How to Stop Dwelling on Mistakes | Gary Vaynerchuk's Top 10 Rules

In this motivational interview, host Evan Carmichael presents Gary Vaynerchuk’s third rule from his "Top 10 Rules for Success" series: stop dwelling on mistakes. Gary expands the conversation with a series of anecdotes and hard‑won lessons from his early days at Wine Library, the rapid growth of VaynerMedia, and countless pivots in digital marketing. He argues that obsessing over past errors stalls progress, while relentless hustle, self‑awareness, and a focus on personal strengths accelerate results. Gary stresses the importance of leveraging the internet’s low‑cost opportunities, ignoring what others have, and constantly iterating—whether that means staying the course on a failing YouTube channel or cutting a product that no longer feels right. Throughout the dialogue he addresses audience questions about motivation, fear, and strategic choices (gap year vs. side hustle), repeatedly urging listeners to align actions with their own "North Star" rather than external expectations. The video closes with Evan prompting viewers to comment on the most impactful lesson and a brief shout‑out to a fan.
Chapters
Dwelling on what you fucked up on is the quickest way for the next thing not to work. All great stuff, especially when you're innovating, doesn't happen right away. Number one mistake so many people make is they care about what other people have. I don't give a fuck what anybody has. If I have more, if I have less, doesn't matter. I worry about myself.
He's an American entrepreneur, investor, and 4 times New York Times bestselling author. He's best known as a digital marketer and social media pioneer. He's an angel investor or advisor to Uber, Birchbox, Twitter, Facebook, Snapchat, and Tumblr. Gary Vaynerchuk, and here's my take on his Top 10 Rules for Success Volume 2. Rule number 3 is my personal favorite, and I'd love to know which one you guys like the best. And as always, guys, if you hear something that really resonates with you, please leave it down in the comments below. Put quotes around it as well so other people can be inspired. Also, when you write it down, you're much more likely to lock it in for yourself as well. Enjoy.
What if I told you this was the last Monday morning of your life? What if I told you you die this week? Would you complain about your crap job or that test you don't want to take? I doubt it. You would go much higher level thinking. Well, that's really what it takes. It takes understanding that if you're not pumped right now, if you're begrudging what you're about to do, if you're not looking forward to it, look, I respect practicality. You gotta go through school 'cause your parents want to. You gotta pay your rent, you got student loans, I get it, but please recognize the world we're living in. We're living in a world where there's so much more opportunity. This internet thing created way more opportunity for all of us, way more. I mean, look, you might not even be alive. Like, your mom and dad could have had sex like 3 minutes later and you wouldn't even exist, and you're complaining. You could have ended up being a bus, a tree. I just don't get the mentality of being head down sad on a Monday morning. I'm gonna make Monday morning my bitch. I'm gonna make you Saturday Monday morning. That's what I want to do every morning, and that's what I want from you. Please, take a step back and think about how awesome it actually is, and then recognize that you can attack the world in a totally different way, 'cause you were lucky enough to be born during this era. So many people come up to me and say, "Gary, it's so hard." I look at their Instagram, and they're not posting any of their content with hashtags, which is a by accident way to pick up exposure in a world where they have no money. When you have no money, when I took over my dad's business, I did $3 million a year, 10% gross profit, $300,000 before expenses. My first year marketing budget was $14,000. When you have no money, and I built that business from a $3 to a $60 million business in 5 years, I had to make every penny perfect. So I was right about email marketing in '96, and I was right, and because of that I had 91% open rates. When Google AdWords came out, the day it came out, I paid 5 cents a click for words before anybody bid me up, and I was super right, and that worked. [Speaker] How much is that luck versus preparation, and do you ever get anything wrong? What do you do when you make a mistake? I get everything wrong, it's just that I can't recall it because once it's wrong, I'm moving on to the next thing. Dwelling on what you fucked up on is the quickest way for the next thing not to work. Right? Yeah. So I think I do everything, I mean, you know this, this is a fun thing to say, some people in the back know this, I was a breakout YouTube star in the first year, 2006. I decided that the right strategy was to leave YouTube completely and go to Viddler Because Vidler offered me equity in their company, and I've left an enormous amount of attention. I deviated from my intention thesis to do short-term economics and equity in a company, and I lost. I lost. When DRock finally came in my life 2 years ago and we started to try to build up my YouTube for the first time, I was sitting on 40,000 user followers in a world where I could have had millions if I just stayed the course. So I make mistakes all the time. I'm re-orging VaynerMedia every day 'cause it's based on a mistake I made the prior year. I just don't give a fuck about my mistakes. Everybody else cares about your mistakes. If you're worried about your own mistakes, you've already lost.
Sometimes a lot of people may try a new initiative and then they don't get an immediate reaction and they think it's a failure.
That's right.
I wanna go back to your YouTube videos with the Wine Library. You know, you had so much content out there. How did you stick in there? How did you keep yourself motivated?
Because I believe in my strategies and I'm patient as shit. Like, all great stuff, especially when you're innovating, doesn't happen right away. This notion that like, oh Gary, I tried it, I spent $500 on Facebook ads, it doesn't work. Well, what if your video sucked? What if your product and service sucks? I tend to do things that are very early. That has been my career. When I do things, I believe in them. I stick with them based on intuition. Even though for 18 months nobody watched my wine videos at all, I knew it was right, I was right. There's been things I've done that I've jumped off of very quickly. I started a GaryVee app, VeeChat, V-E-E. WEE, like WeChat, thought it was funny. For my fans, great CRM one-on-one. Didn't feel right after a week or two. Spent plenty of money building it. Stopped it after, you know, couple months. Wine Library TV, 5 years, every day, YouTube. Decided to change it to Daily Grape, insular app. You could buy stuff, subscription for reviews. It was a lot of fun. Only did it for 5 months, stopped it, 'cause it didn't feel right anymore. It's always hard to know when to jump off something new. But I find that people don't believe in what they're doing. They hear a guru, and they do it begrudgingly, 'cause their boss wants them to, or they're like, well, Gary's right a lot, so let me do it, but they don't believe it. And so then they jump, they're looking for nos instead of yeses. Everything I do, every business development, every event I do, every time I try a new marketing tactic or sales tactic, I'm looking for the yes. I'm looking for the yes, and if the no punches me, Well then I'm like, crap, the no punched me. I believe the majority of people when they try new tactics are looking for the no, and you're gonna be getting a lot of subtle nos immediately. And so I think that's why that happens. You need to care about everything, and it starts with yourself. Look yourself in the mirror and ask yourself, what do I want to do every day for the rest of my life? Do that. I promise you can monetize that shit. If you love Alf, do an Alf blog. You collect Smurfs? Smurf it up. Whatever you need to do, do it. So many people are talking about, I can't monetize, I can't monetize. There's a billion 70-year-old douchebags that are in control right now. But the number 2 person, that 34-year-old lady, she's gonna buy your shit. She's gonna put the advertising on your stuff. It's coming. Stop crying and just keep hustling. I'm desperate for people to start defining their hopes and dreams and wants and needs on their terms, not on what I I say, I don't care if you wanna hustle 18 hours a day. I really don't, I really, really don't. I don't care if you wanna buy the New York Jets. I don't care what you want or need. You need to care about what you want and need. You can't worry about what I'm saying. You can't worry about whoever your flavor of the month is, right? Maybe I'm your flavor of the month right now. Maybe your consistent flavor of the life is your mom's point of view. In front of you is your older brother who's guided you with good wisdom but wants you to be a lawyer, but you don't wanna be a lawyer, you wanna be a street artist, you wanna take the chance of being an entrepreneur, or the reverse, or the reverse. Nobody preaches and loves entrepreneurship more than me, but I think you see me all the time talking about self-awareness. Are you one? This is the golden era for entrepreneurship. People ask me for selfies. This will go away. It may not go away for me, but it's gonna go away. Entrepreneurship, like a rap artist, like a baseball player, Like the heavyweight, nobody cares who the heavyweight champion of the world is right now. Nobody cares who's an active astronaut, but they surely did in 1969 and 1954 for the heavyweight champ. They change, they change, and it will always change, and it will continuously change. And right now entrepreneurship is in this pedestal, it's having its moment, and what I'm fearful I love is that you watch my videos, you see my Instagram quotes, and what I want to clarify for everybody is I hope you understand I am not giving advice to everybody. The only advice I'd like to give to everybody is to do you, to find what your North Star is, to understand yourself, to understand what your work-life balance ambitions are, how much— what your financial ambitions are, what your life challenges are, the problems that you want to try to solve and cure as we all do as humans, trying to climb those different mountains in our lives. What makes you tick? That is all that matters. Don't do, you know, I don't do DailyVee or all these videos for you to be like me. I don't think anybody should be like me. Boy, are there enormous amounts of pressures and sacrifices that I recognize are just not healthy or valuable to anybody else, but it's also not healthy or valuable to me to do some of the things that you want me to do. Like, it's not fun for me to work 9 to 5. Like, I will break. I will be as equally devastated as you would be to work till midnight every day. And so we just need a call to action for everybody to recognize we have to stop judging everybody else. I'm not judging you. I'm creating content for you to use as a barometer to try to figure out what you like and what you don't like, and I'm trying to provide value through my words, my actions, and my content to bring to people to amplify their worlds. And that's really it. That's the clarification. Like, I don't want people to be like me. I don't want people to do me. I want people to do themselves. And they just have to start with understanding themselves and not trying to be like me in this moment or that person the next moment or that person the next moment. The people that most win are in tune with themselves and figure them out. Themselves. The problem is, if you have the greatest hammer, and the greatest screwdriver, and the greatest wrench, the greatest, in front of you, if you don't use them properly, you will lose. If there's a nail that I have to put in that ground, but I take the wrench and I hit it when the hammer was right there, it still comes down to the practitioner. And you have to be good at your craft, and you have to love your— If you don't love sales, If you don't love it, you have no chance. 'Cause it's so hard, it's so painful, there's so much rejection. So those are the things I think about.
So technology is clearly an enabler, as you just said there, though the person is equally important.
More important.
Right, and going back to—
I apologize for jumping in, but let me make it perfectly straight. If I go play Roger Federer right now in tennis, and I have the greatest tennis racket ever, like from, taken from Mars's new resources, and he took a John McEnroe 1974 tennis racket. He would whip my ass. Like, I'm crushing salespeople that have every Salesforce, every one of your competitors, 37 features upgraded, went to every pro conference watching this. I will beat their ass in sales every day of the week. Pure talent. [Speaker] And it was, you regularly say that failure propels you. Are there any instances in your past truly where you couldn't get over it and why? Nope. I mean, by the way, by the way, that's the same answer for everybody in this room. That's what humans are good at. We all fail. We've all failed. Like, my parents haven't been killed, my child, I mean, there's people that have their children die. Could you imagine? The shit I deal, listen, unfortunately or fortunately, depends on how one wants to look at it, I'm a pretty optimistic guy. I lost 3 of my 4 grandparents before I was really, before I knew them. 2 before I was born and 1 very early on. It's easy for me to be happy. I have my shit in the right order. The health and well-being of my family. And there's nothing even remotely close to that. Not even remotely. People have gotten through much worse. This is why I'm trying to recall our grandparents and our great-grandparents. People were persecuted and killed. I just, we do not have real headaches. You know, I don't know why I have this highly emotional and then completely unemotional part of me, but I mix them together to create the balance, and that's what works for me. So of course there's nothing that I couldn't get up from. Like every other human ever besides somebody who now lives in some weird cave that we don't know about. You know what I mean? We are strong as shit. We're really fucking strong. We're just being sold that we're not 'cause there's a lot of money, a lot of money in telling us that we're not pretty enough, thin enough, smart enough, good enough. Fuck that. I want to tell you you're the fucking best. Go do shit. I've been feeling a little bit unmotivated and I've been feeling like I should be doing something or I should be, I feel like I should be pulled and like, I'm feeling uninspired basically. That's my question. How do you get, when you lose inspiration or you lose motivation, how do you get it back? I get it back by remembering that you might die tomorrow. That's true. So I'm inspired by practicality and reality and the truth, which is it is ridiculously impossible to become a human being. I am one. I have other good things going for me as a human being, and I'm just grateful. You're dwelling and looking at what you don't have versus looking at what you have. If you actually looked at what you had, your health, you know, living in America, you know, who the heck knows what would be on your list? If you actually spent all your time looking at that versus I don't have a million dollars, I'm not famous, I don't have this, if you spent all your time on what you have versus what you don't have, you would be the happiest girl on earth.
Should I launch my business on the side or take a gap year and try to launch it?
Both work. Both? Both work.
Which one is best?
I don't know you well enough. You know. You know what I mean? They both work.
Yes.
Which one do you want to do?
I would like to try to take a gap year, but I'm scared.
So take a gap year. Well, that's why you're asking. Yes.
Which one will you do?
I wouldn't take either.
What will you do then?
I can't answer that for you. Fear's holding you back. You know what you want to do. The only reason you're not doing it is because you're scared of doing what you actually want to do, right?
Yes, that's it.
Are you scared to do it 'cause your parents won't like it?
No, my parents actually support me.
Okay, so what are you scared of, failing?
Not failing, but still being at the same place when my friends are at the next level.
Huge mistake. You don't want the same thing your friends want. No. So why the fuck do you care what they have? Number one mistake so many people make is they care about what other people have. I don't give a fuck what anybody has. If I have more, if I have less, doesn't matter. I worry about myself. The fact that you're worrying about other people's accomplishments is already a losing formula. You need to get rid of that first, then you can focus on yourself.
Thank you.
You understand? You know, to be great, I think you have to fight. And I very much think that my success is a product of some level of skill, but I do think I win because I outwork people. I really do believe that. I do believe that 100%, and I'm not sure that if my dad didn't set that example that I'd even have the ability to think one could work that hard. The fact that I've been working 19 hours a day every day for the last 20 years is easy for me. It's the only gear I knew, right? I was poor. I sucked shit at school. It was the only gear I had. You know, I think you need to recognize that your biggest advantage is that you're hungrier than your competitor. And that if you're not applying your one advantage, which is your work ethic and the hours that you have to put into your business, well then you're gonna come up short. I sit here with enormous assumptions around all of you that you're just too soft to beat me. Right? That I think that you've had it better and that that alone doesn't allow you to beat me. People come with the countercultural point of view and be like, Gary, that's cool, but I don't have to work that hard because I'm working smarter. Yeah, me too, asshole. I work hard and smart. Now what? Look, there's a 12-hour, 10-hour, 8-hour, 15-hour workday. You can finish a lot of things in those 18, 12, 9 hours, or you can finish medium amounts of things or lightweight things. People focus on too many way too many people in this room are gonna spend the next 30, 40 years of their lives trying to check the boxes of the things that they're not as good at, and that you're gonna waste a fuckload of time in those. I highly recommend for all you hustlers, 'cause there's a lot of you, there's a lot of you that are always talking about, Gary, I do work hard, and you do, you work for 16 hours. Some people just don't have the attention span or the capacity to remember Or like, there's a lot of things I can't learn. I was a very poor student because the subject matter bored me, and if I was forced to become great at understanding the great artists of the 20th century, I'm in big trouble. And so I would tell people to bet on their strengths. You need to bet on your strengths and don't give a fuck about what you suck at, and to put themselves in a position to win with their strengths, because that is absolutely the straightest line to success. Greatness comes from adversity and looking the challenge in the eye and having the intestinal fortitude to kind of step up and go after it.
Thank you guys so much for watching. I'd love to know what did you think of this video? How do you like our Volume 2 series? Leave it down in the comments below. I'd also love to know what did you learn from Gary today? What did he say that had the biggest impact on you? What lesson is your favorite and you're going to apply immediately to your life or business somehow? Leave it down in the comments below. I'm super curious to find out. Finally, I want to give a quick shout out to Richard Galvez. Richard, thank you so much for picking up a copy of my book, Year One, word. It really, really, really means a lot to me, and I hope you're enjoying the read. So thank you guys again for watching. I believe in you. I hope you continue to believe in yourself and whatever your one word is. Much love. I'll see you soon.
Amy asks, a professor once said to me it's better to be a big fish in a small pond. Do you agree? Amy, this, you know, I'm gonna be very upfront on this question. This is a good way to bang out the show. That sounds like a loser professor to me. It's small-time thinking. I don't subscribe to it. There's a lot of practicality in it, right? It's a lot easier to be the most successful businessman in St. Louis, Missouri than it is to be in the world, right? So I understand the thesis, but honestly, that to me is very conservative, Not in my DNA thinking. That could be great advice for a lot of people who are delirious and think they're better than they are, though I love to drive through self-esteem and optimism, and I think early in your life, you should absolutely shoot for the highest stars that you can. I think as life moves on and time moves on, you need to become more practical. You've got bills and kids and all those kind of things, but to start off one's career in the first 20 years, call it till you're 40, to be in that thinking, I think that limits. There have been so many people who've hedged and settled in their lives, and honestly, I'm not the kind of character that's going to play in that kind of sphere. I'm going in a different direction. It's what comes natural to me, but it's also because I think I could be the biggest and the baddest in any game I play. It's just how I'm wired. I think this comes down to, it's probably very good advice to some, and it's probably atrocious advice to others, and this is why I continue to say if I could inject anything and to anybody, it would be self-awareness because it would help you answer this question. Because for a lot of people, it's probably really solid advice. For me, and for many of you watching this, it's crap advice. Alan asks, "As we've seen, you hate wasting time, but how do you adjust on days nothing is going right?" Well, there's no such thing, luckily. No, I mean, there's no, I mean, I don't remember a day where nothing went right. I mean, first and foremost, the way I really deal with it if we wanna get zen about this, and a lot of you know this, is as long as everybody's healthy, everything went right. I always quantify, when business doesn't go well, I default quickly to, oh, business is bullshit, it's all about life. You know, like when my kids, look how cute my kids are, look how, thank God my parents are alive. Like, I quickly switch from, I don't dwell. You know, I'm not good at dwelling. I love speed, and I don't like wasting time. Dwelling, complaining, wishing, hoping, you know, pondering how you wish it was, is the single biggest waste of time in life and in business. Like, the bottom line is, we all wish things. I wish I was 6'4", the single best looking guy in the world, and the quarterback of the New York Jets that has won 19 straight Super Bowls. I wish that. I mean, I wish that. I mean, I just wish that. I wish that. And in the same way that that's funny is the same way to wish that, like, that deal went through, or that employee took the job, or that person didn't quit, or that concept didn't work out. I mean, I've had multiple divisions, multiple strategies here at Wine Library, at VaynerMedia, that haven't worked in the last 12 months, yet we're dismantling it. And so much like, Anything else, you just, it's like the next, it's the next play. Using artistic stuff, like if you're doing a Broadway play, what are you gonna mess up a line and just stop? And just cry on stage? You just gotta go to the next line. I mean, you just gotta keep moving forward, and so, how do I handle it? Easily, I'm a fucking champ on this issue. I'm a champion. I am an absolute champion on this issue. Meaning like, I'm prepared for the punches in the face. I expect. Things not to go well. It's kind of the way I prep for a Jets game. Saturday night, nobody likes being around me 'cause I'm just devastated. It's all bad. We're gonna lose, this is what's gonna happen, we're gonna lose. You know, like, I'm subconsciously like that, but unlike the Jets where I say that outwardly, these guys can tell you I'm only on winning and offense at all times. Adam asks, I feel like I've lost my hustle. Help, what do I do? Adam, anybody who's losing their hustle has a lot of variables, and there's a lot of variables in this episode This is the variable episodes where there's a lot of context points, it's not just direct answers today. Listen, you might not be passionate about your north star anymore. I've been going through something. Let me actually break some shattering news here. For the first time in my life, I've been thinking about weird things like sabbaticals and building a business school in Haiti for 5 years and Like, I love, listen, I'm still all about buying the New York Jets, and it's the process of that and the game, but it's amazing for me to be in tune with myself, the maturity, like, as you get older, like, just different, like, my kids are 6 and 3 and they're interesting. Like, they're interesting. And like, you start, you know, I start projecting, what do they look like at 13 and 15? Like, it'd be really cool to like, I don't believe in the school system as much as everybody, like, do I just take them and go do something rogue? Like, just different things. Like, you just evolve. And you might have just lost your North Star. The thing that you thought you were going for might not be. It's why I was always happy that I didn't want a million bucks, or I didn't want fame, or I didn't want a car, or a private plane, or all these little things. Like, it was fun to be like, I wanna buy the Jets, and what that always meant to me is I want the process of buying the Jets, which means I get to hustle forever, 'cause that's who I am. Maybe you've lost who you are, or what you want, or maybe you've accomplished accomplished kind of, or maybe you feel it's achievable. I would be crushed if I thought what I wanted to achieve was super achievable. I mean, it happened to me in the wine business. It's happening at Vayner. Like, as Vayner's becoming a player in the agency world, and we're not like, uh, now we're like, uh. And soon we're gonna be like, uh. Like, you know, like, that's not as fun for me. I like being the underdog. I like the climb, you know? I like that. So, maybe that's happened. Maybe you're just tired. I mean, I think one of the things that the New York Jets do for me that nobody understands is those hours, actually you just caught something on DailyVee, right? Me talking to Jeff. That was the first time I talked business during a Jets game in 15 years. I looked at my phone at the wrong time, it was a very big thing, and I only spent a second on it. Like, I am escaped and relaxed. And by the way, I didn't care about it. Like, that's how excited, like, those 3, 4 hours of escapism, maybe you need some vacation time, maybe you need Maybe you need to look at the people around you. Maybe you need to change. Maybe you need to break up with your boyfriend or girlfriend. There's a lot of intense different things that could be happening. Or maybe you can take a step back and really listen to this statement, which is you've lost your hustle because you really are not in tune to why you're doing it, right? You're just not in tune to why you're doing it. That you're maturing and realizing like a Ferrari or a fat watch or courtside tickets or custom Nikes, I just wanted to show them, you know, is not what you're living for. And so, you know, it's funny, tonight I'm going to the Charity: Water gala. I never thought of myself 10 years ago as somebody who would be so involved in nonprofits, sitting on the board of Pencils of Promise, donating. I was, you know, I was old school. I'm 40, I'm older. Like, this new narrative of much better people, and that's what I think you guys all are, I think you're a much better generation. Grew up thinking I'll get rich and when I'm old I'll be giving out money and doing that stuff. So you just evolve, right? And so maybe you, like me, I haven't gone completely, I don't have enough money, my kids can give away all the money, but I can't, I don't have that luxury yet, but maybe you wanna do nonprofit, maybe you wanna build schools for Pencils of Promise and we'll take you in Laos. Maybe you've lost your purpose. So take a good step back, shut down, shut down for 24, 48, 72 hours, go away. Go away like this. This is how I want you to shut down. Go to Airbnb, this is a 2016 way to shut down. Go to Airbnb, find a very remote place, you know, do I have to go? I'm taping something, yeah, I'm just wrapping up the show, sorry. Go to Airbnb, find a very remote place that you can get to at a low cost, like a crappy cabin far away on a 4-hour drive where you can just drive, as you can, or somebody will drive you there, or hitchhike, I don't give a crap. Lowest cost, furthest away, seclusion, and just be with yourself and start talking to yourself for real. For like, really talk to yourself for real. One of the great things I do with myself is I talk to myself for real. Nobody is a harsher critic and a bigger fan of themselves than me. And I think that friction in both directions matters.
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