Young and Profiting with Hala Taha - Matt Higgins on Escaping Poverty, Entrepreneurship, and Knowing When To Quit | Entrepreneurship | YAPClassic

Episode Date: February 24, 2023

Matt Higgins’ childhood was plagued with extreme poverty. He lived in a tiny apartment with three other boys and a single mother who struggled to make ends meet. Ashamed of his family’s financial status and living conditions, Matt started juggling several side hustles, such as selling handbags at flea markets and scraping gum off the bottom of the tables at McDonald’s. Today, he has a net worth of over $150M. In this episode, you’ll learn about the importance of quitting, the benefits of thinking about your own death, and different methods of financing your business.  Matt Higgins is a noted serial entrepreneur, growth equity investor, and co-founder and CEO of private investment firm RSE Ventures. He is also vice chairman of the Miami Dolphins and an Executive Fellow at the Harvard Business School, where he co-teaches the course “Moving Beyond Direct-to-Consumer.” Matt was also a Guest Shark on ABC’s four-time Emmy-Award-winning TV show Shark Tank in seasons 10-11. In this episode, Hala and Matt will discuss:  - Why dropping out of high school was one of the best decisions Matt ever made - The importance of quitting - Why you should reflect on your own mortality  - How Matt built RSE Ventures - Be picky about how you spend your time  - How Matt manages his investments  - Should you look for an investor or bootstrap your company?  - What Matt looks for in entrepreneurs  - Matt’s optimistic view of Gen Z  - And other topics… Matt Higgins is a serial entrepreneur and growth equity investor. He co-founded New York City-based RSE Ventures in 2012, amassing a multi-billion-dollar investment portfolio of leading brands across sports and entertainment, media and marketing, consumer and technology industries – including several of Fast Company’s Most Innovative Companies. RSE has successfully backed many challenger brands from inception, including RESY, an Open Table competitor that American Express acquired in 2019; the world's premier drone racing circuit, the Drone Racing League; and the International Champions Cup, the largest privately-owned soccer tournament featuring Europe’s top clubs.  Higgins is also co-owner of VaynerMedia, founded by digital marketing expert Gary Vaynerchuk, and a partner in the early-stage venture fund Vayner/RSE. He also appeared as a Guest Shark on Shark Tank.  LinkedIn Secrets Masterclass, Have Job Security For Life: Use code ‘podcast’ for 40% off at yapmedia.io/course. Resources Mentioned:  Matt’s Website: https://www.burntheboatsbook.com/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-higgins-rse/ Matt’s Twitter: https://twitter.com/mhiggins Matt’s Instagram: https://www.instagram.com/mhiggins/?hl=en Matt’s Facebook: https://www.facebook.com/ManifestorMindset/ Matt’s Podcast The Manifestor Mindset: https://podcasts.apple.com/us/podcast/the-manifestor-mindset/id1517691358 Matt’s book Burn the Boats: https://www.amazon.com/Burn-Boats-Overboard-Unleash-Potential/dp/006308886X WeCroak App: https://www.wecroak.com/ Sponsored By:  Use promo code YAP for 15% off sitewide at https://justthrivehealth.com/discount/YAP More About Young and Profiting Download Transcripts - youngandprofiting.com   Get Sponsorship Deals - youngandprofiting.com/sponsorships Leave a Review - ratethispodcast.com/yap Watch Videos - youtube.com/c/YoungandProfiting Follow Hala Taha LinkedIn - linkedin.com/in/htaha/ Instagram - instagram.com/yapwithhala/ TikTok - tiktok.com/@yapwithhala Twitter - twitter.com/yapwithhala Learn more about YAP Media Agency Services - yapmedia.io/

Welcome back, Yapam. Today we're replaying my interview with Matt Higgins. Matt is a serial entrepreneur and investor. He's the co-founder and CEO of RSE Ventures, and he's the former vice chairman of the Miami Dolphins. He was also a shark on ABC's Emmy Award-winning show Shark Tank in seasons 10 and 11. Matt recently came on Yap to talk about his new book, Burn the Boats, and that episode comes out March 6th, which I'm super-examined,

excited about. In honor of that, it felt right to replay this interview so you guys can get all of his entrepreneurial insight and life story before hearing anything a layer deeper in terms of business strategy. In this Yap classic episode, Matt tells us his incredible rags to riches come up story. He faced so much adversity growing up, which makes the massive success that he has today even more impressive. We'll learn how he started RSC Ventures, how he first met and became business partners with Gary Vaynerchuk, and what Matt believes makes a great entrepreneur. This episode is chock full of timeless business wisdom, and I can't wait for you guys to hear it before Matt's new interview drops on March 6th. Without further delay, here's my interview

with Shark Matt Higgins. Hi, Matt, welcome to Young and Profiting Podcast. Well, thank you. Thanks for having me. I am so excited to have you on the show. I am a Shark Tank fanatic. It is literally the only TV show that I watch for the past like five years. And, uh, I'm a, you know, I'm a shark tank fanatic. It is literally the only TV show that I watch for the past like five years. And I first found out about you on that show. And you are an exceptional businessman. You know, you're the founder of RSC Ventures. You were working for the Jets, the Dolphins. You've done so many cool things. You're a partner in VaynerMedia, which people don't even really know about. And I can't wait to dig into all of that. But first, I want to start with your childhood. Because I know that it has a lot to do with who you are and how it's shaped you. And a pivotal point in your

life is when you dropped out of high school. So I thought we could start there. And I want to understand, you know, why you decided to drop out of high school, how you came to that decision. And really, to start leading up to that, like, what was it like for you leading up to that? I know you had an ailing mother. She was sick. And I would love to understand that dynamic. So we're just going to go deep, right? We're just going to go. We're just going to start right at the deep parts. Sounds good. So, uh, for those who have you heard this story, I apologize. but my background does have everything to do with who I am today is for most of us, for better or worse.

I grew up in Queens, New York. Shout out to Queens. And with a product of a single mom with four miserable boys growing up in a tiny little shoebox apartment on Springfield Boulevard in Queens. My childhood was framed with extreme poverty, extreme shame, extreme concealment. Because as a kid, you know, the last thing you want people to know, at least back then, is how poor you are.

my early days were through of endless side hustles. I used to sell flowers on street corners. I was that kid knocking on your window. So be nice if somebody's trying to sell you flowers. You know, I would sell handbags at flea markets, $10 leather handbags. And I worked at McDonald's, scraping gum from the bottom of tables. So that was the context. My mother was amazing, worked really hard.

And she had no high school diploma growing up. And, you know, she got divorced when I was around nine. And it always was sort of a hole in her life that she knew she was smart and gifted. but had gone through this terrible childhood and actually didn't even have a high school degree. And so I watched her go from basically on her hands and needs cleaning apartments for elderly homebound senior citizens to getting her GED at the local community college

and then enrolling in Queens College and really fight for years upon years to get first a bachelor's degree and then eventually pursued two different master's degrees and urban studies and library science. So my prism of my childhood was, poverty dysfunction, but also aspiration and watching my mother go through this journey. And around, you know, 13, I would be have all these mixed emotions, which anybody out there

who's suffering alone can relate to, like, is anyone going to help? And does anybody care? And eventually I made a decision that, like, I'm going to take matters into my own hands. And the key is, I need to make enough money to eventually get out of here as fast as humanly possible, right? Because you have a self-est streak as a kid. Nobody wants to be in charge. And so watching my mother do that, get her GED, as an adult gave me an epiphany that there was a loophole back then, that if you could get your GED and do well enough, you could technically go to any college. So they said, right, nobody really does this. But I thought, well, why don't I just do this on purpose and re-engineer and architect my entire life?

And that's why I decided when I was 14. And in order to make sure I would stick with this crazy plan that I made sure I got left back over and over again. So I sat in the same home room with kids with beepers who were pursuing a very different path, you know, dealing drugs or whatever, to sat in the back of that room. And I decided I was going to drop out. And it was the most important decision I ever made because I had the whole weight of the world telling me, one, you're going to be branded a loser. Two, you're never going to be able to get a good job, et cetera, et cetera.

And what I learned from that experience is like maybe true from this educational path may work from where you sit. But as a kid trying to take care of his parents, his mom, this doesn't work for me. and I need to get to college as soon as possible so I can get a well-paying job. And that's what I did. And it was actually the best, most important decision I ever made in my life. Everything I built from that point forward was on top of that one decision. It's so amazing that you had that kind of knowledge at such a young age and you were able to make such a big decision and stick with it, even when people told you that it would be the worst mistake of your life.

I know you were a good student and a lot of your teachers kind of weren't approving of. what you were doing. But in terms of your your parent-child dynamic with your mom, how you had to act like the parent, how do you think that that impacted you later on? Do you feel like that gave you a chip on your shoulder? Do you feel like that made you like super responsible for the rest of your life? Like, how did that positively impact you? Because at the time, it really probably sucked. But now, do you feel like that has positively impacted you in any way? Well, that's a great question. I mean, I think, well, number one, it may be very empathetic. Like, to watch a person literally deteriorate throughout your entire formative years, you know, to jump to the end of the story, I drop out of high school, I go to college.

I go to college for seven years at night. I work and work and work to build myself up. I went from McDonald's earning $3.75 an hour to the time I was 26 years old, 10 years later to being press secretary to the mayor of New York, making six figures. That's a lot of ground to cover, but also she deteriorated throughout that entire path. While I was doing that, living this secret life, I would spend my nights at the ER. You know, we'd literally had no money, and I refused to go on any kind of public service. We would go to the church all the time for food. So what I learned from that, the day I become press secretary, the mayor of New York,

this heady moment when I finally have achieved everything, she dies that morning. So I guess the reality, what I learned from it is that the greatest thing you could do with your time, energy, and money and power is to ameliorate somebody else's suffering. It doesn't mean that you have to devote your life to being a saint, but just from a practical standpoint, if somebody had intervened in that journey in those 10 years, she would not have died. I mean, like, we just were wasting away.

And so that stays with me. Two, there's no cavalry coming. It just is what it is. It sounds harsh, but you have to take matters into your own hands. You have to be an agent in your own rescue. And three, like, if I'm being totally honest, you know, the parent-child dynamic is supposed to be one of sacrifice. Like, at the end of the day, it's a one-way street, right?

Like, if you're doing this because you want your child to fulfill you, take care of you, realize all your unrealized aspirations, you got it wrong. And so I honestly learned a lot from the dysfunction of that dynamic and to resist it because you want to make sure you don't pass on these patterns to the next generation, right? And so, but also at the same time, normally when things are distorted in a parent-child relationship, but it's because of some trauma that has been unrealized or unmitigated or unsynthesized. You know, and so I think that was the case with, with my mother. Like, you tend to pass on dysfunction from one generation to another. So I guess

my real answer is to really be aware of the patterns that govern us so we don't pass that on to the next generation. And that's what I've worked hard on, although I'm probably screaming out my kids and I'm told other ways by probably overcompensating. But anyway, it is what it is. We're all flawed. But I think that's my greatest lesson I took away from it. I love that. So let's back up a little bit. So you had all these crazy jobs. You were scraping in gum underneath seats at McDonald's. You were selling flowers on the street. And then you got your first real job. It was being a reporter at the Queens Tribune or an investigative reporter, right? So talk to us about how you end up getting that first real job. Yeah, that's a great way. You did your research,

too. So I haven't talked about this a long time. I think it goes back to the, every one of us has some kind of gift, some kind of advantage that we could press. But we spend so much energy worrying about what we're not, as opposed to focusing on what we are. So what was I in this little unformed shell of a being at age 16? I could really write. I was gifted with language and with writing. So how do I translate that? So my actually, my path out of poverty is one of education,

but one of communication and pressing that. So first job, even before that, was working for a congressman and doing letters and whatnot. And he said, you know, you really are gifted. There was an opportunity to a newspaper that he owned an interest, and Queens called the Queens Tribune. They were starting this column where people would send their problems in, and I was meant to do muck-raking problem-solving.

But I took that little column and turned it into something a lot bigger. Did big investigative pieces, would often team up with big New York City reporters, and some of them resulted in awards. So I learned how to press whatever advantage was in front of me to turn that into something much bigger. And I say this to millennials all the time. Like, make yourself indispensable at whatever. is you're doing right now because that is the path to do what you ultimately want to do.

So even if you're not happy or you think a job is pointless, press the bet, press the advantage. And that's what I did with them writing. My ultimate aspiration wasn't really necessarily be a reporter, but it was a bridge to where I was going. What I love about you is that because you dropped out of high school so early, you ended up getting so many experiences, so much more hours of work than a normal teenager would have had. And then that puts you ahead of the game. So by the time you were 26, you were pressed up. secretary, which is probably what like a 36-year-old would have accomplished, not a 26-year-old.

By the way, it's a brilliant point that you just raised. Like, you know, Warren Buffett says the most important thing in the world is compounding when it comes to wealth. Like, and I sort of expand the concept of compounding interest to apply to compounding experiences, so the same thought applies. If you could pull forward experience, you have more time for that experience to create exponential growth, right? And that's truly the story of my life.

Because people say, well, how did you do? You've overseen two NFL teams by, you know, 40-something. Shark Tank at 43, teach at Harvard Business School. It really goes back to the fact that I was put in a bad situation, or like a lot of people, but because I pulled forward my evolution, I was able to everything compounded from that moment forward. So I say to folks, like, be patient, but be urgent, because if you can pull forward experiences, they will compound. But that's a great, great point. I'm really passionate about it. If ever there was a formula to what I have pulled off, it's that particular phenomenon. Yeah, I think that's amazing. So I know,

that to get your job as press secretary, you actually quit quite a few times. And I know you just mentioned this thought about being indispensable. And I wanted to add to that that it's be indispensable. And if they don't appreciate it, quit because you can get some leverage that way. So talk to us about the importance of quitting, why you quit, and how you kind of climb the ladder that way. I love this topic too. You're hitting on all the topics I love. So anybody listening out there, point number one, opportunity is a leading indicator of success and recognition is a lagging indicator. So what I mean by that is if you are a successful person and good at something, you will be given opportunity by a person with authority, but the opportunity won't come

with the recognition that you secretly crave, money, title. First, grab the opportunity, and then there's a lag between the time you get the opportunity and the time recognition comes. I'm just trying to reduce this to a formula because I know there's a lot of people out there. Am I being taken advantage of my career saying, you know, shouldn't I get a promote? motion, there's always a delay. That's life. You will have to make the first deposit. But then you have to assess, okay, after a certain period of time, where's the line between natural lag versus exploitation? And so if you are working for somebody who's a taker or withholder or a gaslighter, you know, whatever the category is it, that's when you have to have the courage to quit,

because there's another overarching phenomenon operating on humans, especially in positions of authority, which comes from a place of insecurity, is that familiarity breeds contempt, which really sucks. Because it's like, wait, why are you looking outside this organization for shiny objects, but I'm right here. But you have to be on the lookout for an organization that looks for shiny objects and is contemptuous of its own talent happens more often than not. And that's when you have to quit. So when I was young, this is a little absurd, but, you know, I felt, I think it was 22, 23. I was ghostwriting pieces for the mayor of New York. I was doing all this, like, incredible work. But my official job was, like, handing out newspaper clips like 530 in the morning.

I would like cut clips literally from the newspaper and put them on a eight and a half by 11 and walk around in this drudgery of handing them out to people. While doing this heavy work of writing things, and eventually I felt like the delta between opportunity and recognition was coming too great. And I was like, well, I want to be press secretary. And I want to, you know, that's what I want to do. I want to sit in that chair or not that chair. And then the answer was like, wait your turn, wait your turn. I also had the urgency of trying to elevate quickly to take care of my mom. And then I quit.

And then everyone was sort of horrified. And I went to the most boring job. Mind them. I could hear the blood rushing through my ears, but it paid more. Quitting is not disloyal. That's the, there's a different point. You should be loyal and you should give and give to get. But you should also know your own self-worth and just never be afraid to bet on yourself.

If you're basically saying, I know my self-worth and I want to go because I want to do something with myself, I want to expand myself. It's not, and you're not being mercenary about it. If you're just quitting money because you're for hire, that's different. If you're moving on because you want to progress, nobody can begrudge you. Let's hold that thought and take a quick break with our sponsors. At Yap, we have a super unique company culture. We're all about obsessive excellence. We even call ourselves scrappy hustlers.

And I'm really picky when it comes to my employees. My team is growing every day. We're 60 people all over the world. And when it comes to hiring, I no longer feel overwhelmed by finding that perfect candidate, even though I'm so picky because when it comes to hiring, indeed, is all. all you need. Stop struggling to get your job post noticed. Indeed, sponsored jobs help you stand out and hire fast by boosting your posts to the top relevant candidates. Sponsored jobs on Indeed get 45% more applications than non-sponsored ones according to Indeed data worldwide. I'm so glad I found

Indeed when I did because hiring is so much easier now. In fact, in the minute we've been talking, 23 hires were made on Indeed according to Indeed data worldwide. Plus, there's no subscriptions or long-term contracts. You literally just pay for your results. You pay for the people that you hire. There's no need to wait any longer. Speed up your hiring right now with Indeed. And listeners of this show will get a $75-sponsored job credit to get your jobs more visibility at Indeed.com.com. Profiting right now and support our show by saying you heard about Indeed on this podcast. Indeed.com slash profiting. Terms and conditions apply. Hiring, Indeed, is all you need. I love that advice. So let's talk about mortality because I think this is a really interesting topic

You mentioned earlier that your mother passed away the first day that you were press secretary. I can relate. My father passed away the week that I started my company. And we grew to 70 employees in our first year. He didn't see any of that. But it also really motivated me the fact that he passed away because I realized that life is so short and that we only have one life. And it made me really get myself into high gear. And I knew that you also had testicular cancer, you know, in your,

30s, and that also had you thinking about death, I'm sure. So what is your perspective on death? And how did those experiences shape you? Yeah, I think my first big experience with death was watching my mother pass away and just watching those like desperate last minutes, the bargaining that happens, to be honest with you. And this is, you know, sort of a tough detail, but just in the last, the last couple of days, she's very heavy. She couldn't really get out of her chair. It's just beyond, I couldn't even betray to you how miserable this environment was and oxygen tank. And she was bargaining. Like, she knew and I didn't realize.

I just thought it was another day in hell. You know what I mean? Like, when you're living in like a fever dream of madness, it's like, oh, this is just another day. And she asked me not to go to work that day. Like, please stay home. And I'm like, we have no money. Like, I have to go to work.

I didn't know that day was any different than any other day in our living hell. And so I watched the bargaining, though, in those last days of like, I won't eat poorly anymore. Like, you know, and I didn't know she was bargaining with her maker. And so I witnessed the regret, the overcoming dread you have at the end of life and thought, wow, it really does can end terribly. My mother worked so hard to try to get somewhere in life, never even took a vacation or a plane, and yet still died.

And so, I mean, I say that in such rawness because I don't want to gloss it over. And like, but everything was fine. Like, it was not fine. And it was terrible. And she was worried about being discarded in life, right, after working so hard. So what that taught me is like, you really. really have to be in touch with your mortality and take custody because it does end at any moment and no one's going to at the end of your life reconcile all the things that you didn't reconcile,

you know, the bargaining phase. So that's kind of point one, two, having gone through cancer and going to Sloan Kettering, I was only 20, no, how old was I? How old was I? How old was I? I don't even know, maybe 32. I had just had my son. And I remember once I, my mortality, like, I wasn't dying tomorrow. And I was like, I think we're going to get through this. And what it did is tell me how much of the things I think about every day don't hold up against the prospect of imminent death, which is interesting because I'm like, wait, the idea of death is hanging over us all the time. And yet I spend my time scrolling through New York Times classified sections looking for a bigger house. I was like, oh, wow, so much of our thoughts are meaningless.

And that's a gift to be aware of and hold on to. So it changed my perspective on mortality. Long story short, you know, I have an app on my phone call We Croke, which is inspired by the folks in Butam, who contemplate their own mortality five times a day. And what you find out, when you think of it, about your own mortality frequently, it's not a morbid, actually. It's peaceful because you relieves you of all the aggravation of the daily stresses because they just don't hold up against the prospect of death, which we all live with. And you realize how much of our angst that we go through on a daily

basis is trying to confuse ourselves or distract ourselves from the idea that we don't know why we're here and we don't know where we're going. Now, for those who are very religious, maybe it's a little bit easier, but for the vast majority of people, like, we don't know what we're doing here. And we don't know when it's going and we don't know where we're going. And so I think if we lock in on that, then you say, well, what do I know? Oh, the present. The present is the one thing that I'm guaranteed. The present is the one thing that feels so great and I'm so grateful for. And so I tried to every day bring it back to Sloan Kettering, bring it back to the idea I might die and bring it back to the awareness that mortality. And what, you know, what it makes me do is like celebrate my wife,

who's my best friend, celebrate my kids and just make like, who cares about this stupid email, all this internecern interpolitical fight of nonsense crap that I'm dealing with. So I recommend everybody out there. Download that app. Kids think I'm crazy, by the way, especially when I read the quotes from somebody Voltaire about, you know, death. But it works. We croak. It's called a re croak. Yeah. It's so interesting. Honestly, Matt, you are such a role model. I just want to take a second to just say, like, wow, like you've done so much in your life. You've come over so much adversity. Your mother is probably so, so proud of you. So thank you. Congratulations.

I tell you a little story since you're like you're going so deep on it. Of course. It's a major story, a positive note about my mom because I feel like this can be so grim. But I went back to deliver the commencement speech at my college. And I really wanted to do it because it's where my mother went to school. And when I was a little nine-year-old boy, some of the positive memories I had were sitting in her classroom in the back on a Saturdays watching her sort of take custody of her life as a single mom. So big moment. It's only a couple of years ago.

I'm only 43. They're giving me an honorary doctorate. I went from a PhD to a PhD. And I feel like this is my moment to inter my mother soul on the campus. And I'm going to honor her. And I'm like, how am I going to get through this speech? Such a hard speech to give. So I'm walking in the procession, you know, with all the gear and everything.

And there's an older professor, older gentleman, interrupts the line, say, excuse me, I need to say something to Matt Higgins. And I see his face. And it's the weirdest thing. I'm like, I recognize this face. And he comes up because, hey, I'm professor. Dean Savage. I just want you to know that I had your mother as a student. And she was the best student I ever had. And I'm like, that's the craziest, like, a moment of, and he goes, I'm retiring tomorrow, but I needed to tell you before you give your speech. And now I'm like crying.

So, but what was interesting, she had always worried about being discarded. And here was this professor who 30 something years later is telling me that it was the best. And she would say he was the best professor she ever had. So you can make a big impact on people, even if you have no money, no anything, just by being a good human being. So it ends well, I guess, as my point in the start. I give the speech. And now every year I have a group of single moms that I pay scholarships for for them to go to Queens College,

which is so fun because these are like my LeBron Jameses of people like they're doing what my mom did. They're raising kids and they're going to college. All them have incredible stories of fleeing abusive husband or dealing with, you know, substance abuse issues, whatever. And now they're going to college while they have little kids. And so I sort of took my mom's legacy and I just transfer it now through scholarships. That is so amazing and so positive.

So, you know, you did so much more after this. You worked for the Jets for eight years. You did so much more. But let's fast forward to entrepreneurship. And let's talk about how you got started in entrepreneurship. You say that Gary Vee was the genesis of all of that. So talk to us about how you met Gary Vee. What was that whole situation like?

Yeah, I was overseeing the New York Jets, the business of the team, and it was probably my seven, you know, year, eighth year doing it. And it was not my dream to become a sports executive for life. I used to always say, I've everybody's dream job, but mine. I love the organization, but I'm not like a rabid sports fan where I want to spend, you know, my whole life doing it. But it was a business and it was fun to run it, high-profile the whole bit. And Gary Vaynerchuk was like,

like, you know, this mythical YouTube wine guy who everyone knew was a huge Jets fan and wanted to buy the team. So my guys were convinced that I could sell them a suite. And I even know anything about sports and entertainment. Selling a suite was like impossible. But I told my guys, okay, I'll go, I'll go meet him in Springfield, New Jersey. And I'll try to sell him a suite. So we met for a bagel and a cup of coffee. And everyone knows Gary Vaynerchuk or can easily now Google and see him eight million hours of content. But I meet him and he's wildly gesturing. I'm going to buy the Jets. And he's, you know, whatever he's got out of his mind.

Like, with what money are you going to buy the jet? But then, and I pride myself on doing this. Like, I can look past the packaging and say, and just listen to the quality of the thoughts and the predictions. And in that 30 minutes, Gary laid out a vision for the future that played out. And it sounded like truth to me. So, for example, this is 2009. This is when Twitter is just kind of like taking off.

He's like, look, the future of the world involves every single person will be HBO. and Comcast. They will be both the content producer and the content distributor. The entire world is going to change. And these big stupid corporations are not going to be able to keep up with it. And they're going to be battleship carriers

and I'm going to build a speedboat. And my little brother, AJ, once he graduates college, we're going to build a firm together. It's going to be amazing. We're going to manage people's social digital. And by the end of the 30, I was like, I think Gary like sees the future.

And if I could figure out how to partner with him, we can unlock great things. And that preface, we cut a deal. Why don't we do this? Why don't we take one player on the team and you'll manage their social media and you'll make them like Twitter famous. And if that goes well,

I'll become the first client of what was to become VaynerMedia. And he did. We actually did social for a player. Kerry Rhodes, went and had dinner with, he was the safety at the Jets, went and had dinner with him.

And Gary did a great job managing it. And VaynerMedia was born, gave him four Jets tickets to become the first client. And then when I left the Jets and started up my own venture firm, went back and acquired almost 40% of the firm, and we've been partners ever since,

and the firm is probably the largest social media, digital firm in the country. So the moral of that story, to me, is when you spot greatness, figure out how you can unlock it, and in so doing, you can also change your own life, right? Like, Gary's my brother. I've had tremendous success,

partly because of him in a lot of ways, not entirely because of him. I've done other things, but he's changed my life, and I believe that I made a huge contribution to his. It's so cool. Gary Vee is such an idol of mine. I actually grew up right next to Springfield, New Jersey. And so I've been following Gary Vee for so long. So let's talk about RSE Ventures. It's a private investment firm that you started. You're the CEO. And you've helped companies like Warby Parker. What are the other companies that you've worked on with this one? Actually, Warby Parker is my partner, Jesse. He did that one. But no, but generally speaking, like big picture, the genesis of it was when you, own a sports team, you have so much access to deal flow. So you have an inbound that you could take

advantage of. You also have perspective. You see a lot of emerging consumer trends. You see Pinterest maybe before others might, right? Like you see Snapchat taking hold because these are huge audiences sports teams have around them. And those emerging technologies are always pitching those sports teams to basically tap into them and offering equity. And so the epiphany I had where the Jets was like, we should be monetizing those insights. We should be backing these technologies, but also we then should be using the sports team as a petri dish, basically, to go ahead and help them gain traction.

So that was the general insight. So RSC was born around the Miami Dolphins in early days, and it's morphed into a pretty significant portfolio of great consumer brands. So our formula is generally a great founder, a Gary V type or whomever, who has some degree of magic. is going against convention and could use some support in some way to scale, right? So in the food context, that would be Christina Tosi and Milk Bar has been my partner. We spun that company off from Momofuku with Dave Chang, its own independent company,

funded it, scaled it. Now if you walk down Whole Foods three years later, you'll see milk bar cookies everywhere, right? That's a reflection of my work with Christina Tosi and my team at RSC. We own Magnolia Bakery, which we acquired. I'm giving all the good food stuff because I like that's, more interesting than some of the other things. But really, that's the approach. I wanted to take this interventionist empathetic approach to founders and figure out how to unlock people's potential. Like, I know what you get excited about doing in your life is similar to what I get excited about.

Like, I wish somebody had unlocked me when I was going through whatever I was going through. So I just enjoy identifying like magic and saying, oh, what would it take to truly amplify whatever it is you're great at? Whatever it is, it makes you beautiful. And I get to kind of play with it, kind of behind the scenes. It's why I don't talk much about the Gary partnership, because the truth is, like, there's only one Gary, and Gary is Gary. Like, my role is minor, and I enjoy the minor, the role behind scenes, helping scale. So that's what I do across the portfolio. Version 1.0 was building things from scratch. We helped launch Resi. We incubated that with Ben Levinthal and Gary Vaynerchuk, and now it's about owning significant stakes in great consumer brands. And Resi is like a restaurant

software or something like that? He's a competitor to Open Table that was born. maybe six, seven years ago at this point, and then was sold to Amex, and now Amex owns Resi. But in the early days of RSC, we would build companies from scratch or work with founders from scratch. That gets hard to do over and over again.

Like, you'll have a very short life if you keep doing that. So now it's more a little bit more mature, significant interests, and then helping scale. But more recently, I've been backing great mature brands that I come across through investing in digital native companies or teaching out at Harvard.

So I backed Dapper Labs, which is a big NFT platform company, Thrasio recently invested in. OpenC is another one. So because it's our own investment vehicle, don't report to the Wall Street, don't report to other investors. It's just a partnership. We have the ability to back whatever we find that's interesting. That's so cool. How do we understand something?

And it might be a dumb question, to be honest. But how does the owner of a sports team or managing a sports team, how does that lead to a lot of deal flow, like you being exposed to a lot of deal flow. I don't quite understand that. So entrepreneurs, when they have a consumer-facing technology, for whatever reason, they're always drawn to sports and entertainment to a lesser extent. But if you think about like a big artist, a big artist doesn't really have a platform to communicate or put a brand in front of their fan base, right? But a sports team does. They reach millions of people. Like Real Madrid, right, has like a hundred million people following that. So it's a natural place for a Snapchat in early days or any kind of

social platform or e-com platform to want to tap into to get in front of that group. So you can see them pretty early. And often in those early days, the imprimatur of a sports team or a league is so valuable that they're willing to do equity deals in those early days. That phenomenon will carry on forever because you have a captive audience that's very loyal. So if the NFL or the MBA backs like the NBA did with Dapper Labs early, that gives Dapper Labs a massive opportunity, right? So that's, that's really it. It's just people trying to get through that dedicated core fan base. Got it, got it. Okay, let's talk about VCs and teach my audience and stuff about VCs. So aside from just giving money to people, what are the non-financial things that a VC or a private investment firm would

do for an entrepreneur? Oh, great question. I think money, ideally money is just, way down the list because money is money and you can find money in a lot of places. It really depends if the entrepreneur is self-aware and reflective, which to me is the whole ballgame, right? I think a VC who's been down the road before, especially a VC who's been an operator can be tremendously valuable. And so I would say to those, I have a tremendous bias towards people who have operating experiences because they will be much more sympathetic to the struggles you're going through and much more realistic. It's easy when you think the answers are on an Excel sheet, but the Excel sheet doesn't tell you anything. All the issues you have to deal with as an entrepreneur are really about

people and trying to get the most out of people, trying to deal with people, trying to navigate around people. So to make that a little more, more explicit, like a great VC investor is somebody you can come to and say, I'm really struggling to fill this position. I need a COO. I feel like I can't handle it all, but it's such a hard person to hire because I have this delicate culture in my office. you know, and Sally and Mark are competing for the top spot, you know, whatever, whatever the issues, that VC will help you source that person or will help you synthesize that fact pattern. So to me, number one, it's a place where you can frankly be vulnerable. And oftentimes, that's the whole ballgame. If you could be vulnerable with somebody, your investor, your spouse,

your partner, you then can get through whatever it is you're dealing with. If you need to sort hold back because if you share your vulnerability, you're going to be criticized for it or judge for it, you really can't make progress. So a great VC, will create a safe space where you could share your problems, hiring, you know, fundraising, product, everything that's going wrong. Because if you could voice what's going wrong, you can go ahead and figure out what to do about it. Because I always think the number one predictor I have for whether an entrepreneur is going to be successful is the amount of time it takes them to make a decision that's already become

objectively inevitable. In other words, like, this product is going to fail. Like, it's clear the market has spoken. How long will it take you to kill it and acknowledge it and shift directions? So many things will get in a way of making that decision, fear of being judged, you know what I mean? Like, don't have another answer, you know, too big of an ego. So I think when you have the right level of self-awareness and a confidence and humility to pivot and iterate, when you're backed by people that won't judge you for it, it makes it a lot easier and a lot faster to make those pivots.

But I've seen the reverse when you have investor of investors, you know, wearing their Patagonia vests and staring at the spreadsheets, you know, never had an operating job in her life and like just in it for the money. and they make your life living hell because I don't know what they're talking about because they never had to hire somebody, fire somebody, never been on the line. They just learned about it in a classroom. Like, I don't know. So I have, as you could tell, a strong bias towards people with true operating experience as investors. Yeah.

I think that's a great point. If you've never done it before, how can you give somebody advice who's doing it right now? It's pretty hard to do. Your advice will be cerebral or theoretical, but it's not going to be practical. So how do you have time for all this? I mean, like I said, I'm a huge fan of Shark Tank and you were on two seasons and all the sharks are investing in so many companies. And I always wonder like, I would probably want an investor. I don't have an investor for my company right now.

I bootstrapped the whole thing, right? And I think that's my next. That's an upcoming question. All right. We'll get that. Okay. So if you have 500 companies that you're invested in, how do you have time for all that? And obviously, people are going to start to take priority.

and other people will fall to the wayside. So how do you deal with all of that? And if you're an entrepreneur looking for an investor, should you look for someone who doesn't have their star yet because you might want to be that star for them, if you know what I mean? Yeah, that's a great question. I mean, it is hard at the end of the day

because, you know, you take on more, you have less capacity. Part of my objective is to render myself obsolete wherever that's an option, right? So whether that means hiring a really great person, I really don't try to hold on to things. I try to let them go when I'm no longer useful. I kind of only tend to want to go where I'm useful and serve a purpose.

And when I don't, I'm just not that interested. So unfortunately, that can make me very like, all right, well, there's no more problems here, so I don't really need to work on this right now, right? Like, we're good. So that's number one. Two, I'm very intentional about my time. People always say, are you doing so much?

I'm very, very intentional about what I do. There is nothing that I do in a given day that wasn't thought through and wasn't through being really intentional. I try to send boundaries around the things that matter most to me, so I have a lot of room to roam elsewhere. So, in other words, my kids are the most important thing in my life. You know, my wife happens to be my best friend, so I don't have a need for a ton of friends

and, like, sees who I want to hang out with. So I've constructed my life in a way that enables me to have a lot of room to roam outside of those really hard boundaries around the things that matter most to me. And then three, I scale. So I'm always scaling, trying to see. set myself up to level up beyond that. And yet, I'm really hard on myself about, am I doing what I said I was going to do? Am I executing on the things I took on? Because I don't have a lot of respect for people who my partner calls it as a grasshopper. You jump from thing to thing.

So I'm constantly auditing like, wait, you said you were going to do this. You took this on. Are you doing it? And if you're no longer interested in doing it, have you leveled with everyone saying, I'm going to move on now, right? But you made a great point. It is a delicate a balance. I'm like, I always, I'm sure I'm always pissing somebody off saying, I'm able to get a hold of you. I miss you. I'm like, I'm sorry. I'm just trying to do something bigger, you know, like, I mean, so yeah, it's a great question. I think I've come to believe that the joy of living is in the striving. It's my formula for happiness. I figured it out. I ran my first more marathon. I finished. I was like, why am I so depressed? I'm like, oh, it was the

training. And so I tell, I communicate that to people like, oh, this is how I'm wired. I really enjoy the pressure and the stress and the evolution. You know, I never taught a day in my life. I worked for almost a year to have the opportunity to teach at Harvard Business School. That's life-changing. So with that comes a degree of shedding of other responsibilities in order to level up. Yeah. I mean, that's just the way the cookie crumbles. Like, it is what it is, you know, and you got to focus where there's promise and the other entrepreneurs maybe hopefully get a competitive kick out of that too and maybe level up themselves, you know. So I think. And I also think that like I give this advice to people too. Nobody wants to go on a rescue mission. When you're when you're trying to solicit support from

whether it's a new investor or an existing investor, like come up with discrete actual items that are impactful that make a difference because everybody's guarding their energy and their time. Right. So I feel like it's on everyone else to sort of extract from you what's most impactful, but leave you with enough bandwidth to do what you want to do, right? As opposed to me to be like, I think we're out of money. Like in. two weeks. I'm like, oh, okay. So what's the plan? And I do get some of that in my life, too. I'm like, come on, really? Like, wait, you really are saying you want me to go on a rescue mission? Like, you don't think I have a million other things going on in my life. Because I get that in my,

I tend to get overly involved. And I do feel like I've been through a lot. So people come to me, which I love. But then when people just come to me with a problem without even like a fact pattern that might get us out of it, I can't stand that. Yeah. Can't waste your time. You're a busy man, Matt. So let's talk about when we should look for funding. So I'll give you my example. So I bootstrapped my company. I started my company as a side hustle while I was working at Disney streaming services and marketing. And I grew it for six months. By the time I quit, I had 35 employees all over the world. And now we've, you know, we've hit $2 million in revenue in our first year. And I don't need an investor. My customers are effectively funding my company.

I hit my first my first real client was paying me 30k a month and I feel like he was my seed investor. You know, all my clients are kind of like billionaires, millionaires who I run social media and their podcast for. And yeah, I mean, I don't know. Sometimes we think about should I change the structure of my company and figure out how we get investors and start raising money. I'm a really good salesperson. And a lot of people tell me I should go down that path and figure that out and start raising money. And then internally, we're kind of just like, well, we could probably take this all the way, like how we're doing it, you know? So what are your thoughts there? When should somebody actually consider an investor?

I mean, everything about us is hiring good talent. So if I got money, it would be about hiring better and better people and having unlimited amount of money to innovate new products and hire better people. So what are your thoughts? So a great question, which everybody should grapple with if they don't, because to bypass this critical question, you know, you could end up in a place you never intended to be, right? So I always think a lot of the the, a lot of artist satisfaction in life doesn't come from the wrong answers. It comes from the wrong question or failing to ask a question at all. So this is the question. Should I scale with investment or should I, you know, bootstrap? I think it comes bound to what's the goal,

what makes you content? We, I found this even when I teach at HBS. It's like we have this presumption that the object of the exercise to create a business worth $100 million or a billion like and to have these markers where it's so hard to make $1.1 into 10. to, you know, and to sort of be on your own, a completely autonomous, no boss, and feed yourself. Like, I marvel at that. Like, wow, you went out. So you're already doing it. Like, I think, you know, like you won. So then the question is, what does winning look like to you? Winning to me looks like you're already successful on your own, but winning to you might be like, I really want a big exit. I want an exitable business. A lot of times when you want an exitable business that can get

that you do need the capital in order to scale bigger and so or faster. So to me, that's always a threshold question. And then it's the theory of the case. What kind of leverage am I really going to get at a dollar in today that I couldn't achieve on my own by growing organically? So if you told me that you're going to start this new media property, right, and you need it to raise $500,000 to create this media property. But with that $500,000, you're going to be within the next three months able to hire 10 people. You're going to get it up to 10 million impressions a month within a year and you're going to get, you know, a whatever, five X multiple on yada, yada, yada, and now that thing's worth 20 million bucks. And that matters to me. That would make sense

because it's going to take you a long time to generate $500,000 and free cash flow to fund that media property. Number one, two, if you said, and this idea is really time sensitive, because if I don't do this media property today, somebody else is going to do it, so I need cash, right? So it's a blend of what's my objective. Do I want an exitable business? Because oftentimes times if I do, I probably do need to raise capital. What's the leverage I can get on a dollar in today? And is there an urgency that requires me to scale now as opposed to scale organically? We'll be right back after a quick break from our sponsors. What's up, young and profitors? I remember when I first started Yap, I used to dread missing

important calls. I remember I lost a huge potential partnership because the follow-up thread got completely lost in my messy communication system. Well, this year, I'm focused on not missing any opportunities. And that starts with your business communications. A missed call is money and growth out the door. That's why today's episode is brought to you by Quo, spelled QUO, the smarter way to run your business communications. Quo is the number one rated business phone system on G2 and it works right from an app on your phone or computer. The way Quo works is magic for team alignment. Your whole team can handle calls and text from one shared number, and everyone sees the full conversation. It's like having access to a shared email inbox, but on a

phone. And also, Quo's AI can even qualify leads or respond after hours, ensuring your business stays responsive even when you finally logged off. It makes doing business so much easier. Make this the year where no opportunity and no customer slips away. Try Quo for free plus get 20% off your first six months when you go to Quo.com slash profiting. That's QUO.com slash profiting. Quo. No missed calls, no missed customers. Hello, young improfitters. Running my own business has been one of the most rewarding things I've ever done. But I won't lie to you. In those early days of setting it up, I feel like I was jumping on a cliff with no parachute. I'm not really good at that kind of stuff. I'm really good at marketing, sales, growing a business, offers. But I had so many questions

and zero idea where to find the answers when it came to starting an official business. I wish I had known about Northwest Registered Agent back when I was starting Yap Media. And if you're an entrepreneur, you need to know what Northwest Registered Agent is. They've been helping small business owners launch and grow businesses for nearly 30 years. They literally make life easy for entrepreneurs. They don't just help you form your business. They give you the free tools you need after you form it, like operating agreements and thousands of how-to guides that explain the complicated ins and outs of running a business. And guys, it can get really complicated, but Northwest Registered Agent just makes it all easy and breaks it down for you. So when you want

more for your business, more privacy, more guidance, more free resources, Northwest Registered agent is where you should go. Don't wait and protect your privacy, build your brand, and get your complete business identity in just 10 clicks and 10 minutes. Visit Northwest Registeredagent.com slash yapfree and start building something amazing. Get more with Northwest Registered Agent at northwest registered agent.com slash yapfree. Those are all super great thoughts that I'm going to noodle on. Yeah, that's for me. I'm just like, I don't know if I need an investor yet. I feel like I need some like other huge idea that I need funding for because as of now, I'm able to kind of pay for what I need.

Well, I also think about an agency, if you're going to run a pure agency, then, you know, most of the time the answer is you don't need investment. You build it or again, you win the contract, you hire. You hire, once you have some more free cash flow, you can hire slightly ahead of demand because you know the demand will come. I think that's a bigger threshold for an entrepreneur who's building an agency to overcome, the willingness to hire slightly ahead of demand and have the confidence to know demand will come. I believe philosophically that problems beget solutions and people have it all wrong.

People think solutions beget the willingness to undertake a problem because you've identified how you're going to solve it. I do the opposite. I like to create the problem for myself and then know that we have an infinite capacity to get ourselves out of situations. And so I placed myself in a problem. So to you, I'd say, I'm going to hire three people. I'm not sure how I'm going to pay them, but I know I trust myself. I'm going to get the business to pay them. That's more important and taking an outside capital, actually. That's exactly what we're doing right now. And I'm just like booking sports start dates and months ahead.

And I know the clients are coming. I mean, Gary Vee, when Gary did his deal with me back in the day, that money didn't go into the firm. It just went to him and to AJ. So truth, VaynerMedia is really 100% bootstripped. We a little bit of money went into acquire Purao, but really actually Gary, Gary built that with the hustle of getting clients and stuff like that. So it can be done.

The biggest thing to overcome is the willingness to hire a head of demand. Yeah, it's so true. It's so funny. That's exactly what we're going through right now. Do I have a future in this? Should I go? Yes. Let's talk. Let's talk. Listen, VaynerMedia has always been my dream. Don't get me started. I'm about to be on Claude Silver's podcast too. Oh, cool. Such a sweetheart, by the way. Yeah, she's so nice. She's been on my podcast, she was on my podcast like a year or two ago, and now I'm going on her, so I'm excited.

So let's talk about entrepreneurs and what you look for in an entrepreneur. So let's start there, and then I have a couple follow-up questions. So maybe I put on kind of the Shartan context, but I think it applies to everything for my time when I was on Shartang. I look for probably signals more than anything. I really believe, I think the Italians have a phrase, you know, the fish rots from the head. I just think everything is about the integrity of the mind and the alignment of everything going on in your head. And so I spend a lot of energy really trying to look under the hood.

And what am I looking for? I'm looking for number one, like I mentioned earlier, self-awareness in an entrepreneur. And it's like, don't sound like empty words, but we all can pick up, we can pick up signals of self-awareness. One of them being, for example, if you're on the set of Shardtank, will you acknowledge that you don't know something? Do you have the confidence to say you don't know? something. I'm looking for conviction, though. I'm looking for somebody who doesn't simply capitulate to me because that's expedient. So how would that show up on Shark Tank? Cuban would say, like, your name sucks for this company or your packaging stinks after

like we've looked at it for 10 seconds. And a person's like, would all due respect, like, I actually think, and here's why, as opposed to, sure, I'll change it. Whatever you want, I just want you to be my partner. So I look for a degree of conviction, right? I also look for humility, use of the we in the language rather than I all the time, those little signals that say to somebody, and the reason why that matters, not because I want you to be the nice person in the world, people will follow others who bring them along, right? So if it's talking about I, I, I, I, that tells me your ego is very fragile. You may be a narcissist. You're going to be unlabel to recruit people to your cause, including vendors and employees, and you're going to be

less successful. So I look for that conviction. I look for the self-awareness, right? I look for the ability to bring other people around, right? And of course, I look for master. of subject matter. People who are looking to like delegate everything or outsource it, who don't have respect for what happens in the weeds, you know, who don't want to sort of sit in a stream of data, they tend to not be successful over time. So I really do look for a degree of willingness to be involved in minutia, right? And the things that get away with that be ego, while it's beyond me, or I just want to outsource all that. So I look for mastery of the facts. I can be unforgiving. If I think there's something you really should know and you don't know,

that does say I do judge that pretty harshly. So if somebody were to go on Shark Tank, for example, and they're starting a restaurant or whatever, or somebody comes to me, and I asked them, what's your forewall, what's your cogs, right? What's your occupancy cost?

All these things are really important when you have a restaurant, food business. Your occupancy costs, for example, should be no higher than 10% of your total gross revenue. If you tell me you're the chef, I kind of just handle the food.

I leave that to build to do it. It's like, no, no, no, like food. Like, we'll just cook in your kitchen. Like, the option you have to make a profit. your restaurant. So I can be unforgiving when you don't have mastery of the things I believe you should. I could also be unforgiving if you bullshit me and act like you do when you don't. You know what I mean? So it's new on. We can do this all day about what I'm looking for.

But my overall point of this philosophical discourse is I try to get under the hood of the head. The worst deals I've ever done in my life are when I partner up with a private equity firm and they've got like billions of dollars under management and they bring in all these experts to do these expert reports. And then like I'll go on a day one, I'm like, Did you notice that the CEO is delusional? Like, I mean, the reports are really great, but like a great product will never eclipse or overcompensate for a bad CEO, a bad founder, right? Whereas the other thing is true. It's actually the reverse is actually true.

A great founder can eclipse a really bad idea and iterate to a better one, but the reverse is never true. It's so interesting. So something else that I've heard you say is that you feel like entrepreneurs today might be too overconfident. And that's because they have Google, they can search anything, you know, anybody can be an entrepreneur, you don't need an office, you have Slack, you have Zoom. So how can we prevent ourselves from being overconfident? And why do you think that entrepreneurs are so overconfident these days? Yeah, well, I think number one, I think we do a disservice to some extent because we fetishize this idea of being an entrepreneur. And like it's now the hierarchy, you know, everybody wants to be the hoodie wearing, you know, maybe not Mark Zuckerberg.

But like, you know, there's a mythology around. entrepreneurism, and because everyone has the ability to have a side hustle. We confuse side hustle with the idea of having a business. And so there's just not a lot of honesty about the drudgery and the pain of what it takes to create a business, but also the skill sets that are required to be successful. I mean, you know this because you've had to manage people now. If you were passive, aggressive as a leader, you'll ultimately fail because you're going to hate the conflict. You're not be able to tell people and give them feedback. You're not going to be able to manage higher slow, fire fast, all the things that go in to be a great leader. So my point being, we've made

entrepreneurism sound a lot easier and more accessible than it is. And we've also made people feel bad if they don't have an idea or some creative impact. We've almost devalued what it means to be part of a team and how precious that is to serve for the greater good, how valuable that is. And so those are my kind of my big overall takeaways. And as a result, we place less of a premium on experience. And I think that's everything about life boils down to pattern recognition skills ultimately. That is your greatest gift about getting older. Downside of getting older is we get more wrinkly and maybe we don't process information as fast. The upside is our pattern recognition skills are way stronger with every year of growth we have. And it takes us less time to recognize a pattern.

So we tend to now discount that. We discount age. I'm not saying this because now I'm a little older. I really believe in it. We discount the growth and the pattern recognition that comes with that. And I see it shows up, but entrepreneurs a little bit like, well, I'm going to have Google. I mean, I already know that. I'm like, no, it's different from knowing something in the abstract and having imprinted on your cortex.

So that's what I'm saying. And that was a very long way of saying it. No, yeah. I totally agree. I don't know if this exactly relates, but I understand what you're saying because when I was 25, I was, a first-time entrepreneur, and I failed. I had great brand. I was, you know, almost got a show on MTV, all this cool stuff, but I couldn't monetize what I was doing. I didn't know what I was doing. Then I ended going into corporate, and I had a lot of years in corporate, and then became an

entrepreneur, and now I'm successful because I had those experiences to learn off the back of another company, basically, big companies, right? And so, like, what I tell people on my show is, like, let's say you failed as an entrepreneur. Don't be like too cool or something to go get a real job after that and learn from somebody else who's doing it right. Yeah, I know. 100%. I am an amalgam of that which came before.

It would be impossible now to pull in a little bit of Buddhism, right? Like, what is the book? Is the book the words on a page, the author who wrote the book, the tree that created the book, the water that fed the tree? I don't know. So I am an amalgam of all that which came before. and a lot of that included jobs, drudgery, also getting it wrong.

In my 20s, when my whole identity was about being like Dugie Hauser and younger than everything, right? And also just being the hero, took care of his mom and all this, like, that was my whole construct and my personality. It didn't involve working through other people. In fact, like, I just would like, let me just tell everybody what to do because I have the answers kind of,

and I don't mean that like egotistical way. That's just was the formula, right? And then as I get older, I get so excited to submit to the greatness of others. I love being humbled. by somebody's magic. Like Gary, for example, he's so self-possessed, and he sleeps eight hours.

I'm like, God, if I could sleep two hours. Like, he's so reconciled to who he is as a person, whether you like him or not. He doesn't care. And I'm amazed by that. I get to submit to the greatness of his self-possession. I seek out opportunities to do that everywhere professionally. So that has unlocked more value for me and my family

and my professional success than my 20s when I thought that I was the, you know what I mean, the star of the show. And so that's my point. It's a time for me to know that. It's a pattern recognition for me to realize, I think I'm more successful when I submit to the greatness of others than when I ruminate my own success, right?

Like, I seem to get further and seem to enjoy life when I'm humbled by somebody else's mastery of a topic because it tells me that I have more room to grow. There's another marathon to finish, right? I haven't hit the ceiling myself. And so a long way of saying that we unfortunately devalue experience and pattern recognition, which doesn't mean simmer down young person.

It just means value, seek out what you don't know and get excited when you discover that you didn't know something. So as we wind down, I have a couple more questions for you. I want to talk to you about Generation Z because a lot of people who are older generations, they look down on Generation Z and they think that they're, you know, lazy or whatever they want to call them. But you actually think that they have great values. So talk to us about what you love about. Generation Z and maybe what you think they could do differently because I have a lot of Gen Z listeners.

Oh, I love that topic. I feel really passionate about this general idea that when you're on, I use this tacking metaphor, but I won't get into it, but I did a speech called tacking if you want to look it up, but that when you're sort of on the ground, you're in the middle of things, things look like they're getting worse, you know, or life is getting worse. But if you take a step back and you look at it from 30,000 feet, you realize the world is always getting better. And I think Gen Z is a perfect manifestation of our world getting so much better, and it's manifesting in the values of Gen Z. This generation, in my view, is relatively colorblind. And I mean that in a negative way, understanding, obviously, you know, all the different experiences we've had depending upon

our background and making, you know, accommodations for it. But at the same time, just this vision of equality that pervades Gen Z is amazing. Same with sexual orientation is amazing. And so I look at my kids and the values they now espouse and their classmates. And I look at what I grew up around and Queens. And I'm like, it's breathtaking and makes me so happy for the future. So it's honestly, and I'm 46. So I can, I can, you're not out old at all. No, I can malign myself as my only point. So I'm going to malign myself in anybody my age. I really think it comes from a place of insecurity of the dying of the light. Like, it's hard when you get older. You get like, it's uncomfortable. Like, what is this TikTok? Like, dancing videos and, and, and, and, and, and, and, and, and,

And, you know, we can't relate. But that's on each of us as we age to refuse to become obsolete and instead embrace or question or wonder or dip our toe into what's going on. You know, if TikTok makes you uncomfortable, then go open an account and see what's going on there. So I think this sort of, this happens almost in every generation. Millennials used to be maligned and now Gen Z is maligned. But what is unquestional to me is the values that Gen Z espouses.

And this isn't just academic. Putting that energy out into the world, we're like, no. People get to identify however they want to identify. They get to live their life, however they want to live their life. We need to make amends for the past. We cannot act like we did not commit the most tremendous, atrocious crime in humanity or among them with slavery. And that has longstanding repercussions. We need to come to turns with them.

We are destroying our environment. We're all going to hell. These are important conversations that Genzi is stimulating and spurring them. So I think most of the maligning comes from this sort of discomfort with like the world seems to be changing so fast. and TikTok's so stupid. So I don't know. I find any time I have that attitude, I'm like, well, no, no, check yourself.

That's just you becoming obsolete. You just don't like it. So I listen to my beautiful kids, my son talk about what's going on in school and just how he views his friends and identity and whatnot. I just think it's breathtakingly amazing. So that's my view.

Way to leave on a high note. And the last question I ask all my guests is what is your secret to in life? I really think it's being intentional. I think that if you look at what's one of the worst emotions we go through, it's not anger, it's not sadness, it's regret, because it's the one self-inflicted emotion that you can completely avoid.

And so the antidote to regret is intention. So I think the secret for me profiting in life is I'm always working backwards from my deathbed and my epitaph. What do I want my epitaph to read? and what am I going to feel on my deathbed? And if you think long and hard, you can actually project. I'm like, oh, yeah, it was that. I didn't do this.

Most of it is I didn't do this, not I did this. It's kind of, because most things when you're in 80, are you really going to care that you did this? It's mostly I didn't do this. And so the cure of making sure you don't have too many, I didn't do this, is to be really intentional. So I ask myself every single day, what is the highest and best use of Matt today?

Right? It's like a concept I take from land use. We do that with a piece of property. You're always asking, what's the highest and best use of this piece of land today? It evolves as the context evolves. You evolve as your context evolves. So you have to audit. What's the highest and best use?

I've changed. I'm not who I was yesterday. My cells are dying, but my brain is growing and my experiences are, you know, are blossoming. Who am I today? And then I set my intentions based on who am I today. And that's why when you look at my crazy life and my crazy repertoire, it's because of that pattern is constantly playing out. Oh, my gosh. I love that advice.

I would recommend that you guys go rewind that right now. And where can our listeners go to learn more about you and everything that you do? I'm spending a lot of time on LinkedIn. That's kind of my favorite place. And I am, so Matt Higgins on LinkedIn, and I have a book coming out. Not for a while, but we'll talk more about that. All about these topics, it's called Burn the Boats, be out in about another year, Harper Collins. So find me on LinkedIn.

Awesome. Cool. Have you back on when you have your book launch. I can't wait for that. Thank you so much, Matt. This was such an awesome conversation. Well, thanks for having me. You're amazing. Your questions are amazing. It's so thought-provoking, and I appreciate it.