If you can go to that one place where you think you, whether it's your mom or dad or best friend or spouse, where you're like, "Hey, I'm actually starting a journey "of self-awareness and I know that I've always been "the kind of person that can get very defensive "or it can lead to a fight, or you just love me so much "you don't want to hurt my feelings, but no bullshit.

"Can you just answer a couple questions for me? "You know how everybody says I have all this talent? "Am I lazy?" If you can get a person that loves you to a place where they'll tell you the truth, you can really start to unlock some conversations that can give you some affirmation on something you've been fighting off.

- Hello, and welcome to All The Hacks, a show about upgrading your life, money, and travel. Now, many of you might already know Gary Vaynerchuk, but the conversation we have might surprise you. While he might be best known for his hustle and savvy in entrepreneurship, I want to focus on a side of Gary you might not have seen before.

But having known Gary for over a decade, I think it might actually be more a part of who he really is than anything else. That's a conversation about kindness and happiness and self-awareness. We'll talk about ways to transform your life by digging deep into the importance of kindness and making amends with people, and how you can use self-awareness as a superpower, some important life lessons to instill in your kids, and a lot more.

And before diving in, if you could give us a thumbs up, it'd really help the algorithm. And if you're new here, please consider subscribing. All right, let's do it. (upbeat music) - Gary, thanks for being here. - Are we rolling? - Okay. Gary, thanks for having me here. - Thanks for having me on your show, brother.

- Yeah, yeah, it's good to be in this office. So many people that I told I was coming to chat with you associate you with hustle. What are they getting wrong when they make that assumption? - The nuances of it, right? Like, yes, I believe in work ethic. I think it's a variable.

But I don't think it's as, it kind of reminds me of what's just kind of going on in the world, right? We're so into headline reading. I think there was a couple of viral posts on Medium written about me on hustle porn, and that kind of like cemented a point of view that even the writer of that article, three years later, DM me to apologize, because he spoke to the agenda he had at hand, and realized he was making certain variables convenient to the story he was trying to tell.

And I really appreciated that, by the way. I think that takes a lot of humility and courage. And honestly, I really do love the idea of understanding that work ethic is a variable, but there's so many other variables. Like, for example, from the first book I wrote, "Crushing," when I wrote it in 2008 and came out in '09, in that exact book, there's like, hey, if you work nine to five, and you make $48,000 a year, you've won if you're thrilled, if you live within your means and you're super happy.

And so I think what people get wrong is, I'm excited and I enjoy what I do, and I put in hours towards it, but it doesn't define me. I'm completely, utterly detached from financial success, from notoriety. I just love my game. The people that know me best know the same vigor I talk about like, hey, you can have a career that you love, I bring that same vigor to 6 a.m.

on a Saturday to go garage sailing 'cause I love it, or competing in basketball or pickleball, or watching a Jets game. I think what they get wrong is, unlike a lot of people who don't even use that word or even deploy that energy, I have tons of friends who are seemingly calm, speak all the right speak for acceptance, but are absolutely, incredibly overly driven by money, by fame, and are detached to that and I think that's why there's a lot of anxiety in the world.

And so I think the nuances of how I think about it, plus I also spoke about that concept during an incredibly down market in the economy, when the internet was hitting an incredible inflection point in 2008, '09, '10. So I think just the nuance of it, the word, when I use the word hustle in 2008, '09, '10, the intent is like, hey, there's opportunity and you can go get it.

I'm thrilled to change that word to tenacity, or grit, or work ethic. So I think the semantics of it all. And I am a communicator that I'm incredibly self-aware that the way I communicate with the excitement level, with the energy, with the Jersey chat of it, I'm very aware and genuinely compassionate and understanding to why people may take the extreme take.

And I also don't have the audacity. I deploy enormous humility when I'm about to say what I'm saying. I would never expect someone to spend five hours to double click into it and actually understand what I'm about and what I'm saying. And so I guess at the end of the day, what are they missing?

They're not missing anything if they're just doing a drive by and reading a headline. If they've spent two or three hours on me through content or interaction or people that really know me, I doubt they'd be missing anything 'cause I think they would contextualize it. - Yeah. Do you think that work ethic you have, that grit, that tenacity is something that can be taught or learned, or is it just something that's part of your DNA?

- I think it's a combination of both. I think it's clearly in people's DNA. There's many people that are either born with too little or too much that deploy it immediately to quote unquote prove something or see an opportunity, especially for immigrants. It's so easy for me to go at it.

I was born in the Soviet Union. My parents lived their entire childhood and into their early 20s there. So I lived in a household that really understood, like shit, man, America's pretty epic. This is pretty cool. You don't go to jail for trying to make a better life for yourself in entrepreneurship.

So it was very easy for me. On the flip side, I've seen a lot of people be affected by the osmosis of work ethic. It's kind of like what's going on with me in the gym. It became so not natural. As natural as it comes to me to sell lemonade or sports cards or run businesses or be nice to people, it comes equally not natural to me to work in the gym.

But we've known each other a long time. Somewhere around 38, I decided to put in the work 'cause I wanted to live longer and just thought it would be better. And through osmosis practice, I'm now someone who goes to the gym. I still don't love it, which is why I really do talk about how important passion is to actually get to that state where it's so easy 'cause you love it so much.

I really do wish for everyone that the job they had was similar to their favorite hobby. For everybody right now who's listening, they can take a step back and whether it's skiing or cooking or playing video games or sailing or garage sailing or watching movies or what have you, if they could do that 24/7 and sustain their life, a lot of people would be happier and would enjoy that.

But on the flip side, for a lot of us, just like me for the gym, sometimes you have to put in that work if you want to accomplish something that you think is good. To me, I'm actually very focused on people living within their means versus creating frameworks that require them to work harder, to make more money, to live within the means that they think they need to live in.

I don't think you need a BMW. I don't think you need a six-bedroom house and I think that is where that conversation gets interesting but at the end of the day, I think it is something that can be taught but I don't think it's something that can be taught in this scenario.

I've gotten better at basketball even in the last year. I've put in more work. I'm not an NBA player. So I think there is a level of DNA that caps out everyone in every genre but I think the capacity to get better in everything is quite high. Like I can't sing for a lick.

I have a feeling if I got a voice coach and really put in the work and like worked on it for a decade, like I think I would be better at karaoke than I am now and so that's interesting to me, the things you can control versus the things that you can't.

- So I'm guessing you don't wanna sing which is why you haven't done that but you did wanna build-- - So I have a new song out with Snoop. Everyone go check out, it's not a joke. Go check out on Spotify. Please take a step back, Snoop Dogg and Gary Vee.

17-year-old me is still freaking the fuck out. - But you did wanna work out. - Yes. - You said you're 38. I'm 38. I don't have a great fitness regime. You know, was it just putting in the work or are there things you did that made it more possible?

- I think I was also in a five-year window where I was really hitting it hard, traveling a lot, going hard. I was really enjoying it but I did recognize like hmm, like this is really like not sustainable. Like I don't think I have good eating habits. I have great mental habits.

I'm incredibly calm and happy. I sleep, the hustle thing that always makes me laugh is like I sleep six, seven, eight, nine hours a night depending on the night. So I have good sleeping. I have good lack of anxiety because I am detached from the work stress but I knew that my eating and muscles were nowhere and so my back had been hurt as a child working in my dad's liquor store.

So like that was something I wanted to fix 'cause it was really uncomfortable and back to like kid's life, you start like not wanting to carry your kid 'cause you're worried your back goes out. Little simple things like taking luggage off of the top of like a plane and like having to use your right side 'cause you're scared your left side will go out.

There was these little nagging things. My neck, you know, like would get stiff at times. I was like, well, I'm way too young for all this and I plan on like really quote unquote going hard. I mean, I enjoy what I do. I'd like to be 65 and fly somewhere for a meeting or, you know, and so, you know, for me, I just said, I've got to do this.

This is very clear. Like there are certain things that are just very clear. Back to how we started this. Like work ethic is one of the variables that helps somebody build something meaningful, right? Well, you know, eating well and going to the gym like genuinely gives you a higher propensity of like having a longer life and a more enjoyable life in your 60s, 70s, and 80s.

So it was just a very logical conversation. I also got to the financial place where I was able to hire a babysitter and the big unlock for me was I'm not accountable to myself, I'm accountable to others. The reason I think I'm a very good boss, the reason I think I'm a good friend is like I like being there for people.

For my own self, I just kind of take it for granted. I like, I don't want to like beat my own record on how much I, how fast I ran or how much iron I pumped. So by hiring Mike Vacanti to be my full-time babysitter and like the person I was accountable to, it really worked for me.

And it's what I'm still doing 10 years later. - It's funny, the sharp decline in my exercise happened when Kevin Rose stopped riding the Peloton because we had this fierce competition of like, I'm gonna be, I didn't care about beating my record, I cared about beating his record and he cared about beating my record and then he kind of like gave it up and I lost.

- I think that's a huge insight for you. I think you can replicate that. You've got other Kevin Roses in your life, you can find a Kevin Rose on Twitter right now. And so I think that's epic. And by the way, same with me, like who I am on a basketball court or a tennis court, the level of effort and work I put on in that environment versus what I do in the gym is like 10 to five.

Like 10 on the court, five in the gym. So I understand that and I think that that's something you should try to figure out. - Yeah, I got some ideas. - Good. By the way, anybody who's listening to this podcast, just hit up Chris and like be like, I'll be your Kevin Rose.

- Yeah, just get on the leaderboard. - Yeah, that's it. - I wanna push, like we would basically be like, let's push until we might throw up on this bicycle. - By the way though, building this podcast, which you have care for 'cause you put a lot of effort to making this date work and I appreciate your tenacity and I apologize that my schedule is the worst, I'm so pumped we're here and it's always great to see you.

You're such a good dude. I think you should build the community of this podcast. I think you should get, I guarantee you, 73 of your listeners right now are fired up right now and you can build a whole community on this. - Yeah, so we, it's funny, we haven't had the conversation about this, but we launched a membership.

There's like 150 people right now, actively, starting a book club, like in the city. - In this membership, 39 of that 150 or 150 others that haven't gotten into the membership yet are all about this Peloton challenge and like something we're thinking about. - Yeah, I like it. Okay, so first book, focus on Crush It.

Most recent book, much more on the softer skills. - Yeah. - You said you'd rather, or my takeaway was that you'd rather be known for kindness than hustle in the long term. That's a focus. Why is kindness so important to you? - Well, because at 47, it's clear to me that that's an equal variable to work ethic that's brought me to the place that I'm at.

And the thing that I watch and admire in others who are in similar places. I think there's an incredibly disgusting concept in society that says nice guys finish last. I think it's an awful thing. As a matter of fact, I really need to make a hoodie and start rocking it that says nice guys finish first 'cause I really believe that.

Because I think it's what are you judging? Like cool, you made $83 million in the bank and you die and nine people show up to your funeral was like that good? I would argue it's not. And so, you know, when I wrote Crush It, what was obvious to me at that point was the internet had a huge opportunity.

Influencers were gonna be big. People laughed at that concept. That work ethic was a requirement. You know, I was 34. All I knew was my dad and myself worked our faces off to like build the American dream. And that finding something you liked would make it not feel like work, which would eliminate the anxiety of the work.

At 47, when I write 12 1/2, I've now built a 2,000 person global company. I know why it's working. I know why it's indisputably gonna disrupt the marketing industry. It's because people wanna be here forever. I looked back at Wine Library and be like, wait a minute, that's the same thing that happened there actually.

And then I just think about like my life. And then also I think about the hundreds of companies I've invested in, the ones that have worked, the ones that haven't. The thousands of companies I've consultant, the ones that work, the ones that I don't. And you know, I think again, back to the way this podcast started, if you started it with like, Gary, nice guys finish first.

Like what are people missing? Or if you went the other way and said, hey, Gary, you really hate the nice guys finish last. What are people missing? It's similar to the hustle conversation, the work ethic conversation. There's multiple ingredients. It's why the book is subtitled Ingredients. There are multiple ingredients that I think stand out as a consistent North Star blueprint that have sustainable, enjoyable success attached to them.

And I think work ethic, and I think kindness, and I think curiosity. And several others are pretty standard. Now, some people are stronger than others. And that's why there's so many variable differences of so many different things out there. But it works for me. And like, I really enjoy being nice.

Like I like the way that, you know, you know this as well 'cause you've watched this journey from me being like someone, a couple people knew to a lot more people know. You know, I've always enjoyed the fact that even today, like the people that know me best have the best feelings towards me.

That's a nice feeling, especially when you've become a public figure. And a lot of people have a lot of different takes. There's a sense of like calmness that comes along with, well, like as people get closer to me, they have a better taste of me. I'd be much happier with that than the reverse, which I think a lot of people in the world have, which is they may be liked optically on the outside, but as you get closer to their inner circle, it gets more rotten quickly.

- Yeah. The interesting thing about kindness is it feels like the thing that most people probably think they have. And when you double click, there's aspects of their personality. And I'll even like open up, like there are times where I find myself saying things like, "Ah, this person's annoying." Like, you know, we're not...

Is cutting all negativity? Does that like level it up? Or how do you really own kindness? - I think it's understanding negativity versus cutting it out. We're all humans. I mean, I'm gonna go to the garden tonight and the things I'm gonna say to Jimmy Butler are gonna be completely inappropriate.

Though I love Jimmy Butler, represents so much of what I believe in. But for those three hours, I will not be kind. It's the context. And like, you know, like every human's gonna gossip a little bit or like talk to their best friend in the office about somebody else in the office.

I think the question becomes, why? You know, I ask myself, why do I not spend a lot of time tearing down other people? It starts with because I'm not tearing down myself. I don't really have a whole lot of envy. You know, I don't deploy a lot of jealousy.

I don't hold resentment towards my parents or other important figures in my life for anything that I deem that they did that wasn't good. Right? And I think that's a very common trait for the masses. I think, I mean, I know people who just can't let go. Just spend all their time on jealousy, envy, and resentment.

And then it manifests. It's in their subconscious. And then like every day to day, if they see someone who's happy, they get triggered to make, to kind of point out what they're not good at or what they're unhappy. So I think we're all human and we, everyone has it.

But I think getting to a place where you figure out your relationship with yourself, I think can be quite powerful. And I think always has a direct indication of how people feel about others. I always believe that the bullies in the world, the nasties of the world, the not able to be civil with others of the world are always in a really tough spot with themselves.

- So kindness, it's funny. We always think about kindness as like, I'm kind to people. But it sounds like the like unlock is realizing you need to be kind to yourself and you need to understand yourself. You've said, I think self-awareness is like a superpower most people don't realize.

- In a way that really matters, brother. Like in a way that's like, man, if I could wish anything for people on earth, besides good health, for everyone who's listening in this great community, 'cause I know the kind that you would cultivate. I just think to myself, like who's a listener of this based on I know good amount about you.

And like, I've been watching you for a long time. Like, you know, there's like a really high standard of human on here. But I think a lot of them are blind to certain aspects. And I think the biggest one is like, just be like easier on yourself. Like the extreme level of judgment people put on themselves because they play the game of comparison.

Like, the enjoyment I get to see Kev or Tim Ferriss or I mean, anybody like Sarah Blakely in spec. Like, I don't know, like you, like anybody. Like I get thrilled when I see people are winning as if that's coming out of mine. I've always been baffled by people's inability to understand that the world is abundant and nobody, nobody is taking out of yours.

If 50 people showed up tomorrow that are incredible public speakers, not a dollar is taken out of my pocket. There's plenty of speaking gigs I could do. You know, and so I think I really, I really wish people understood that. And I think understanding who you're trying to accomplish for is also very important.

There's a lot of people listening here who are still trying to make their parents proud, even though their parents are not capable of ever giving that, you know, co-sign to their child because they themselves never got it from their parents. So a lot of people blame their parents and haven't done the work of figuring out that they should actually be blaming their grandparents, which then leads them to actually realize they should be blaming their great-grandparents.

And it becomes this game where you can give your parents a lot more leeway, which actually a lot of times for people is an unlock. And it's kind of like, you know, you can get it off your chest. And, you know, I think, yeah, I'm very passionate about this subject matter.

- Are there things people can, that are listening can do to start to build better self-awareness? Is there like a training regimen or some activity that you've seen be helpful? - I think one is to really start to make the people closer to them, feel comfortable with giving them truth and candor.

So like finding that best friend where like, if you can go to that one place where you think you, whether it's your mom or dad or best friend or spouse, where you're like, hey, I'm actually starting a journey of self-awareness. And I know that I've always been the kind of person that can get very defensive or it can lead to a fight.

Or you just love me so much, you don't wanna hurt my feelings, but no bullshit. Can you just, you know, like answer a couple questions for me, like, you know how everybody says, like, I have all this talent. Like, am I lazy? Like, if you can get a person that loves you to a place where they'll tell you the truth, you can really start to unlock some conversations that can give you some affirmation on something you've been fighting off.

- It's funny you say this. I remember, I hope he's okay with me talking about this. Kevin had this, went through this process and actually hired someone to call a bunch of his friends and have that kind of like performance review conversation and be like, you know, I'm gonna keep this anonymous.

I'm not gonna sign it to you, but like, Kevin wants to know like, what can he improve in? Like, where is he letting his friends down? What would you tell him if, you know, you knew he wouldn't be able to know it was you? And it sounds like, you know, not everyone needs to hire someone to do that.

You could, you know, it's hard. Sometimes your friends don't wanna be honest. - No, I think what you just said is a viable and maybe even a cleaner data set than what I'm referring to. And, you know, I'm just very aware that most people can't afford to hire someone to do that, right, or even think of it, but like, look at- - But even a friend, like, ask a friend, can you just call these five people and ask, you know?

- I like it, I like it. To your point, in my version, I'm not asking that most inner person to give it to you. To your point, maybe that inner person is the one that cultivates the data. I think it's fascinating. - Or an anonymous Google form. - I think, I like that too, I like that too.

I think people have to be ready, right? I had to be ready at 30. For eight years, I knew health and fitness was something I wanted to be, but it was finally on a flight from Houston to New York with my head against a window where I was like, it's time.

You know, like, for a lot of people right now, they're hearing this and they're pushing against it, like, nah, because they're not ready. For another listener today, this was the moment. Like, in the last week or two, they just got ready of like, you know what? I just want my life to be happier, and this is part of the equation.

Like, look, out of all the things, work ethic, passion, kindness, I will say that accountability, I would argue, is probably the quickest indicator to how happy you are. If you are truly interested in being accountable. - To yourself? - Yeah, to the whole thing, to yourself, to everyone around you, to every situation, to every relationship, to the truth.

Like, when, you know, I'll give you a good example. In my 20s and 30s, I would struggle so much with firing people and giving them candorous feedback that almost every exit at Wine Library and early VaynerMedia was sloppy. They stayed a year longer 'cause I wrestled with it. And then when I would do it, it would just be a shit show.

Like, it would be, I'd ask my cousin Bobby to do it, even though I was the one who interacted with the person every day, 500 days a year. I would flub it. I would go in quick and get out with any, you know, I would over, I would talk for three minutes about how they're the greatest and be like, but that being said, we're gonna have to let you go, and they'd be confused.

And so, there was two, 300 people over a 20-year period, back to what I said earlier, that were close to me and did actually know me, who did not have a good taste towards me. What did I do in my 20s and early 30s? I would blame them. I'd be like, how could that person be mad at me?

They were so, like, they were the worst. They were so incapable at their job. I was such a good guy for letting them even be in the company for another year or two. Look what's happened. They've not been successful in their last two places. And it took me getting into my late 30s and really actually into my mid 40s.

Fuck my late 30s, not my late 30s. It got into the last three or four or five years where I was like, you know what? My lack of candor is the kryptonite to the thing I said 15 minutes earlier, which is I love that people that know me like me a lot.

Asterisk, people that have worked for me that were not good at their job in my subjective opinion, that I let sit around 'cause I was too scared or was not interested in conflict. And I created so much resentment and passive aggressiveness that eventually it boiled over and then they were fired.

That group of 100 to 200 people on earth don't have the same good taste towards me than the 10,000 that have been close to me in my life. That took me being accountable to like, that's on me 'cause I struggled with candor, which is why in the book, the last book that you're referencing, the reason I wrote "12 1/2" was strictly at the end of the day to talk about kind candor.

This concept that I rebranded it to myself and now I'm better at candor, but it took a lot of professional and personal losing for me to get to that point where I could be accountable and be like, hey, okay, tough guy, you're good at a lot of shit, that's nice, or a lot of people, this is something you stink at and will continue to be a problem in your life unless you're able to build.

And I'm proud of where I'm at with candor now. I'm a five, I'm a 4.7, I'm a 5.2. That's a lot better than a one. And I gotta tell you, in the last two, three years at Boehner X, the holding company, Boehner Media, the agency, the company's much stronger 'cause of it.

My greatest pride as a leader was eliminating fear. I got this, I got this, I got this. I got you, we got this. And I delivered for years, but what really was rock bottom for me was when I realized, wait a minute, there's a lot of people walking around scared 'cause they don't know if out of nowhere they're just gonna get fired because I'm like, everything's great until it's not.

And then I have to start giving more candor along the way and my organization does it better because I do it better and it's been a big growth for me. - Have you, you mentioned earlier that you liked that that reporter reached out to you three years later. Have you reached out to those 100 to 200 people?

- I've reached out to many people. I have, I like making amends. Luckily for me, and this is just like, so the answer is several. Luckily for me, there was a lot of good in what happened until the end. And so for a lot of people, when they've gone on to have two or three other work experiences, they were able to contextualize what I was doing well.

And so to the credit to a lot of those people, a lot of those 100 to 200 people, two, four, five years later have reached out to me. And then, because I was still on my journey, I wasn't there yet. And then to me, when they did that, I would come so hard and say, hey, Jimmy, Sally, thank you, but hey, I need to own a piece of this as well.

Over the last two, three, four years, I've been better at starting that conversation versus being the follow-up to that. - Yeah, I mean, I appreciate you being vulnerable, saying, I'm not good at this thing. 'Cause I think from the outside, everyone's like, Gary must be great at everything. - Yeah, and honestly, from the outside, I think a lot of people, back to the way we started this podcast, assume I'm not good at a lot of things.

For example, people are blown away when they hear that I don't like conflict, because on public stages and in podcasts, especially 'cause I always talk about innovation and breaking things, seemingly, I like it. So, there's different versions. I think the other thing for everybody who's listening is like, look, a very important thing, back to judgment, is I don't make assumptions about anybody.

Like every person I know that I don't know, I make almost no assumptions. You don't know if they're aunt. I'll give you an example of shit I think about when somebody's judging someone. Like, oh, someone famous like Ryan Reynolds has the best life ever. You don't know if the most important person in that person's life was his aunt who was a mother figure and she's been diagnosed with terminal cancer.

How do you think that person's walking around right now? You know, or in your office, like that person got the promotion. They're so lucky. Are they? You don't know that their spouse might be dealing with alcoholism currently right now. You know, so, you know, I think it's, I'm glad you brought that up.

I think another thing that really works for my temperament, for my peace of mind, for my joy, is my lack of capacity to make assumptions about other people's lives. Like I just, there's nobody I think has a great. It's inconceivable. Everyone's a human. It's inevitable. And by the way, even when someone does have a great, and people have had, I've had 'em, people have had 'em, eight year, nine year, six year, 12 year, 20 year runs.

Life is too challenging. I know friends who I know intimately and know well enough to say the following, great 10, seven, 12 years, and then boom, child sick. Great 10, 12 years, and boom, father was the rock of the family, gone, heart attack. So, you know, this concept that somebody's got a great life is like just incredibly judgmental and lacks like the nuances I think are required.

And I think we are at a hyperbole of this judgment world now. We are full headline reading. We are full cancel culture. We are full assumptions. We are full envy. And I don't think this is a social media thing. This is what's always happened. We're just hearing us talk it out.

You know, people in well-to-do neighborhoods for years have envied the person that's the richest or the handsomest husband or the, like people just, you know, really need to get back to like being insular, loving themselves, thus allowing them to start to love others. - I mean, you said earlier people would be happier if they weren't chasing money.

They weren't chasing dreams. They weren't chasing status. - Dreams you should chase. - Okay, fair. - Right, like I want to be the best surfer. That's fun. Like dreams are fun when you don't beat yourself up on accomplishing it. When you champion yourself on trying to accomplish it. And then you being realistic about it.

But go ahead, what was your thought? - No, part of that was you said people were doing what they love and weren't as focused on money. They'd probably be a lot happier. I want to spend a couple minutes on something that you've talked about before, but to someone listening who's like, okay, I want that.

I can learn to detach from the need to be as good as I might perceive someone to be, which might actually, you might be completely wrong. On the figuring out what you should be doing front, have you seen people make that discovery of like that's the thing that I should be doing?

And are there things they did to get there? - Yes, I've seen it a lot because of what I talk about and how many DMs and emails I read for the last 15 years. So far, it all happens from extremes. Horrible divorce. Now, whomever the wife or the husband is in like a financially challenged situation, like life's different.

And they're forced into doing something. And they just happen to be consuming mind and other positioning of like, if you're gonna do this, do something you like. And all of a sudden, they have a business making kites. This is a real one. And it was just really therapy 'cause there was so much pain.

And kites, I mean, I remember this email vividly. Kites were a big part of their childhood and they enjoyed. And it was really nasty. Like not, it was very challenging. The father that flew kites with this person passed and then six months later, divorce. And then like really in a challenging spot.

And this person decided to follow the passion route versus getting a job like everyone told them. And she sold kites on Etsy. And like four years later, was selling like $400,000 a year in kites. And so like that or the complete other side, someone just hearing the message in the right way and realizing in their early 20s, you have nothing but capacity for risk and decided to like run into it, which is like, and I've seen a lot of versions, just being very humble and aware that they are in a financial family that allows them to go full risk for passion.

Just having a parachute and a landing route. The reverse, so pissed at their often Asian or immigrant or Indian parents of like, I'm not gonna be a doctor or engineer you fucking assholes. Like I'm going for it. So like in extremes, I've seen it in extremes. I'm hoping to get those edges into the middle a little more.

I'm hoping someone right now who's just like, to me the dream state is the person who's listening now that's making 210 and living a 250 lifestyle. They make $210,000 a year. They live a $250,000 lifestyle. And they realize that if they lived $100,000 lifestyle, it would take the golden handcuffs off of them to maybe take the leap and go for it.

So they're obsessed with cooking and they want their own little like bakery, but they don't have any savings. 'Cause again, their apartment's too expensive. Their car's too expensive. Their vacations are too expensive. Their nights out are too expensive. They order bagels on Seamless and Postmates. Like do you know how many people buy $30 bagels currently?

Chris, like a lot. - I don't, I want to not. - Well, but we know this like, and this is more like the Uber thing that we learned years ago. Like people will pay for convenience at scale. There are people right now who are buying $30 bagels and don't even realize it, right?

They're buying an $8 bagel on Postmates or Seamless or Uber Eats, but then there's the surcharge, the charge, the delivery fee. They kind of are blindly on the tip 'cause they want to be a good person. Like you kind of wake up and it's a $28 bagel. Like, and that person is, that same person is buying a $28 bagel 'cause they make $210,000 a year.

But deep down, they're like, they hate being in this law firm more than life. Like literally can't wait to five or six o'clock every day. Truly can't. Yet want to own a bakery. Yet like want to start a podcast on Star Trek. Yet like, and I believe they can, but do they have the humility to move back in with their 50 or 60 or 70 or 80 year old parents?

Probably not. Do they have the humility to like get a roommate? Probably not. Like do they have the awareness to say, I should move out of New York and maybe move to a suburb of Wisconsin because I actually like the outdoors and my lifestyle there can afford it? Like, especially right now, I got one, I haven't thought about this until this exact microsecond.

We are living right now in a world where a lot of companies will let you work remote. I've been talking about this whole quit your job, start your life by going humble. How about don't quit your job, ask for a move. And so you literally go from New York, LA, San Francisco, Dallas to literally lower cost, deep suburbs of those places.

You know, my parents live an hour and a half from this office. Living in Hunterdon County, New Jersey, you can live for a lot less than living in Manhattan. Could you do that? And could you take those savings, could you cut out the $30 bagel? Can you take one less vacation?

Could you trade in the car you have now for a downgrade? And can you take all those savings on that 210, now you're living a 130 lifestyle, right? And can you stack 30,000 savings three years in a row to give you that $100,000 nest egg to go? That's a level of practicality around passion that I hope becomes a bigger norm.

- Totally agree. I actually have been thinking about this as you're talking that my new hypothesis is that once you start doing the thing that you really like, you actually probably will care less about all these other things going on, right? If you hate your job, like of course you're like, oh, I need these other things to make me happy, my friends have these things.

- It's all in, all out. - Yeah. - Like when I work out, I eat better. If I don't work out in the morning, I eat worse. So it's an all in or all out. When you like what you do, the majority of your life, aka your job, well then all of a sudden you aren't spending $50 on cocktails after work to deal with what's going on.

You don't have seven streaming services to escape what's going on. You like don't find band-aids. You get, you know, like you don't find band-aids for the issue and the issue is your relationship and your job. And like figuring that out is massive. - I got two final things. One, so you're all in on the, let's say you're all in on something, which I kind of am on this podcast.

It's like I found the thing that's me. It's my calling. Once you love it so much, you know, I know you have kids. How do you find this balance of I love what I'm doing? A part of me is like I could spend every waking hour thinking about it, but I also love this other thing.

I have these two big ambitions. - You wanna mitigate regret. And like anybody who has kids realizes like you don't wanna wake up when they're 20 and realize your relationship isn't strong and they don't wanna see you anymore. And like they were accustomed to living without you being in their lives and like it's devastating.

And so I just think you're thoughtful. I think, look, there's no such thing as balance. There's your subjective opinion of balance, right? I love when people like judge other people's work-life balance. You don't know their family. This goes back to a lot of things we talked about. So I think for every person here, be willing to adapt.

I've changed and ebbed and flow multiple times over the last 15 years on it. All here, this, more there, less, weekend. Like, you know, I think everyone's got their own thing. Like, you know, I work very hard Monday through Friday, and I'm pretty checked out on weekends and holidays.

And when I say pretty checked out, I'm checked out. Like, unless there's a super fire, right? And so other people may work nine to six or nine to five during the week, but they're also working on the weekend on their phone the whole time. Like, everyone plays it different.

And by the way, you may go all in for three years on this podcast 'cause there's a moment right now, right? And, but then in three years, you may be like, wait a minute, I've done that. So like, look over here, these little ones are getting big. And like, wait a minute, I'm worried.

And so you can go all in there. Like, people can find balance in extremes. You can't judge yourself on a day-to-day basis on these big issues. It's a bigger thing than that. You know, look at all the people that reconcile with their relationships years later and have great, I mean, I have a friend who didn't speak to their father for 40 years, and now has had an incredible five years.

And that's because they've leaned into forgiveness. You know, like, I think you gotta, I think it starts with forgiving yourself. You know, back to your question. Like, there's a lot of parents right now who have 17-year-olds who are like, oh, too late. No, not too late. Like, there's never a bad day to start doing the right thing.

- Yeah. - Like, if you're 62 and you've never been good at health and wellness, good news. Tomorrow is a good idea to do it. If you have 18-year-old twins and you've worked on just your career for the last 18 years, and you can sense they're about to go to college and they don't give a shit about you.

They love you, but they're accustomed to not having you be a big part of their lives, good news. You could visit them every weekend at college. Probably a bad idea. They might not like that. But, like, you could start today to put it in. If you are angry at your mother and you've got 20 years of resentment built up, like, good news.

Today is the day you can start therapy. Today is the day you can go have a canterous conversation that is built on compassion for your mom, that gets some of the poison out. Like, there is never a bad day to start doing the right things that are most upsetting you.

- I love it. The last thing, kids, you know, everyone listening could share this with their parents. They could share it with their spouse. They could start to think about these lessons. I can't go share this with a one, a three-year-old, probably not a five, six, seven-year-old. Are there things you're doing to try to instill, let's take your kind of 12 and a half lessons.

- Self-esteem. - That's the thing. - That's the thing. And not delusional self-esteem. - Okay. - If your seven-year-old loves Beyonce, but when she's running around the house singing, like, literally, you have to put earplugs in 'cause it's the worst sound you've ever heard, it's probably a bad idea to tell her she can be Beyonce one day too.

It's not a bad idea to say, if she puts in a lot of work, she could be better at singing than she is today. These sort of, so to me, it's self-esteem. Also, what do you compliment your kids on? If you're complimenting your kids constantly on how attractive they are, you're so beautiful, you're so cute, you're so handsome, you're instilling affirmation on that, which is gonna affect them when they're in their 30s, 40s, 50s, and 60s 'cause that's gonna be their self-worth.

If you're telling them that they're remarkable because they're getting A's in school, you're teaching them to conform to systems that aren't real once they become 22. Might not be the best idea. You know, eighth place trophies bother me, not because I'm so competitive, but because you're telling your kids that losing is bad.

Like, kids are smart. Kids are smart. So they realize the reason they're getting an eighth place trophy is like you, as the parent, don't want them to feel losing. Losing is bad. The problem is losing is such a fundamental part of life that you're teaching kids to be scared of it instead of leaning into it.

So I think, for me, it's practical self-esteem, truth. - What do you compliment your kids on? - Their humanity. Whenever I see them interact with humans and are kind, compassionate, empathetic, when my son will go over to somebody who gets hurt, I mean, he drilled a line drive off of when coaches were pitching two years ago when he was eight.

He drilled. He was very good at baseball between like six and 10. Drilled a line drive that drilled the head coach. He ran, you know, he hit it, so he started running towards first base and he stopped and like in the middle of the base path and asked the head coach if he was okay.

You know, after the game, the coach came up to him, he's like, "Look, I've been hit a lot of times "in the history, I've been doing it for 30 years." He's like, "I've never had a kid just stop and do that." And I bring that up to my son every day.

Like, do you know how good of a person you are? Even though you're so competitive in baseball as your passion, like you did that. The humanity of it versus the thing. So I try to focus on those things. - I love it. I feel like this is not the conversation I think a lot of people thought we were gonna have and I like that.

Any final words or where people should go to see more Gary? - You know, I think building off of what you just said, I think it was a theme of everything. Like, books by covers is a real issue in our society right now. I think, you know, for me, I think to your point, I think 90% of your audience will be like, "Oh, that was interesting.

"Didn't see that going that way." I think for 10% of your audience, when you just said that, they're like, "What are you talking about, Chris? "That is Gary." Why? Because they've allocated the time to go deeper. I think, you know, we are really in it in our society right now, politically, socially, nationalism, geopolitically.

There's a lot going on. And we're also affected by the last 30 years of parenting where I do think we over swung too far in certain areas like eighth place trophies, which has made a lot of people anxious. You know, so what I would say as a final thought is, if you find yourself thinking that in this interview or any other of Chris's interviews, it's definitely what made me think about the world.

Like when I started going through my 20s and 30s and meeting people that I had different thoughts of. And then when I got to double click in, either in person or through content consumption, I'm like, "Ah, right." And so I think, you know, that will lead to a much happier life.

But like the theme of this whole podcast, it starts with yourself. Finding how to not judge yourself for your shortcomings and accept yourself for your shortcomings. And champion and be proud of your strengths is a really nice framework to be able to do it for others, especially your children, your spouse, your parents, and then going to your friends and acquaintances.

And then just the world. I think this world desperately needs more civility and warmth. And I think people are looking for others to provide it. And I think back to accountability, it starts with yourself. And so I think you're capable of it. I really do, whether that's therapy or listening to different things or starting a regimen of health or wellness or mindset that gets you to that place.

And I think you should do that 'cause it's a lot more fun to live life happy because final thought, you were dead for a long time, aka not born, and you will be dead forever. And so I think it's a good idea to maximize your hundred years, God willing.

And so consider that. - I love it. Reach out if this was helpful. I'm sure they can reach out to you online. Gary's easy to find on the internet. - Thank you so much for being here. - Thank you.