Young and Profiting with Hala Taha - Shark, Matt Higgins: Attacking Entrepreneurship | E145

Episode Date: December 13, 2021

Ever wonder what investors look for in up and coming entrepreneurs? In this episode we are talking with Matt Higgins! Matt Higgins is a noted serial entrepreneur and growth equity investor as co-founder and CEO of private investment firm RSE Ventures. He is also vice chairman of the Miami Dolphins, an Executive Fellow at the Harvard Business School, where he co-teaches the course “Moving Beyond Direct-to-Consumer,” and was a Guest Shark on ABC’s four-time Emmy-Award-winning TV show Shark Tank seasons 10-11. Matt 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 early-stage venture fund Vayner/RSE. In today’s episode, we hear about Matt’s childhood and journey to entrepreneurship. We’ll also discuss Matt’s work with NFTs and how he began RSE Ventures. We’ll also hear Matt’s thoughts on “The Great Resignation” during COVID, and what he looks for in entrepreneurs! If you want to level up your entrepreneurial skills, keep listening! Sponsored By: Charles Schwab - Learn more at Schwab.com/plan    Jordan Harbinger - Check out jordanharbinger.com/start for some episode recommendations Shopify - Go to shopify.com/profiting for a FREE fourteen-day trial and get full access to Shopify’s entire suite of features. StoryWorth - Go to storyworth.com/yap and save $10 on your first purchase! Social Media: Follow YAP on IG: www.instagram.com/youngandprofiting Reach out to Hala directly at [e-mail] Follow Hala on Linkedin: www.linkedin.com/in/htaha/ Follow Hala on Instagram: www.instagram.com/yapwithhala Follow Hala on Clubhouse: @halataha Check out our website to meet the team, view show notes and transcripts: www.youngandprofiting.com Timestamps: 00:47- Matt’s Childhood and How It Molded Him 08:39- Matt’s First Job and How He Got There 11:19- The Importance of Quitting 16:46- How Mortality Has Shaped Matt 23:50- Matt’s Journey to Entrepreneurship 27:42- The Future of NFTs and Matt’s Work With Them 35:57- RSE Ventures and How It Began  44:27- How Matt Manages His Investments 50:08- When to Consider an Investor 54:47- What Matt Looks for in Entrepreneurs 01:03:51- Matt on The Great Resignation Post COVID 01:07:75- Matt’s Take on Gen Z 01:11:12- Matt’s Secret to Profiting in Life Mentioned In The Episode: Matt’s LinkedIn: matt-higgins-rse Learn more about your ad choices. Visit megaphone.fm/adchoices

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stores. Taxes and other fee still apply. You're listening to YAP, Young and Profiting Podcast, a place where you can listen, learn, and profit. Welcome to the show. I'm your host, Halla Taha, and on Young and Profiting Podcast, we investigate a new topic each week and interview some of the brightest minds in the world.

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Our subject matter ranges from enhancing productivity, had to gain influence, the art of entrepreneurship, and more. If you're smart and like to continually improve yourself, hit the subscribe button because you'll love it here at Young & Profiting Podcast. This week on YAP, we're chatting with Matt Higgins. Matt is a well-known entrepreneur and is the co-founder and CEO of the Private Investment firm RSE Ventures. Matt is also an executive bellow at the Harvard Business School and was a guest shark on ABC's four-time Emmy award-winning TV show, Shark Tank,

back in seasons 10 and 11. In today's episode, we'll hear about Matt's childhood and inspiring journey into entrepreneurship and how he became the youngest ever press secretary to the mayor of New York when he was just 26. We'll get into the importance of self-worth, knowing went to quit, and we'll also hear Matt's thoughts on the great resignation, and why so many professionals are leaving their nine to fives

to start their own businesses. If you're looking to feel motivated and get the courage to leap into entrepreneurship or start a side hustle, you've got to tune into this one. 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 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 wanna 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 gonna go deep, right? We're just gonna go, we're just gonna start right at the deep parts.

All right, sounds good. So, for those of you who 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 Spring Fable of Arn Queens. And my mother had been through a ton of stuff that I only really found out about later on after she had passed away that kind of contextualized everything I went through as a child, but my childhood was framed with extreme poverty, extreme shame, extreme concealment,

because as a kid, the last thing you want people to know, at least back then, is how poor you are. So my early days were endless side hustles. I used to sell flowers on street corners. I was that kid knocking on your windows, so be nice if somebody's trying to sell you flowers. You know, I would sell handbags at flea markets, $10 a leather handbags, and I worked in 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 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 to 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 knees, cleaning apartments for elderly home-owned senior citizens to getting her GD 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 pursue 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 is suffering alone can relate to, like, is anyone going to help and does anybody care? And, you know, there were so many different lightdowns as a kid, no intervention, and like, doesn't everybody see how difficult the situation is? And plus, as a kid, you just don't want to be in charge. And the whole parental dynamic was turned on. It's head when I was growing up. So I was sort of the parent. And as the parent, 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-restrict as a kid. Nobody wants to be in charge. And so watching my mother do that, get her GD as an adult gave me a piphany that there was a loophole back then that if you could get your GD 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 reengineer and architect my entire life. That's what 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, dealing drugs, whatever, to sat in the back of that room. And I decided I was gonna drop out. And it was the most important decision I ever made because I had the whole way to the world telling me, one, you're gonna be branded a loser, two, you're never gonna 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 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 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 made me very empathetic. Like to watch a person literally deteriorate throughout your entire form of years, 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 of night, I work and work and work to build my stuff up. I went from McDonald's earning 375 an hour to the time I was 26 years old, 10 years later to being press secretary of the Marinery York, making six figures. That's a lot of ground to cover, but also she deteriorated throughout that entire path. So while I was doing that, living this secret life, I would spend my nights at the ER. We 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 of the mayor of New York, this

heady moment when I finally 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 humiliate 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, we just were wasting away. And so that stays with me to there's no cavalry coming. It just is what 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. You know, your parent, 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 you're unrealized aspirations, you got it wrong. And so I honestly learned a lot from the dysfunction of that dynamic and to resist it.

It's because you wanna make sure you don't pass on these patterns to the next generation, right? And so, but I also to the next generation, right? But now, at the same time, normally, when things are distorted in a parent-child relationship, it's because of some trauma that has been unrealized or unmitigated or unsynthesized. I think that was the case with my mother. You tend to pass on dysfunction from one generation to another. 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 we're taught on. Although I'm probably screaming out my kids and I'm told other ways, I probably were compensating. I'm probably not a helicopter parent. There's a go-free, you know, I'm told. 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 scragged, fin 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 Queen's 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 to do research too. So I haven't talked about some a long time. I think it goes back to every one of us has some kind of gift, some kind of a damage

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 shallow of 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 like, and whatnot, and he said, you know, you really are gifted. There was an opportunity to newspaper that he owned an interest in and Queens called the Queen's Tribune. They were starting this column where people would send their problems in and I was meant to do muk-breaking 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 you know, some of them resulted in 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 guess as to millennials all the time, make yourself indispensable at whatever it 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 bad, press the advantage. And that's what I did with them writing. My ultimate aspiration wasn't really necessarily to 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 end 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 press secretary, which is probably like a 36 year old would have accomplished not a 26 year old.

By the way, it's a brilliant point. You just raised, like I, you know, warm buffets as 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, which is 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 around Shark Tank at 43, teach at Harvard Business School. It really goes back to the fact

that I was put in an ad-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, be patient, but be urgent, because if you can pull forward experiences, they will compound. But that's a 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. I know you just mentioned this thought about being indispensable, and I wanted to add to that that it's being 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 that a lot of people out there am I being taken advantage of my career, you know, shouldn't I get a promotion? 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 with holder or a gas lighter, you know, whatever the categorism, 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 I fell, I think it was 22, 23.

I was ghost riding, pieces for the Mayor of New York. I was doing all this incredible work, but my official job was like handing out newspaper clips like 5.30 in the morning. I would cut clips literally from the newspaper and put them on a 8.5 by 11 and walk around in this drudgery of handing out to people while I'm doing this heavy work of writing things. And eventually I felt like the delta between opportunity and recognition was coming to great. And I was like, well, I want to be press secretary. And I want to, you know, I want to, you know, that's what I want to do. I want to sit in that chair and 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 yeah, and I went to the most boring job. Mind I'm gonna hear the blood rushing through my ears, but it paid more. And then four months later, I got a phone call

to come back, deputy press secretary, paid for my law school, everything I had wanted. So I always remember that story. Like, you don't want to be, 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. So I actually did that twice. I did it again. And the second time I did it, you know, it was like, you know, you're not coming back. Like, that it, you know, I was like, you're not coming back. Like, that's, you know, we love you. Like, I'll bless you.

A year later, I was in the youngest press secretary in New York City, that's very 26. So. That's amazing. So I guess my big question to you is people quit all the time, but people burn bridges, right?

So how do you quit without actually burning the bridge? So they want, they feel okay to kind of put their tail between their legs and ask for you back. That's a great point. Well, I think it begins with the end of the spendability. If you're quitting from a place where you want indispensable, people will remember that.

Like, oh, that was the ultimate utility player. Can't believe they got out the door. Two, people admire those who know their own self-worth. It's just the fact we train people how to treat us. My wife always says that, which is true. So 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. And then you just keep those lines of communication open. There's a way to manage yourself. But if you quit from a place of bitterness, what makes people bitter is when you believe that somebody else's job to take care of your career trajectory, right? I find it happens. So people are like, okay, but I really like it here. But I want to be in charge of everything. I'm like, well, that's not going to happen just yet. If you get bitter because of that as opposed to taking agency and custody of your own,

that's what happens. If you leave and you're not bitter and you're just doing it to progress, eventually people don't begrudge that they admire that because they kind of want to operate the same way you're operating, right? I know that's convoluted, but it's a nuance, but it's so true. Expunge all bitterness because nobody owes you anything. You owe yourself everything. Yeah, and I would say do good work to the day you're gone.

Make sure they remember you on a high note. That's what I would say. Yeah, I'm in awe of hard work. I go to places and I see people working so hard. I'm in awe and I really need this. I'll go to hang out in my local 7-11. God, you're working so hard. I find it so hard to smile today.

I'm gonna be such a miserable boss. And here you are, cheerfully, whatever context. So my point is people in positions of authority know anybody who is doing exceptional work at any level. And you will eventually catch the attention of somebody who's good-natured who wants to tap into your magic and promote you, elevate you.

And if you don you, elevate you. And if you don't, and you quit. 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 a high gear. And I know 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. I'm just watching those desperate last minutes, the bargaining that happens to be honest with you. And this is a tough detail, but just in 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 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? When you're living in 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. Please stay home. And I'm like, we have no money. 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 now in those last days of like, I won't eat poorly anymore.

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 and like never even took a vacation or a plane and yet still died. And so I mean, I say that in such a raw mess

because I don't want to gloss it over and like, but everything was fine, like it was not fine and it was because I don't want to gloss it over in life, 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 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, too, having gone through cancer and going to slow and catering. I was only 20, now, how old is I? I don't even know, maybe 32. I just had my son. And I remember once I, my more talent, 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 what 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, I have an app on my phone call We Croak Which is inspired by the folks in New Tam who Conniplate their own mortality five times a day and when you find out when you think about your own mortality frequently It's not a morbid actually. It's peaceful because you relieves you of all the aggravation and the daily stresses because they just don't hold up Against the prospect of death and mortality which we all live on 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're, 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 to end. 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 try to every day, bring it back to Sloan Ketter and bring it back to the idea I might die and bring it back to the awareness that mortality. And what it makes me do is like, sell my wife, who's my best friend, sell my kids, and just make like,

who cares about this stupid email, this internet, some interpolitical fight of nonsense crap that I'm really with. So I recommend everybody other download that app. Kids think I'm crazy, by the way, especially when I read the quotes from somebody, Voltaire about death, but it works. We croak, it's called We Croak.

We croak, yeah. So interesting, honestly, Matt, you are such but it works. We croak, it's called We Croak. Yeah. 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 congratulations.

Thank you. Are you a little story since you, you're bringing, like you're going so deep on it? Of course. I'm very, a positive note about my mom, because I feel like this is so can be so grim, but I went back to deliver the commencement of 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 go in from a PhD to a PhD and I feel like this is my moment to in term my mother soul on the campus and I'm going to honor her. I'm like, how am I going to get through this speech? Such a hard speech to get. So I'm walking in the procession, with the gear and everything. And there's an older professor, older gentleman,

interrupts the lines, 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 I'm like, 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 gave your speech. I was like, I'm now like crying. Like, 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 at one point, to start, I give this 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 James's, of people like they're doing my mom did, they're raising kids, and they're doing my mom did, they're raising kids and they're going to college. All of them have incredible stories of fleeing abusive husband or dealing with substance abuse issues, whatever. And now they're going to college while I have little kids. And so I sort of took my mom's legacy and I just transfer it now through scholarships. Hold tight everyone. Let's take a quick break and hear from our sponsors. Young and profitors, do you have a brilliant business idea but you don't know how to move

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This is possibility powered by Shopify. 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. Let's talk about how you got started in entrepreneurship. You say that Gary Vee was the genesis of all of that. Talk to us about how you met Gary Vee.

What was that whole situation like? Yeah, I was overseeing the New York Jets to business of the team and was probably my step in year, eight, you're doing it. And it was not my dream to become a sports executive for life. I used to say I have everybody's dream job, but mine. I loved it, my organization, but I'm not like a rabid sports fan

where I want to spend 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 this mythical YouTube wine guy who everyone knew was a huge sheds fan and wanted to buy the team. So my guys were convinced that I could sell him a suite. And I didn't know anything about sports and entertainment selling a suite was impossible. But I told my guys, okay, I'll go meet him in Springfield, New Jersey. And I'll try to sell him a suite is like impossible. But I told my guys, okay, I'll go meet them and sprinkle New Jersey. And I'll try to sell them a suite.

So we met for a bagel and cup of coffee. And everyone knows Gary Vaynerchuk or can easily now Google and see an eight million hours content. But I meet him and he's wildly gesturing. I'm going to buy the jets and he's, you know, what I'm, he's still out of his mind. Like, with what money are you going to buy the jets?

But then, and I pride myself on doing this like I can look past the packaging and 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 and it's but it sounded like truth to me so for example this is 2009 this is when Twitter is just kind of 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 gonna build a firm together. It's gonna be amazing. We're gonna manage people's social digital. And by the end of the 30, I was like, I think Gary sees the future. And if I could figure out how to partner with him, we can unlock great things. And that breakfast, 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 to Had dinner with,

he was the safety of the Jets, went and had dinner with him. And Jerry did a great job managing it. And VaynerMedia was born, gave four Jets tickets to become the first client. And then when I left, the jets 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 why 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 V is such an idol of mine. I actually grew up right next to Springfield, New Jersey. And so I've been following Gary V for so long. So I know you and Gary are doing an NFT project. Can you talk to us about this project

and what you think about in terms of the future of NFTs? Yeah, I think I have gone deep into NFTs. Well, first, like so many people listening to this over the age of 30, dismissed it. Like, with JPEGs, like, what, what am I really buying? And I remember Gary, wasn't that long ago, during a pandemic, I had dinner with him, and he's like, open your eyes and you, like, what, what am I really buying?

And I remember Gary, wasn't that long ago, it was during the pandemic, I had dinner with him, and he's like, open your phone right now, and you are gonna buy five crypto punks right now, and they are gonna be worth an extraordinary amount of money, and whatever, I'm like, I open my phone, I'm like, I'm not buying this. Like, are you out of your mind?

I was like, 30 grand at the time. I was like, this is silly. Of course, big mistake, right? Like Julia Robertson, you know, that she walks up big mistake. So I just not have done that. But anyway, I pride myself on reflecting, especially when I get things wrong.

It's not that I didn't think they might take off, it just didn't feel like it was, you know, for me. And in the summer, I had a little bit of a window, free time I decided to go deep down the rabbit hole, and just really understand like, what is the fundamental activity happening here with NFTs? Like is there something there and I just became convinced that the metaverse is going to transform the universe that this underlying activity around NFTs appeals to so many different things that resonate with people that do feels to our desire to collect right rare items. It appeals to our desire to have prestige and have a rare thing and portray that, you know, to an external audience. It appeals to the desire to gamble, to be honest, right?

Like, and to invest and to be part of a community, which is the easy part to dismiss. If you don't spend time on discord in a round and NFT project, you don't understand what's happening with NFTs. If you do and you immerse yourself and you see how enriching it could be to go deep into an NFT community, you begin to understand it. And then gaming, I think that NFT gaming is going to be a multi-billion dollar industry and it's happening in real time and it's so easy to miss. So for fun, I've been onboarding people of,

you know, all different stripes to a different NFT projects that I really like, and when I find across the board, one, everybody becomes addictive. Like, I don't care if you're a lawyer, a CEO, you're a skinic, a septic, a curvangian, it has a certain gravitational pull, and that tells me that it's pretty significant.

So I think OpenC could be the next Amazon, and there's going to be basically an arms race to figure out which becomes the winning platform. And in particular, NFT gaming is just going to explode. So in fact, you're not Gary, I'm Gary. It was just that we create our NFT fun together, and we've been putting money to work. Is that already launched, your NFT fun, Gary? Yeah, we've launched. We've been added for,

we kind of keep it sort of quiet, you know, we don't brand it, we just do what we do, you know, and invest in projects. We're an axi, we're in a ton of different things. I feel like we've got pretty great. We also buy some art, so we own an ape, which has done pretty well in crypto punks, but my only point for those out there,

like don't dismiss it, dismiss it at your own peril. Actually spend some time and have fun with it. And you'll discover that it's quite real. And this is the internet in 1996. So how would you suggest that somebody actually get started? You mentioned go on Discord, which for those who don't know, it's a social audio app.

So go on Discord, start listening to some conversations. Most people don't have 30 grand lying around. You don't know, it's a social audio app. So go on Discord, start listening to some conversations. Most people don't have 30 grand lying around to invest in. Yeah, so what's like an investment amount that we should think about, and also how does somebody get involved? Okay, great question. So just point number one, remember complexity

is a proxy for opportunity, because it means it's early. So it is literally ridiculous to onboard yourself into the metaverse. It's so abstract and you get so mad like, why do I need a corn base to happen? What the hell is MetaBask? And what is a wallet? I have a wallet. You know, like, I say you need to like shake it off. And go into this knowing like it's so stupid how hard it is. But that's the opportunity because in 1996, I had all these ideas for like these domain names and I was like, I'm going to do it and then I didn't bother going through the process to register

because it was so complicated and there went millions of dollars out the door. So stick with it. So point number one, if you can find a friend who's into it, so probably a gamer, somebody in your world has gone into, they might be 12 years a gamer. Somebody in your world has gone into, they might be 12 years old, but somebody in your universe has gone deep and asked them to mentor you and onboard you. Everybody will do it because they want the population to grow. So if you, but if you don't happen to have that person, it's a couple of simple steps. You download, you know, the Coinbase app, right? You send some money to Coinbase. Now you'll learn the world of annoying fees, but you, you've sent somebody to Coinbase. Now you'll learn the world of annoying fees, but you

you've sent some money to Coinbase and then you download Metamask, which is your wallet. You need these two things. Don't use the Coinbase wallet, in my opinion. It's not good. The Metamask wallet and send some coin because you'll convert your cash to Ethereum and then you send some Ethereum to Metamask. Now you're in. You will buy Metamask through the platform called OpenSea. That's where that's the Amazon of Metamask at the moment. And your Metamask is hold your money, called Ethereum. And that's where you'll buy your NFT there. There's tons of projects where you can spend

a few hundred bucks to get started. You don't need to spend thousands. You want to do your research first by downloading Discord. If you like some pretty objects, just spend some time look at the depth of the community, the passion around the community, do the developers of the project, do what they say they're going to do. Everybody puts out what's called a roadmap, most of them are foolish yet.

So just like you want to look for these little signals of execution, a one-up, but you don't need $1,000 to get started. I would say the opposite. Like you can do it for a couple hundred bucks and do what's called minting, which means you're there from day one where you buy an NFT from the beginning. So I know what I said is complicated. I wanted to give you at least the general framework. No, it's helpful. And I'm a YouTube, but I think the modese, just like, so what I do now, I'm going to

get it wrong. But you know, you teach somebody to fish, right? They'll have food for the rest of their life. So anybody I bring in, my friends from Queens, and like teach divinity in a T-land, but they have one obligation, which is to onboard somebody else that I send to them. So now I just, I've created this, you know, this group of people that onboard other people. So find somebody. Very, very cool.

And honestly, you de-complicated it. It sounds a lot easier than I thought it would be, although more steps than I realized in terms of like, how you have to like, where you have to get your money and how you have to buy it. But it seems doable until your point. That's the opportunity. The fact that it's so hard and so few people

are gonna actually get in early because they're gonna be overwhelmed by it instead of just figuring it out step by step. I'll give, and again, I'm going to simplify this. So it's not so complicated. But because it is so early and so few people doing things, but so many new ways of transactions have been opening up just to make one simple example.

All these games and platforms produce their own coins, their own cryptocurrency, so to speak, that has an utility within their world. You'd use this coin to buy a new type of skin for the NFT to change its color, whatever the utility of the coin is, right? But in order to stabilize the coin, they need what's called liquidity pools,

just something to back up these things. There's a whole ecosystem out there where people are basically providing liquidity to these bulls and earning 20%, 30%, 40% APY. It is so early. So my message is here I am, I teach at HBS, I'm supposedly an adult, ideally I'm not through my trauma, I'd reconcile myself, whatever, I'm like a teenage child playing with NFTs. So there's something there, it's my only point. Don't dismiss it. You've definitely changed my mind. I have to say. By the way, I'm an O'omba or onboard you as a case study. So by the way, I would love to. I would love to. I'm literally, I want we're done. I'm going to set you up so that the next time

you're doing a podcast, we'll see if I've made you addicted to it or at least a believer in it. Yeah, I'd love that. So let's talk about our SE Ventures. It's a private investment firm that you started, you're the CEO, and you've helped companies like War Reparker. What are the other companies that you've worked on with this? Actually, War Reparker 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 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 when offering equity. And so the epiphany I had with 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. 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 Christine Atosi a 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 Christine Rapose and my team at RSA.

We own Magnolia Bakery, which we acquired. I'm giving all the good food stuff because 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 that 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 there's only one Gary.

Gary is Gary. My role is minor, and I enjoy the minor, the role behind the curtain, not behind the curtain, because that's not true, behind scenes, helping scale. That's what I do across the portfolio. Version 1.0 was building things from scratch. We helped launch Rezzy. We incubated that with Ben Lovebidol and Gary Vaynerchuk. And now it's about owning significant stakes and great consumer of brands. And Rezzi is like a restaurant software or something like that.

Rezzi is a competitor to Open Table that was born, maybe six, seven years ago at this point, and then was sold to Amix. And now, Amix owns Rezzi. But in the early days of RSC, we would build a company 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 interest 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 at Harvard. I backed that for Labs, which is a big NFT platform company, Thrasio, recently invested in. OpenC is another one. 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 can 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 set. But if you think about like big artists, a big artist doesn't really have a platform to communicate or put a brand in front of their 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. So it's a natural place for like Real Madrid has like a hundred million people following. So it's a natural place for a Snapchat and 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 have a, you can see them pretty early. And often in those early days, the impromotor 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 NBA backs like the NBA did with Dapper Labs early, that gives Dapper Labs a massive

opportunity, right? So that's really it. It's just people trying to get that dedicated core fan base. Got it, got it. Okay, let's talk about VCs and teach my audience some stuff about VCs. So aside from just giving money to people, what are the non-financial things that a VC or private investment firm would do for an entrepreneur?

Well, 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 aren't 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. To make that a little more explicit, explicit, like a great VC investor, somebody who can come to and say, I'm really struggling to fill this position. I need a C.O.O.I. 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 and, you know, in Sally and Mark or competing for the top spot, you know, whatever, whatever the issue, that VC will help you source that person or will help you synthesize that fat 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 of hold back, because if you're sharing 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, 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 notchpreneurs 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, this product is going to fail. It's clear the market has spoken. How long will it take you to kill it and acknowledge it and shift directions and so many things will get in a way of making that decision, fear of being judged, you know what I mean? Like, you know, if we 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 see in the reverse,

when you have in bunch of investors, you know, wearing their Patagonia vests and staring at the spreadsheet, you know, never had never had an operating job in their life. And like, just ended 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, they've 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 buy start to 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, is that going

to be practical? So how do you have time for all of 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 bootstrap the whole thing right and I think that's my that's what upcoming question. Okay, so if you have 500 companies that you're invested in, how do you have time for all of that?

And obviously, people are gonna 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 wanna 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 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, you know, 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 like, 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. My wife happens to have my best friends. So I don't have a need for a ton of friends and see what 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 in three, I scale. So I'm always scaling trying to 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, by partner calls, 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?

So, but you may as a great point. It is a delicate balance. I'm like, I always, I'm sure I'm always pissing somebody off saying, I'm gonna be able to hold you, I miss you. I'm like, I'm sorry. I'm just trying to do something bigger. 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 and I was like, why am I so depressed?. 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 the 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'd give this advice to people too. Nobody wants to go on a rescue mission.

When you're trying to solicit support from whether it's a new investor or an existing investor, like come up with discrete, actionable 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 too to sort of extract from you what's most impactful, but leave you with enough bandwidth to do what you want to do,

right? I'm supposed 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 know, 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, you know? Because I get that in my, I tend to get overly involved. And I, 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, 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 bootstrauffed my company. I started my company as a side hustle while I was working at Disney streaming services

in marketing. And I grew it for six months, but as high my quit, I had 35 employees all over the world. And now we've hit two 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 30 K 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 they're podcasts 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. A lot of people tell me I should go down that path and figure that out and start raising money. Currently, we're kind of just like, well, we could probably take this all the way, like the way 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, you 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 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, a lot of artists' 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. I found this even when I'm teaching HBS, it's like we have this presumption that the object of the exercise to create a business worth $100 million or a billion to have these

markers where it's so hard to make $1.00 into two and to be on your own completely autonomous, no boss, and feed yourself. I marvel at that. Like wow, you went out. So you're already doing it. Like I think 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 are 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 there, you're going to start this new media property, right? And you needed to raise $500,000 to create this media property. But with that 500 grand, 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 a whatever, five X multiple on Yadda Yadda. 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 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, or kind of,

or can I? Those are all super great thoughts that I'm gonna 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 don't think I'm on an agency. If you're going to run a pure agency, then most of the time the answers you don't need investment. You build it again. You win the contract, you hire one, you have some more free cash flow, you can hire slightly ahead of demand, because you know the end 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 office that I like to create the problem for myself and then know that we have an infinite capacity to get ourselves out of situations. So I place 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 pay them. That's more important in taking an outside capital, actually. That's exactly what we're doing right now. And I'm just like looking 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 a really 100% bootstrap. We were a bit of money went into a choir pure out, but really, actually, 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. Okay. So, I do I have a future in this. Should I? Yes. Let's talk. Let's talk. I listen. VaynerMedia has always been my dream. Don't get me started. I'm about to be on Cloud Silver's

podcast too. Oh, 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 of follow up questions. Oh, okay. So maybe I put on kind of the Shark Tank context, but I think it applies to everything my time and I was on Shark Tank. 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 a number one, like I mentioned earlier, self-awareness in an entrepreneur. And it's like, those 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 sharp tank, 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 the president's like, what all do 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 the others who bring them along, right? So it's all about I be eye-to-eye. That tells me your ego is very fragile.

You may be a narcissist. You're going to be unlabeled 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. I look for the ability to bring other people around. And of course, I look for mastery of subject matter.

And people who are looking to delegate everything or outsource it, who don't have respect for what happens in the weeds, 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 things are going to weigh with that be ego,

well, 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 this is 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 ask them,

what's your for-wall? You know, 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 cost, for an example, should be no higher than 10% of your total gross revenue. If you tell me you're the chef, I kind of just handled the food, I leave that to build,

they do it, it's like, no, no, like food, we'll just cook in your kitchen. The opposite of the other thing is to make a profit on 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. I'm the worst deals I've ever done in my life or when I partner up with a private equity firm and they've got billions of dollars on the management and they bring in all these experts to do these experts reports.

And then I'll go into the deal and then the day when I'm like, did you notice that the CEO is delusional? I mean, the reports are really great, but a great product will never eclipse or overcompensate for a bad CEO, a bad founder, right? Whereas the other thing is true. Is 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.

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for 15% off an annual membership. Masterclass.com slash profiting. 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 it to service 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 entrepreneurialism, which, 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 acquired to be successful. I mean, you know this because you've had to manage people now. If you are passive aggressive

as a leader, you'll ultimately fail because you're going to hate the conflict. You're not going to 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 into 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 greater good, how valuable that is. And so those are 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 I know 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 in entrepreneurs a little bit like, well, I'm going to have Google. I'm going to already know that. I'm like, no, it's different

from knowing something in the abstract and having an imprinted on your cortex. So that's what I'm saying. And I 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. Now, I'm successful because I had those experiences to learn off the back of another company, basically, a big company. And so what I tell people on my show is, let's say you failed as an entrepreneur, don't 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, you know?

Yeah, I know. 100% I have an amalgam of that which came before. It would be impossible now to pull in a little bit of Buddhism, right? Like, what is a book? Is the book the words on a page? You ought to have 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. When in my 20s, when my whole identity was about being like, doogie house and you know younger than everything right and also just being the hero took care of his mom and all this like that was my whole construct of 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 and like, God, if I could see 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 see got 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, and me in 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 see it 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 on myself. And so, 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. Hopefully you still have some time. So there's a thing called the great resignation happening right now. We're 40% of the workforce after COVID

has decided to become an entrepreneur. I'm one of those people, right? Started a business during COVID. What do we do as startup businesses and small businesses, especially service-based businesses to actually recruit people to work for us when there's so many people who don't wanna work anymore. They're either getting a welfare check or maybe that's not the right word, but some sort of a check

from the government or they're trying to start their own business and they're not interested in working for someone else. So do you have any tips for actually recruiting entry-level employees? No, it's fascinating what's happening and quite real. I mean, it's a combination of different forces of work. It's this notion that that we don't have to go back to work that everything can function on, you know, on 60% optimization. Like, that's eventually gonna show up somewhere. So that's number one, too.

I think it's partly a reflection of a moment in time where the all clear has not been issued, right? And we're in this sort of, this interstitial, where you kind of wear a mask when you walk into the restaurant, but then if you sit at the bar, you can take it off, even though you're surrounded by a hundred people. Like, nothing makes any sense. And so we're still, I think, reconciling the aftermath. If we were in the movie, you know, we would still be gathering for the big speech an Independence Day, but like the speech hasn't happened yet. So what my point is, this can't last,

right? It won't last. This notion that we can have absolutely everything is not true, because eventually people will want to get ahead, will want to put in more time, whatever. I think the part that is permanent is frictionless behavior in the workplace and in our home life. So what I mean by that is like no one's going back to commuting for no purpose. If there's no being in the workplace and in our home life. So what I mean by that is like no one's going back to commuting for no purpose If there's no being in the office you cannot get people to come to the office and so what I love now is the idea that That so many meetings the default is still zoom so the amount of you know energy that that unlocks the amount of productivity is pretty extraordinary But the reality is I actually don't have answers on their courting front. I've encountered the same exact thing

I'm amazed by some of the things people say that would be like But the reality is I actually don't have answers on their recruiting front. I've encountered the same exact thing. I'm amazed by some of the things people say. I mean, I'm really interested, but I've been taken up the scuba diving class. So I just kind of feel like I want to and I'm like, what? What's going on? I just think in another six months, it doesn't look like this. It doesn't look like a hybrid. I do think that the all clear. I think it's important for our leaders politically to say, doesn't look like this. It does look like a hybrid. I do think that the all clear,

I think it's important for our leaders politically to say, all right, we've hit a threshold. It's time that we get going again. Where's the, come on, America. Let's get back to it. We gotta get out of the state of suspended animation. I think it happens in six months is my guard. So over those who will hear this,

this little time capsule, we are in the year 2021. What's the date today? So we tell everybody. October 21st. All right, October 21st. So I think I'm gonna give myself by to next May, by next May, we're back to normal, not to back to how it was.

We're back to normal with a hybrid, where people are all working and how, going about our lives again. Oh my gosh, I hope so, but I'm so glad there's no more commute. And I'm so glad that I'm an entrepreneur and I never have to take the New York subway ever again in my life. I'm so happy for that. Oh my god. Funny, you, I always say that's so corny, right? But you really do need to know your why. Like, what are you fighting for? And no matter who you are in life and whether you're an entrepreneur.

But my why has always been to achieve more freedom and autonomy because I perform better and I will do more in this world if I have more unfettered ability to pursue what's in my head. And I've wanted it since I was a kid. I've wanted less subjugation, less control over me. And I wanted more mastery of my own decisions

because I'm a vision. And the more unfettered ability I have to implement the vision that better off, I believe the world will be, but the better off I will be. That's my why is autonomy. So it's like, what's your why? It sounds like your why is also freedom and autonomy. Yes. 100%. Not a little shit stuff like commute, which I get. As we wind down, 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 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. I love that topic. I feel really passionate about this general idea that when you're on, when you're, and 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, 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 color blind. And I mean in a negative way, understanding obviously 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 in their classmates and I look at what I grew up around in Queens. And I'm like, it's breathtaking and makes me so happy for the future. So it's honest, and I'm 46. So I can, I can not outbuild at all. I'm not going to align myself as my only points. I'm going to align myself at 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 it. Like it's uncomfortable. Like what is this TikTok? It like dancing videos and, and, and, and, you know, and like, we can't relate. But that's on each of us as we age to refuse to become obsolete and instead embrace our question or wonder or tip our toe into what's going on. You know, if TikTok makes you uncomfortable, then go open and 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 years 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 and humanity or among them, but slavery, like, and that has long standing repercussions, and we need to come to terms with them. We are destroying our environment. We're all going to hell. Like, these are important conversations and Gen Z is stimulating and spurring them. So I think most of the maligning, maligning comes from this sort of discomfort with like, the world seems to be changing so fast and TikTok so stupid. I don't know. I find anytime 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

an 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 profiting 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 in 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 or you're really going to care that you did this, it's mostly I didn't do this. So the the care to 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 blossoming. Who am I today? And then I set my intentions based on home 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? Well, I'm spending a lot of time on LinkedIn. That's kind of my favorite place. And I am so mad against 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 at HarperCollins. So find me only dead. Awesome, cool. Have you back on when you have your book launch? Can't wait for that. Thank you so much Matt. This was such an awesome conversation.

Oh, thanks for having me. You're amazing. Your questions are amazing. So thought provoking and I appreciate it. And there you have it, young and profitors. My first interview with a shark in the books. And it was so surreal to interview Matt Higgins. I love Shark Tank.

I'm like a fanatic of that show. I've watched like every single episode. And then I got Matt Higgins on the show. It is unbelievable what you can achieve when you just put your mind towards something. Like the people I get at interview, sometimes I have to pinch myself that I get to interview these people.

It is amazing. And I promise you, young and profitors, this is not gonna be the last shark I have on the show. I'm gonna have Mark Cuban. I'm gonna have Barbara Corcoran. You bet, I promise you, this won't be the last shark on the show. And when it came to this episode,

we covered a lot of ground. Matt's story, to say the least, is truly inspiring, from his beginnings and queens to his decision to drop out of high school at 14 to then being the youngest press secretary to the mayor of New York at the ripe age of 26. And now look where he is today. He's one of the most prominent businessmen in America. He's on national television. He's one of the most prominent businessmen in America. He's on national television. He's invested in some of the biggest companies in the world. Matt has accomplished so much and he did it all by betting on himself.

That is the main takeaway from today's episode is you've got to bet on yourself. Matt covered a topic that I think is really important for people to hear, knowing yourself worth. He told us that when you know what you're good at and when you know what you're worth to your company, you can gain some leverage, whether that's leverage in negotiating a raise, leverage in a promotion or a title, or even leverage to quit. Ultimately, he told us to never be afraid to bet on yourself. I hope you remember that. And aside from that beautiful advice that Matt provided, he also gave us some great insightful

tips for business and leadership that I want to revisit. I specifically want to recap what he looks for in an entrepreneur when making investment decisions. The first thing he looks for is conviction. Having the ability to stand by your idea, even when someone is challenging you, remaining confident in your product speaks volumes. And number two, humility, always giving credit to the people around you, and using we instead of I gives insight to not only who you are as an entrepreneur, but as a person as well. And number three, Matt believes in the power of saying, I don't know.

Being able to have the confidence to say you don't know something, instead of lying or blaming someone else, gives us a chance to look at your willingness to learn and take responsibility. This was truly an inspiring conversation with Matt, and I hope you guys enjoyed it as much as I did. Thanks again to Matt for our conversation and thanks for listening to Young and Profiting podcast. Be sure to connect with me on social media. You can find me on Instagram at Yapp with Hala or LinkedIn. Just search for my name, it's Halataha. Big thanks to the amazing Yafteem as always,

this is Halah signing off. Are you looking for ways Asois, this is Hala, signing off. Are you looking for ways to be happier, healthier, more productive and more creative? I'm Gretchen Ruben, the number one best-selling author of the Happiness Project. And every week, we share ideas and practical solutions on the happier with Gretchen Ruben podcast. My co-host and happiness guinea pig is my sister Elizabeth Kraft. That's me, Elizabeth Kraft, a TV writer and producer in Hollywood. Join us as we explore fresh insights from cutting-edge science, ancient wisdom, pop culture, and our own experiences about cultivating happiness and good habits.

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