Dedicated to every single entrepreneur, founder, executive, manager,employee, mom, dad, and older sibling courageous enough to become

better leaders to those who look up to them.



Title Page



My Half: Kind Candor

Part I: The Emotional Ingredients

➣ Gratitude

➣ Self-Awareness

➣ Accountability

➣ Optimism

➣ Empathy

➣ Kindness

➣ Tenacity

➣ Curiosity

➣ Patience

➣ Conviction

➣ Humility

➣ Ambition

Part II: Real-Life Scenarios

Part III: Exercises

➣ Gratitude

➣ Self-Awareness

➣ Accountability

➣ Optimism

➣ Empathy

➣ Kindness

➣ Kind Candor

➣ Tenacity

➣ Curiosity

➣ Patience

➣ Conviction

➣ Humility

➣ Ambition


The Inspiration Behind This Book



About the Author

Also by Gary Vaynerchuk


About the Publisher


Years ago, I had the most difficult conversation with a client that I’ve everhad to have in the course of my career.

It was with a top executive from one of the biggest brands we wereworking with at VaynerMedia, a contemporary creative and media agencywhere I’m the CEO. The executive called me and asked if we could meet inMidtown Manhattan. She wanted to talk face-to-face.

That day, an entry-level employee at my company had accidentallyposted a tweet from the client’s Twitter account, thinking she was loggedinto her personal account. It was a very negative tweet about anotheragency that VaynerMedia was working with to support the brand. To theworld, it looked as if the brand had made disparaging comments about theother agency.

It was a very quick meeting. The executive told me that she expectedthis not to happen again and asked me to put the proper protocols andsystems in place to ensure that.

Then she said to me, “The only way our company sees that we can goforward working together is if you fire the individual who posted thattweet.”

It took me about a hundredth of a second to think it through.I said to her, “I can’t do that.”I had to be able to run my own business and make my own decisions

about my employees. The executive had every ability to fire us if that’swhat she felt was necessary. But it had to be my decision what theramifications of that tweet would be.

She was surprised. That brand represented about 30 percent of our totalrevenue at the time.

I was mentally prepared for them to fire us, but at the time, I knew thatwe had just enough new business coming in that we could afford a yearwith no profit. I also had enough saved up that, if we lost money that year, I

was willing to help bridge the gap if needed. If we could weather thatstorm, it would be a clear indicator to our employees as to what we reallyvalue.

This conversation was one of those interesting moments when you haveto decide what you’re going to stand for. We scheduled a call the next day,and I stood my ground. Luckily, the client didn’t fire us.

I tell that story because modern society’s definition of a “smart businessdecision” is disproportionately predicated on analytics. Business leaderstend to find safety in the “black-and-white.” They find safety in theacademics, math, hard data, and what looks good on spreadsheets.

It’s harder to gauge the 30-, 60-, 90-, 365-, or even 730-dayeffectiveness of empathy, kindness, and self-awareness in an organization,but their results will play out. When you can eliminate fear from yourorganization, very good things happen. If employees don’t have to spendtheir time trying to outmaneuver one another, trying to kill one anotherpolitically, they may actually achieve the task at hand. I don’t know whichsix-year-old girl in Tennessee is going to invent the system to score this, butat some point, it will be mappable. This level of common sense and humantruth will play out.

In big companies especially, many decisions are predicated on ninety-day numbers. That practice comes from Wall Street and business school,where you’re being judged every quarter on performance. It can lead toshort-term behavior, even though many of us are still planning to be inbusiness over the next five, ten, twenty, or even fifty-plus years.

Unfortunately, the bias toward short-term metrics can also makeemotional intelligence a “nice to have” rather than a requirement. It createsa scenario in which a leader looks the other way when one employee makeseveryone else in the office miserable, just because that employee happens tobe bringing in the most revenue. It makes people think negative behaviorand a poor EQ (emotional quotient) are just side effects of being “good atbusiness.”

The business world I entered in the late nineties put the black-and-whiteon a pedestal. At that time, it wasn’t recognized that soft skills could be thekey to building a successful company. I don’t recall hearing these traitsbeing emphasized in the mainstream business community. Business was“dog-eat-dog,” an endeavor where “only the strong survive.”

Ironically, I also believe that only the strong survive. I just believe thatleaning into your humanity is the actual strength that will help you surviveand flourish. Not yelling at someone else in a conference room. Not being atough negotiator with aggressive words. To this day, I think the strongestperson is someone who’s able to deploy kindness in the face of theopposite. The twelve ingredients I describe in this book (we’ll get to whatthe half means later) are some of the traits that have led to my success andhappiness over the years, in addition to others that I’ve observed andadmired: gratitude, self-awareness, accountability, optimism, empathy,kindness, tenacity, curiosity, patience, conviction, humility, and ambition.The black-and-white is still wildly important, but in my opinion, it’s adistant second to mastering soft skills.

I couldn’t be more aware that there are fifteen to fifty other ingredientsthat could’ve made it into this book. But these twelve stood out to me afterseeing other leaders fall short in deploying them and how that gap madepeople around them feel. Many people in conference halls, dinners, lunches,buses, and flights would tell me stories of these twelve ingredients beingneglected. One of the sad things about human nature is that negativity islouder than positivity. It’s been one of the driving forces of my life to makepositivity louder. One of the reasons I’m writing this book is to cheer forthese traits and put a spotlight on them in business.

My greatest challenge has been extracting these ingredients andarticulating them. They’re not tangible. They can’t be tracked or measuredon a spreadsheet. In fact, in May 1998, when I walked into my dad’s liquorstore, I didn’t understand their significance.

My dad’s not a big talker, but on Thanksgiving weekend in 2020, whenI had started writing this book, he told me that he hadn’t believed in“company culture” back when I first started working with him. Comingfrom the Soviet Union, he thought that fear and money were the mosteffective motivators. That’s how he drove his career. But today? Now hebelieves in positive company culture over everything. Even though itdoesn’t come naturally to him and he struggles in explaining it to hisfriends, he told me that he knows it’s crucial. I find it poetic, especially ifyou realize how rarely my dad tells me stuff like that.

This book is cathartic for me because it allows me to do what I can’t onsocial media, given the fragmentation of my communication style. I thinkhumility is one of the biggest reasons for my success, yet if you watch a

one-minute video of me pontificating with uncanny conviction around anopportunity within a TikTok environment, you might say, “Fuck this know-it-all.” As you’ll find, you can be humble and curious but also haveconviction in your beliefs. It’s not either-or.

In part II, you’ll see me combine these twelve ingredients into complete“meals” and show you how they can be used together when you facedifferent challenges in business. For example, accountability and convictionare often seen as opposites to empathy and kindness; they’re traits that havemore “teeth.” Traits like humility and conviction, ambition and patience,and gratitude and accountability might also be interpreted as opposites. Thisbook will help you understand how many ingredients that might seem likeopposites actually work together.

Developing these twelve ingredients individually is the starting point,but knowing how to cook the meal is the real takeaway. Even if you haveall twelve in a solid place naturally or you were lucky enough to havelearned some of them by experience, you still have to know how to usethem together. You still need to be the “chef” who “cooks” them.

There’s a time and a place for a Big Mac, but I wouldn’t serve a BigMac if I were planning a meal for twenty-five strict vegans. Every dish youmake needs to be made in the context of the situation it’s being served in.These twelve traits have to be used in different mixtures in every businessscenario. That’s all I’m ever doing.

Let’s say you’re the head of a law firm and you’ve hired a kid who grewup on “the other side of the tracks.” He or she doesn’t know the protocolsfor a fancy dinner with a client, and you end up losing the deal as a result.This is where you have to pull gratitude and accountability from the “spicerack.” You need to be thankful for even having the opportunity to own abusiness and land this new account. You show accountability by realizingthat you’re the one who hired but failed to properly train that person. All ofa sudden, everything else becomes secondary.

It’s impossible for any of these twelve ingredients to work withoutpatience at the core. If you’re baking a pie, patience is the crust. Peoplemight think ambition contradicts patience, but I think patience is the path toyour ambitions.

People often don’t achieve their ambitions because of their owninsecurity. In their desperation to put wins on the board so the audienceclaps for them, they end up taking shortcuts. It’s hard for such people to

build a meaningful business because they’re so focused on making a milliondollars and buying clothes, boats, and other fancy things without havingcultivated patience.

Whatever you do professionally is normally going to be something thatwill take up most of your life, so patience is a practical way to get to yourambition. Lack of patience is a huge vulnerability, and it has led to morebad decisions than any other factor.

Sometimes, I notice this with my buyers at Wine Library when we makedecisions and negotiate deals. It’s imperative to realize that the sellers we’rebuying wine from are going to be our partners for the next fifty years.That’s why I’ve left dollars on the table when negotiating a wine deal. If Ihad ground the sellers to the bone every time, they wouldn’t have had thesame relationship with me, and there would have been fewer opportunitiesin the future.

This was something I observed early in my career with one of ourbuying managers, who was a formidable negotiator. As I watched ourrelationships with the wine suppliers, I noticed that (1) they reacted to thebuying manager’s negotiation style by raising the starting price, and (2)they started taking their wines to other stores. By leaving some dollars onthe table, I got many more of the best wines and had a better starting pointin every negotiation.

As a CEO or manager, you also need patience as you watch youremployees develop. Many of my partners and hires didn’t start out great inthe role they became best at.

Most important, you need to be patient with yourself as you developthese ingredients. Those who think they’re running out of time get franticand become vulnerable to bad decisions. When I was watching The Queen’sGambit on Netflix, I noticed that as the chess timer got lower and lower,players got more frantic. When I watched videos of the greatest chessplayers, I noticed the same thing. Their body language and decision makingbecame more frantic when time became part of the equation.

I believe the majority of people starting and building businesses do nothave a good relationship with time. They misunderstand it. They’re basingtheir choices on low-probability events, like getting hit by a bus. Theyforget that they may live to ninety or a hundred as life expectancy increases.Patience has kept me from dwelling on bad deals I’ve made and allowed meto work in a family business when I wasn’t making the salary I could’ve

been making elsewhere. It’s what has allowed me to take steps backward inthe micro and macro without getting crippled by discouragement.

I think I have a lot more time to play. Whether that’s actually true ornot, I feel an enormous amount of day-to-day happiness as a result of thatbelief.

My Half: Kind Candor

Patience and ambition, gratitude and accountability, empathy andconviction—I balance a lot of these traits in mixtures. I’ve started to workon balancing my kindness with candor. I realized that kindness withoutcandor was creating entitlement within my organization. By giving positivereinforcement again and again without critical feedback, I created delusion,which led to entitlement.

I have a visceral reaction to confrontation, and so I was very bad atgiving critical feedback for most of my career. After twenty-four years as abusiness operator, I’m heartbroken that there are people out there who don’tfeel great toward me because I wasn’t able to be candid with them. I wouldfire them without giving them enough feedback, or I would create situationsthat forced them to quit.

I didn’t see the beauty of candor, the humanity in it. I didn’t realize thatcandor actually is kindness. I can think of many times when some kindcandor would’ve taken my success to a higher plane. All my unhappiness inlife and business has resulted from my inability to deploy kind candor whennecessary. That’s why I’m calling it my half. I say “half” because nobody’sa zero on anything. No matter how bad you think you are, the fact thatyou’re even aware of a weakness or a gap has already started your processof becoming better at the underdeveloped skill.

My half convinces me of the importance of the other twelve ingredients.Knowing that I’m not good at kind candor yet, at least at the level of beingable to cook the whole meal, makes me realize that lack of any one of thetwelve is going to hurt you. It’s going to limit you. It’s the indicator of yourvulnerabilities.

As you go through this book, I don’t want you to be depressed whenyou find out what your halves are. I want you to be thrilled because, as youimprove on those halves, more good things will happen for you. You mightrealize that you’re unhappy because you don’t have kindness to give. Youmight start understanding why you yell at your interns. You might startuncovering reasons why you’re being selfish at work. You might learn thatyou’re not “full.” Personally, I feel grateful to be working on kind candor, atremendous addition to the other twelve ingredients.

The growth potential of most businesses is limited by the emotionalintelligence of their leaders. That goes for sports teams, families, andsovereign nations. Every single person who has a child is a leader. Anyonewho has a younger sibling is a leader. Anyone who has a pet is a leader.Anybody who has even one person to manage is a leader.

This book will help you refine your ingredients and improve yourleadership capabilities. The quality of your dish depends on the quality ofyour ingredients and the way you use them in combination.

All twelve are important. If one ingredient is secondary to another, thedish won’t be good. What’s more important, the fish or the salt? What’smore important in baking a cake, the flour or the eggs? The answer isalways both. They’re equally valuable but must be deployed in differentproportions in different situations. As you navigate every second of yourlife, you need to add different ingredients at different times.

So much has worked for me in creating outsized success because I gottwelve of these down. The reason I didn’t have every dish tasting perfectwas that kind candor was missing.

How This Book Is StructuredAs you begin part I, you’ll notice that I define each ingredient and explainhow it can affect your career and your life as a whole. I’m emphasizing akey concept, which may be the most important sentence in this book: Whenyou actually understand how unimportant business is in the grand schemeof your life, it allows you to enjoy it and potentially get better at it. Peoplethink of me as an entrepreneur and businessman, but if I were melted downand read in book form, I think most people would be shocked to see howlittle I ultimately care about business.

Before you get into the following pages, you need to know that whenyou value life as a whole over success in business, the game gets

dramatically easier and wildly more enjoyable. When you put happinessover money, stock shares, and public admiration, your day-to-day workbecomes sustainable over the long haul. I believe some entrepreneurs,managers, and founders of successful businesses sometimes go throughburnouts and crashes because they haven’t implemented these ingredients.

In part II, I’ll take you through a variety of different real-life scenariosto show how these ingredients can be used together in varying mixtures.You’ll also have the chance to reflect on your reactions to challengingsituations in your career and what you would do differently today with whatyou’ve learned from this book.

In part III, I’ll give you real-life exercises to help you develop eachingredient, including kind candor. These exercises will enhance yourconviction around your strengths and help you identify insecurities, uncoveryour halves, and grow in those areas. For a full list of supplementalresources, visit

It’s a shockingly simple point of view. I think of business as an art. Ithink it can be as beautiful as a symphony or a painting when executedproperly.

For it to ever have that place in society, we must realize how the twelveand a half emotional ingredients in this book can be the catalysts for successin business.

Part I

The Emotional Ingredients



The quality of being thankful; readiness to show appreciation for andto return kindness.1


If there were a list that ranked everyone on Earth in terms of overallsuccess and happiness (from 1 to 7.7 billion), where do you think you’drank?

Write down your answer here: __________________ out of 7.7 billion.Got your number? Great.According to the World Health Organization, 785 million people

globally lack basic drinking-water services.2 That’s a little over 10 percentof the world’s population, and even two million Americans don’t haveaccess to safe drinking water or basic plumbing.3

Do you have enough food to eat every day?More than 820 million people in the world were undernourished in

2018.4No matter how much you hate your job, do you have even the slightest

potential or ability to get another one? According to the Global SlaveryIndex, 40.3 million people were in modern-day slavery in 2016.5 Theyreally don’t have the option to quit.

Do you have a proper toilet at home? Around 60 percent of the world’speople (4.5 billion of them) don’t have a toilet that properly manageshuman waste.6

Do you have high-speed Internet at home? About three billion peoplearen’t even on the Internet.7 Even twenty-one million Americans lackbroadband access.8

And we haven’t even started talking about income yet. According toCNN’s Davos 2017 Global Wage Calculator, the global adjusted averageannual wage is $20,328.9 In Russia, it’s about $5,457 per year; in Brazil,$4,659; in India, $1,666; and in Malawi, $1,149.

Obviously, there are too many variables to identify your exact rank outof 7.7 billion. However, by throwing all this data at you, I hope to get youto understand what’s actually going on in the world outside your directsurroundings.

I’m completely driven by perspective and gratitude. I was born in theformer Soviet Union in Belarus, so I deeply understand how much worselife could be. In fact, I might not have even been able to get out, had it notbeen for the following event:

In 1970, sixteen Russians plotted to hijack a small plane. The crewpretended they were going to a wedding but secretly planned to fly theplane to Sweden to escape the Soviet Union. Their eventual goal was toarrive in Israel. But the plan didn’t work out, and the participants gotarrested and thrown in jail for treason.

However, that event drew global attention to the human-rights issues inthe Soviet Union during the Cold War. The media in the United Statescovered the hijacking plot, and it changed the political landscape. Due tothe increased attention and pressure, the Soviet Union loosened itsregulations and eventually let more Jews leave.

I believe those sixteen people changed the course of my life.Luck is an interesting word. I probably would attribute most of my

success to my tenacity, ambition, and other emotional ingredients ratherthan luck, but the fact that I was able to escape the Soviet Union at a youngage certainly involved luck.

People don’t understand the reality of what’s happening in the worldbecause their communities are so insular. Many people look at a milliondollars as the entry point of success. Many twenty-somethings are trying to“make it” before thirty. When you’re living in a Los Angeles apartment or ahouse in Greenwich, Connecticut, it’s tough to wrap your head around thefact that women in Africa collectively spend two hundred million hours a

day collecting water.10 People look upward at those who rank higher, butthey don’t look downward at the billions ranked lower.

Anybody who owns a business in a First World nation is already livingan extraordinary life. I don’t think most entrepreneurs realize how blessedthey are. Even if it’s a grind. Even if it’s hard. Even if there are bad days.

Don’t forget—over half the world doesn’t even have a real toilet.When you develop perspective, the timelines you set for your goals

naturally shift. As I write this, life expectancy in the United States is aboutseventy-nine years. In 1930, it was fifty-eight. In 1880, it was thirty-nine.11

Although 1880 feels like a long time ago, it really isn’t. A grandparentwho’s ninety-one in 2021 probably knew of family members who died atthirty-nine or so. If you lived during that time, of course you needed to haveyour life figured out by thirty. You’d die nine years later!

Even in 1930, people died at fifty-eight. By age thirty, their lives werealready more than half over.

As our life expectancies increase, shouldn’t our timelines for goalsincrease too? Shouldn’t you be OK with not having everything figured outuntil later?

With advances in modern medicine, I believe many of you will live toninety or a hundred years old. If you’re twenty-seven and hate your jobafter working your way up for five years, it’s fine to take a step backwardand find another job. If you’re thirty-three and decide to start your ownbusiness from scratch after getting a degree in something you’re notpassionate about, you’re not “too late.” You’re actually the luckiest of thelucky. You get to be alive during an era when the math shows you probablyhave another sixty years to play. Regardless of what happened yesterday orevery day before that, you still have a generous amount of time ahead ofyou.

Be thoughtful and honest with yourself about your missteps, but don’tstart dwelling on them. People beat themselves up and obsess aboutsomething that happened thirteen years ago—a business partnership thatdidn’t work out, a startup that failed, or a boss they didn’t like—and itbecomes the jail they live in. With all the time you have left, there’s zerovalue in getting bogged down there. If I ever get into that mud, I’mgrabbing my gratitude hose to wash it off.

I’ve had major disappointments in my career that I’ve dwelled on formaybe an hour. Maybe a day, if it was really a gut punch. How can I be

upset about such a small thing for so long? I’m playing my life’s mission.I’m doing my thing. Of course I’m going to lose every now and then. It’slike losing a playoff series in basketball. It’s going to happen. In the face ofdisappointment, gratitude is my chess move to limit dwelling on it.

Actually, as long as we’re talking about dwelling, I need some help:send an e-mail to, and title it “The value ofdwelling.” I need to know what it is.

I’m not talking about the value of mourning. I’m not saying youshouldn’t give yourself time to mourn. I just think we should reservemourning for the death of people, not bad business decisions. What’s thevalue of dwelling? What could possibly be productive about beatingyourself up for weeks, months, or years over a bad outcome?

I get it. Susan broke your heart in college, but it’s over. She’s forty-seven now, with three children.

One of the biggest points I’m trying to make in this book is that positiveemotional ingredients provide more sustainable fuel than negative ones. Ifyou draw energy from gratitude, you’ll find that it lasts much longer thanenergy drawn from insecurity, anger, or disappointment.

I understand why people like to use the dark side as energy. I love beingan underdog and having a chip on my shoulder too. Why do you think Ilove being a fan of the New York Knicks and the New York Jets? I lovelosing. I’m motivated by it. But I’m more motivated by the light than thedark. That balance matters.

Anger can give you a short-term energy boost, whether it’s anger towardyourself or others, but once you achieve the gratification you’re looking for,you’ll often find that it’s not as fruitful as you imagined it to be. A lot ofpeople are motivated to “stick it” to their parents for doubting them, but bythe time they do it, things are different. The situation has often changed, theparents are no longer around, or maybe they’ve mellowed. Insecurity andanger can be tremendous drivers of success—but I don’t believe they leadto happiness.

Anger and resentment are heavy ingredients to carry around. Gratitudeis light.

I’m fascinated that people think that gratitude creates complacency.There’s a reason why complacent and grateful are two different words. Thedefinition of complacency is “a feeling of smug or uncritical satisfactionwith oneself or one’s achievements.”12 They’re not the same.

For example, I can separate my gratitude from my requirements for thefinancial structure of a business deal. If those requirements aren’t gettingfulfilled, I know I’m in control of making a decision on whether I sign thedeal or not. Same thing applies if you work at a company: you can begrateful that you have a job, but if you feel it isn’t paying you enough afteryou’ve delivered results for three years, you can take another job instead ofdwelling on it.

As you’ll see in part II, you can be grateful and ambitious. You can begrateful and tenacious. These traits don’t have to come at the expense ofone another.

Want to know where my energy and smiles come from when you see meon social media? They come from gratitude. If I wake up in the morningand nobody I love has passed away or come down with a terminal illness,then my day starts off great. If the people closest to me are OK, I’m good. Iwon. Nothing else can truly faze me beyond that.

If you’re truly grateful for what you have instead of being envious ofwhat you don’t have, you’ll be a dominant force in business and, way moreimportant, in life.



Conscious knowledge of one’s own character, feelings, motives, anddesires.13


If there’s anything that I could wish upon society aside from good health, itwould be a new drug to help everyone develop these emotional ingredients.If I were the FDA, the first one I would prioritize would be self-awareness.

The value of self-awareness first hit my radar in 2011 to 2013 duringthe explosion of interest in entrepreneurship in popular culture. When I sawsome students and executives become startup founders, it struck me—howdo they not realize that they have no chance? Why are they trying to be anumber-one (a CEO)? How do they not realize that they’re better suited tobe a number-two, number-three, or a number-twenty-seven player in anorganization? Do they not realize that they’re making this jump becausethey think it’s cool, instead of doing it because it’s their calling?

There are many reasons why humans try to become someone they’renot. Sometimes, it’s just delusion. (I don’t say that in anger; I say it withempathy.) Delusional people lack awareness about their strengths andweaknesses.

However, what surprised me was that many of them aren’t delusional—they’re actually very self-aware. They do recognize they have no shot, sothey overcompensate for their insecurities by propping themselves up witha job title like CEO. They’d rather put “entrepreneur” in their Instagram

bios to appear successful in the eyes of the world than lean into theirstrengths and passions and start building sustainable, long-term happiness.

Many of those who dream of being entrepreneurs today would’vedreamed of being astronauts and pilots back in 1957 or rock stars in 1975.

Self-awareness has a close relationship with self-love and self-acceptance. I’m realizing right now that it’s one thing to be self-aware. It’sanother thing to look in the mirror and say, “Hey, you’re not good at X.”That doesn’t mean telling yourself you’re a piece of shit. It just meansacknowledging a weakness.

Insecurity often leads to avoidance. People tend to be the most avoidantwith their own flaws.

If you tell yourself, “You’re not good at running a business,” thatdoesn’t mean you’ll never have a successful, fulfilling career. Maybe youcan build a personal brand for yourself as an influencer. Maybe you canmake your impact as an executive. Maybe the reason you’re not good atrunning a business is that you don’t enjoy managing people, and you canbring in a partner with a complementary skill set.

When you fully accept yourself, you’re no longer scared of otherpeople. On social media and in real life, humans tend to feel uncomfortablewhen they feel out of place. They feel that others are superior or that aninsecurity they’re trying to hide will be exposed. For me, a combination ofself-awareness and humility is why I love being around people. Nobodyscares me.

Therefore, I don’t feel the need to use my ambition as a crutch to getacceptance from others. Self-acceptance helps one embrace self-awareness,not avoid it.

For a lot of people, a little more self-awareness could help them bemore secure in their titles at work. Outside of the financial benefits that cancome with more senior roles, chasing titles is one hundred percent tied tocaring what others in the organization think of you. For me, the job title hasbeen an afterthought in many of the companies I’m involved with. What Icare about is bringing value to every single person I interact with.

I will say, out of fairness, that your job title does become an importantleverage point when you plan a move to a different company. When peoplein my company meet with me and ask for a different title that I can’tprovide, I often tell them to come back to me when they want a differentjob, and I’ll give them a double title increase to leverage on LinkedIn.

But within the organization? Those who care too much about job titlesare largely worried about other people’s opinions.

Looking back, I see I’ve always had self-awareness, even in my youth. Iknew I was a businessman, a purebred entrepreneur. When I made athousand dollars as a sixth grader selling stuff, I knew I was going to be OKeven if I got D’s and F’s in school. It wasn’t just my opinion that I was atalented businessman—I had affirmation from the market.

I was an entrepreneur then, and I’ll still be an entrepreneur if and whenit stops being cool a decade from now.

Confidence makes self-awareness easier. I’m willing to take a hard lookin the mirror and acknowledge all the problems I have in my life. I’mwilling to separate who I am from who I wish I could be, a challenge forthose who are insecure.

The best part of acknowledging your weaknesses is that you can thenstart navigating around them. For example, I don’t have the work ethic toput up a painting on a wall, because I don’t like doing it. So, I’ll findsomeone else to do it.

But I do have the work ethic to spend fifteen hours a day on mybusiness, because I love it.

I can’t read long texts or e-mails, so I have quick five-to-fifteen-minutemeetings with my team instead. I don’t say to myself, “Oh no, I need to geta tutor.” Instead of taking my reading skills from bad to OK, I’d ratherspend that time taking my strengths from great to supernova. That takesself-acceptance and self-love.

That said, I think you do have to improve your weaknesses. To a point.You need to be capable enough. My kind candor was so weak that it

created issues with some current and former employees, so I had to improveit. But I don’t overstress this point, because most people work only on theirweaknesses, not their superpowers. Yes, I want to level set my weaknesses,but I’m more interested in taking my strengths to the moon.

You might not be able to completely punt your weakness as I puntedschool. You might need to get it to an acceptable baseline, but it’s often toomuch work to go from acceptable to good. Even more often, the juice is notworth the squeeze. I want you to triple down on what you’re naturally goodat. Ironically, you’ll find that it actually compensates for your weaknessesmore effectively than trying to turn a weakness into a strength. In other

words, the net business outcome is greater when you triple down on thosestrengths because of time-impact arbitrage.

I needed my kind candor to be at an acceptable level, but I know I willnever be the greatest at it. I’ll never be as good at it as I am at an ingredientlike empathy. Never ever.

If at this exact moment you stop reading and start learning more aboutself-discovery from other teachers and formats, then this book is the bestone I’ve ever written. That’s how much I believe in self-awareness.



The fact or condition of being accountable; responsibility.14


People love to deflect blame from themselves onto other people. Thegreatest misconception is that avoiding accountability will lead tohappiness, when in reality the reverse is true.

“It’s my boss’s fault I’m not getting paid enough.”

“Sally messed up my project.”

“That’s on Rick for not communicating.”

“The market collapsed the day before our launch.”

“Well, if the client hadn’t made these demands . . .”

When you blame others, you’re admitting to yourself that you’re nolonger in control. You give leverage to the person(s) you’re pointing yourfinger at, and you become a victim of the situation you’re in.

Instead of pointing a finger, consider pointing a thumb back at yourself.

“I need to ask my boss for a raise or get a new job.”

“I have to set a better framework to work with Sally in the future.”

“I need to set up quick check-in meetings with Rick.”

“If I hadn’t been looking for the gold rush (or if I had moved quicker during the gold rush), thiswouldn’t have happened.”

“If I’d been more up-front with the client, I wouldn’t be in this situation.”

I think of accountability as the brakes. It stops the momentum of painthat comes from blaming others. If your business partner screws you andyou go into a dark spiral of blame, accountability gets you out of it. If youlisten to two people arguing, you’ll notice that the entire conversationalflow changes the second someone takes a step toward accountability.

No matter what challenge I’m facing, I have to accept that in some wayI made a decision that put me in that situation. Even if the decision I madewas to ignore the situation until this moment, I need to hold myselfaccountable for that, too. It gives me great calm and comfort to feel thatevery issue in my life is 100 percent my fault. It excites me to know thatnobody else is in control. If I created the issue, then I have the power to fixit. If I didn’t create the issue and it’s bigger than me or purelycircumstantial, I can still decide how I absorb it.

Accountability is the most challenging ingredient for most people,because their self-esteem is predicated on the outcomes of their actions. It’shard to take blame when you’re not kind to yourself or optimistic about thefuture; taking it leaves you completely vulnerable to other people’sjudgment.

People fear others’ opinions, so they develop an ego-defensemechanism against their own mistakes. It’s a form of avoidance disguisedas a solution.

I cheer for people. I show my admiration for them. However, I don’tthink others are better than me. I also don’t think I’m better than them.When you don’t overvalue your own opinion, it’s easier to not overvaluethe opinions of others. It frees you to be accountable. It’s easy to tell theworld, “It’s my fault,” because there’s nothing anybody can say about methat can affect my self-esteem.

You might be able to trick certain people by deflecting accountability,but you can’t trick those with stronger emotional intelligence than you.People who have a high EQ are typically the most liked or the mostsuccessful, and it really sucks if you can’t win with that group.

To them, it’s obvious when you’re passing blame. Unfortunately, manypeople would rather live their lives tricking other emotionally weak players.They’d rather win with those who are ego-driven and fear-based.

I do have empathy for those who avoid accountability, because for along time, I also avoided kind candor and one-on-one confrontation. I wenttoo far in the direction of being empathetic and taking accountability forothers’ weaknesses or mistakes, which meant that some employees didn’trealize they also had room for improvement. My avoidance of kind candoralways led me to a situation I didn’t want to be in. In the short term, Iavoided conflict, but throughout my twenty-plus years at VaynerMedia andWine Library, some employees left because I didn’t give proper feedbackon how they could grow.

I’m continuing to learn that leaders need to mix kind candor withaccountability. Too much accountability can give way to entitlement andresentment down the road for both managers and employees. Perhaps kindcandor can make it easier for you to embrace accountability: it means youdon’t have to passively accept all blame.

If you’re having friction with a business partner, you can takeaccountability for putting yourself in that position but still give feedback tothe other person when necessary. You can do both.

Of course, in business, financial stability is the big variable that canmake it easier to be accountable. That’s why saving money is crucial.

As you work on developing this ingredient, I encourage you to askyourself this important question: Can you quit your job tomorrow?

A lot of people can’t. It’s one thing if you’re twenty-two years old andfresh out of school with no debt, but when you start adding otherresponsibilities, it’s not just about you anymore. Even if you feel that youcan live in a smaller house without fancy things, maybe you have kids, whoeach need their own room to study. You might have a significant other whowants a different lifestyle.

Do you feel trapped? If so, a good start toward taking accountability islooking at your expenses and seeing where you can save money. Can youmove an hour away from your office to save on rent, now that morecompanies accept remote work? Can you sell some things you don’t useanymore?

As I get older, I realize how much of my happiness comes from being incontrol. Financial control is only one aspect of being in control. It’s alsoabout being in control of how I use these twelve and a half ingredients.

When you genuinely feel that you’re in control, you don’t fear theoutcome. If you have savings, you can feel safe, because you can take care

of yourself. If you’re still working toward that security, you can still feelsafe in the fact that you can always get another job. There are always moreopportunities. The world is abundant, and you’re in the driver’s seat.

Much of the day-to-day angst people face comes from a feeling ofhelplessness. Accountability can potentially reverse that.

I wish this book were called Thirteen, but it’s not. It’s called Twelve anda Half because I’m still in the process of addressing my kind-candoringredient. If you know that accountability is one of your halves, I hopeyou’ll begin to do the same right now.



Hopefulness and confidence about the future or the successful outcomeof something.15


On December 13, 2020, I posted on Instagram a video of a deer skippingacross a beach. I gave it this title: “all I want is for you to be as happy asthis baby deer . . . that is all.”

Visit to check it out.

Someone left a comment on that post, saying, “Till that lion comes.”I responded, “And then he will get smart and avoid the lion, too many

are scared of the thought of the lion without realizing you’re capable ofnavigating it!!! Fuck the lion.”

Optimism is a word that has become controversial in some ways.There’s a misconception that it means the same thing as delusion. Astunning percentage of people (probably including the user who left thatcomment) believe that optimism is just a setup for disappointment and loss.Those who are scared and hurt are afraid of optimism because they don’twant to be let down, so they confuse it with naïveté.

Take a second and reread the definition at the beginning of this section.In contrast, here’s the definition of delusion: “a false belief or judgment

about external reality, held despite incontrovertible evidence to the contrary,occurring especially in mental conditions.”16

Notice how they’re different?The opposite of optimism would be pessimism. Here’s the definition of

that: “a tendency to see the worst aspect of things or believe that the worstwill happen; a lack of hope or confidence in the future.”17

Does it make sense that with hope and confidence about the future, youhave a higher chance of reaching your desired outcome? I think so. Moreimportant, you have far more control of your perspective than you haveover the trillions of variables that make navigating the universe so tricky.

Choosing optimism over pessimism is, at the end of the day, wildlypractical. It doesn’t mean being naïve or blind to the downsides in businessor in life. In fact, I’m more aware than most about what could go wrong. Ijust believe that I’m capable of navigating any challenge. For example, ifyou think you’ll be genuinely happy running your own business, I’m notgoing to lie to you and say that it’s going to be easy. However, I’m excitedthat you even have the opportunity to try. Your grandfather couldn’t start acompany on the side with his smartphone. Gratitude can fuel optimism. Doyou know how lucky you are?

Optimism is being thrilled about your next at-bat, while acknowledgingthat you’re not guaranteed to hit a home run.

If this is hard for you, ask yourself what your defense mechanism iswhen something doesn’t go as planned. Do you default to blaming othersand getting upset? Do you lack accountability? Do you use ego as a shield?Do you crawl into a shell because you’re dwelling on the past and beatingyourself up? Is your self-esteem entirely influenced by what other peoplethink of you?

Or do you take accountability? Do you deploy gratitude to limitdwelling? Do you have perspective on life as a whole, outside of yourbusiness or career? Are you kind to yourself?

The other emotional ingredients will help you deal with losses moreeffectively, so you won’t be let down as often. When you know you won’tbe let down, optimism comes naturally.

Rewiring your emotions takes time. Start by surrounding yourself withoptimistic people, and limit interactions with people who drag you downmentally. Fill your ears with positivity through podcasts and videos—24/7,365.

Groups who have been historically oppressed tend to draw optimismfrom other successful people who look like them. That’s one of the reasons

why representation is so important.My grandparents would always point to the TV if there was a person on

it with a Jewish last name. They’d say, “Wow, a Jewish person is on TV!”They lived under oppression in the Soviet Union. I didn’t understand

then, but now I see why they were thrilled to see successful people wholooked like them—they were a source of hope.

I think of optimism as a map. It helps me see my destination. It’s one ofthe many reasons why I value the journey over the outcome. Optimismmakes the journey so much more fun than pessimism. It’s exciting to wakeup in the morning and play my game when I have hope and confidence inachieving my goals. Optimism makes playing the game more enjoyablethan winning it.

I talk about how I want to buy the New York Jets one day, but I wishyou could understand how little I actually care about it. Of course, it wouldbe amazing if it happened, but I’m comfortable if it doesn’t happen.

What I’m not comfortable with is not trying.That’s why I believe optimism is a perfect teammate to tenacity. How

can you be tenacious if you don’t think you can achieve what you’re settingout to achieve? How can you put in the necessary work? More important,how can you sustain success once you achieve it?

If I’m climbing a hill and I tell myself I’m not going to be able to makeit to the top, it’s not as much fun to push through. But if I believe I can, I’llgenuinely enjoy the process of climbing—even if naysayers say I can’t. I doacknowledge that, much like Darth Vader, you can use pessimism withtenacity to achieve your goals, but it’s not sustainable. If you haveconfidence in a positive outcome, and you pair your optimism with tenacity,success has a better chance to come true and be sustainable.



The ability to understand and share the feelings of another.18


Let’s call out the elephant in the room.I named my wine project Empathy Wines. In 2019, it was sold to

Constellation Brands, but it will always have a special place in my heartand soul.

When I hear the word empathy and read its definition, I get emotional.Empathy is a powerful ingredient that has accelerated much of my successin business and life.

Empathy is the reason why I invested my life savings in Facebook andTwitter in the early days. It’s why I’m bullish on the future of NFTs (non-fungible tokens, unique digital assets that exist in a variety of industriesfrom digital art to virtual real estate to collectibles, and more). It’s why Iknew CryptoPunks would grow in popularity, and that rappers like Gunnaand DaBaby would have successful careers. It’s why I knew the Internetwould change my dad’s business back when many thought the “informationsuperhighway” was just a fad.

I’ll continue to do that over the next several decades of my career.Eventually, I think I’ll be looked at as someone who had an uncanny senseof human behavior.

Empathy is my ear to the ground.It naturally pairs with curiosity, as you’ll learn when you get to that

section. Curiosity is the work I put in to get educated about NFTs. Empathy

is my intuitive feeling that they are going to be a big part of your life in thefuture. When it comes to NFTs specifically, I get the same feeling I got inthe early Web 2.0 era in 2005.

I have empathy for individuals sitting across from me at a conferencetable, but I also have empathy for the masses. For me, it’s as easy to sensethe feelings of the person next to me as it is to sense what all of you arefeeling as you’re reading this book. It’s crazy and almost overwhelming tome that I can feel all of you collectively, with all your different nuances,perspectives, and backgrounds. It helps me communicate contextually.

When you’re empathetic, you recognize why people behave the waythey do.

Why do you think I react with compassion for those who leave hatefulcomments on my content, not with anger or frustration? If somebody’staking the time to come to my account, consume my content, and then leavea negative comment saying I suck, then that’s a reflection on them. They arein enough pain to want to drag me down to their emotional level.

Somebody once commented to a piece of content, “Gary, this isridiculous, you’re not that special.”

I replied, “That’s not what my mom says.”And after looking through that user’s account, I added, “Your

photography’s remarkable.”I deploy empathy and kindness against hate because I know it takes

more strength to be empathetic. From the outside, people think that thosewho come with negativity and aggression have the advantage in theinteraction. I know it’s the reverse.

If I were working in a corporation with a toxic boss, I wouldimmediately go to empathy. The boss might look as though he or she iswinning on the outside and may trick casual observers into thinking thatstepping on others is how you get ahead. But that boss, likely cynical orinsecure, is going home and secretly popping pills or drinking to escape. Orhating Mom and Dad and the whole world.

For me, it’s simple to deal with those scenarios. I feel bad for the boss.How could I not, when that human being must be in so much pain?

Empathy is the ingredient that provides the answers to the test. Whenyou can feel what another is feeling, you develop an extraordinary ability tomanipulate human beings. I believe it’s the ultimate superpower. You cancreate carnage with it, or you can use it to uplift the world, as I’m trying to

do for you with this book. I’m trying to inspire you to be happier bydeveloping these ingredients for business success. In reality, this is aboutmuch more than just helping you win in business. It’s what the worlddesperately needs.

However, it’s one thing to have empathy. It’s another thing to use it.There are mothers, fathers, CEOs, managers, and leaders out there who

have the capacity for empathy at the highest levels. Yet they themselves areinsecure, so they hold back.

A mother might intuitively feel that her young daughter hasentrepreneurial ambitions, but they might live in—say—a remote part ofTexas where cheerleading and pageant life is everything. The mother knowsher daughter isn’t interested in that, but if the mother herself lacks self-esteem, she may subconsciously force her kid to become a cheerleader toavoid judgment from other moms. If you don’t have self-awareness (withself-acceptance and self-love, by association), then empathy might be oneof your halves. Your own insecurities are like anchors weighing you downand preventing you from truly bringing value to others.

In a business context, my biggest challenge with deploying empathy isbalancing it with letting others learn on their own. Two employees on myteam had a conflict with each other last week. I know the answers to thesituation and what they each should’ve done, but do I tell them? There aremuch-needed lessons for both employees, but should I go in heavy-handedand just let them know?

If I do, they might start becoming fear-based. Or I might be justapplying a Band-Aid that doesn’t create lasting change. They might need tocome to those realizations themselves. But withholding feedback can createentitlement. As you’ll see in part II, when we dive into real-life businessscenarios, I’m always trying to figure out when and how to jump in withfeedback.

Empathy is like a cheat code in business and life. I actually think itmakes the other eleven and a half ingredients easier to use. You can handleany situation if you can feel the feelings of others involved.



The quality of being friendly, generous, and considerate.19


At Wine Library, I once had an employee I was really close with steal$250,000 worth of wine.

What would you do in that situation?People think of kindness as an ingredient to deploy toward people

they’ve disappointed, hurt, upset, or put in a precarious spot. For me, it’sabout being kind to those who have put me in a difficult position. I’ve beenkindest when associates have been rude to me or fucked me over inbusiness and two years later pretended nothing happened.

I often tell my friends with big potential that being kind is easy whenit’s easy. Being kind when you’re under pressure is tough. It’s easy to blastoff and curse people out when you’re feeling stressed. It takes internalstrength to be the bigger man or woman, but it’s an important trait that candifferentiate you from others.

On a daily basis, I rely on kindness to get me through anxious andchallenging moments in business. The people closest to me have had theluxury of seeing it. But I’m sad that my aggressive communication style infront of the camera creates some confusion about my obsession with thisword.

You don’t have full context on anybody else. You don’t have 100-percent insight into what’s going through their mind or the events in their

childhood that molded them into who they are today. So how can you judgethem?

By the same token, when other people judge you, how can you take thatjudgment to heart when they don’t have all the context on you? Those whojudge themselves harshly tend to judge others harshly too. Those who arekind to themselves tend to be kind to others.

When I first got news that an employee had stolen from us, it felt like agut punch. I knew that my dad would be resentful of the open, inclusiveculture I’d created that (in his mind) enabled one of our own to takeadvantage of us. Immediately, I went into protection mode.

First, I reminded my dad that people have stolen from us in the past,even when he did have an “iron fist” over the company. It’s just the natureof a retail business. Then, I asked myself: “Is that employee OK? Why dothis? Is there something I don’t know about?”

There was. That person was addicted to pain meds, desperately neededmoney, and so stole from the company.

Believe it or not, I feel a sense of gratitude and guilt in these situations.I’ve been so fortunate in my life to not be hurting. How could I not lean intoempathy and kindness to find forgiveness for that individual? How could Inot feel bad for them?

That doesn’t mean you can’t hold that person accountable. Peopleconfuse the definition of kindness with the definition of pushover—“aperson who is easy to overcome or influence.”20 They’re not the same at all.

You can be kind, be candid, and hold your ground all at the same time.When you’re in a confrontation with an employee, vendor, or client,kindness will let the other party open up to you in a way that wouldotherwise never happen. I’m passionate about practicing kindness to createa safe environment when delivering bad news or having difficultconversations.

If you’re too empathetic and kind without balancing it with candor,however, you set yourself up for resentment later in life. When you’reoptimistic about the future, you can be the bigger person when others dowrong by you, but when time starts running out, you start lashing out.

If I hadn’t started developing kind candor as an emotional ingredient,resentment would flourish in my old age. I’d deploy the opposite of theseingredients in my eighties and nineties.

Kind candor was always challenging for me because I don’t care aboutwhat most people care about. I’m not transactional. I’m an emotional giver;therefore, I have a larger capacity to deal with resentment. But at the sametime, I know I have to balance that with other ingredients. For you, it mightbe the opposite—even if you’re great at candor, you might be missing thekindness element.

There’s a reason why I added the word kind in front of candor. Howyou deliver the medicine matters. One of the reasons many people chooseone doctor over another is bedside manner. It’s not about only theknowledge of medicine. It’s a lot easier to swallow a grape-flavored coughsyrup than to drink it raw. It’s more fun to be in a humorous, laughing moodbefore getting a shot than to have tears running down your face. You’re stillgetting the shot.

Don’t use candor as an excuse to not be nice.During the Steve Jobs era, I literally watched nice kids create a harsh,

rude management style in their organizations as an ode to Steve. It struckme deeply, and it became one of the reasons why I wanted to talk moreabout kindness. In fact, it was a catalyst behind this book, and why I wantedto put these twelve and a half ingredients on a pedestal. I wanted to maketraits like empathy, kindness, and gratitude cool—just as being a jerk wascool during that era.

I’m not trying to have an argument about whether or not being a toughboss increases productivity and output. I’m just trying to say that, at the endof the day, I believe kindness beats rudeness. I’m sure we can point to manysuccessful organizations that had dark management styles, and I get it.Tough coaches can create successful teams. But if you look underneath thehood, there’s a lot more love there than people from the outside realize.There’s more context that people have internally.

I don’t know all the details around Steve, but I know how the youth inSilicon Valley interpreted it and how it became lore. My intuition is that hehad a lot more love and good intentions than his reputation at that pointsuggested.

Even the toughest coaches in the NBA or NFL have players who lovethem. Many also speak of the coach being a totally different person behindclosed doors than how he or she is perceived by the media.

There’s a reason for that.

The concept of kindness as a strength is one of those things that societyreally struggles with. It’s just not the way that trait has been positioned. Iintend to push the narrative of kindness as a strength and see what kind ofimpact I can have.

It genuinely, genuinely works.



The quality or fact of being very determined; determination.21


We live in a world where the word hustle has been manipulated and evendemonized. To some it means burnout and fatigue, and I’m devastated whenanybody wants to associate those words with me.

If you want to be successful in anything, I do believe that tenacity isessential. However, it should never come at the expense of your peace ofmind and happiness. Tenacity should never equal burnout. I’m sad thatsome people haven’t been able to separate those two words.

But I have empathy for them. A lot of people view tenacity in the sameway I viewed candor. Throughout my life, I’ve been unable to separatecandor from the negative way I saw it deployed in my life, so I avoided itcompletely.

When I see people confuse hustle or tenacity with burnout, I’m not mad.I get it.

But there’s a clear difference between the two: Burnout is physical ormental collapse caused by overwork or stress. Tenacity is determination.

The reason I talk about enjoying the process of achieving yourambitions is that people burn themselves out by chasing a million dollars, aMercedes-Benz, a Chanel bag, or a private flight. The reason that thiscommonly leads to burnout is that such people are almost always trying toachieve those things for the approval of others, not for themselves. Whenyou’ve put yourself in a position to base your happiness on outside

validation and on material proxies of success, you will always, and I meanalways, be on the cusp of burnout. This is why I try to communicate thatthese can’t be the goals we put on a pedestal.

Instead, what if you work on something you genuinely love? What ifyou work toward a goal truly for yourself, instead of trying to buysomething to prove something to someone else?

Being tenacious is about telling yourself, “I enjoy my process so muchthat I am able to push through what others normally view as obstacles alongthe way.”

For example, in my mid-twenties, some of my former classmates wouldstop by at my dad’s liquor store. These were people who graduated andbecame doctors, lawyers, or Wall Street professionals. They would buyexpensive champagne, I’d walk into the basement and grab it, bring thecase back up, ring them up at the register, carry the case out to their car, andput it in the trunk. In their eyes, I remember seeing a mix of pity and ego. Iwas that kid who was still working at his dad’s liquor store.

It was my tenacity and conviction that allowed those moments tomotivate me rather than to devastate me. It became a healthy chip on myshoulder.

As you’ll see in part II, my immediate reaction to challenging scenariosnormally involves a mix of soft traits like empathy, kindness, and gratitude.But as Raghav Haran (my partner on this book) just pointed out as we werewriting this, this time in my early twenties was one of the few times in mylife when I went with a little more teeth, a little more ungh, with tenacityand conviction. But very quickly behind that, I deployed empathy andpatience. How could I expect my twenty-five-year-old friends to know howstrategic and thoughtful I was at that age?

They didn’t know that my obsession at the time was to spend over adecade building up my dad’s business as a thank-you to my parents for allthey did for me. How could they? That was a rare decision to make in thosetimes and continues to be extremely rare. They didn’t know I had a stronggrasp of what eighty, ninety, and one hundred years looks like. I hadpatience and perspective. The thought of working in my dad’s liquor storefor a few years didn’t scare me. I never felt I was “behind” or “off-track.” Ihad to empathize because they didn’t know I was going to the greatestheights.

At that point in my life, I had tremendous perspective about time. Mythought was that I would make a “deposit” with my time—from the age oftwenty-two to thirty-two—for my family. It seemed incredibly easy in aworld where I get over ten thousand DMs (Instagram direct messages) amonth from people who are “struggling” because they haven’t figured it outat twenty-six.

I found it interesting to hone my craft in the trenches of Wine Library, aretail business where I was interacting with customers for fifteen hours aday. I was sharpening my skills as a communicator because I had to worryabout sales every day. The business was our livelihood; it was how we ate.But I also knew that one day, I wouldn’t be working there. By building abrand that my dad could leverage in perpetuity, I wouldn’t feel sadness inmy forties and fifties that his business disappeared after I left. How couldanyone understand all that? The point is, it didn’t matter if they did. I knewit. And that fueled my drive.

Conviction and tenacity work hand in hand. When you have convictionin what you’re doing, it’s easier to be tenacious.

Throughout the process of writing this book, I’ve ironically been thinking a lot aboutcompetitiveness, a word that’s surprisingly not found often in my content over the lastdecade. However, I’m realizing that I probably sell short how much tenacity, conviction,and my internal fire to win in my process are foundational to who I actually am. Myintuition at this exact moment as I’m writing this tells me that tenacity is the seed to thenext book.



A strong desire to know or learn something.22


I’m struggling to write this section right now because of how excited I’mfeeling about NFTs. I can feel the chemicals in my body as I’m sitting in mychair. I genuinely believe that NFTs will create a revolution in humancreativity, and I’m so excited to learn more.

After spending the latter months of 2020 focused on VaynerMediaoperations, I’m willing to lift my foot off the gas pedal a bit in early 2021 tomake more time for research. That might mean my business won’t grow asfast, but I can’t let this opportunity with NFTs pass. I’ll have far biggerregrets if I don’t see this through.

When people lack curiosity, they dismiss new opportunities instead oftaking the time to explore them. A lot of people thought that playing videogames wasn’t a practical way to make money. Today, top-earning gamersand e-sports content creators are making millions of dollars every year.

In the early days of social media, many experts dismissed it as a fad.They said the same thing about Web 2.0. When I started talking about therise of sports cards as an interesting alternative investment, people didn’tbelieve it was practical.

Now, in early 2021, we’re at the dawn of an era when artists will be ableto generate livable income through NFTs. Yet, many people believe beingable to draw isn’t a practical skill. There are many passionate, talentedartists who are accepting jobs they’ll eventually hate, not realizing that they

could’ve made a living doing what they loved as a child. Instead, they’ll begoing through the motions, working as executives at a bank.

The word curiosity is underrated in our society. It feels fluffy, academic,and childish, but I believe it’s one of the most important characteristics forsuccess in business.

In the wine world, my curiosity manifested in reading every post onMark Squires’ Wine Bulletin Board in the mid- to late nineties. Throughempathy and curiosity, which I think are foundational ingredients to myintuition, I felt that Australian and Spanish wines would rise in popularity,based on the info I’d gathered. And I was crazy right.

In a way, it’s similar to what an A&R rep (artists-and-repertoirerepresentative) from the music industry does. My curiosity led me toputting in work to learn (like going to clubs to discover artists, as A&Rpeople did in the seventies and eighties), and then I used empathy to pickwhat was going to be hot, betting on artists who’d go on to build big bands.That’s essentially what I do for a living.

Curiosity mixed with empathy can lead to intuition. Then, afterexperiencing or “tasting” that intuition, you can develop conviction.

My curiosity ultimately led to my belief that sports cards would explodein value in certain categories. Same with NFTs.

I’m an anthropologist by nature. I watch. I deeply observe humanbehavior, which leads to what some consider predictions about emergingtechnologies and industries. In reality, I’m not making predictions. I’m justpaying closer attention to what the market is already doing and executingfaster than most.

When you have curiosity, you need to protect it with humility at allcosts. I don’t put my successes on a pedestal in my head because doing sowould undermine my curiosity. It would trick me into thinking I don’t havemuch left to accomplish. In my mind, I’m still young. I’m still just gettingstarted. I’m still “in the dirt.” If you have an inflated ego, curiosity getssuppressed.

The two words that stand out to me in the definition of curiosity arestrong and learn. To maximize the value of curiosity, you need a strongwork ethic. You need a strong desire to continue learning, no matter howmuch you’ve accomplished.

If more athletes leaned into their curiosity, they would be excited whenthey retire, not sad. Instead of thinking, My career is over, they would

think, Wow! I’m only thirty-five. What else can I do for the next fifty or sixtyyears of my life?

Athletes could leverage their talent, reputation, relationships, andknowledge to explore new areas of life—whether building a brand or justbecoming a better parent. Players in the Hall of Fame are younger than Iam, and I think I’m a baby. Imagine what I think about them—they’re so, soearly in their careers.

If you’re an ambitious person who retired at sixty-five before the era ofsocial media, then curiosity can lead to a brand-new career. If you want toget back on the field, sixty-five to ninety can be like playtime. What if youshared your knowledge from over sixty years of life? What if you couldenhance your legacy by communicating to the world on social media,taking advantage of an opportunity you didn’t have in the prime of yourcareer?

In addition to optimism, one of the driving forces behind my love forthe journey is curiosity. I wonder how big a business I can actually build. Iwonder how many people I can have an impact on. I wonder how many willshow up to my funeral one day.

I’m fascinated by how big all this can get. I want to see it through.The second crucial word in the definition above is learn.Those who follow my content on social media are often confused by my

perspective on education. I believe education is the foundation of success,but I also think we should question the way it’s sold in America today.

If you live and breathe entrepreneurship and truly have potential to be abusinessperson, then it’s worth debating whether taking on college debt isworth it. More students, parents, and organizations need to reconsider thevalue of college for their specific ambitions.

That said, the reason I’m on the board of Pencils of Promise is that theybuild schools in places like Ghana, Laos, and Guatemala. In less-developedcountries, school can be the gateway to opportunity in the same way thatthe Internet and social media are in the United States.

Learning can come in different forms. You can learn by DM-ingsomeone you admire and asking to work for them. You can learn by goingto a class. You can learn by consuming content on Twitter and YouTube, asI’m doing to learn about NFTs. Curiosity is the inspiration for that workethic.

People who lack curiosity often trick themselves into thinking they’redeploying conviction. You might not want to learn about new technologies,platforms, or opportunities because you’re “sticking to one thing.” I respectit if you don’t like to juggle too many balls at once—a lot of people don’t—but be careful not to put your past accomplishments on a pedestal or operatefrom ego and call that conviction.

I don’t want to rank the ingredients in this book against one another, butif I were forced to pick, I would put curiosity and humility over convictionand tenacity.



The capacity to accept or tolerate delay, trouble, or suffering withoutgetting angry or upset.23


When I hear this definition, I smile ear to ear.My community is probably tired of hearing me talk about patience. But

I have terrible news:I will continue to drill this fucking word into the skull of every person I

ever meet. Patience has been such a beautiful gift in my life. Raghavpointed out that he didn’t expect to see “tolerate  .  .  . suffering withoutgetting angry or upset” in the definition, and I didn’t either. I feel a closeassociation with this word and how it’s defined.

If heaven is a place where they give you a word on your chest, I knowthat this will be the one for me. Patience is a core ingredient to the lightnessI feel inside. When you have a good relationship with time, the pressure islifted and you can do so much more. If I have my way one day, patiencewill be in the K–12 curriculum everywhere.

I wish more parents realized that patience is one of the most importantingredients that children need to develop. We would have much happierchildren who wouldn’t need escapism to cope with the stress thatimpatience creates. A staggering number of people from eighteen to thirtyfeel anxiety about their careers because they don’t have a good relationshipwith patience.

I’ve watched dozens of employees come through companies I’ve beeninvolved with who seemed destined for great things but were underminedby their impatience. They expected astonishingly high raises, demandeddouble promotions without results, or made other unrealistic demands tofeed their short-term insecurities. They unfortunately derailed their long-term potential within the organization because they were in such a rush andlacked self-awareness.

Insecurity festers without the fertilizer of patience.When you’re desperate to prove something to other people in the short

term, you don’t give yourself a chance to enjoy the process. When youdon’t enjoy the process, you become more vulnerable to burnout. If you’reforcing yourself down a path just because you think you’re going to make amillion dollars by thirty and you don’t, you’re setting yourself up for majorself-esteem issues at thirty-one.

Worrying about other people’s opinions of your accomplishments whenyou haven’t even achieved them yet is a common mistake. Patience allowsyou to deal with judgment from others in your twenties and beyond. Whenmy financially successful friends came to my dad’s liquor store and lookedat me with pity, my patience is why I was able to deal with it so effortlessly.

Those who are patient aren’t any less ambitious or tenacious. In fact,patience can give you permission to dream bigger.

Let me be very transparent with you: I have not even come close toachieving what I want to achieve. Not even the same realm.

I’m also aware that I’ve achieved a lot so far in the eyes of others. Butto myself? Just like you, I feel there’s so much more to be done. At forty-sixyears old as this book comes out, I’m still patient. I’m not in a rush torealize my dreams in the next few years—I’m excited about the next forty-six.

You can imagine why I try to shake up kids at conferences intounderstanding that they have the greatest asset: time. For all you twenty-two-year-olds, if I could trade everything to switch places with you, Iwould.

I also want to remind the sixty-six-year-old that twenty-five more yearswith modern medicine is plenty of time to achieve what you dreamed aboutat thirteen, twenty-three, or thirty-three. There’s still time to lean into yourcuriosities. I view patience as foundational not only to the entry-levelintern, but also to CEOs, COOs, and senior executives.

When you’re patient as a leader, you can give your employees room togrow and develop over time. All of a sudden, you don’t get angry at smallmistakes they make in their first few weeks on the job. You’re morecomfortable with training and developing young talent over time. You’remore willing to look at their performance in aggregate, rather thanovervaluing how they did in week one or week ten. When you’re patientwith yourself, you can be patient with others.

Like many of the other ingredients, however, patience needs to bebalanced with kind candor. By being overly patient, you risk sowing theseeds for resentment. When my patience ran out in the past, it led to murky,sloppy exits. If and when people prove they’re incapable of doing the jobthey were hired for, kind candor needs to come into play.

I have an interesting insight for all of you: Almost every time that I putout content about patience, a stunning amount of the comments say, “Easiersaid than done.” I want to remind you, as you uncover your halves, that allgreat things should be hard.



A firmly held belief or opinion.24


Why would I go on the public record and write that NFTs are going tocreate a revolution in human creativity? Why would I put myself in aposition where I could be so wrong in front of so many people, when NFTsare still so early?

Stating your convictions out loud is a vulnerability. You might bewrong.

To me, though, conviction is like religion. I’m aware that’s a powerfulstatement, and I’m not trying to ruffle feathers. The reason I say that isbecause it’s a strong belief. I believe in my business convictions like areligion. When I’m convinced about something, nothing can stop me.

Conviction is the north star that keeps you on track, helping you betenacious throughout your journey, despite the inevitable difficulties.Without conviction, you’ll miss big opportunities and lose because of otherpeople’s opinions, which is the most devastating of all.

If Elon Musk, Warren Buffet, Oprah Winfrey, and Jeff Bezos all walkedinto my room right now and said NFTs have no long-term potential, youcouldn’t imagine how little I’d care about what they have to say. Despite alltheir business successes and innovations, their subjective opinions wouldn’tbe able to penetrate my conviction.

But if nobody buys NFTs seven years from now? That data from themarket might change my mind. What won’t change my mind is the opinions

of four people, no matter how successful they may be. Even if they weresuccessful in the past, that’s not always a guaranteed indicator of theircorrectness about the future.

That’s why I don’t pontificate on subjects I don’t know about. I have noopinion on Mars. I have curiosities and hypotheses about virtual reality, butI need more insights from the market before I go on the record with myconvictions. I need to “feel” the end consumers’ behaviors.

Augmented reality excites me because Pokémon Go already happened. Isaw people pull over to the side of the road and jump out of their car tocatch a nonexistent Pikachu in the woods. Which means it did exist. There’sno doubt in my mind that we’re going to live in a mixed-reality universe.AR might not be at scale yet, but it’s going to happen. It already has.

When I saw nerds talking to each other from their basements in 1994through this thing called the Internet, I knew it was just a matter of timebefore the whole world did it. When I saw kids playing Fortnite or buyingdigital goods, I knew it was just a matter of time before adults started doingit too. In fact, I did see adults do it. It was called Farmville on Facebook in2010.

I often find my beliefs to be in contrast with reports and official studies.My question is always, “How’d you get to the results in that report?”

Is it a true representation of market behavior? Or did you conclude that—say—67 percent of Americans think coffee is delicious because youpolled 91 people and claimed the math was significant?

I’m trying to live in constant osmosis with all 328 million people in theUnited States. I want to feel the pulse of the culture. I’m living in a constantstate of curiosity and empathy, which lay the path toward strongconvictions.

Because my beliefs come from my intuitions, I don’t think I’m “right.” Ijust think I’m old enough to know that my intuition has a strong trackrecord.

I’ve won that game a lot. People start by telling me “No,” which thenturns to “Maybe,” and eventually turns into “You’re such an innovator” or“How did you predict that?”

That’s been the foundation for my career. Doing a focus group of ahundred people won’t always get you those results.

When you follow your convictions against society’s pushback, one oftwo things will happen: either you’ll be right, or you’ll be happy you saw it

through. If you quit your well-paying law-firm job to start a clothing lineand it fails two years in, you don’t need to feel ashamed for not keepingyour job like your mom told you to. You can feel relieved that in youreighties and nineties you won’t be asking yourself, “What if I’d taken theleap?”

I prefer dying on my own sword over dying on someone else’s. I holdon to my convictions until the market tells me I’m wrong. And when I’mwrong, I make adjustments with conviction too.

Over time, I’ve matured in rounding out my convictions to be morethoughtful. I believed in hard work—for example—and I still do, but now Ican paint a more complete picture after seeing how the market hasmisinterpreted my message about hustle. I’ve started emphasizing that youneed to love your work first, because hard work isn’t sustainable withoutlove and passion. I work as hard as anybody I know today, but I had zerowork ethic in school because I hated it and it didn’t map to my ambitions.

That was me with school, but that might be you with your job. Thatmight even be you with entrepreneurship. Maybe you want to work within astructured system. If you own a business, you take on more pressure thananyone else in your company. Maybe you don’t enjoy that. Maybe you wanta boss or CEO to worry about the future of the company, so you don’t haveto. This is where self-awareness can lead to conviction about yourambitions.



A modest or low view of one’s own importance; humbleness.25


I actually hate this definition. Why is humility considered a low view?Fuck that.

I do agree that it’s a modest view of oneself. I would argue it’s a fairview, even a compassionate one. I have all-time ambitions for my career,but I’m not confused—even when legendary cultural icons (like Prince andDavid Bowie), celebrities, or influential politicians pass away, we mournfor a period of time but then move on. I recognize how little I really matterin the grand scheme of things, and that’s humbling to think about. Nomatter how many accolades I receive, no matter how much praise peoplethrow on me, I never let myself believe that I’m more special than everyoneelse.

Humility is a requirement if you want to cultivate a lasting positivereputation and leave an admirable legacy. Leaders can’t sustain successwithout it. That doesn’t mean they can’t ascend to senior levels and makemoney. Depending on the organization, leading with ego may landpromotions and raises—but those leaders will inevitably be talked aboutpoorly behind their backs. If you want your reputation to endure the test oftime, you absolutely need humility.

It’s one of the most attractive traits human beings can have.Let me ask you this question: Would you want to have the people who

know you the least think you’re the best, and the people who know you the

best think you’re the worst? I genuinely believe this is a question mostpeople need to ask themselves. Many are confused when they see successstories of people who aren’t great human beings. But were they actuallysuccessful? How did they feel when they were on top? And more important,how will they feel in their last days?

It would be the greatest devastation of my life if I achieved my financialand professional goals, but the people who knew me the best spoke aboutme the worst. I never want that legacy. It would crush me.

Because my humility is the least obvious ingredient in my content, Ithink it’s the one that wins over those closest to me. Most people confusemy passion with my ability to have compassion. People who consume mycontent on social media may think my aggressiveness and competitivenessovershadow my other traits.

We didn’t include competitiveness as an ingredient in this book, but itwas right on the precipice. If I ever write a sequel with new ingredients, I’msure it will make it. Or maybe the reason I’m holding it back is thatcompetitiveness may need to be a whole book by itself.

It’s funny how I think about competition. I want to bash mycompetition’s collective face in when I’m playing them on the field, but if Ilose, I immediately deploy humility. I lost. I can’t be delusional. It’s theingredient that allows me to enjoy the merit of business, whether I win orlose.

Humility creates a comforting feeling of safety that can help you movequicker in business. If I lose everything, I’m humble enough to live in acheaper apartment. I’m not joking when I say I could literally live in a boxin Kansas. I would wake up, use my charisma and work ethic to shower forfree somewhere, and start all over. I can downsize my lifestyle withouttaking an ego hit, so I’m not scared to take calculated risks in business. Myhumility keeps me safe at all times.

What are people going to say? That they can’t believe I dropped somuch? That they saw it coming? That everybody who believed in me gotfooled?

If I were forced to live in a shitty apartment due to a financial situation,I would take full accountability. Clearly there was a flaw in my operatingsystem that led to catastrophically bad behavior and a series of mistakes.With humility and the self-love that comes with self-awareness, it would beeasier to take accountability. Of course, I never want to be in such a tough

situation, but at the same time, I’m not afraid, because I know how to usethese twelve and a half ingredients to respond to every scenario. Humilityhelps bring out the flavor of many of the other ingredients.

Almost everyone reading this can find ways to spend less money, andyet they don’t think so. Downgrading your lifestyle makes it more realisticto follow your passion or take a calculated risk in your career. You don’thave much to fear. But for some people making $248,000 a year, thethought of making $200,000 sends shivers down their spines. They’re notwilling to trade in their car, sell their home, or give up a luxury vacation tolive a bit more humbly. You can replace those numbers with $80,000 and$68,000, or with $40,000 and $34,000. It’s still the same game.

If you’re willing to go backward financially for the short term, youdon’t need to fear losing your job or shutting down your business after threeyears. All of a sudden, taking the leap to run your small YouTube channelfull-time isn’t as scary anymore. You’re not fazed by your colleagueslooking down on you for quitting your job as an executive to build a vlogaround your passion for root beer.

When you have a fair, modest view of yourself, you have a significantadvantage over others, because you’re willing to do what they aren’t. Forthose of you looking to build your brand, you need humility to post a videoof yourself on the Internet for the first time.

Humility keeps you from overthinking the aspects of content creationthat slow most people down: Does my picture look nice enough? What willpeople think of these colors?

You can also change your mind more easily when faced with new data.For example, managers and leaders tend to fire bad employees too slowlybecause they have more pride in being “good at hiring” than in running agood business. If you’re humble, you can admit when you misjudged thecandidate.

Because of my humility, I don’t feel the need to stay consistent withdecisions I’ve made. I can change my opinion in two seconds, and I do it allthe time. I’m so hot on my NFT projects right now, but if more importantthings come along, I’ll have zero hesitation in shifting NFTs to a lowerpriority.

My definition of humility would be “a comfort in one’s ownunderstanding of one’s position in the world.” I feel that’s more accurate.Fuck you, Oxford English Dictionary. 😉



A strong desire to do or achieve something, typically requiringdetermination and hard work.26


You know what will happen in eleven years if Sally Thompson buys theJets instead of me?

The whole world would make fun of me. Can you imagine what thosesocial-media posts would look like? I’d get completely shit on.

I’ve put myself in a position where if I don’t pull off that highlyunlikely feat, I’ll be considered a failure by the masses. Even if I do make$2 billion. Even if I become one of the most accomplished businessmen. If Idon’t buy the Jets, the world will say I lost.

Strangely, it excites me. Because one of two things will happen:I’ll buy the Jets and create one of the most inspiring life stories ever. Or

I won’t, which would give me the opportunity to teach the world importantlessons through my actions—that you should do it for the journey, not thedestination.

No matter what the outcome is, I’ve already won. Setting a goal to buythe Jets gives me the opportunity to build and grow businesses my wholelife, which is what brings me joy. It’s so much fun to strategize and put allthe pieces together; it’s like a big puzzle that I get to solve.

My thirty-year mission is to buy major brands when they’reunderpriced, grow them, flip them for billions of dollars, and buy the Jets. Ibuilt VaynerMedia as a strategic step in that direction. Our work with

Fortune 500 brands helps me learn how they operate. I needed to build thatfoundation so I can use VaynerMedia’s capabilities to grow brands I acquirein the future. It could also help in starting new brands, or something I don’teven see now, but having VaynerMedia’s infrastructure allows me to scalethe opportunities of the future.

People tend to have an unhealthy relationship with ambition partlybecause they use it as a cover-up for their insecurities. Some people setgoals to build successful businesses or secure prestigious titles inorganizations so they can prove something to their parents, their significantothers, or their high school friends who doubted them. Their ambitions aregreat, but their motivation is based more on insecurity than curiosity or self-awareness.

That’s why people set time constraints for their goals. I was neverdesperate to buy the Jets by my thirties or forties. I was always workingtoward it for myself, nobody else. I’ll be thrilled if I get there in my sixties,seventies, or beyond.

Just as I couldn’t separate candor from negativity in the past, and just assome can’t separate tenacity from burnout, another group of people aren’table to separate being ambitious from being mean. They see leaders drunkwith ambition destroy everything in their path on the way to their goals. It’swhat I’m trying to change with this book. Winning at all costs hasconsequences.

Life is a joy when you have good relationships with your ambitions. Iwake up every morning and chase my dream, yet I’m so not in need ofachieving it. It’s a beautiful blend of conviction and humility. I fully believeI’ll make it, yet I don’t need to make it. Ambition is like a healthy “carrot.”

Ask yourself what you want to achieve, and more important, why youwant to achieve it. Are you telling everybody you’re going to own a sportsteam because you want their respect and admiration? Do you really justwant a cushy nine-to-five job and three vacations a year? Do you actuallywant to deal with the headaches that come with being a CEO? Do you justwant to leverage that title on Instagram and LinkedIn?

At the other extreme, are you afraid of telling others about yourambition because you fear they’ll think you’re delusional?

I love talking about my ambition publicly, in front of the world, becauseit holds me accountable. Doing so also gives the whole world permission tolaugh at me if I fail.

But here’s where all the ingredients tie in together. Ultimately, I’m notdoing it for anybody else but me.

Part II

Real-Life Scenarios

I’m fascinated by how a steak, fish, or salad is entirely at the mercy of theingredients used to make it. A salad can taste wildly different depending onthe type of dressing you use or the mixture of toppings you add. Not usingenough salt can make food taste bland, but too much can overpower theother flavors.

Likewise, the ingredients in part I are effective only when they’re usedin appropriate mixtures. What you’re about to read is my perspective onhow to use them in combinations to respond to various real-life scenarios,like:

➣ negotiating a raise,➣ getting your boss to recognize your efforts,➣ watching your colleague get a promotion over you,➣ confronting a business partner who stole from you,➣ voicing mental health concerns at work,➣ improving your team’s enthusiasm, drive, and overall performance,➣ being thrust into a management position unexpectedly,➣ staying ahead of the curve with new innovations, and➣ deciding whether to stay at a job or pursue a side hustle full-time.

And more. Some of these scenarios were inspired by messages from mytext community (text 212-931-5731 to sign up). Others were inspired by

comments on social media, conversations from real life, or questions I getat keynotes.

As you read how I’d use the twelve and a half ingredients in thefollowing scenarios, I don’t want you to blindly think I’m right. By readingmy perspective, I want you to develop your own way of using theseingredients in the combinations that are right for you and the scenarios inyour life.


Scenario 1: You and your coworker Brandon started working at the company around thesame time. You believe that you’re both pretty similar when it comes to your skill set,personality, and drive. Out of the ten people on your team, you two are the best. However,the promotion slot goes to Brandon, not you. What would you do?


The first ingredient that came to mind for me was kindness. I genuinelybelieve that if you start your reaction by being happy for your coworker,you feel lighter inside. When you feel light inside, the conversation thatneeds to happen next becomes easier. To get honest feedback, you can setup a meeting with the decision maker (i.e., your manager) and say this:

First of all, Brandon is amazing, and I’m so pumped for his promotion. I respect the decisionyou made, but I’d like to be educated on how you’re thinking about this. What made you chooseBrandon?

Regardless of what the answer is, remember that it’s not a definitivestatement about you. It’s one person’s subjective opinion when a choice hadto be made. It’s not a scarlet letter or a final judgment on your capabilities.The manager’s making a call based on what he or she is able to “see.”

On my personal team, either I or Andy Krainak (who runs my team) hasmade a decision on who’s good or not good. Even though I’m alwayswatching how my team members are performing and I’m highly intuitive,I’m still missing a large amount of data on my employees. I don’t have 100-percent context on what’s happening. No manager or leader does. Don’t feelbad about yourself just because one or two people subjectively decided thatBrandon is better than you at work.

Keeping that in mind, what you don’t want to do is come into theconversation with guns a-blazing. Anybody who starts the meeting withanger or aggression instead of kind candor has already set the foundationfor an unfavorable outcome. It becomes an event that’s far more detrimentalto one’s career than any perceived lack of accomplishments. If you come inhot, it’s over before it starts.

As you’re reading these scenarios and my suggested reactions, you might be thinking thatthey’re noble but hard to execute. In other words, “easier said than done.” If that’s you,you have to understand that you’re a triggered human being. I have empathy for that; weall have challenges in developing these ingredients. For some, it’s more difficult than it isfor others. There are people whom I love inside out who would find it impossible to doalmost everything I’m suggesting in this book. It just means that your emotional capacityisn’t strong enough to handle challenges on initial contact. This weakness comes from amillion different things, including both nature and nurture.

If the following scenario reactions feel unnatural for you, deploy self-awareness andtake a big step back. If you have to, put the book down, light a candle, and think. Askyourself if you feel that there might be value in this book. Could this be the way to uncoversomething that’s holding you back in business, or even life? Why did you even pick thisbook up? As you go through part II, maybe you realize that going to therapy is the bestanswer for you. Maybe it’s having a conversation with kind candor with a parent, orsomeone in your life who created a framework for insecurity. Maybe it’s deploying moreaccountability—pointing your thumb at yourself instead of your finger at others.


Scenario 2: Your manager, Olivia, says she needs to see more proactiveness from you.You’re surprised, because from your perspective, you’ve been putting in extra effort tocome up with ideas to improve your team’s performance and output. You’ve been sharingthose ideas with other team members consistently. What would you do?


When your manager or client gives you unexpected negative feedback, howyou deliver the following line determines what will happen next:

Hey, Olivia, can you give me more clarity on your feedback?

I want you to read that line out loud seven times.

Read it like someone who’s pessimistic about getting another job. Readit like someone who’s resentful or angry. Read it like an egotisticalemployee who looks down on the manager’s skills. Read it like a bigspender worried about the payments on a luxury car.

Then, read it like someone who’s optimistic about the future. Read itlike someone who’s humble, curious, and wants to learn more. Read it likesomeone who doesn’t default to blaming other people.

See how different that same line sounds? The emotional ingredients youdeploy in this situation can change your tone of questioning and potentiallythe outcome of the meeting.

A lot of employees in this situation would jump to the assumption thatOlivia is sitting in her ivory tower, clueless about what’s actually happeningwith her team. Whether that’s true or not, starting with that assumptionmeans you’ll react poorly to critical feedback. You’re not setting yourselfup for a productive discussion. The truth is, you don’t know what’s goingon in Olivia’s head. You don’t know what’s going on in her home. Youdon’t have full context on what’s going on behind the scenes.

Instead, you could start with empathy and curiosity. Empathy andcuriosity give you a chance to listen to what the manager has to say beforeyou make a decision on what you do next. It sets the tone for a more fruitfulone-on-one.

When you’re receiving positive or negative feedback, you have todeploy your conviction and keep in mind that the feedback is subjective.You’re at the mercy of another human being’s opinion about you in thecontext of this job. One of the reasons I’ve always loved being anentrepreneur is that the business results are the judge of whether I’msuccessful or not—not any one human.

However, there are many times when we have to deal with subjectivefeedback. For example, you see it in boxing matches when there’s noknockout. You see it in the Olympics and even the school system where ahandful of “judges” can dictate the outcome.

Feedback from a manager or a colleague is often subjective. It’ssomebody’s opinion of your work, and although it may be informed bydata, it doesn’t necessarily provide the full picture.

When you think about it, that realization is actually liberating. So manyemployees who receive critical feedback at work end up going home and

drinking a bottle of whiskey, smoking a blunt, or dealing with it in otherways—all because one person said, “You’re not good at what you do.”

That doesn’t mean you should ignore feedback, but when you realizethat it’s just an opinion, you can put it in the proper context. It’s not adefinitive stamp on your level of talent by any means.

For example, if one person told me I’m bad at tennis, and that personhappened to be my dear friend Ryan Harwood, who is clearly much betterat tennis than I am, then that makes sense to me. That’s black-and-white.

The scenario we’re talking about here is not black-and-white.If you see Olivia as your mentor and she says you’re not being proactive

enough, then you can make adjustments with optimism. But if you don’t seeher as a mentor—if you feel that she’s motivated by insecurity, ego, or badintentions—you can take that context into consideration when you hear herfeedback.

For example, is she giving you negative feedback right before a raisecycle? Is that because Olivia secretly doesn’t want you to make moremoney? Could she have been feeling anxious one day because she receiveda mean phone call from her sibling, and now she’s overreacting to a smallmistake you made? Or even worse, is Olivia dealing with a serious healthscare that has changed her behavior recently? Does she extract value fromher employees because she knows there are hundreds of others willing totake their places?

Remember, being optimistic doesn’t mean being naïve.By starting with empathy and curiosity, you can get clearer feedback.

Then accountability and conviction can help you decide what to do next.I want people to be more thoughtful. Some reading right now will be

ready to quit a job they hate. Others are uncovering deep-seatedinsecurities, but after confronting them, they’re about to start gettingpromoted for seven straight years.


Scenario 2 Follow-Up Question:“From the manager’s perspective, what’s one thing Olivia can do to get the bestperformance out of the employee?”


Deploy gratitude.

As a CEO, I’m very grateful that my employees choose to work for me.People have options, especially in today’s world, where remote work hasbecome more acceptable after the year 2020. I’m genuinely flattered when anew hire joins my organization.

People talk about how employees should be grateful to have a job, butit’s also true that companies should be grateful to have employees. Whencompanies feel entitled, they build a transactional atmosphere that doesn’tgive people a reason to stay or do their best work.


Scenario 3: You are the founder of a direct-to-consumer kelp noodle company. Althoughyou believe kelp noodles are a popular trend and a healthy alternative to spaghetti, you’vegotten very little traction so far. You’ve worked for seven years, spent your own money onthe business (money you saved up from your previous job), but haven’t been able to raiseany outside capital. You have $13,000 in the bank after starting with $216,000. Whatwould you do?


This is the scenario new entrepreneurs worry about. What if you spendyears trying to launch a new business but you wake up on April 19distressed and almost broke?

That’s the moment you lie in bed muttering, “How the fuck did I gethere? I used to have $216,000 in savings. I was doing great. My job wasfine, I had time for my friends, and I was fifteen pounds lighter. What did Ido? Who did I think I was? Why did I have to start this company?”

It’s the beginning of a dark path. People then start beating themselvesup and sinking under the weight of past decisions.

Worst of all, they start blaming others, which makes the problemsignificantly worse. “Why did GaryVee have to tell me to be anentrepreneur? All these fucking people on Instagram  .  .  . Why did my dadpush me to do this? Why did my mom not stop me this time?”

People quickly start pointing fingers. But if you’re in this scenario,pointing your thumb back at yourself is what will keep you positive thatmorning of April 19:

I really wanted to see if I could do this. It was ultimately my decision. I’m running out of savingsnow, but I’m grateful I gave it a shot.

When you’re eighty-three years old, you’re going to be ecstatic aboutthe seven years you spent building this business. You clearly quit your dayjob for a reason. If you had stayed and collected that paycheck, you mighthave more money, but you’d be crushed by the what-if.

The what-if is poison. It’s a source of regret and emotional pain in yourold age. As soon as you wake up and start going down a bad path, call anaudible fast:

No, it’s not anybody’s fault that I’m down to my last $13,000 from $216,000. I’m grateful. I’mhappy I did this, because I’m not going to feel regret in my old age.

People always debate over what the “right” decision is in a situation likethis. Should you lean into humility and go back to your day job? Or shouldyou stick to your conviction and keep trying until your savings run to $0?Let’s play it out together.

OPTION 1: You decide to go back to your day job in law, a field that doesn’t excite you.

OK, so you want to stack up some more savings.When you step back into the office, you’ll have to deploy a crazy dose

of humility. You’ll have to talk to that work friend who made a snarkycomment that your business would fail. You’ll have to admit your friendwas right. Your mom might have never come out and said it, but you knowshe was never on board with the idea either. You’ll have to talk to her too.

Let’s make option 1 even tougher: nineteen months after you went backto your day job, kelp noodles spiked in popularity after a few famousYouTube influencers made videos about them, and a major health reportcame out that caught America’s attention. Suddenly, your number-threecompetitor, who was lagging behind you, ends up dominating market share.You watch Kraft Foods buy your competitor’s company for $200 million.

If you choose option 1 and this happens, you’d need humility andgratitude to protect yourself against dwelling and self-criticism. You neededto give this opportunity a shot. Even though you didn’t win, you got to tryfor seven years—so much more than most people ever get.

Alternatively, option 1 could play out the opposite way. Kelp noodlesmay never become mainstream. Your competitors may also fail. You maygo back to your law-firm job, build your savings back up, and meet a new

lifelong friend at the company. Maybe your friend invites you to an eventwhere you meet your future spouse or a fellow parent whose child becomesyour child’s best friend.

Success in business is just one part of life. What if your kelp noodlecompany failed, but your personal life actually improved?

You can’t predict the events that give you the best overall outcome inlife. That’s why I love leaning into optimism. Even if I missed out on ahuge investment opportunity, who knows what would’ve happened if I’dgotten it? What if getting that opportunity meant I would have to fly acrossthe world to give a conference, and on the way my plane crashed, and Idied? What if I actually avoided a catastrophe because I missed out on adeal?

In January 2020, we all got the devastating news that Kobe Bryant andeight other people had died in a helicopter crash. If America’s COVID-19lockdowns had started in January 2020 instead of March, would they still bealive today? Imagine, that tragic event might never have happened.

That’s how I think about it. You don’t know if an event is “good” or“bad” because you never know the alternative. Quitting your business mighthave led you to something incredible (like a lifelong friendship) or helpedyou avoid something horrible (like an accident or a disease). I prefer to lookat life through the lens of optimism.

OPTION 2: You stick with your kelp noodle company until your savings completely run out.

Going to zero is a very lonely feeling. Countless people have gone toAtlantic City or Las Vegas with $400, got down to $80, dreamed of turningthat $80 back to $400, went to zero, and had to borrow money from theirfriends to get a cab.

In this scenario, your last $13,000 in savings will likely end up going tozero.

But I’m asking you: When you’re seventy-one, will you feel betterabout yourself for going all the way to zero before going back to your law-firm job, or will you feel better about saving that $13,000?

Cutting your losses is important, but limiting regret is important too.Even if kelp noodles never become mainstream, your competitors neverexplode in growth, and Kraft Foods never makes a $200 million acquisitionin the space, you can feel proud at seventy-one that you left it all on thefield.

There is no right decision here, which depends on your own goals inthis scenario, but here’s my ultimate point:

If you look at every decision you make through the lens of optimismand layer it with kindness to yourself, there’s almost never a wrongdecision. If you look at it through pessimism, there are problems with everydecision. That’s why I’m always happy in the grand scheme of things.


Scenario 3 Follow-Up Question:“My natural instinct is to be pessimistic rather than optimistic. How do I fix that?”


By hanging out with optimistic people. The more time you spend withpractical, optimistic people, the more you’ll shift your mind-set.


Scenario 4: You’re a mother of two children who had a lot of ambition early in your career.After having children, you happily decided to be a stay-at-home mom. One day, yourgrandmother passes away, at ninety-three, after living a long, fulfilling life. You alwaysadmired her, and you launch a blueberry-jam company as a side hustle inspired by herhomemade recipes from your childhood. The business exploded in growth in its first year,but you’re trying to balance that with raising your two kids, currently twelve and fiveyears old. What do you do?


Self-awareness comes first. Where do you want to take the business? Doyou want to sell it? Bring in a partner? Continue growing it to millions ofdollars a year?

Then you absolutely need to be kind to yourself. As a stay-at-homemom, you’ve been the CEO of the household. Now that you’re also theCEO of a company, the likelihood of dropping balls is high.

You might be seven minutes late when picking up your five-year-oldson from soccer practice, when you’re normally on time. You might haveenough time to sign up your five-year-old for only one extracurricular whenyour twelve-year-old was part of three. You might feel guilty because you

can’t spend as much time helping your twelve-year-old with homeworkbecause you have to pack shipments, and now she’s getting a C in sciencefor the first time after being a straight-A student.

You’ll also receive judgment from other parents, maybe even your own.Your mom might say that you need to focus more on your kids (hergrandkids) and ditch your business. Maybe your mom sacrificed herentrepreneurial aspirations to take care of you, and now she expects you todo the same for your kids.

One way to react is to say, “I am going to shut this jam business down.I’ll do it when the kids are done with school.”

If that’s genuinely what you want to do and what makes you happy, thenthat’s a perfectly fine decision. However, a lot of moms in this scenario shuttheir businesses down out of guilt. Over time, they’ll develop somethingmuch worse: resentment.

Resentment builds up when you suppress your own happiness for thesake of others. Shutting down your business so your daughter can get an Ain science might lead to conscious or subconscious resentment of her or thepeople who pushed you into that decision.

Instead, consider looking at the situation through an optimistic lens. Youdon’t realize that your daughter is watching your every move as you’rerunning your business. Through your actions, you’re inspiring a young girlwho will one day believe she can become president of the United States ifshe wants to. You’re teaching her patience and ambition. Other moms mightjudge you for letting your daughter get a C in science, but you’re setting herup to win at life.

You need to be kind to yourself to keep external judgment from gettingto you mentally. Day-to-day losses will happen frequently in this scenario.

Here’s another challenge you may deal with: Your twelve-year-olddaughter frantically calls you on a Friday night from a sleepover. She wantsto come home because some of the other girls are picking on her andpressuring her to drink alcohol.

You think, Oh shit, I’m packing all my items tonight and I need to shipthem out tomorrow, so customers get the orders in time for their events.

But it’s your daughter, so you stop packing and drive over immediately.When you get back home, she wants to sit down and talk, and you want tobe there for her. You don’t get your packing done, and you ship yourblueberry-jam orders out on Monday instead.

On Friday of that week, you get e-mails, calls, and messages on socialmedia from customers who want refunds. Since you sent the shipments twodays late, some of the orders didn’t arrive on time for their event.

In this example, you beautifully chose to support your daughter insteadof supporting your business. But that was your decision. Don’t lie there onFriday night and start blaming your husband for not helping you packboxes. Don’t blame any of your customers for not supporting you, even ifsome of them happen to be good friends of yours.

When people are hurting on the inside, they lash out by blaming others.They desperately look for a coping mechanism, which usually comes in theform of pointing fingers.

It might not seem like it at first, but accountability is the cure. “I madethat decision.”

You also need patience. “This is one bad day in the grand scheme of afifty-plus-year business. It doesn’t mean anything.”

And conviction. “I’m still going to build one of the greatest blueberry-jam businesses of all time.”

And especially gratitude. Take a step back here and realize that yourdaughter was being bullied and peer-pressured to drink. That night could’veended terribly. Imagine if she died of alcohol poisoning, and you found outon a panicked four a.m. phone call from the sleepover host’s dad. Youwould’ve been able to spend Friday night packing boxes to get the orderssent on Saturday. But at what cost?

When you scare yourself into having perspective, you can put yourproblems in their appropriate context. It doesn’t feel good to get refundrequests from customers when you’ve spent hours making your blueberryjam, but how does that challenge rank in comparison to everything else thatcould’ve gone wrong that night?

I know in these scenarios I’ve used some pretty aggressive examples as what-ifs, like medying in a plane crash on the way to a conference or your daughter dying of alcoholpoisoning. They may seem too extreme and unlikely, but these are things that actuallyhappen in the world. I find that most of us dwell on stuff that ultimately doesn’t matterbecause we lose the context of how lucky we are when these extreme events don’t happen. Iapologize that I’ve been aggressive so far, but I will continue to be this way because it’s mytruth.


Scenario 4 Follow-Up Question:“It’s tough to feel gratitude when you’re in the heat of the moment. How do you do that?”


Many people misunderstand gratitude. They think you should be gratefulfor material things—a nice car, a mansion, a fancy watch.

Gratitude is best when it’s grounded in simplicity. I’m grateful that thepeople closest to me are healthy and alive. Naturally, I’m happy every day.All I truly care about is that one thing. Everything else is secondary.


Scenario 4 Follow-Up Question:“How can a stay-at-home parent overcome judgment from others when starting abusiness?”


A stay-at-home mom might hear the following statement from her mother:“I had so many business ideas, but I didn’t pursue them because I wanted tomake time for you.”

There’s a lot of context missing. Maybe her mother had a spouse with ahigh income, so she didn’t have to work. Maybe her mother didn’t havestrong business aspirations, didn’t have a strong entrepreneurial itch.

People who judge you or compare your situation to theirs don’t have allthe context. There are a million variables in play.


Scenario 5: You’re a student at one of the best business schools in the world. You have ahigh GPA, run a couple of student organizations, and are well positioned to get lucrativejob offers. Most of your fellow students are interviewing at investment banks, managementconsulting firms, or Silicon Valley tech companies. You believe that you could land thosejobs too, but after setting up an e-commerce store last summer, you’re fascinated by theidea of selling your own hoodies full-time. Your online store is currently bringing in onlyabout $5,000 per year on the side, and you’ve got $61,000 in student loan debt. Whatwould you do?


If you’re going to make this jump, the first thing you have to realize is thatthe world is going to tell you, “No!” You’re going to feel pressure fromyour parents and friends, who may be coming from a good place. Peoplewill look at the last three, five, ten, or thirteen years of your life and say thatyou’re “throwing it all away”—not maximizing the investment in yourdegree.

The reason I keep talking about redefining success is that I think we’reapproaching the dawn of the era when people actually believe what I’msaying. Which is, it’s much more fun to make $130,000 a year and be happythan make $470,000 a year and be miserable.

If you’re going to make the jump to run your hoodie business full-time,you’re going to need a large dose of optimism. You would need to believethat in thirteen years you’re going to achieve a better money-to-happinessratio than you’d achieve as an SVP at a bank.

From there, you’ll need to pair tenacity with conviction to get throughall the booing. It’s kind of like going for it on fourth down in a criticalplayoff game on home field. If you don’t convert, eighty thousand peoplewill boo you.

Do you have the stomach for that? There’s no doubt that you’ll getbooed if you follow this path, but conviction along with tenacity can carryyou through.

You’ll also need patience. It’s going to take many exciting years foryour store to go from $5,000 a year on the side to a place where you won’tfeel anxiety on a $61,000 loan. I say exciting because I knew that going intomy family business in my early twenties wasn’t going to allow me toaccelerate as fast as my other twenty-something friends.

I had to have patience, tenacity, and conviction in those days. I reallywish I’d had a vlog back then. I wish everyone could see all the mundanework I did just waking up and being at a liquor store for fifteen hours a dayevery day. I was stocking shelves, building an e-mail list, saving money,and doing actual work.

People think that fast money is the answer. It’s the greatest trick of life.Freedom comes in either extreme wealth or extreme perspective. Extremewealth is extremely rare, and even then, many find that destination to be

less of a cure-all than they had imagined. Extreme perspective is trulyliberating.


Scenario 6: You’re a fitness influencer who started creating content on Instagram early.You were able to quickly grow to a million engaged followers and build a community. Youthen started a successful business selling protein supplements and workout apparel.However, as the platform matured from 2015 to 2021, your growth has stagnated, andsales have declined for six straight years. You passed 1.0 million followers quickly, but sixyears later you’re only at 1.7 million.


During the seven-year period from 2015 to 2021, we all observed thefollowing changes:

1. The explosive growth in podcast listeners.2. The increased maturity of the direct-to-consumer space.3. The mass advancement of influencer marketing.4. The emergence of new platforms, like TikTok and Clubhouse.

In 2015, a person with a million followers on Instagram had one of thehighest forms of leverage in modern society. If you were in that position,you could’ve easily leveraged those followers to develop new businessconnections or directed followers to your different channels to build thoseup. You could’ve used that following to build an ecosystem on YouTube orTikTok. You could’ve built a following on Clubhouse early.

This sounds like a story of complacency, which is why accountabilityand humility are the two important ingredients to deploy.

If you have ambition to grow, you’ll have to eat some humble pie in thissituation. From 2015 to 2021, while your business stagnated, you probablywatched others grow from 50k to 5.2 million followers because theystrategized more effectively, executed more consistently, or had more talent.

If you’ve been kind to others on your way up, then this is where thatkarma can come back to help you. When people are at their peak, theyunfortunately tend to be unkind or indifferent to others. But as the saying

goes, the people you meet on the way up are the same ones you see on yourway down. If that influencer who built an audience of 50k up to 5.2 millionremembered your kindness back in the beginning, then maybe thatfriendship could turn into a partnership.

Accountability and humility can help limit your frustration, anger, anddisappointment. If you’re aware of your weaknesses and recognize thatyou’re not that special to begin with, then you’re not stunned when otherinfluencers start outperforming you. When you accept that you made thedecision to not diversify your following across social platforms, there’s noone else to blame. You made the decision to be one-dimensional withInstagram. You’re in control, and you have the opportunity to change thecourse of your business from 2021 to 2027.

In this scenario, accountability can lead to optimism and kindnesstoward yourself. Sure, your business declined, but you still pulled off anincredible feat. Very few influencers ever reach a million followers onInstagram and build a business on the back of it. You’ve accomplished morethan the vast majority of people on Earth.

Moreover, if you did it once, you can do it again.Sometimes the perfect platform for your creative strength comes along

at the right time. Maybe you’re a model and it came naturally to you to posein a bikini or show off your six-pack abs. Instagram was a visual-centricplatform that over-indexed for models and fitness experts because theycould show off their bodies and fitness results. That might have led to yourrapid growth to one million followers on Instagram. But YouTube, TikTok,and Clubhouse require a technical skill set in your craft. In fitness, thatmight mean sharing your knowledge on topics like fascia, protein, oromega-3 supplements.

You can still grow on those platforms, but it might take a differentcontent strategy. You could deploy your humility and, even if you’re thirty-seven now, educate yourself on the technical aspects of health and wellnessso you can reboot your brand in fifteen months. Maybe you could reinventyourself as a B2B fitness guru and charge companies $10k per month for acoaching program that all their employees can access.

Most of all, you need to lean into your self-awareness and ambition. Imade the assumption that this scenario was a story of complacency, butmaybe it was a story of falling in love. Maybe you decided to spend the lastthree or four years building your relationship, and you’re fine with spending

less time on the business. Maybe you just worked way too hard in the earlydays to build your social account to a million followers, and you struggledto find balance. Maybe you were too obsessed with buying a Mercedes-Benz, a second home, or a Gucci bag, making you vulnerable to burnout.

I would actually argue that many people are happier with a slow-growing, sustainable business. It can create a more harmonious work-lifebalance if you can maintain the business size while living your life. Youmight be happier accepting your current lifestyle, without aspiring for abigger house up the hill.

However, you may not realize this if you’re not full mentally oremotionally. You see other businesses growing, and you feel you’re laggingbehind what you should’ve achieved at your age. That’s where humility andself-awareness come in. You don’t want what other people want. So why doyou care what they have?

Take a massive step back and think about what it was that slowed downyour growth. Did you misplay a chess move somewhere? Or was itsomething out of your control for a personal reason? Either way, it’s OK.

If it’s your fault, great. You can be accountable, optimistic, and kind toyourself. You can pivot and reinvent your business.

If it’s out of your control, great. You can still focus kindness onyourself. You had to slow down for a personal reason. Don’t listen to other,“successful” influencers or personalities who judge you for that. They don’thave all the context, and they have different ambitions than you. No matterwhat the reason is, there’s no solution that involves beating yourself up.


Scenario 6 Follow-Up Question:“How do you go from being an Instagram fitness model to a business owner?”


This is a challenging transition for many for an obvious reason: it’s hard togo from being a horse to being a penguin.

There’s nothing similar about them. They’re ridiculously different.Some influencers who start out as personalities or models actually do

turn out to be great businesspeople. Others aren’t so good at it. It takes alevel of talent and passion that many influencers don’t have, but because

entrepreneurship has been so glorified, every influencer wants to be a CEOor a COO.

If you’re struggling with business, you may need the humility to say,“Hey, I crushed it as an Instagram fitness model, but I really don’t have thepassion for advertising or operations. I need a business partner.”

If you can deploy self-awareness, humility, and optimism, you can findyourself a partner, to whom you can give 5 to 49 percent equity. Self-awareness and humility can lead you to making that decision, whileoptimism helps you trust that person after vetting him or her.

You’ll be far happier because you will no longer have to work in Excelspreadsheets or build out infrastructure for shipping logistics. Your partnercan handle that, and you can just be a personality, posing for photos andpublishing content.

Furthermore, owning 50 percent of a business that makes $2 million ayear is better than owning 100 percent of a business that’s making $300,000and declining.


Scenario 7: Your wife met a woman at a new mother’s group who eventually became herbest friend. The friend invites you and your wife out to a double date. You haven’t beenout that often since the new baby, so you’re excited to get out of the house. However,you’re a little nervous because you’ve never met this couple before. When you sit down atdinner, your wife’s friend and her husband start talking about NFTs. You have no ideawhat they are. What do you do?


Ask! Lean into humility. Don’t dismiss them as a nerd couple talking aboutsomething weird or assume that NFTs are a scam because you don’tunderstand them. Even if you’re not interested, be kind by listening and notchanging the subject. Don’t overstate your premature beliefs.

Curiosity is the single biggest unlock for you in this situation. Youcould go home and go on Wikipedia and Google and do some realhomework on this. Many people have heard friends, colleagues, oracquaintances talking about something new that could’ve been the biggestbreakthrough in their professional life, but their ego stopped them from

spending the ten or twenty hours to get a bit more educated. In today’sworld, Google alone can get you far.

This is exactly what I did with NFTs. I watched a bunch of YouTubevideos and followed a handful of people on Twitter, and I knew enough tobe dangerous within a week. That knowledge is going to be the foundationfor some big NFT projects.

That’s curiosity.If you go home from that dinner and Google NFTs, watch fifty YouTube

videos, and follow fifty people on Twitter, you might be on the verge ofchanging your life in a week or two. I’ve done this. For the record, I’vebeen that person at dinner talking about something new many times:

Sports cards. Dismissed by friends and acquaintances.Startups. Dismissed by friends and acquaintances.The Internet. Dismissed by friends and acquaintances.

All of whom looked at me later with admiration but, more important,regret.

Curiosity is a rare ingredient but maybe the most powerful of them allwhen deployed with a dose of humility on the front and the back. Here’swhat that looks like:

Have the humility up-front to stay curious and not divert the convowhen you hear something you don’t know about. Then, be curious enoughto learn more. Add some more humility to put in twenty-plus hourslearning, not two minutes.

One of the things that irks me the most is people saying “I don’t havetime” when I ask them to try something new. I have found that people whoclaim their “time is valuable” actually have the least-valuable time. I’vebeen humbled even at high levels of success with how much more I can dowith my time, even though it’s a finite resource. Innovation is based oncuriosity.

In addition to curiosity and humility, layer on patience and conviction.Innovations take time. I’m learning about NFTs in 2021, but I don’t expectthis category to truly materialize for another decade.


Scenario 8: The upper management at your company noticed your tenacity and potential,so they promoted you to a managerial position where you have to lead a small team. Oneof your new employees, George, is more than fifteen years older than you. He’s beenworking at the company longer than you have. From your initial interactions, you can tellthat George doesn’t have confidence in your ability as a manager and believes that he’sbetter at making decisions than you are. What would you do?


New managers typically deal with this situation by going out with theirfriends, popping bottles, celebrating the promotion, and making fun ofGeorge behind his back. It hurts me. I’m actually getting a little emotionalas I think about it now.

If I were in this new managerial position, the first person I would thinkabout is George. It must be so tough for him to watch a newer employee getpromoted. How’s he feeling? What are his ambitions? How can I get him onmy side?

I would be able to lead George easily because I’d deploy empathy,kindness, and humility. I wouldn’t try to prove to him, my boss, or my otherteam members that he’s wrong for doubting me. That’s what a lot of peopledo in this situation. Their insecurities surface in the face of doubt, and theybecome confrontational with George instead of deploying these ingredients.

Either through formal or informal communication, I would let Georgeknow that I’m on his side. The best way to communicate depends on yourstyle. You might be the kind of person to sit down with him over a two-hourbreakfast to build rapport. For me, it would be through the warmth of myactions.

In my first team meeting as a manager, I would say, “George is right,guys. Let’s not forget, he’s been here a long time, and his experiencematters on this team. I wouldn’t be here today without observing some ofthe subtle things George did. I’m going to lean on him in many areas for hisexpertise.”

If you deliver those lines in a meeting without George knowing they’recoming, they can have more impact than any one-on-one meeting. Georgemight think you’re just “checking the box” if you only speak with himalone over breakfast.

As I talked this out with Raghav and David Rock (a videographer on myteam), their reactions were quite powerful—I could tell from their faces that

the reaction I painted above hit a nerve. I believe most books written aboutmanagement and leadership would have said the right answer is to “sitdown with George and address all the issues up-front.” But I think thereaction that I just played out is more realistic.

You might be the type of person who prefers to sit down one-on-one andtalk with George, which is perfectly fine if that’s your style. But what I’mtrying to communicate is that business isn’t about the black-and-white. It’sabout the gray—it’s nuanced.

Let’s make this situation even tougher: let’s say the first project Iexecuted as a new manager failed horribly, and George started whispering“I told you so” to everyone else behind my back.

That would get me excited, not deflated. I was very happy that theKansas City Chiefs beat the Buffalo Bills to go to the Super Bowl in 2021.They were down 9–0 early in that game. That’s a scary score to start offwith, but Patrick Mahomes was telling the team to calm down. He wassaying, “We got this.”

That’s how I would react as a manager: 9–0? Good. 29–0? Good. 78–0?Good.

Through self-awareness, you will develop a sense for where you sit onthe scale of insecurity and confidence. If you’re insecure, it’s harder to leaninto kindness in tough situations. Without confidence, the weight of yourown emotional problems is too much to bear, and you default to making funof George to prop yourself up instead of taking time to empathize with hispain.


Scenario 9: You notice that Sally, an employee on your team, has strong potential andtalent, but she’s not able to perform as well as other team members yet. You’re trying toset an example and show her how to do her work properly, but she doesn’t seem to get it.What would you do?


First, you need to take on accountability as a manager and realize thatyou’re making a mistake. Doing the work for somebody is almost never theright answer. Doing the work for somebody without that person involved is

never the right answer. Ever, in the history of time. I don’t like using theword ever, but it’s true. People don’t grow when you do all their work forthem, especially if they’re not included in the process.

My mother washed all my clothes for me when I was young. When Iwent to college and started living on my own, I literally didn’t understandwhat people were talking about when they asked, “When will you pick upyour clothes?”

I didn’t even know what a hamper was. I’m serious. I was not evenaware of the existence of hampers because, when I was a kid, I would dumpall my clothes on the floor and miraculously they would be clean the nextday. Also, my immigrant family would never spend money on a hamper.My clean clothes were always folded on a chair.

My mother is an incredible woman who worked her face off as a stay-at-home mom, with no help and no maid her whole life. But it still wasn’thelpful in the context of learning how to wash my own clothes.

When you do someone’s job without having them as part of it, thatperson doesn’t get a chance to develop his or her skill set. In the scenarioabove, Sally will never learn how to execute her projects on her own. Inaddition, the manager will develop resentment, which may lead to Sallygetting fired. That’s what managers don’t realize until it’s too late.

Instead of doing the employee’s job, tap into self-awareness to map outhow you could teach. Teaching is how you empower others to execute. It’sthe way to scale your talent, so that you don’t have to do everythingyourself.

First of all, are you even a good teacher to begin with? Or are youtricking yourself into thinking you’re a good teacher because yourgrandfather or aunt was?

Next, take a step back and see how you can navigate from yourstrengths. For example, my companies have never had significant formaltraining systems. I prefer to teach through what I call osmosis. In otherwords, employees build their skills over time through my energy and byworking with one another, which helps my organizations move faster.Nevertheless, at the time of writing this book, we are building internaltraining capabilities at VaynerX and VaynerMedia, because we have over athousand employees. At this size, the free-flowing nature of osmosisdoesn’t always reach the entire company.

If you’re not a good teacher, consider meeting with HR or your managerto work on hiring an external trainer—a vendor, a specialized agency, or aspecific person.

Next comes the part where many leaders struggle: giving Sally thefreedom to fail. This is where you need to deploy optimism. Optimismleads to trust, which is imperative when you’re training people. When youmake Sally “earn your trust” instead of giving it to her up-front, she’ll movemore slowly. Empowering your team members to make decisions is howyou scale.

If Sally does happen to fail, deploy accountability and self-awareness.Take the blame and figure out your style of giving feedback. Personally, Ilike to deliver playful zings and razz people a little when they makemistakes. People laugh, and the point still gets across without coming off astoo harsh. If I can tell from the employee’s reaction that the razz didn’t land,then I might set up some time for a one-on-one conversation to clear thingsup. I also have to make sure that my razz isn’t a reflection of passive-aggressive behavior or resentment that needs to be cleared up with kindcandor.

Maybe for your style, setting up a one-on-one convo right away is moreauthentic, in which case you can deliver feedback with kind candor(something I’ve been leaning into more and more recently).

Optimism is one of the biggest differentiators between managers whobuild successful teams and ones who don’t. I’ve listened to some peoplecomplain about their employees constantly, but after spending fifteenminutes with them over a cocktail, it’s very obvious that their insecurities,fears, and cynical points of view are actually the core issues. Somemanagers think their employees will leave if they’re trained too much.Some fear the ramifications of the mistakes their employees will inevitablymake, so they put heavy restrictions on what they can and can’t do. Somelead with ego and suppress those under them so that their employees don’tbecome “too” successful and leave. Some managers go even further andassume that their employees are trying to steal from them.

How can you grow your own career as a leader if you’re alwaysmicromanaging and restricting those under you? You’re limiting yourpotential too.

I’ve always had employees leaving my organization to start competingcompanies or work for other competitors. My companies still grow like

crazy because I don’t fear these exits. In fact, I propel employees I adoreeven further—I give them more leverage in our relationship than I have.

There are plenty of business owners and managers who struggle withscaling because they can’t teach. They can’t teach because they don’t trust.They can’t trust because they’re inherently cynical and fearful instead ofoptimistic. Lack of trust leads to managers doing their employees’homework for them, then to resentment and failure.

In many of the scenarios I lay out in this section, you’ll note that mydefault viewpoint is abundance: opportunities are everywhere. If Sallymesses up and you take the blame and you get fired, be kind to yourselffirst. Then lean into conviction and tenacity to find another job, whichmight even pay more. A few colleagues close to you may have seen howyou trusted Sally and took accountability for her mistake. They’ll rememberyou and could be business partners down the road.

Someone’s always watching. Developing good karma is practical.With these twelve and a half ingredients in your spice rack, you can

navigate any situation, which means you can always be on the offense.You’re in control of how you absorb the situation and respond to it. There’sno reason to fear.


Scenario 10: A customer e-mails you, sounding disappointed in your product. You cancelyour next meeting so you can jump on the phone and talk with the person. You find thatthe customer actually wasn’t dissatisfied at all, that you just misinterpreted the e-mail.You’re relieved, but it’s throwing off your day. What would you do now?


Something similar happened to me yesterday.I got a text from a couple of people on a creative team at VaynerMedia

saying, “Can we talk?”They’ve been with me for a long time, so I felt that something was off. I

ended a meeting early, FaceTimed them both on the spot, and ended upbeing five minutes late for the next meeting, which was an important one.

That next meeting was a little less efficient than I wanted it to be. Thedetails of the FaceTime call hovered in my mind for the next two or three

hours, until I had a meeting with the team members I wanted to talk toabout it. For those two or three hours, my meetings weren’t great, because Iwas in another place mentally. The preoccupation “threw my day off.”

Instead of FaceTiming those two people, I could’ve set up a meeting inthe next week or so. But I wanted to know right away, and I tookaccountability, knowing that it’s what I chose to do. In that sense,accountability was a gateway to acceptance. How could I be upset when Imade the decision that I wanted to make?

When you choose a customer or an employee over yourself, it’s neverthe wrong idea.

Adding optimism to the mix can also help. Even if your day was thrownoff, it’s just one day out of so many. You have three hundred–plus days in ayear and many years in a long career. Don’t judge yourself based on a badday, a bad week, or even a bad year.


Scenario 10 Follow-Up Question:“Is there a way to keep your day on track after an unexpected negative e-mail? How doyou prevent your day from being thrown off?”


One of the reasons I’m not a huge fan of e-mail is that the written word canbe misinterpreted. Tone is completely lost in written form. When peopleread e-mails, their insecurities, pessimism, or optimism can cloud theirunderstanding, and a misunderstanding can throw off the rest of the day.People read written feedback through the filter of where they’re at mentallyand emotionally.

Throughout this book, I’m trying to help you understand yourself. I’mself-aware enough to know that when one of my employees tells me thatsomething’s off, I’m not able to focus on those next few meetings anyway.The quicker I can address the problem, the more efficient my day becomes.It was actually more practical for me to FaceTime those two employeesimmediately instead of waiting a week to have a meeting, even though itdid make my next few meetings less productive.

It was still more efficient than the alternative.


Scenario 11: You’re a tenacious employee eager to prove yourself in the organization andmove up the ranks. However, after a couple of years in, you feel that you want to reduceyour work hours and take more time off. You have trouble vocalizing mental healthconcerns to managers, because “burnout” feels like a taboo subject and you might have totake a step back in your career. In the meantime, your output is getting worse and worse.What would you do?


No matter when you’re reading this book, your memory of the COVID-19years is very fresh.

This situation reared its head often as people were adapting to a remotework environment. Video conferencing and other remote work processescreated some remarkable efficiencies, and some employees struggled toadapt. They couldn’t go out and grab coffee with a coworker or spendseventeen extra minutes by the watercooler in conversation with a friend.

Although remote work increased productivity for many organizations, Istill think that those seventeen-minute convos are important for culture andcamaraderie. Unfortunately, employees around the world lost that privilegeas their organizations went virtual, and many struggled to find their balanceas they worked from home. People found themselves working far more thanthey used to, and some of them had kids to take care of at the same time.Fatigue and burnout occurred more frequently.

In this scenario, I would deploy two seemingly opposite traits: patienceand ambition.

Ambition is a beautiful trait, but like all the other ingredients, it’sineffective when it’s out of balance. Patience helps balance ambition.

When you’re a young, tenacious employee, you’re ambitious by nature.Cultivating patience along with ambition helps you realize that you don’tneed to get your next big promotion this year. You can be a year or twoolder when you move up to your next role or get your next raise, and you’llstill have a fulfilling career.

Patience helps take the pressure off. People put so much pressure onthemselves to hit arbitrary timelines. They think they have to be at a certainplace in their careers by the time they’re twenty-two, thirty, forty, fifty-five,or sixty-five years old. How about being happy instead?

If you work in a company that demonizes you for taking a quarter stepback after working hard for a year or two, then you’re working in the wrong

place.On the flip side, if an employee gets lazy for a full year or so, that might

create enough sustained issues that the manager needs to deliver feedbackwith kind candor. However, if you get engaged at twenty-seven after twoyears of slaying it at work and now you need a little more time off to planyour wedding, that should not be frowned upon.

I wish more leaders would look at the whole picture of an employee’sperformance instead of asking, “What have you done for me lately?” In myorganization, people might have periods of time when they work tirelesslyand then have periods of time when they’re more passive. How many hoursyou put in at work depends on the serendipity of what you’re working on,the stage you’re at in your career, what’s going on in your personal life, andany number of other factors. Leaders need to be fair when they evaluatetheir employees’ performance. They need to review it in aggregate.

If you’re living this scenario and you’re afraid that you might get firedor reprimanded for voicing your concerns to your manager, consider gettinganother job. If you’re an ambitious, tenacious individual, chances are you’recapable of creating more options for yourself. You might be able to get ajob that pays more, or even one that pays less but gives you the work-lifebalance you’re looking for.

By saving money, you can open up even more opportunities. So manyemployees out there are living paycheck to paycheck because they boughtan apartment in DUMBO* or downtown San Francisco based on theircurrent savings and $237k per year salary. Once they handcuff themselves,it’s harder to go down to, say, $150k per year and take on less responsibilityfor a more interesting role.

I’m sad that people choose fake luxuries instead of the real luxury,happiness. By living more humbly, you can take a financial step back. Youcould take a job that pays $8,000 less but gives you more downtime tospend with your family. You could afford to spend a few months or a fewyears building a side hustle instead of always feeling tired after work.

If a company evaluates your performance and potential entirely on yourlast at-bat, work somewhere else.


Scenario 12: You’re working on a team that’s constantly short-staffed. You talked to yourmanagers about this, and they keep saying that they’ll hire more employees, but none havebeen hired in the past several months. You’re stressed out in your role, and you’rethinking about quitting and getting a job at another company for more work-life balance.However, you love the people you work with, and you don’t want to add more stress andresponsibilities on their plate by quitting or setting strict boundaries on your time. Whatwould you do?


For many employees in a short-staffed situation, it’s tempting to jump to theconclusion that management genuinely has malicious intentions. Themanagement could be subconsciously or consciously taking advantage ofall the employees to maximize margin, or it could be a different reason.Maybe they just haven’t gotten around to hiring the right people. As a CEO,I’ve learned over the years that hiring people quickly withoutthoughtfulness often hurts the team even more. The management team inthis scenario might be working behind the scenes to find the right people.

Maybe management is dealing with headaches you don’t know about.Perhaps there’s a lawsuit from a former employee that’s keeping them busy.Maybe two of the people on your team are actually underperforming andneed to be trained up before the management team can afford to hire morepeople. Maybe you’re even protecting those two underperformingemployees because they’re your friends and you don’t want to see them getfired, but that’s creating the inefficiency.

Employees struggle to have empathy for managers in a situation likethis, but an empathetic conversation can uncover the underlying issues. Youcould schedule a meeting with your boss and say something like, “Hey,we’re short-staffed, and it’s taking a toll on our team. You and I havediscussed this before, but I know I don’t have all the context. I don’t knoweverything that’s happening in your world. Can you help me understandwhat’s going on?”

Delivering that line with kind candor, curiosity, and empathy instead offrustration could lead to a breakthrough in the conversation.

Depending on how the meeting goes, you could turn in one of twodirections:

One, you could decide that you’re just going through a rough patch atyour job. Just as with your sibling or your significant other, you may have a

rocky thirteen months because you got into a fight. Work isn’t family, butsome coworkers do end up becoming like family, and you might go throughthree, six, or twelve months when the environment is not ideal. Peopleusually don’t take into account the possibility that, if they just stay patientfor seven months, the issues could work themselves out. You could begoing over a bumpy part of the road to something beautiful.

Two, you have the option of quitting and getting another job. It’s nice tolove your teammates, but you also have to be accountable to yourself andyour family.

The reality is, when you complain about something, you’re giving itmental leverage over you. Wouldn’t you rather take accountability and putyourself in a position to make a decision about what you’ll do next? We livein a culture where so many of us cast blame for enjoyment. We cast blameout of our own insecurities and pain. If you can afford to buy this bookinstead of pirating it off the Internet for free, that tells me you have theability to leave a job.


Scenario 12 Follow-Up Question:“But what about the coworkers? Would it be right to quit in a situation where the team isshort-staffed and stressed?”


If I’m worn down mentally and emotionally, I’m not going to bring anyvalue to my coworkers anyway.

The greatest gift you can give to someone, in my opinion, is not puttingyour baggage on their shoulders. The way I see it, quitting your job isactually very admirable in this scenario. You’re being kind by getting adifferent job; now you’re not going to bring others down with yourresentment and frustration.

Here are the steps I would go through in navigating this situation:

1. Accountability: “I’m in control, and I’m capable of making adecision” ➙ Eliminates victim mentality.

2. Empathy: “I don’t have full context on what’s going on” ➙ Preventsyou from blaming your boss.

3. Curiosity and kind candor: “So, what actually is going on?” ➙ Setsthe framework for a productive conversation.

4. Accountability: “I can either stay or leave” ➙ Empowers you to makeyour own decision.

If I do decide to leave, I would have another conversation with my bosswith an undertone of kind candor:

I wish you nothing but the best. I know you’re going through a challenging time. Unfortunately,I’m in a position where something I think is better for me and my family came along, and I felt itwas the right time for me to make that move.

When quitting the job for another opportunity, don’t disparage thecompany on your way out in front of your coworkers. You might have hadthe luxury of getting another job, but one of your teammates might be indebt and might be insecure about his or her skill set. Instead of makingSusan or Rick feel worse for staying there, walk out gracefully.


Scenario 13: You’re a young entrepreneur working on building a following around yourhobby on social media, but your parents don’t believe in what you’re doing. You have atrack record of starting different projects and not following through, so they think thatyour current project will turn out the same way. You keep trying to explain to yourparents that you’re playing for the long term, but they don’t seem to get it. What wouldyou do?


If I were in this scenario, I would go straight to empathy and accountability.If you just roll up on your parents and start talking about Ethereum,

sports cards, being a professional esports player, or becoming an influencer,you’ll sound foreign to them. The concept of becoming a social-mediainfluencer or starting up an e-commerce store is relatively new. It’s obviouswhy most parents struggle with understanding the practicality of thoseoptions. They didn’t grow up with them.

Regardless of what they say about your dreams and aspirations, yourparents love you. It’s in their DNA. But just like everybody else, parents are

either confident or insecure.I have empathy for parents because they were also parented. You might

be mad at your mom, but have you looked carefully at how your grandmaraised her? Have you thought about the insecurities that your mom mighthave developed in her childhood? And if that made you mad at yourgrandma, did you think about how her parents raised her?

Accountability is imperative, because in this scenario, you’ve takenlosses before. That’s why this next sentence is something more youngstersneed to internalize: Keep your mouth shut.

People tend to spend more time telling everybody how rich andsuccessful they’re going to be than actually building their business. If youhave a big mouth, you need to be accountable when everybody points afinger at you for your failed cannabis business or clothing line. You setyourself up for it.

For me, the reason I don’t keep my mouth shut is that I don’t needanybody’s affirmation. In fact, I’m weirdly excited when the worldunderestimates my capabilities. But if you’re in a mind-set where others’opinions still affect you, then work toward your ambition quietly.

Unfortunately, nine out of ten e-mails and DMs I get from youngsters inthis situation are on their parents’ payroll. Their mom or dad is subsidizingtheir lifestyle by paying for rent or a gym membership, or even financiallysupporting their business. If you can avoid taking even a single dollar fromyour parents, then you don’t need their affirmation to continue buildingyour business. You won’t feel the subconscious urge to appease them in theshort term.

Stand on your own two feet, and you have all the leverage. You’ll haveto take the subway instead of Uber, and you might have a shittier apartment,but that’s much more fun than being psychologically controlled by yourparents.


Scenario 13 Follow-Up Question:“I think being upset with my parents is a good motivator. Can’t I use it as fuel to provethem wrong later?”


Many people can have short-term success without deploying these twelveand a half ingredients, or even by deploying their opposites. Insecurity, fear,anger, and hatred are powerful drivers for those who make money in theshort term. If you’re angry and you want to stick it to the world, you canabsolutely use that as fuel.

The question is, will it last? And more important, will you be happy andjoyful in the end? These emotional ingredients are the foundation forsuccess that lasts. Anger and insecurity can create short-term boosts, butthey’ll rarely sustain you. In some cases, they can lead you to a dark placementally over time.

It’s like Star Wars. The dark side has success too, just not as much asthe Jedis. Never in the end.


Scenario 14: You’re growing a service business. You’ve been consistently pitching newprospects, and you find that they’re always excited at first, but once you mention yourprice, they typically disappear, and you never hear from them again. You’ve had clients inthe past who were happy to pay your rate and satisfied with your work, but you’re notsure how to find them consistently. What would you do?


In this scenario, one of three things has happened:

1. You’re dwelling on someone who said no, and you need to move on toother clients.

2. You’re not selling with empathy and humility, so your clients don’t seewhat’s in it for them.

3. The market has adjusted, and clients are only willing to pay you, say,$100 instead of $200.

Here’s where you need to deploy: patience, self-awareness, andconviction.

You have to have the conviction that you’re worth $200 per photoshoot,$100 per haircut, or $400 per landscaping service. On that same note, leaninto self-awareness and humility to make sure that your conviction isn’t

grounded in delusion. Do you have the talent to be able to charge thatmuch? Or are you trying to fake it till you make it?

If you’re a comedian, I would love to hear you have conviction thatyou’re going to make it on SNL and become one of the biggest comediansin the world. At the same time, are you self-aware enough to know if you’refunny or not? Do you know whether or not you have foundational talent tomake it that far? If not, do you have the humility to admit that you don’t?

I, Gary Vaynerchuk, will never make it to the NBA. No matter howmuch I love basketball, it’s just not going to happen. You need the self-awareness to know whether your talent and skill are worth the price you’recharging.


Scenario 14 Follow-Up Question:“I know I’m worth what I charge, but clients still try to negotiate me down. What do Ido?”


Take accountability. You can always say no.I’ve said no over forty times in the last month to speaking engagements

that wouldn’t pay me the fee that I wanted. I secretly wanted to do a lot ofthose, but I decided not to take a lower rate due to timing, brand protection,and a number of other factors.

If you’re not happy with the price a client is willing to pay, you canalways make a counteroffer or decline to work with them.

But here’s the most important point: if and when you decide to say yes,act as if they’re paying you double.

So many service providers ask for $200, accept $100, and then sulk.They become confrontational with the client, provide a lower-qualityservice out of resentment, and beat themselves up the whole time for beinga bad negotiator. Then their brand gets tarnished because of the substandardwork and because nobody likes a sulker. That leads to poor word-of-mouth,which leads to more clients who don’t want to pay as much—or don’t wantyour service at all.

If you ask for $200 and agree to $100, think of it as $300. Up until thatpoint, you have permission to go through your emotions, but once youagree to getting paid, all your disappointment, anger, and resentment has to

disappear. Replace it with tenacity and optimism. That’s the only way youcan get back to making $200 in the future.

Gratitude, humility, and kindness are also partners in crime here. If youcharge $350 an hour and agree to $300, you’re not a loser and the clientdidn’t “get you.” Be grateful for $300 an hour, and be kind to yourself. Howmany people ever get to charge $300 for sixty minutes of their time? That’san insane amount of money!

Deploy humility and appreciate that they paid you anything at all.


Scenario 15: You’ve been working at a company for several years. People around youappreciate your work, but you still feel that you’re underpaid. You know that the companyis having budget cuts, so you don’t want to be insensitive, but you also feel that youdeserve more money, given the value you bring. What would you do?


I would walk into my boss’s office and deliver the following line withkindness and empathy as the undertones:

Hey, I don’t want to seem insensitive, and I’m extremely grateful for the opportunity you’vegiven me in this organization. But here’s what I think I’m actually worth, and here’s why.

Then, the boss can reply with what he or she thinks.Negotiations don’t have to be contentious. You can tell the company

what you want in a kind manner, and they can tell you if they see it thesame way or not. Then you can deploy accountability, patience, conviction,humility, and gratitude in your response.

If my boss says no, I can either stay and work harder if it’s worth it, or Ican leave on good terms and get another job that will pay me more.Gratitude and humility would help me absorb the news, then accountabilityand conviction are the ingredients I’d use to do something about it. I willaccomplish 0.0 things by staying and complaining that I didn’t get a raise.

What this book will help you with is knowing that you’re in control.Your place of employment doesn’t owe you shit, other than what thecontractual agreement outlined. The company doesn’t owe you a 100

percent increase in your salary or a promotion ahead of your manager. Suchthings are predicated on the value you deliver.

The company’s judging you all the time, but you owe it to yourself tojudge the company, too. Evaluate management’s ability to make smartdecisions and judgment calls. If you feel that another company would be abetter fit for you, you can move on.

When you resent your job and view it as a jail, you’re actually resentingyour own life decisions that are keeping you trapped in that job. You’reresenting the fact that you bought a house or a car you couldn’t afford.You’re resenting your own cynicism and insecurities that keep you fromtrying something new. This isn’t the communist Russia that my parentsgrew up in. Everybody reading this book has options.


Scenario 15 Follow-Up Question:“Why would you deploy kindness in a negotiation? Aren’t negotiations aggressive?”


People tend to confuse confrontation with aggression when they’reoperating from a place of fear. When people negotiate, they fear that theywon’t get the outcome they want. They’re afraid of hearing candor from theother side.

But the reality is, most people already know the truth. Most peopleknow whether the designer sitting to their left is more or less talented thanthey are. Most people know whether or not the person to the right isworking harder.

People know. In many cases, they just don’t want to admit the truth andtake accountability. That’s why complaining is so rampant. It’s their copingmechanism for pain. In this book, I’m trying to get you to fall in love withthese twelve and a half traits so that instead of complaining, you can takecontrol and do shit.


Scenario 16: You’re starting out on a new career path. To get experience, you messaged ahundred executives on LinkedIn and asked them for an opportunity to intern directly forthem. Five of them responded to you and one wants to schedule a call to talk more. You’re

excited and want to make sure that you bring value and build a relationship. What wouldyou do?


Some people take jobs or internships where they can’t actually bring valuebecause they want the short-term result—whether that’s money orvalidation. This is where your patience needs to balance out yourconviction, tenacity, and ambition.

Let’s say the call is with a fashion designer.During that call, I’d ask questions about what exactly he or she needs

help with and use self-awareness to gauge whether I’m the right fit. Whenyou consider a new opportunity, it’s not just about the title and the money.You need to first consider whether or not you can actually perform in thatrole.

If that fashion designer told me that I would have to manage a calendarbut I know I struggle with detail-oriented work, I’d deliver these lines withkind candor:

I’m a high-energy dude, but sometimes I miss crossing my t’s and dotting my i’s. Is it going to bea dealbreaker if I book one of your meetings at the wrong time, or misplace a paper here andthere? I just want to be straight up with you that I have a little of that in me. Are you going to beOK in week three when I make a mistake, or would you treat that like The Devil Wears Prada?It’s your business, and I just want to tell you up-front.

It’s not always easy to admit something like that—especially if youspent two full days sending out those initial hundred messages, five morehours following up, and finally got a phone call from someone you admire.

But if I take this job, I know I’m going to mess up a calendarappointment in the first week. I know I’m going to make a wrong entry onan Excel spreadsheet. If you take up an offer to be an administrativeassistant when you know you’re terrible with details, that will damage yourreputation with that fashion designer, and that’s worse than being up-frontand moving on to another job.

I need to be patient and optimistic enough to know that I can get moreopportunities just like this one. If the fashion designer says being detail-oriented is a requirement, then I can be tenacious in sending out moremessages to others in the industry. I’m just going to have to put in morework.

People take jobs that they know they can’t do because they’re insecureabout their ability to get more jobs.

In real life, I get DMs like, “But, Gary, I’m burnt out! I’ve been lookingfor an internship for five and a half weeks. I finally have one. Easy for youto say that I shouldn’t take this opportunity.”

On the record, I don’t care whether you do or not. To the person readingthis sentence, I don’t know you and your specific situation. But I do knowthat if you take a job that you know you can’t do just because you’redesperate for an offer, then you’ll create bigger self-esteem issues in sixweeks when you get fired.

People trick themselves by saying, “I’m going to learn to be detail-oriented.”

They compromise on their self-awareness with delusional hope. Whyaccept a job where your performance is entirely predicated on how muchyou can improve on your weaknesses?


Scenario 16 Follow-Up Question:“What if you accepted the job but realized it was a mistake three weeks in? What wouldyou do then?”


Too many people stay at a job for longer than they want to because theywere told by their parents or guidance counselors that it looks “bad on yourrésumé.” That’s the biggest horseshit of all time.

If companies ask you about it in the future, you can explain to them thatyou leaned into your self-awareness to recognize that it wasn’t a good fit.You learned three weeks in that you weren’t going to bring value, so youhad the humility to resign. There’s nothing bad about that.

If you feel uncomfortable resigning so soon, if you feel that’s not a nicething to do for the business you’re working for, you can ask a few morequestions up-front to make sure that your role is in line with your strengths.Get full clarity on what you’d be doing, whom you’d be working with, andwhat the business is trying to accomplish.


Scenario 17: You’re running a business with a partner, Bob, fifty-fifty. You’ve worked withhim for a long time and feel you have a sense of who he is. Bob brings a lot of value to thecompany and his skill set complements yours. He’s been working with a bookkeeper tokeep the finances in order, and you blindly trust him with that side of the business, whileyou’re focused on driving revenue. However, one day Bob says that he’s going to payhimself an extra bonus, so you decide to contact the bookkeeper yourself and see where thefinances are at. You notice that he’s been taking extra money from the business formonths, paying for personal things, vacations, home improvements, and more. Whatwould you do?


No joke, the first thing that goes through my mind is, I deserve this.Businesses are run with numbers. I love Bob, and I might initially be

disappointed and hurt, but the first ingredient I would use is accountability.I had the ability to reach out to the bookkeeper every day of my life. I couldhave looked at the numbers anytime, but I didn’t.

Accountability is the antidote to anger. Being angry and feeling like avictim are terrible ways to start because they don’t create room for aconversation. It’s also what most people do. Accountability would help mefeel better here, because it’s not like I wasn’t in control.

At the same time, I wouldn’t beat myself up for not checking with thebookkeeper. In this scenario, clearly I’m not the kind of person who’sinterested in monitoring the day-to-day finances. I was the revenuegenerator on the offense. Self-awareness would lead to the understandingthat I don’t enjoy monitoring the numbers, and I trusted a partner whocomplemented those skills. That’s OK.

I’m not going to dwell and tell myself, “I’m an idiot” or “I’m beingtaken advantage of like a loser.”

Believe it or not, I would actually be worried for Bob. I wouldempathize.

Is his marriage falling apart? Are his kids sick? Is there a midlife crisisgoing on? Is Bob sick with a terminal illness and he’s just trying to enjoyhimself? Is there something else I don’t know about?

Don’t confuse this kind of optimism with naïveté or delusion. Optimismin this scenario doesn’t mean naïvely believing that Bob was stealingmoney for vacations “by accident.” It means believing that there’s potentialto get through this in our relationship. There might be an explanation thatmakes sense. This could just be a blip on the radar of the character I know.

Whether that turns out to be true or not, starting with that perspectivesets the framework for a safe conversation.

If you react with anger, all you’re doing is giving Bob a reason to puthis guard up and be defensive. That wouldn’t set the foundation for apositive outcome.

But come at him with an opener like this:

Hey, Bob, I’m sure there’s an explanation for this. I’m struggling to see it on paper, but we’vebeen working together for a long time. I don’t understand this trip to Cabo, these homeimprovement purchases, or these private plane trips. Help me here. What don’t I understand?What am I missing?

That changes everything. By starting with empathy and accountability,you’ve given your business partner (who’s probably in pain) a sliver ofbreathing room to break down and come clean to you.

There are many individuals in partnerships who’ve faced similarindiscretions but have actually gone through with forgiveness. There arepartners who stole money from each other who go on to have a betterpartnership after having that discussion. It doesn’t necessarily have to be theend of a relationship. Maybe after talking it through, I realize that it’s OKby me, and I can keep the partnership going.

On the other hand, some people could never get past that and couldn’tcontinue the partnership. If that’s you, that’s beyond understandable. Youcan have a discussion about letting Bob go, buying him out, asking him topay the money back, or any number of moves. Once you’ve had a safeconversation, you can go back to accountability and make a decision.

For me, if I decided to look past this, will the relationship ever be thesame? Of course not. Would I keep a closer eye on the finances? Probably.Could I set up a system that sends me text alerts when deposits andwithdrawals are made? Sure.

This is about putting yourself in a position to make a decision on yourown terms. You don’t have to end the partnership just because you “gottaken advantage of” in the eyes of the world. You also don’t have to stay inthe partnership and work things out if you can’t get past your resentment.

When you’re playing your own game, you make the rules. Theseemotional ingredients put you in control to make a decision that you want tomake.


Scenario 18: You’re a young buck working at a company your uncle owns. You have twomentors, Charles (your manager) and Sarah (your manager’s manager), whom you workclosely with and admire. You’re part of a seventy-person sales team. On a Mondaymorning, you walk into the office and find out that both of your mentors have left to starta competing company. Even though they want to hire you, you respectfully decline becauseyou don’t want to leave your uncle’s company. You’re thrust into a leadership position atyour job, heading a fifty-eight-person sales team (after twelve left to join the newcompany), and you’re trying to develop an action plan. What would you do?


Start with self-awareness and empathy. Empathy would help you feel whatyour new team of fifty-eight is feeling. Some people may have wanted towork for Charles and Sarah but weren’t asked. Some may have wanted tostay because they enjoy the stability of your uncle’s company. Others mayhave been asked but decided to stay because they’re loyal to theorganization.

Empathy will help build confidence and inspire the team. It would playa vital role in the next six months or year, when the situation is murky—especially the next six to ten weeks.

Self-awareness can help in understanding how to lead. The mistakemost people make when they move into management positions is trying tobe like the managers before them. If Charles and Sarah used to runmeetings in a free-flowing way but you need more structure, you don’t needto copy them. You may not be as charismatic or extroverted. You may nothave as much conviction when you communicate. You might stumble overyour words a little bit. Despite all that, you can still be a strong leader.

Not every leader needs to be extroverted with high energy. If you leaninto self-awareness, humility, and empathy, you can address yourdifferences from the prior leaders up-front.

For example, on that Monday morning, you could call a meeting withthe entire team and say something like this:

I know I’m young. As you know, this is my uncle’s company, and I’ve been coming here since Iwas a kid. I’m as devastated here as anybody else about Charles and Sarah leaving. But now,it’s my responsibility and our responsibility to beat them.

It’s like sports. Just because they left, it doesn’t mean that they’re the mortal enemy. Itdoesn’t mean we’re fighting to the end. We don’t need to gossip and whisper about them or the

twelve people who went with them. I don’t need to hear rumors over the next three weeks thatJohnny from our team texted with someone from the other team.

Teams trade players. Sometimes players leave, and sometimes they sign with different teams.I’m not saying it’s fun. If somebody went from the Jets to the Patriots, that’s a rivalry. But is itreally a problem?

We might be in a rivalry now with Charles and Sarah, but remember, that’s only in thecontext of business. You can still be friends with Karen’s husband, John, who left to work for theother company but happens to be your best buddy.

Sure, we want to beat them on the field in business, but let’s not make it too dramatic. Youcan still be friends with any of the people who went over there, including Charles and Sarah.

At the same time, remember, you’re wearing our jersey right now. And while you’re wearingthis jersey, we’re trying to slay them and everybody else that competes with us. We don’t need tomake this political. We don’t need to make this weird. But we do need to go out there and sell.


Scenario 18 Follow-Up Question:“When thrust into management positions, what skills does one need to develop?”


Emotional intelligence helps, no matter what you’re doing, but it’s evenmore valuable for managers because they affect more people. When youhave employees or team members that you’re responsible for, youremotional skills and failings are magnified. If you’ve developed thesetwelve and a half ingredients or other ingredients you admire, people willnotice. If you haven’t, people will notice.

You might be better than other managers in technical skills, but if you’renot optimistic, you’ll face challenges in scaling your team. If you’re notempathetic, you’ll struggle in getting people on your side. If you’re notcurious, you won’t innovate as quickly.


Scenario 19: You work in a big city at a finance job you hate going to every day. You havea family, and it’s important for you to have enough income to sustain their lifestyle. Eventhough you hate your job, it pays the bills. On the side, you’ve been working on a blog thatreviews gelato restaurants in your city, and you’re just coming to the point where you haveenough money from affiliate revenue to feel comfortable quitting your job. Then, Googlehits your site with an algorithm update, and it tanks in revenue. What would you do?


If I’ve relied strictly on Google and haven’t built a brand and traffic fromsocial-media content or other avenues (like press or direct mail), then Ideserve this. I should’ve had traffic from channels like LinkedIn, Instagram,TikTok, or others, so I’d take on that accountability.

Next comes optimism.In this scenario, I’ve already achieved so many things. I’m making good

money at a job in a big city, and I clearly have the ability to build a revenuesource of my own. I would be optimistic that what took me a few years tobuild up on search is something I can build up faster on social media. Iwould start the process of building a multidimensional traffic generatorbased on several social-media channels, e-mail, affiliates, and influencersand building my SEO (search-engine optimization) back up.

Self-awareness also plays a big role here. I’m clearly unhappy in thissituation. I thought I was almost out of this jail financially. In this scenario,I’m going to have a conversation with my significant other, express how Ifeel about all this, and maybe I would move out of the big city for a whileto reduce my expenses. Where I live might not matter as much, especiallyafter COVID. I would deploy self-awareness and reconsider how much itreally matters to me and my family to live in such an expensive location.

That might mean I commute farther to my job and convince thecompany I work for to let me work remotely and come in a couple of days aweek, since COVID has made remote work more acceptable. I could grinand bear a two-hour commute twice a week and put in more work on myside project on the other days with lower lifestyle costs.

Or if I love being in the city, going to restaurants, and being out till oneo’clock in the morning, that’s OK too. I could continue living in the citywith my family and having higher expenses. I would just have to deploypatience and accept the fact that it might take me longer to quit my job.


Scenario 20: You’re a sales manager at your company, and your team’s beenunderperforming. For the last three quarters in a row, your team has been in the lowest 25percent of overall performance in the organization. In this quarter, you’ve been warned byleadership that if the team doesn’t improve, they might have to let you go. What would youdo?


I immediately assume that it’s my fault. Even if my employees areunderperforming, I’m their leader. I’m in control of how I manage and leadthose who are working under me. If my team’s underperforming, there’sonly one place to look: the mirror.

Accountability is the trigger that would put me in the driver’s seat.Instead of thinking, I wish I had a smarter team or Sally’s only winningbecause she was handed the best talent, I can proactively start makingdecisions. I would start by assessing every salesperson I manage. Who arethe weak links? Are there any toxic employees? Who are the topperformers?

I would set up an off-site meeting with my team and have a deepconversation about what I can do to make the environment better. Thatmeans empathizing and taking a step back to get a feel for what drives eachindividual on my team.

This approach also requires humility. Even at VaynerMedia, I genuinelydon’t feel that my employees owe me anything. It’s my job to put them in aposition to succeed. It’s my job to prove to them that I care. It’s not aboutbeing transactional and expecting them to work hard just because they get apaycheck. So what if they get a paycheck? They can get one from anycompany. That’s why I always say that I work for my employees, not theother way around.

In this scenario, maybe I learn that my team is a competitive bunch, andthey like competing with one another. Maybe some of them preferdeveloping a deep camaraderie. What motivates them? What do they wantto accomplish in their careers?

There are many directions this conversation could take. For example, Imight learn that the top performer on the team is the actual reason the teamis underperforming overall. The biggest earner might have a toxic attitudethat makes the rest of the employees miserable and dread coming to workevery day.

If that’s the case, I would give that person feedback with kind candor. Ifhis or her behavior still doesn’t change, I’d take a hit and let that person go.That might put my overall results down 50 percent but getting rid of thatcancer could lead to the rest of the team bringing back that 50 percent.

There might also be underperformers on the team who need some extratraining in sales. I would go back to the basics and make sure everyoneunderstands how to sell, even open leads for them myself to help themimprove.

I would lean heavily into curiosity here, because curiosity leads tocreative ideas. Clearly, in this scenario, I need an idea to spark the team.These ideas could come from what I learned in my conversations withthem. For example, if I learn that my team is competitive, I might create alittle game within our crew for them to play against one another. If theywant camaraderie, I might set up a dinner party over a video call or atsomeone’s house, so there’s a more human connection.


Scenario 21: You’re working in a strategic role as a manager where you have to do detail-oriented administrative work about 10 to 20 percent of the time. The challenge is, you’verealized that you’re not organized, and you struggle with that part of the job. You tend tomiss e-mails and calendar invites that people send. You don’t have the budget to hire anassistant, and you notice that team members under you are getting frustrated with yourlack of attention to detail. What would you do?


Whether you’re an entrepreneur or an employee, you’ll likely find yourselfin many situations throughout the course of your career where you have tomanage communications with those above and below you.

In this particular case, you have a weakness that’s creating friction withteam members, and your managers are probably noticing too. This is whereself-awareness and humility can give others a sense of your good intentions.Those two ingredients make it easier for others to empathize with you.

Self-awareness not only helps you uncover your strengths andweaknesses, but also provides clarity on where you’re actually capable ofimproving. Once you’re aware of your weaknesses, humility comesnaturally. When you’re self-aware and humble, you’ve laid the foundationto be accountable instead of blaming your team members or dwelling onyour mistakes.

Accountability can help you advance up the ranks in any organization.Some people remain stuck in the same role for years and years because theirmanagers think of them as complainers rather than problem solvers, eithersubconsciously or consciously. When you’re accountable, you come to yourcoworkers and managers with solutions rather than complaints.

If it were I, that’s what I’d do first. I would set up a one-on-one meetingwith my boss and map out solutions beforehand.

Before the meeting, I’d have a one-on-one with a team member whoworks under me and say, “Hey, do you have bandwidth to help me withsome admin work? Is that something you’d want to do?”

It could be an opportunity for somebody on my team who’sunderperforming in their current role. By helping me with admin work, thatperson could bring value in a different capacity that’s more in line with hisor her strengths and potentially more valuable to the organization as awhole.

Adjusting the roles of people on my team would be far more practicalthan going to my boss and asking for extra dollars to hire an assistant. Evenif I did get approval to hire a personal admin, I’d have to be empathetic toother colleagues at my level who don’t have one. That might create largercultural issues in the organization.

Once I have conversations with two or three team members underneathme and find a way to allocate 10 percent of someone’s time to admin work,I’d feel comfortable walking into that meeting with my boss.


Scenario 21 Follow-Up Question:“What if your boss doesn’t like your solution and says you need to figure it out yourself?”


OK, so let’s assume the boss says, “We can’t have one of your employeeshelping you with your calendar.”

My go-to ingredients would be patience and optimism. I can eithercome up with another idea or just get better at detail work. Maybe I decideI’m close to the “good enough” level, and I want to try to improve. I couldalso be tenacious and get a job at another company if I decide that I havezero interest in becoming more detail-oriented. I’d be practically optimistic

that I could find a job that either pays me more or pays less but has a workenvironment that’s geared more to my strengths.

For example, maybe I could get a job as a car salesman and enjoy mylife so much more because I wouldn’t be spending 10 or 20 percent of mytime doing what I hate and spending the other 80 or 90 percent feelinganxious about that 10 or 20. The funny thing is, going all in on my strengthswould lead to higher performance and more happiness, which couldultimately yield more promotions and substantial raises.


Scenario 22: You’re a business owner who’s consistently been putting out audio, video, andwritten content on social platforms for the past two months. You’ve noticed a little bit offollower growth, but you haven’t had any customers come in from social media. You’retrying to understand whether you’re on the right track or not, whether you should keepgoing or adjust your strategy. What would you do?


I would use every single one of the emotional ingredients in this scenario.The most significant opportunity on Earth for every human being is

communicating to the world through social media. I believe contentcreation on the twelve to fifteen platforms that hold the most attention is theultimate gateway for opportunity, whether you’re trying to get a new job,grow your business, or run for mayor.

I’m going to throw the whole spice rack at this scenario:

Gratitude: I would be grateful for the opportunity to speak to the world. Ask your grandmawhat she was able to do to get customers for a business. Or what side hustles she could work onat night after she put the kids to bed or got home from work. We have so much opportunitybecause of the Internet.

Self-Awareness: I would ask myself, am I putting out content that is in line with my strengths?Maybe you aren’t getting traction because you’re publishing blog posts when you should befilming yourself. Maybe you’re trying to imitate my high-energy video content on social media,but you’re introverted and feel awkward on film. You might be a more effective writer. I wish Icould write, but I can’t. Instead, I use my self-awareness, so I’m sitting in a room right nowwriting this book through audio with Raghav.Accountability: It feels really good to know that everything is on you. That means you’re incontrol if you want to fix anything.

Optimism: It’s a lot more fun to say “Tomorrow’s the day when I make a post that will changethe course of my business” instead of the opposite. Telling yourself “I’m never going to make apiece of content that works” is a self-fulfilling prophecy.

Empathy and Humility: I would ask myself, “Why should somebody watch one of my videos?They have other things going on. Who am I?” There are a million videos in your stream. I’mjust one person.Conviction: At the same time, I know I’m the fucking guy. That’s why you should listen to me.Conviction is about believing in the content you’re creating. It’s about believing that you knowsomething others don’t know about law, landscaping, wine, or how to play chess.

Kindness: When I’m attempting something new, kindness toward myself is imperative. I’mtrying.Tenacity: It’s only been two months. It’s clear that I need to stay determined. Nobody breaksthrough on their first at-bat. Most people don’t break through on their first fifty at-bats. Or fivehundred. Or even five thousand. In the early days of Wine Library TV, nobody watched. I evenhad an e-mail newsletter sending out episodes to subscribers, and still nobody wanted to watch.Building a business takes time.

Curiosity: I actually don’t think I need curiosity here.Patience: If you follow my content on social media, you know how much I believe in patience.It complements tenacity. I need to be patient to get through the five hundred to five thousand at-bats.

Ambition: I would ask myself, “Why am I even trying to grow this business in the first place?”

Actually, I just now thought of how I would deploy curiosity:In business and life, I’m genuinely intrigued. How deep an impact can I

have on the world? How much can my business grow? How muchadmiration can I get? Can my birthday be a national holiday?

It’s not about ego; it’s genuine curiosity. It’s partly what drives myambition. I can’t help but to ask myself, “How big an effect can I have onsociety?”

This book is called Twelve and a Half. In three years, will the next onebe Sixteen and Two-Thirds? Are there more emotional ingredients to startapplying in my life?

I’m curious.And you’re curious too. Will your next post be the one that eventually

leads to a show on Netflix?


Scenario 22 Follow-Up Question:“What emotional ingredients would you use to analyze what content is working on socialmedia?”


Self-awareness, then accountability.If you’re self-aware, you’re willing to see the truth. From there, you can

look at both the black-and-white and the gray.The black-and-white is the quantitative data. It’s how many followers,

likes, and comments you’re getting from each post.The gray is the nuance. Are you feeling positive? Are you gaining

internal momentum? Do you feel you’re onto something?I use quantitative data for validation. It’s how I know I’m growing. But

for me, it’s secondary.If I feel I’m onto something, if I like the way I feel, I’m far happier. It’s

like working out at the gym and eating well. As soon as you start doing it,you know you’re on the right track. You can tell by how you feel. That’s thegray.

You can always monitor the black-and-white. Are you getting moremuscles? Do you poop more regularly? Over time, you’ll see actual resultsthat you can measure.


Scenario 23: You’ve been running your own business for some time now. You genuinelylove what you do. The business gave you the revenue you needed to quit your job, andyou’ve enjoyed growing the company. You have ambition to continue scaling the companyto a much higher level. However, you wake up one Tuesday morning and you just don’tfeel like going to work. What would you do?


Let’s talk about judgment.I believe all those reading this will nod their heads when I say that

people who pass judgment on others aren’t dealing with a full deck ofinformation. When you judge someone, you’re usually looking at only afew specific behaviors or actions. You don’t know that person—and even ifyou do, you often don’t know what’s going on in their personal life. Youprobably haven’t spent the years necessary to map out what happened inthat particular childhood. You don’t have full context. That doesn’t mean

you shouldn’t hold people accountable for their actions through kindcandor, but it’s not smart to judge them for it.

People who judge others harshly tend to deploy the harshest judgmentagainst themselves and their own actions. We beat ourselves up way toomuch. To be kind to others, you first need to be kind to yourself.

If I were in this scenario, I would tell myself, “I’ve been working hardall this time, and I’m just not feeling it today. It’s OK if don’t crush it thismorning.”

Many ambitious entrepreneurs would grind through that Tuesday. I’m abig fan of grinding too, and I would lean into self-awareness to gaugewhether or not that’s the right move on a certain day.

It’s like working out. Out of the approximately 320 days a year I workout, I don’t really feel like it on about 290 of them, but I know if I can justget through the first five or ten minutes, I’ll get into my flow. Recently,after about six years or so of a solid exercise routine, I’ve been easier onmyself and taken a day off now and then when I really don’t feel likeworking out. That’s been a healthy addition for me.

Maybe you’re the kind of person who needs to drag yourself out of bedand push yourself for five or ten minutes before you start enjoying what youdo. Or maybe you’re at the point where pushing yourself would lead toburnout, and you really just need time off. As long as someone’s well-beingisn’t affected, I actually think more entrepreneurs should give themselvespermission to wake up and say, “Hey, I’m going to watch cartoons today.”


Scenario 23 Follow-Up Question:“At what point does taking time off become laziness?”


Out of about 250 days that I work in a year (excluding weekends), there areprobably 7 to 23 when I think, Fuck this!

It could happen for any number of reasons. Occasionally, I get hit withthe right pattern of four, five, or six disappointing events all at once. I cantake a punch, but if you hit me like Buster Douglas in his prime, I’m goingdown. That has happened.

On days like that, I deploy gratitude, humility, tenacity, and optimism.Gratitude puts every business problem into perspective: Is my family

healthy? Then I’ve already won. Humility gives me comfort with myposition in the world. I need to be humble enough to take the punches. I’mnot above that by any means. Gratitude and humility put me in the propermind-set to absorb stress, while tenacity and optimism help me go on theoffense to attack the problem. I also take weekends off, and I’m completelyoff-grid during vacations. That disconnected time helps create balance.

You always have the option to go to work anyway, even when you’reuninterested. Keep in mind, though, that it’s not about the hours you put in;it’s about what you put in those hours.

For example, let’s say you had to deal with sadness in your personal life—your grandma got diagnosed with a terminal illness. You wanted to takesome time off, but you tenaciously showed up anyway, despite youremotional pain. In that situation, you risk offloading your own hurt ontoyour team members. You might be angry, frustrated, or passive aggressivethat day, and you could create issues down the road with your staff. What ifyou snapped and yelled at a colleague for miscommunicating a message?What if an employee wanted to talk about personal issues but you didn’tmake them feel heard because you were coping with yours?

No matter what, I try to be kind to myself in this scenario so I can be astronger leader. If that means I take time off, great. If that means I just gothrough the motions at work and lollygag all day, great. I wouldn’t judgemyself. For me, it’s most important to be kind to everyone I interact withthat day, whether that’s my vendors, customers, or most important, myemployees.

Patience is a secret ingredient here that helps balance ambition. Don’tlet your ambition put you in a mental space where you overanalyze youroutput every single day. Focusing on your journey over the course of a yearor five or ten years is more valuable than worrying about being lazy on afew days here and there. Maybe you had an ineffective day. Maybe you hadan ineffective month. Or maybe something devastating happened that threwyour whole year off. The key is being kind and patient with yourself firstand being aware of how much more time you have left.

If somebody in your family got diagnosed with an illness and you needto take personal time for that, that’s appropriate, not something you shouldfeel guilty about. If you just wake up on a Tuesday morning and decide youdon’t want to go into your business because it’s a gorgeous day outside andyou’d rather spend it at the beach, don’t judge yourself for that either.

If you find yourself always getting the urge to take time off, then youshould assess whether you still enjoy running your business through self-awareness. However, don’t overvalue your day-to-day output. Your overalljourney is a more accurate reflection of where you’re headed.


Scenario 24: Let’s say you have a small company that you’re scaling up and, in thatprocess, you’re trying to hire an assistant to manage your calendar. You’ve gone throughfive assistants already, and they’ve all quit or underperformed and been fired after severalmonths. The lack of continuity is making you scale slower than you otherwise would.


I’m realizing that I’m far more obsessed with accountability than I thought.I’m the one who’s hiring the assistants, so I would start by

understanding that this is all my fault. I can’t cast blame or judgment on myemployees for not performing well or for not staying around. I need to takea deeper look at my hiring process or how I’m operating as a leader.

It’s also important to balance that accountability with optimism. I’vetried five assistants, but there are billions of people on Earth. Just because itdidn’t work out five times doesn’t mean that it will never work out or thatI’m not capable of getting better at my process.

Still, if five assistants have quit or gotten fired, I need to take a look atmy own shortcomings. Maybe I’m not being patient enough in their trainingprocess. Maybe there’s something I need to fix about my communicationstyle. Maybe I need to be more candid in the interview, so they know whatthey’re getting into. Their reaction could help me make a better judgmentcall on future hires.

When I’m hiring my sixth assistant, I would lean into humility in thoseconversations and talk about my shortcomings as a manager, even tell somehorror stories from the last five. I could share up-front my perspective aboutwhy things failed. Humility would allow me to have much more in-depth,fruitful, and contextual conversations that would help me make a betterdecision on who’s the best fit.

When you react with accountability and humility in this scenario, yourlosses can actually set you up for a much bigger win down the road. After

examining yourself, your shortcomings, and how you can create a betterinterview process to find your next assistant, you can go back to optimism. Iwould believe optimistically that my next assistant will stay for six yearsinstead of five months because of what those prior experiences taught me.


Scenario 25: You’re trying to build your reputation with the leaders in the organizationyou work for so you can eventually land promotions and move up the ranks. However, inthe past several weeks, your coworker Rick has often been stepping on your toes andtrying to do your job for you, whether he realizes it or not. It feels as though he’ssubconsciously trying to take over your job. You’re frustrated and feel that his actions willlimit your career growth and take away your chance to be noticed by your manager. Whatwould you do?


In business and life, people are quick to jump to conclusions.Here’s one example: A lot of people assume that just because someone

owns a business, they’re killing it. You see Bob the Business Owner’s nicehouse, Mercedes-Benz, and company with thirteen employees, and youassume things are going well for him. You don’t see that he’s underwater onhis car loan, his revenue’s declining, and he’s barely making the mortgagepayments. Bob doesn’t post that part on Instagram.

There’s little empathy in a world where none of us really know what’sgoing on in one another’s lives. Bob’s employees might resent him for notgiving out raises, but they don’t know that he’s been putting his ownsavings into the business just to keep it afloat.

The team might say, “Fuck Bob. He’s got a Mercedes.”The reality is, Bob’s about to lose his Mercedes.I don’t mean you have to prioritize Bob’s well-being over your own, but

I do mean that approaching decisions with empathy instead of resentmentchanges everything. You don’t have all the context on your colleagues’lives, so why confront them through negativity?

Going back to the original scenario, it’s tempting to assume that Rickhas bad intentions. But if you deploy empathy, you realize that Rick istrying hard, just like you. He’s trying to do right by his ambitions, his

family, and what he thinks he needs to do for his own success. How can youget bent out of shape because somebody’s working toward their ambition?

(Sorry to go on a tangent, everybody, but I’m just going to plop this inhere because it’s where my mind went: I think it’s crazy that bosses get madwhen employees ask for raises. I know a lot of those bosses. Youremployees are supposed to ask for raises! They’re trying to supportthemselves and their families. You can always say no if you feel that’s theright response.)

This is also where self-awareness plays a key role, along with empathy.Maybe it really is true that Rick is overstepping the boundaries with thewrong intent. Or maybe you’re slacking and Rick’s trying to cover for you.Maybe your ambition is entirely selfish. Maybe he has bandwidth and he’sfiguring out how to use that time.

If you’re insecure and cynical, you paint a picture in your mind thatRick’s trying to ruin you. If you’re self-aware and empathetic, you see thathe’s trying his best, and you can start having conversations with him insteadof digging your heels in.


Scenario 25 Follow-Up Question:“What would your conversation with Rick sound like? What would you say?”


Communicating with a mix of empathy, accountability, self-awareness, anda bit of curiosity would work like a charm in this scenario:

I appreciate the tenacity, conviction, and ambition you’re coming with, but you’re bleeding intomy world a little bit. Is there any way we can figure this out? Do you have enough workload?Do you enjoy what you’re doing? Do you want to do more of what I’m doing? Is theresomething I could improve on?

Maybe after that conversation, I could take a step back and realize thatit’s an opportunity for me to work on more exciting projects, since Rick cancover some of my current workload. Maybe I decide I need to take onaccountability and step up my own performance. I could have aconversation with my manager or with HR if I still feel that he’soverstepping.

Many employees in this scenario make the assumption that theirmanagers don’t notice what’s happening. At VaynerMedia, I’ve had peoplewalk into my office to complain about a colleague overstepping, and they’resurprised to hear me agree that the other person has the wrong intentions.As a manager, I’m watching too.


Scenario 26: You’re building a new company with a couple of employees who have knownyou for a long time. Over the years, they’ve gotten to like you, your personality, yourintent, and your vision of what you’re trying to accomplish in the industry. As you hirenew employees, they’re surprised when they see that the older team is so invested in yourrelationship with them. You notice the new team making fun of the original team membersbehind their backs, saying they’re “brainwashed” and are “drinking the Kool-Aid.” Thenew employees have talent, so you want to keep them around, but you don’t want them todamage the culture. What would you do?


Many organizations create poor work environments for employees. Thereare unfortunately plenty of CEOs, managers, and leaders who don’t use thetwelve and a half ingredients in this book (or any of their own). Theyunintentionally create politics and fear in the workplace out of their owninsecurities, so employees use cynicism as a protective measure whenjoining a new organization.

Humans fear disappointment. People don’t want to trust a manager orlove their company, only to be let down later. I have empathy for that.

When people join VaynerMedia and see how tight my relationships arewith those who have been around for eight, ten, or more years, it’s veryhumbling for me. On very rare occasions when a new employee thinks theolder ones are brainwashed, I don’t get upset; I actually feel flattered. I’malways humbled in this scenario when I notice it happening at my companyonce in a blue moon.

Believe it or not, one of the most powerful ingredients I would use hereis patience. If my older employees truly love the organization and theenvironment, then the new ones eventually will too. They’re cynicalbecause they don’t have all the context yet.

Whether it’s seven months or two years, they’ll learn there’s no“drinking the Kool-Aid.” It’s just water. It’s good for everyone, newcomersincluded.


Scenario 26 Follow-Up Question:“But the new team is making fun of the others for being brainwashed. Doesn’t thatdamage culture? How would you handle that?”


Writing this book is fun because I can feel the difference in how I’d react tothese scenarios now compared to years ago. Now, I have kind candor in myrepertoire.

Instead of just letting the situation play out, I can set up one-on-onemeetings to help the new team with the crossover. I’d meet with each ofthem and say:

Hey, I totally get where you’re coming from. I’ve been working with the other guys and gals foryears. They know me, and I know them. I hired you so that in a few years, you’ll feel the sameway about this work environment as they do. Over that period of time, it’s my job to show youwhy “drinking the Kool Aid” doesn’t exist here. It’s actually just water, and it’s delicious andgood for you. That responsibility is mine, not yours. If you don’t have confidence in me or thisorganization yet, I fully respect that. But I would ask that you be kind to the others.

In running VaynerMedia and building a personal brand, I deal with thisheadache in real life. If a new employee had the luxury of great parents orshe’s inherently optimistic, it’s easier for her to trust. Employees like herbuy in to my message and VaynerMedia’s culture immediately. Others whowere let down by their mom, dad, society, or past companies or otherwisehad an upbringing that led them to be pessimistic tend to viscerally pushagainst me and my personality. They look at my energy and optimism andthink, He’s going to let me down big.

I always respond with empathy. If you have genuinely good intentionsas a CEO—if you’re deploying these twelve and a half ingredients—employees who start out cynical will change their opinions. It’s incrediblyrewarding to earn people’s trust, regardless of how much else you’veaccomplished.


Scenario 27: You have two employees, Jim and John. Jim has a way of directlycommunicating his feedback, and John doesn’t like it. John says Jim always speaks to himrudely, while Jim says John needs to have every piece of criticism sugarcoated. Jim wasraised to believe it is kinder to deliver criticism swiftly and clearly. Assuming you’re theirmanager, what would you do?


When managers face this situation, many get upset because they lackpatience. Patience helps in navigating this scenario because solving adisagreement between two people takes time. It may or may not besomething that you can resolve in one meeting.

Before I meet with Jim and John, I’ll think through what decisions I canmake. Maybe I can split them up and put them on different projects. If oneof the two is clearly the source of the issue and doesn’t correct his behavioreven after receiving feedback, then I might consider letting him go. But I’dbe optimistic that they just have a difference in perspectives with nomalicious intent and it could be worked out.

I’d approach the meeting with optimism, conviction, and an undertoneof kind candor:

Look, John and Jim, this is just a moment in time. Even if you’ve both had issues in every singleconversation you’ve had in the past, we’re now in the process of trying to fix it. Now that we’resitting down and talking about it, the disagreements between you both won’t last forever. I’m notsaying everything will be perfect after this meeting. You might still have problems, but if ithappens in three out of thirty-three interactions instead of three out of three, we’re winning. Iknow you didn’t start out on the right foot, but that will change.

Think about the way managers would typically respond in this situation.Based on the messages and e-mails I get from my community, I believemany would say, “You two need to figure this out or I’m going to let one ofyou go.”

That’s what happens in the business world, and it stuns me that peopleaccept that as the right answer. It’s rooted in short-term thinking,impatience, and lack of kindness. Why does it have to be so cold? Whycan’t managers give a little love to their people for twenty minutes? Whycan’t managers instill a feeling of safety instead of fear?

Let’s say the manager tells John and Jim to figure it out betweenthemselves or one of them gets fired. Now, the issue becomes far worse.Jim might start planning how to outmaneuver John. John might try to

protect himself by damaging Jim’s reputation behind his back. They’dproduce lower-quality output because they’re more stressed.

Imagine how much more effective they would be if the manager madethem feel a little safer. Instead of navigating company politics, they couldfocus on their actual jobs.

Remember, this isn’t a therapy book. It’s a business book. Deployingthese twelve and a half ingredients in different mixtures can help you builda more emotionally efficient team and a more profitable company as aresult.


Scenario 28: You have a big client you closed that will add a sizable percentage to yourcompany’s revenue. You have personal relationships with this client, its people trust you,and your top priority is for this to go extremely well. You put your best team on it.However, Susan, an employee from your team, has a moral objection to working with thecompany. She tells you that she’d like to opt out of the project. What would you do?


I’ve actually gone through this four or five times in the course of buildingVaynerMedia. Every time, it’s a tricky one.

Empathy first. I’d ask myself, “Would I ever decline the opportunity towork with a client because of the industry it’s in or the products it sells?” Ifthe answer’s yes, then I have to be empathetic to my employees feeling thesame way because of their religious, social, or political beliefs.

In the past, I’ve made my own subjective calls on whom we work with.We’ve had some big clients I’ve passed on because I didn’t believe in theirproducts or services. So, I can’t be a hypocrite when an employee wants todo the same.

If not—if you blindly think, Money is money, and you’ll work withanyone—then at least you have a leg to stand on in this scenario. But don’tbe hypocritical.

Whenever this situation reared its head at VaynerMedia, I sat down withthe employee who had that objection and had a fruitful conversation whereI explored why he or she felt that way. I’m actually curious what makesthem say they want to opt out of the project.

As a leader, you need to figure out if there’s a different underlyingreason why Susan doesn’t want to do it. Is her moral objection a cover-up?Is she actually tired or burnt out? Is she making an excuse? Or is therelegitimacy and good intention behind it?

Sit down with Susan in a one-on-one meeting and say, “Hey, tell memore. Show me why you can’t work on this. I want to learn and understandwhy.”

Then you’d be at a fork in the road. Either Susan comes to the meetingwith a compelling case, or she doesn’t. If the conversation is intriguing, youcan spend time exploring your own feelings on the subject.

The other outcome is that Susan comes with a weak argument and can’tcome up with good answers when you poke and prod. Maybe she read asingle headline on Twitter and came to a fast judgment that wasn’tthoughtful. Maybe she actually just doesn’t have bandwidth, and she’scovering up. Maybe she doesn’t feel confident enough to take it on.

From there, you have to make a different kind of decision: Do you buildSusan up? Do you give it a mulligan and let her sit this one out? Is there abigger issue here that you have to do something about? This is a person’scareer we’re talking about, and you’re paying a salary. What should be yournext move?

Let’s keep playing it out: Suppose Susan didn’t have a compellingreason, but you decide to let her sit it out anyway and replace her withSarah for this particular project. Everything’s going well, but one day youoverhear Susan at the watercooler saying Sarah is a terrible human beingfor working with this client. What do you do now?

In my early years, if I’d faced this situation, I would have deployedaccountability and fired Susan, or I would’ve been delusionally optimisticthat it would blow over. In this situation, she declined to work on a projecteven though she didn’t have a compelling reason, I still let her sit out, andyet she’s soiling the company’s culture and trying to cancel Sarah. That’sjust not acceptable. If I were faced with this situation now, I would use kindcandor first in a one-on-one conversation:

Hey, Susan, good to see you. Listen, I’ve got to be honest. I don’t think you gave me a verycompelling reason why this client project goes against your personal beliefs. I appreciate thatyou don’t like the brand, but I think it’s a project you could’ve still supported in some capacity.However, even after I accommodated your request and replaced you with Sarah, I’ve noticedyou’re damaging our culture. You’re poisoning the well by going out of your way to tell the team

that Sarah’s not a humanitarian, and you’re making her feel uncomfortable. We have a realproblem here, and I want to explore what we can do about it.

Now, instead of firing her outright or not addressing it at all, I’d firstmake it clear to Susan that I notice her negative behavior. I’d give her anopportunity to fix it. If she still continues, then I’d probably let her go.

I would understand where she’s coming from, because she’s adamantlyagainst this client. Unfortunately for both of us in this scenario, I was not,and it put us in a precarious spot. However, at this point I would have tosuffocate the options. If she has decided she doesn’t want to be at thecompany anymore, she must leave, or if she stays, she at least has to notsoil the culture based on the decision we made.


Scenario 28 Follow-Up Question:“What if Susan did come to your initial conversation with a compelling reason why shedidn’t want to work on the client project?”


Then we’re good.In any interaction, I try to first understand the other person’s intent. If I

believe Susan’s being genuinely thoughtful and well-intentioned, then we’regood. Forever. That’s why I react so viscerally when I feel that people areacting with bad intentions.

At the same time, I know I don’t have all the context. That’s whyaccountability and kind candor are crucial for both the CEO and theemployee. As a CEO, it’s my responsibility to create an environment whereSusan feels safe enough to share her honest feelings, thoughts, orinsecurities with me. But Susan needs to also be accountable as anemployee and communicate with kind candor if she feels that the companyisn’t doing right by her.

Your job is just one part of your life. If you’re not giving kind candorthere, are you avoiding it in other areas too? Could your marriage improvewith more of it? What about your relationship with your kids, yourneighbors, your friends, or even yourself?

Finally, I would say this: there have been multiple times in real lifewhen I have decided against working with a client, and there have been

multiple times when an employee’s feedback was the driving force for us towalk away.


Scenario 29: You’re twenty-three and just finished four years of art school. COVIDlockdowns are in place, businesses are struggling, and you don’t have a job. You startdriving for Uber and Lyft while you’re looking for an opportunity. One day, after notgetting many rides, you go on Twitter and start noticing people talk about these thingscalled NFTs. After about five hours of reading on social media over two days, you realize,“Holy shit, I can do this!” What would you do next?


One of my favorite things about innovation is that it sometimes gives newopportunities to people who haven’t had them in the past.

For example, social media created significant opportunities forinfluencers. Please go read the New York Times bestseller Crush It! WhyNOW Is the Time to Cash In on Your Passion. I spoke about it twelve yearsago. People are now able to make $120,000 a year being an expert onstretching, or $90,000 a year being a chef on the Internet.

People didn’t anticipate the long tail, or the money you could make withyour expertise. Cash in on your passion. It couldn’t have been moreaccurate.

In this scenario, I’m going to basically write Crush It! all over again.NFTs are going to do for artists what social media did for people withpersonalities.

Artists would normally think about finding jobs in the advertisingindustry, Hollywood, or some other “creative” field. The truth is, they needto compromise their creativity when they take up those jobs. They’re notcreating what they want to create at work, not even at VaynerMedia.

This person needs to reassert the ambition of youth. He or she needs togo back to the mind-set of the thirteen-year-old who said, “I’m going to beBanksy one day,” the one who at eighteen dreamed of being Michelangelo.Tap into that ambition.

My advice for that artist? This is your moment. This is the time to betenacious, both in your output and in your networking. Don’t underestimate

the power of humility. When personalities tried to become influencers onsocial media, they dreamed of making millions, but many didn’t have thehumility to land at $88,000 a year and enjoy the shit out of the fact that theyget to be social-media influencers.

The same thing will happen to artists. Would you rather be an executivemaking $110,000 and hating your Monday through Friday, or would yourather make $59,000 per year being a working artist? Do you have thetenacity to fight for your art when you’re about to turn thirty in a few weeksand you’re still living with a roommate? Or would you compromise and geta job you hate making logos at a brand?

I know millions and millions of artists are going to be benefited byNFTs. It’s the option economy: they have new ways to monetize theirpassion now.

The number of people pre-NFT who could earn $219,000 a year asartists is a fraction of those who will be able to in 2031. Creatives at adfirms or on Broadway who now earn $110,000 a year to make thingsthey’re not passionate about could potentially replicate that same incomemaking what they dream of making. Or they could earn $59,000 and still beso much happier.

Technology is about to create an opportunity that we haven’t seen in thehistory of mankind. I’m so happy and excited for all you artists who arereading.

Tenacity is the most important ingredient here. I don’t want anyone togive up along the way. When an artist launches his or her first NFT projectand it sells zero pieces when it cost money to mint them, that person willcurse me out in an e-mail ( and say, “Fuck you,Gary! You inspired me to do this, but I lost.” That’s when tenacity shouldkick in.

Dear artist, here’s my message back to you:DO NOT E-MAIL ME UNTIL YOUR 49TH PROJECT HAS FAILED.

Don’t even consider it. Otherwise, you’ve completely missed the point oftenacity. You want to be a working artist and you gave up after one time?Let me get this straight: You want to spend your whole life drawing,painting, coloring, or doodling, and you gave up because nobody paidattention to your very first project? Get out of here.

I want every single artist to have patience and understand that they mayhave sixty or seventy more years of living if they’re starting out at twenty-

nine. In that context, what is happiness? Is happiness having your ownapartment? Is it having nicer clothes?

Please don’t map your actions to fulfill your mom’s and dad’s ambitionsfor you to be at a certain place by thirty.


Scenario 30: You’re a forty-seven-year-old who’s crushed the last seven years at the officedue to some really smart work. You’re the head of marketing of an insurance company.You stumbled upon GaryVee five years ago, and your LinkedIn game has improved.You’re making $250,000 per year, up from $130,000. You’re even starting to get even morevacation time, and your work-life balance is perfect.

But every time you go to sleep at night, you think, What if I branched off and worked formyself? You know there are a couple of people at the company who’d be interested inquitting and working with you. The thought of owning 33 percent of your own businessalong with two partners sounds far more lucrative and exciting. What would you do?


The beauty of this scenario is that you have options. Many people don’t, sothe first move is gratitude.

I wish more people in this situation were optimistic. I’m often confusedwhy people in great situations don’t try to achieve something greater whenthey have the itch. The reality is, if you quit your job, work for yourself,and fail in two years (which often happens), you’ll go back into theworkforce as a more attractive candidate. You won’t just have impressivecorporate experience; you’ll have entrepreneurial experience too. In severalyears, that will continue to be valuable. When you start with gratitude,patience, and conviction, you can deploy tenacity to chase your ambitions.

I actually believe this is a no-lose situation. If you’re a well-paid seniorexecutive who has the humility to live a lifestyle with low expenses, youcan save money to give yourself eighteen to twenty-four months of runway.You can take the leap, scratch your itch, and if you realize you weren’tmeant to be a founder or CEO, you can get a higher-paying job.

In forty years, the regret of not following your dreams is going tooutweigh the pain of quitting your job and failing. Maybe you’ll have tolive a little more humbly than you already were. Maybe you’ll have to takeon a small amount of credit card debt after always having money in the

bank. Whatever it is, it’ll be less painful than being eighty-seven, sitting byyourself, and thinking, Why did I not start my own company?

If you felt the chemicals rising in your body when you read thisscenario, ask yourself the following question: When you look back at yourlife in this exact moment, do you regret not asking a certain boy or girl out?

The answer is yes for everybody. Now that you’re in your twenties,thirties, forties, or fifties, what was so scary about Sally McGee or Tyrone Jsaying no?

Let me save you time: nothing. That’s exactly how you’re going to feelin your old age. You’re going to ask yourself, “Why didn’t I take the leap?”

Please call a ninety-year-old you know. Call him or her and talk aboutthese scenarios. Regret is the ultimate pain. Use conviction, ambition, andtenacity to push yourself over the edge in your mind to make the jump youwant to make. It might take many conversations with yourself to do it. Ihope the words on this page help.


Scenario 31: You’re a small-business owner who took a bank loan to build your businessfrom scratch. That loan took you almost a decade to pay off. However, you’re now debt-free, and the business is finally turning enough profit for you to upgrade to a slightlylarger apartment for you and your family and to improve your lifestyle. Soon after, anatural disaster comes through your town and destroys your office building. What wouldyou do now?


I would give myself some time to mourn. I wouldn’t beat myself up forneeding some time off or for feeling the loss.

Then, I would deploy gratitude as a weapon against thatdisappointment. I would feel so grateful that I’m still alive and that myfamily is OK. I don’t control Mother Nature, and there’s nothing I could’vedone about the disaster. It is what it is.

Gratitude limits the amount of time I’d spend dwelling on the situation.Then, I’d start going on the offense with conviction and optimism. “If Icould build a successful business from zero once, I can do it again. I canabsolutely build this up again, and I will.”

From there, I would go into accountability. Accountability in this case isasking yourself, “What can I do right now?” You can use it to put yourselfin control.

In this case, maybe I could start a YouTube show documenting thecomeback. I could e-mail the links to journalists at every local news outlet.If they pick it up, it could become a national news story that might lead toexposure for a grand reopening, a GoFundMe, or something else. I wouldhold myself accountable to get myself into a mode of building my life backup.


Scenario 32: You’re looking to grow to a senior leadership position with moreresponsibility, but you’re not getting chances to work on new projects that will expandyour skill set. A few colleagues on your team are getting most of the new opportunities,and you suspect your manager is picking favorites. What would you do?


To have a healthy, productive discussion with my manager (with kindcandor), I would need to get myself into a positive mental state. I’d use amix of gratitude and optimism first. In a world where millions of peopledon’t have a job, I actually have one. Even if I’m going through a roughpatch, some disagreements with my boss, I would never let myself beconfused about my rank out of 7.7 billion people in terms of overall well-being. I have a job in a world where millions of people don’t have one atall, and that means I have an opportunity to improve our relationship.

Imagine if your immediate reaction was the opposite:

“Oh, the boss is just picking favorites again.”“He doesn’t know how to spot good talent.”“This company’s leadership is clueless.”

If you walk into a conversation assuming that the other person is quietlyundermining you, you’re setting yourself up for an unfavorable outcome.Your emotional ingredients will show through in your tone and energy, andthe smart ones around you will intuitively sense it. You can’t trick theemotionally intelligent.

That doesn’t mean you shouldn’t stand up for yourself. However, far toomany people walk into meetings with employees, bosses, or team membersthey’re having disagreements with and “fight for what’s right” withouthaving a single conversation about it first. People approach these convoslike an after-school fight.

At VaynerMedia, I’ve watched employees storm into my office with firein their eyes, but the second they give me awareness of a difficulty orchallenge they’re facing, they’re stunned how I immediately get on theirside. The conversation turns in a positive direction as soon as they bring itto my attention. The fire turns into hearts.

Meanwhile, I wonder how long they’ve waited to communicate thatissue. Have they been sitting on it for seven days? Seven weeks? Sevenmonths? Seven years? How many people left the company without givingthemselves or the company the chance to create a fantastic situation?

People allow resentment to fester in their minds while they toss and turnat night, or dump their anger on their parents when they call. It could not beunhealthier.


Scenario 32 Follow-Up Question:“What would you say if you were to sit down and talk to the manager? Would you ask formore opportunities?”


Before asking for anything, I’d gut-check it with humility and self-awareness. There’s too much entitlement in the world today.

I’ve had employees come to my office guns a-blazing, asking forpromotions at twenty-two years old, with no experience, having been at thecompany six months. Some people ask for more responsibility on importantprojects even though six of the last seven clients they worked with didn’trenew. I could still give those people one out every five or six projects, butas a business owner, I’m concerned. Will our growth slow down if I handthem more responsibility when they haven’t delivered?

In this scenario, humility and self-awareness are effective filters. Whatare you actually asking for? Do your results back that up? Or have youbecome delusional because you have an upcoming wedding, so now you’reexpecting a business to take care of you? Have you done a little rope-a-dope

in your own mind that you deserve a promotion or a raise because of yourown life events?

With humility, self-awareness, gratitude, and optimism, you can deliverthe following lines to the manager:

Hey, manager, I know there are a lot of new initiatives at the company, and there are manytalented people in this organization. But I just wanted to bring this to your attention: I noticedyou’re giving most of the new projects to Bob. I’m not going to be able to show you how great Iam unless you give me opportunities too. Is there anything I can do to earn that?


Scenario 33: You’re the owner of your own company, and you’re in the process of buildinga new product offering for your customers. You have a release date for the product in thecoming weeks, and you’ve prepared an e-mail blast to let your customers know. It’s veryimportant for the company that this launch goes well. Unfortunately, a junior teammember, Sally, accidentally sends that e-mail blast out a week early, before the product iseven available. What would you do?


Right before Sally walks into my office, I’m probably screaming, “Fuck!”This scenario is a tough one. I like to say that 99 percent of things don’t

matter. Most of the issues people face in business are blown out ofproportion. However, this scenario is really painful. You never get a secondchance to make a first impression, and messing up a product launch can bevery detrimental to the company.

As the owner of the company, I would truly be disappointed. I wouldimmediately scream “Fuck!” because I would need to release mydisappointment before talking to Sally.

After you get such news, maybe your style is to take a long run or havea hard workout. Maybe you punch a punching bag. You need to get yourfrustration out, so you don’t blow up on your employee.

Then, I would assess the situation through the lens of accountability. Ihired the person who hired the person who hired the person who hiredSally. I created the framework that allowed her to make that mistake. Howcan I fall into a spiral of blaming others when I’m the source?

My top priority at that moment wouldn’t be to give the team criticalfeedback. It would be to make Sally feel safe. She’s probably terrified and

spinning out of control, thinking, I’m about to get fired.The best way to react is with a huge dose of empathy. As soon as she

walks into my office or as soon as I make that FaceTime call, I’d quicklyput her at ease by saying, “Everything is going to be OK.”

That conversation is my opportunity to create safety. If you want todeliver feedback to the junior team member with kind candor, you can do itlater, when things have cooled down. Giving feedback when you’reemotionally on tilt could have a more pernicious influence on the team.

Shouting “You all ruined this for me” is just going to instill more fear,which means the team will feel inhibited. People will be looking over theirshoulders, casting blame instead of taking accountability, holding back newideas out of fear. The company will grow more slowly, which would be afar bigger problem than one failed product launch. When people feel safe,they go on the offense. Going on the offense leads to growth.

Once safety has been created, the question then becomes, “How can wespin this into a positive?”

This is where gratitude comes in. Now that I’ve gotten my frustrationsout and had conversations with my team, I’d have an improved perspectiveon the mistake and recognize that it’s not that serious. Maybe I could makea fun video bantering with my junior employee and send it out to my e-maillist:

Me: “This is Sally. She hit Send by accident. Jeeeez! We’re really sorry; wedon’t have the product yet. We’ll be back next week with the officialannouncement and a special discount code for you: SallyMessedUp. Lookfor it! Right, Sally?”Sally: “Ha ha. Right, boss!”

There’s always an opportunity to make lemonade from lemons.


Scenario 34: Over a three-year period, you and your husband turn a side hustle sellingvirtual art classes into a full-time company. You both have been putting out content onInstagram, TikTok, and LinkedIn. The business has rapidly grown to $300,000 in yearlyrevenue. You and your husband have complementary skills and a successful fifty-fiftypartnership. However, your husband is now happy with where the company is at, whileyou have ambitions to grow it to seven figures and beyond. What would you do?


I watch so many people struggle in marriages, business partnerships, andrelationships because they’re frustrated with their partner’s level ofambition.

In this scenario, your husband has new data. He now feels that he wantsto enjoy a little bit of his money. He might say, “You know what, I’m happymaking $180k profit on this $300k revenue. Instead of reinvesting it to getus to a million, I want to do things like go to Disney World with the kidsand stay at a nice hotel.”

As his wife and business partner, you might find those words difficult tohear, especially if you had conversations in the early days about how thetwo of you both would take this business to $10 million in revenuesomeday.

When you’re in a partnership, though, empathy and humility come first,not conviction. When you sit down to have a talk with your husband aboutyour different ambitions, you can’t be in an aggressive, ego-driven mentalstate. Notice how ingredients like conviction, tenacity, and ambition arealmost never the first go-to reactions in difficult scenarios. That’s becauseyou can’t counter aggression with aggression right away; you need todefuse it first.

Starting with empathy and humility sets you up to have a productiveconversation. When you’re empathetic and humble, it’s hard to aimnegative energy at other people. In this scenario, that means recallingeverything your husband has done for the business to help you get to$300,000 per year. Even though you have differing opinions now, youwouldn’t have gotten to this point without him.

It’s OK that your husband is content with the current revenue. It’s alsoOK that you want to take it to a million. You don’t need to compromise onyour goals and happiness. You also don’t need to convince your husband tochange his. Together you can create a two-part structure to make this work:

1. Hire someone to do your husband’s job.2. Look at the bigger picture of everything your husband is helping you


The first part is easy. You sit down with your husband, break downeverything he’s doing to help the business, and hire someone, so he can takea break.

At first, you’ll feel relieved because you found a solution. Seven monthslater, when you’re burning the midnight oil preparing for an art class afterputting the kids to bed and your husband is sitting there playing Call ofDuty with his time off, you’ll feel like wringing his neck.

That’s when you need to take a step back. Look at how he’s helping youin life, not just in the context of business. Is he taking care of thehousehold? Is he picking the kids up from soccer practice while you doyour virtual sessions? Is he helping them with homework while you’rerunning the company?

Even if he’s not directly involved in the company, he could be settingyou up to win at life in a different way.


Scenario 35: You’re fifteen, and you’re making about $1,400 a week from trading sportscards. You’re a straight-A student at school, but your grades are now starting to slip.You’re also less interested in lacrosse, even though you’re a freshman on the varsity teampositioned for Ivy League schools. Your new sports-card addiction is keeping you up lateat night, and you’d rather spend time trading than studying, playing lacrosse, or enjoyingcasual escapism like Fortnite. What do you do?


This scenario is a fun one for me. I have so many kids hitting me up aboutsimilar situations in their own lives, scared they’re screwing up theirfutures. Somewhere around seventh to ninth grade, a framework wasestablished: I’m an exceptional lacrosse player, and that’s my life path, orI’m an exceptional student, and that’s how I’m going to win.

Usually, this is the result of a family dynamic that can be healthy insome ways but unhealthy in others. Some parents look at their fifteen-year-old kid like a product. They say, “This is my Harvard daughter,” or “This ismy lacrosse-player son.”

Depending on what the parents do for a living, they may have differentsubconscious ambitions for their children. If the parents are entrepreneurs,

they may be comfortable with their kid trading sports cards. If they’reacademics or executives, it may make them uncomfortable.

Here’s what I would tell the kid in this scenario:

Have empathy for yourself. It’s OK to have these feelings. Maybe you’re actually anentrepreneur, or maybe you have entrepreneurial tendencies. Either way, have empathy for yourparents. They have an ideology for you, and you’re fucking it up. You need to be empathetic soyou can absorb their criticism and any attempts to manipulate the situation.

For example, they might tell you, “We’ll pay you $1,400 a week. Don’t even worry about thecards.” You need to be accountable and self-aware and realize that will lead you to a spoiledlife. Don’t let that happen.

The reps you’re getting in the trenches are worth more than the money. Focus on patienceand conviction. You need to be OK with getting B’s instead of A’s for the time being.

At the same time, you may go through this sports-card phase for twelve months and grow outof it by sophomore year. You may have to work harder to improve the grades that you let slip atfifteen. You’d need conviction that you can get back to a decent GPA if you double down insecond semester sophomore year, if and when you stop caring about sports cards. Take thesteam out of the anxiety that comes with choosing between two options. You’re not choosingbetween grades or sports cards; you’re choosing in the short term. You can catch back up.

One example of this is my physical well-being. I was behind everybody in my twenties andthirties, but strong execution with a personal trainer for seven years allowed me to catch up,although probably not all the way, compared to where I’d be if I’d been training hard from myearly twenties. But my point is, people are fearful of choosing, but in reality, the decision isn’tfinal. It’s not either-or. You can do both.

When your peers make fun of you for getting worse at lacrosse and letting your grades fall,use a combination of humility, conviction, self-awareness, and accountability to deal with it.You’re the one who wanted to trade sports cards. You’re the one who followed your beliefs andmade the decision to let other areas of your life slide for the time being. Even if your sports-cardphase throttles your ability to play lacrosse at a top college while your friends are gettingrecruited, recognize that it wasn’t a waste of time. Nor was it the worst thing that ever happenedto you.

Even if your goals change in junior year compared to where you are at fifteen, you’lleventually become more aware of how valuable the lessons were from your sports-card years.As a junior or senior, you might be pissed at yourself for screwing up your freshman year onpaper, but at twenty-five when you join a startup, those skills you learned from fifteen to sixteenare going to come to the fore. Patience.

Look at your life in a hundred-year window, not a hundred-day window.


Now it’s your turn. Post a video on the social-media platform of yourchoice describing a challenging real-life scenario you faced in your career,how you handled it then, and how you would handle that situationdifferently today. Use the hashtag #ScenariosGaryVee when you post it.

Part III


Before you can properly combine these ingredients in your own lifesituations, you need to develop each one individually. Here you’ll find ahandful of exercises you can use as a starting point to build your emotionalcapacity and improve on your halves. You’ll find exercises to help you withevery ingredient listed in part I, including kind candor.

Some of these exercises will be easy for you. Others might be morechallenging.


Turn on your phone’s selfie camera and record a video sayingsomething like this:

I’m making this video to tell you the five things that are most important to me in the world.These are things that I’m so thankful and grateful for. I want you to send this video back to meanytime I complain about something minor.

Text that video to the five to fifteen people you talk to the most.I want to compel you to care about the health and well-being of your

family over everything. When gratitude is grounded in that, you’ll see howeasy it is to navigate through challenges in your career.


For this exercise, I want you to answer a few questions about yourselfand how you’d typically respond in a variety of different situations in bothbusiness and life. Then, send those questions to the ten people closest toyou professionally and personally through an anonymous Google Form thatthey can fill out.

This way, you’ll get a sense for your level of self-awareness and howyour perception of yourself compares to how others see you. Head over for the full instructions (including the questionsand how to set up the Google Form).


Think about a time recently when you deflected blame on someone elsefor something that was your fault.

Post a video or photo on the social-media platform where you have themost followers and apologize for it. Use the hashtag#AccountabilityGaryVee. I’ll be scrolling through and giving love to asmany of you as I can!


Open your phone contacts and find the five people in your address bookwhom you deem the most optimistic.

Text them and ask to set up a fifteen-minute conversation. Ask themwhy they’re so optimistic. Ask them to use specific examples.

I believe that the more you hear other humans talk about optimism, themore you can formulate your own context and understanding of it. I’vehoned many skills in my life by surrounding myself with people who arestrong in those areas.

P.S. This exercise could also lead to a conversation with somebody youhaven’t talked to in a while. That’s always nice too.


Call one close family member and one close friend from work.Ask them, “From our interactions in the last few years, can you give me

an example of a time when you were upset about something, and myreaction didn’t bring you value? Was there a time when my reaction to anevent poured lighter fluid on your stress or anxiety? Tell me the story.”

You’ll hear about a time when another human being was hurt becauseyou were unable to empathize, being more focused on yourself than theother person.


Practice allocating part of your time and part of your finances forkindness:

1. Go on and donate what you can afford to a cause thattouches your heart.

2. Donate your time and your skills. This is one I’ll challenge myself ontoo. If you’re fortunate enough to have achieved great financialsuccess, it’s easy to donate $1,000, $10,000, or even $100,000 to acharity. That’s why I’ve always felt that the kindest acts I do are therandom one-hour meetings I give to people. Even though I still makethose financial donations, the greatest value I can give is my time.

Kindness is based on the recipient’s terms. Not yours.

Kind Candor

Kind candor was actually the most difficult ingredient for me in thisbook. It’s still a half, not even a full ingredient.

For this exercise, think about someone in your life you need to talk towith kind candor. Then write out an e-mail as though you were talking tohim or her in person, and send it to


Go on YouTube right now and type in “good form push-ups” and watcha video to get educated. Then do as many push-ups as you can in a row, andpost a video on your social-media platform of choice with how many youdid.

I want you to do push-ups every day for fifty-five days. On the fifty-fifth day, make another video talking about how many push-ups you can dothen, and use the hashtag #GaryVee55Days at that point, so I can find it!

I believe that the mind and body are deeply intertwined, and thatphysical exercise can have profound effects on your mental state.


On your social-media platform of choice, post a video telling yourfollowers that you’re on a curiosity mission. Ask them to send you a link toa Wikipedia article or a YouTube video of something they’re passionateabout but don’t think you know about. Use the hashtag #CuriosityGaryVee.

Allocate twenty hours to reading, listening, or watching videos ontopics you’ve never considered before at the recommendation of those whoare somewhat close to you. Make a commitment to curiosity, even if thatmeans what you’re learning about isn’t the most interesting. One subtleinput may trigger something that benefits you in an unexpected way.


1. Using a calendar tool (Google Calendar or some other app), create anevent titled “You still have plenty of time.” Set it so that it pops up onyour calendar every six months at 9:00 a.m. for the next ten years.

2. Post positive statements about your ten-, twenty-, or thirty-year goalson your favorite social-media channel. Communicate how excited youare to still be on your journey decades from now. Use the hashtag#PatienceGaryVee.

I make a lot of comments about how I’m going to be an OG in myseventies or how I’m just getting started at forty-six. These stories I tellmyself create a beautiful narrative around patience. I don’t picture myselfbeing eighty and sick in a retirement home. I picture myself at eighty givinga keynote, looking at all the fresh faces in the crowd, and feeling just ascurious about what they’re thinking as I’d feel now.


Write down one strong belief that you’ve doubled down on over time:

Write down a belief you had that you’ve wavered from:

From this exercise, what did you learn about conviction? Make a quickvideo with your thoughts, post on your social-media platform of choice, andhashtag it #ConvictionGaryVee.


Spend five minutes writing down every single thing you’re not good at.Then cut out the page and hang it on your fridge, frame it in your bedroom,or put it next to your mirror. I want you to look at it every day. When you’redone writing, take a picture of this page and share it on social media with#HumilityGaryVee.


I want to challenge you to record a selfie video talking about yourbiggest ambition in life. Post it on social media using the hashtag#AmbitionGaryVee.

In this exercise, I’m trying to make you accountable to your ambition.By putting yourself in a vulnerable position where others can make fun ofyou if you don’t achieve your ambition, you can work on not beingmentally vulnerable to that judgment.


When you develop these twelve and a half ingredients to your maximumpotential, working from nine to five might even be too many hours in theday. Seriously.

As you develop kind candor, gratitude, self-awareness, accountability,optimism, empathy, kindness, tenacity, curiosity, patience, conviction,humility, and ambition, you begin to work with minimal friction. Yourcolleagues feel safe, happy, and calm around you, speeding up execution.

When these ingredients are instilled properly throughout anorganization, team members won’t have to spend thirty minutes in a seven-minute meeting. They won’t feel the need to invite eight extra peoplebecause of insecurities and politics. Those who need to be in a meeting canbe there, others can focus on their tasks, and projects can move faster.

By taking accountability for your actions, you can skip the two-weekdark spiral of blaming others for a bad business decision. With self-awareness, you can focus on your strengths instead of spending your wholelife checking the boxes on your weaknesses. By practicing gratitude, youcan limit the time spent dwelling on mistakes. With empathy, kindness, andhumility, you won’t be fazed when insecure people try to drag you down.When you’re optimistic, curious, and patient, you can lead with trust andcreate scale. With kind candor, you can communicate feedback beforeresentment develops. All those ingredients will help you operate withtenacity and conviction as you move toward your ambitions.

The funny thing is, even though your job won’t take forty hours a week,you might find yourself still working at eight p.m. because you’re having somuch fun. Strong emotional structure leads to speed in business and life. Bymixing these ingredients appropriately, you can move without your fearslimiting every step.

When Raghav read off the ingredients to get my initial take on each forpart I, my immediate reaction was always “This is the one. This ingredient

is the foundation for success.”That reminded me that every one of the attributes I laid out is essential,

and they are all interdependent. None of them can operate in silos. Thescenarios in part II were my best attempt at thinking through how theywould be deployed in the realities we all go through. It’s the mixture thatwill lead to success. You’re the chef.

I’ve always emphasized tenacity in my content, because it’s the mostcontrollable variable for most people. It’s often more challenging to becomeempathetic, humble, or self-aware. Developing these ingredients takes a lotof practice if they don’t come naturally to you. The exercises in part III arejust a starting point. You might have to analyze your childhood, maybe evengo to therapy. I’ve been aware of my lack of candor for over twenty years,but I’m just now developing it in my mid-forties. This stuff takes time.

For most people, it’s easier and faster to put in a few extra hours toachieve their ambitions. However, tenacity out of balance iscounterproductive, because it can bring fatigue, burnout, or lack of sleep. Itneeds to be used in combination with self-awareness and conviction.

As you begin to use these attributes in the workplace, you’ll start usingthem outside the workplace too. All of a sudden, you’ll notice that youdidn’t buy something you didn’t need, because you’re patient. If theneighbor’s dog runs over to your yard and takes a shit, you’ll make a jokewith kind candor and bond over it, instead of fighting.

Imagine the typical reaction to that classic Americana story. Unhappypeople will compound their own unhappiness by shouting at the neighborfor not keeping the dog on a leash. The relationship gets smeared, and itbecomes awkward every time they see each other in the backyard. All forwhat? Because the neighbor came home after a long day at work and forgotto put the dog on a leash?

This entire book could’ve just been one line: “Are you insecure?” Thiswas my effort to put a mirror in front of you and ask you that question indozens of different ways through real-life scenarios and exercises.

You can see why I always deploy the most empathy and kindness to thenastiest people. They’re adding to their own unhappiness with their badbehavior. Those are broken, insecure individuals who often project theirown unhappiness onto somebody else who’s also unhappy, and they bothstart arguing. That’s what happens at many companies, and that’s what I’mtrying to change with this book.

I’ve noticed that people sometimes demonize business. Occasionally,society sees businesspeople as the opposite of these twelve and a halfingredients. I’m sad that people think business leaders are egotistical, takeadvantage of others, and use their success as an excuse to be mean toeveryone around them. It’s actually why most customers are afraid to trustbusinesses. If I can use my popularity and this moment in time to changehow business is branded, I can change a lot of things.

Some reading this sentence right now are ready to quit their jobs, andit’ll be the best thing they ever did. Others are currently uncovering theirinsecurities and will come into the office tomorrow slightly humbler. Stillothers are about to get promoted for the next seven straight years becausethey’ve realized they’ve been complainers, but now they’ll start being moreaccountable.

But best of all, their lives will feel lighter.There are different forms of privilege in society, but the ultimate

privilege is peace of mind. I hope this book will help you get there.

The Inspiration Behind This Book

The time lag in releasing this book after Crushing It! was large in my authorcareer because I felt at the time that my next book had the potential to bethoughtful. It had the potential to be deeper than anything I’d ever written. Icould just sense it.

I had a lot of different topics I was debating. If you follow my social-media content closely, you know how excited I am about writing aparenting book from the perspective of a child who’s incredibly happy withhis parents. I continue to give a lot of thought to a book to be called Jab JabJab Left Hook, a sequel to Jab Jab Jab Right Hook. The concept of makingcontextual creative for platforms continues to be an incredibly importantconversation as platforms like TikTok and Clubhouse emerge and platformslike LinkedIn and Snapchat evolve.

However, when I was at USC, I met Mikey Ahdoot, a young man with alot of passion and gusto whom I intuitively felt good about. I’ve met manyhigh-energy people who pitch me many things, and I don’t always feel greatabout it. They’re mostly coming from a place of self-interest, which is OK,but you can’t come only from a place of self-interest. In this case, I felt itwas a bit bigger.

Mikey has a company you should check out called Habit Nest, whichproduces guided journals that help people build better habits. Habit Nest’sinitial pitch to me was that we need a GaryVee journal to break down someof the loftier concepts I talk about in a more tactical way. The idea ofcreating a journal or a textbook for my audience was intriguing and a goodcomplement to the other content I put out.

Over the years, I’ve found myself being in two different kinds ofprojects:

1. Projects that flow fast from idea to production. Going from idea toproduction sometimes can be very quick even for big projects like myK-Swiss deal, my first book deal, The #AskGaryVee Show, orOverrated/Underrated.

2. Projects that I have to work through. For example, WineText was inmy own head for years before I launched it for my dad.

This book was the second kind. Habit Nest worked on some initialversions with Team GaryVee over the course of a couple of years and madesome important contributions. However, as Raghav and I worked on it, itevolved into a very different book—one that tries to map the emotionalintelligence that I think is required to win in the next century of business.The concepts in this book will become a massive conversation in culture.

I wanted Mikey and Habit Nest to be recognized for contributing to thisproject.


First, I want to thank my family, whom I love more than breathing.Second, I want to thank Raghav Haran: my writer for this book, my

collaborator, and my right hand throughout the entire production process.This book could never have been what it is without him.

I want to also thank Mikey Ahdoot, Habit Nest, and everyone on TeamGaryVee who contributed.

Finally, thank you to Hollis Heimbouch and the entire HarperCollinsteam, who have, once again, been true partners in releasing this book.


1. “Gratitude,” Lexico, Oxford Dictionaries, WHO Global Water, Sanitation and Hygiene Annual Report 2019 (Geneva: World Health

Organization, 2020), Zoë Roller et al., Closing the Water Access Gap in the United States: A National Action Plan

(Oakland, CA: US Water Alliance; Los Angeles, CA: Dig Deep, 2019),

4. Cindy Holleman, ed., The State of Food Security and Nutrition in the World: Safeguardingagainst Economic Slowdowns and Downturns (Rome: Food and Agriculture Organization,2019),

5. Walk Free Foundation, Global Slavery Index 2018, “Highlights” (Perth, Western Australia: WalkFree Foundation, 2018),

6. “7 Fast Facts about Toilets,” UNICEF, Nov. 19, 2018,

7. Joseph Johnson, “Global Digital Population as of January 2021,” Statista, Hamburg, Apr. 7,2021,

8. “21 Million Americans Still Lack Broadband Connectivity,” Pew Charitable Trusts,Philadelphia, June 2019,

9. “Global Wage Calculator: Compare Your Salary,” CNN Business, 2017,

10. Thalif Deen, “Women Spend 40 Billion Hours Collecting Water,” Global Policy Forum, NewYork, Aug. 31, 2012,,40%20billion%20hours%20per%20year.

11. Aaron O’Neill, “Life Expectancy (from Birth) in the United States, from 1860 to 2020,” Statista,Hamburg, Feb. 3, 2021,,to%2078.9%20years%20in%202020.

12. “Complacency.” Lexico, Oxford Dictionaries,

13. “Self-Awareness,” Lexico, Oxford Dictionaries,

14. “Accountability,” Lexico, Oxford Dictionaries,

15. “Optimism,” Lexico, Oxford Dictionaries,

16. “Delusion,” Lexico, Oxford Dictionaries, “Pessimism,” Lexico, Oxford Dictionaries, “Empathy,” Lexico, Oxford Dictionaries, “Kindness,” Lexico, Oxford Dictionaries, “Pushover,” Lexico, Oxford Dictionaries, “Tenacity,” Lexico, Oxford Dictionaries, “Curiosity,” Lexico, Oxford Dictionaries, “Patience,” Lexico, Oxford Dictionaries, “Conviction,” Lexico, Oxford Dictionaries, “Humility,” Lexico, Oxford Dictionaries, “Ambition,” Lexico, Oxford Dictionaries,

About the Author

GARY VAYNERCHUK is a serial entrepreneur and serves as the chairmanof VaynerX, the CEO of VaynerMedia, and is the creator and CEO ofVeeFriends. Gary is considered one of the leading global minds on what’snext in culture, relevance, and the internet. Known as GaryVee, he isdescribed as one of the most forward thinkers in business—he acutelyrecognizes trends and patterns early to help others understand how theseshifts impact markets and consumer behavior. Whether it is emergingartists, esports, NFT investing, or digital communications, Garyunderstands how to bring brand relevance to the forefront. He is a prolificangel investor with early investments in companies such as Facebook,Twitter, Tumblr, Venmo, Snapchat, Coinbase, and Uber.

Gary is an entrepreneur at heart—he builds businesses. Today, he helpsFortune 1000 brands leverage consumer attention through his full-serviceadvertising agency, VaynerMedia, which has offices in New York, LosAngeles, London, Latin America, and Singapore. VaynerMedia is part ofthe VaynerX holding company, which also includes VaynerProductions,VaynerNFT, Gallery Media Group, The Sasha Group, VaynerSpeakers,VaynerTalent, and VaynerCommerce. Gary is also the cofounder ofVaynerSports, Resy, and Empathy Wines. He guided both Resy andEmpathy to successful exits—they were sold to American Express andConstellation Brands, respectively. He’s also a board member at CandyDigital and a cofounder of VCR Group.

In addition to running multiple businesses, Gary documents his lifedaily as a CEO through his social media channels, which have more thanthirty million followers across all platforms. His podcast The GaryVeeAudio Experience ranks among the top podcasts globally. He is a five-timeNew York Times bestselling author and one of the most highly sought-afterpublic speakers. He serves on the board of MikMak, Bojangles Restaurants,

and Pencils of Promise. He is also a longtime Well Member of charity:water.

Discover great authors, exclusive offers, and more at

Also by Gary Vaynerchuk

Crushing It! How Great Entrepreneurs Build Their Business and Influence—And How You Can, Too

Jab, Jab, Jab, Right Hook: How to Tell Your Story in a Noisy Social World#AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness

The Thank You EconomyCrush It!: Why NOW Is the Time to Cash In on Your Passion


TWELVE AND A HALF. Copyright © 2021 by Gary Vaynerchuk. All rights reserved underInternational and Pan-American Copyright Conventions. By payment of the required fees, you havebeen granted the nonexclusive, nontransferable right to access and read the text of this e-book on-

screen. No part of this text may be reproduced, transmitted, downloaded, decompiled, reverse-engineered, or stored in or introduced into any information storage and retrieval system, in any formor by any means, whether electronic or mechanical, now known or hereafter invented, without the

express written permission of HarperCollins e-books.

Cover design by Kyle NguyenCover photograph © Anton Starikov/Shutterstock


Digital Edition NOVEMBER 2021 ISBN: 978-0-06-267470-8Version 09222021

Print ISBN: 978-0-06-267468-5Print ISBN: 978-0-06-314379-1 (International Edition)

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  • Title Page
  • Dedication
  • Contents
  • Introduction
  • Part I: The Emotional Ingredients
    • ➣ Gratitude
    • ➣ Self-Awareness
    • ➣ Accountability
    • ➣ Optimism
    • ➣ Empathy
    • ➣ Kindness
    • ➣ Tenacity
    • ➣ Curiosity
    • ➣ Patience
    • ➣ Conviction
    • ➣ Humility
    • ➣ Ambition
  • Part II: Real-Life Scenarios
  • Part III: Exercises
    • ➣ Gratitude
    • ➣ Self-Awareness
    • ➣ Accountability
    • ➣ Optimism
    • ➣ Empathy
    • ➣ Kindness
    • ➣ Kind Candor
    • ➣ Tenacity
    • ➣ Curiosity
    • ➣ Patience
    • ➣ Conviction
    • ➣ Humility
    • ➣ Ambition
  • Conclusion
  • The Inspiration Behind This Book
  • Acknowledgments
  • Notes
  • About the Author
  • Also by Gary Vaynerchuk
  • Copyright
  • About the Publisher

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