Matt Higgins - CEO & Co-Founder of RSE Ventures | Burn The Boats

Welcome to Success Story. I'm your host, Scott DeClaire. The Success Story podcast is part of the HubSpot podcast network which has other amazing podcasts like Business Made Simple hosted by Donald Miller. Business Made Simple takes the mystery out of growing your business to make sure you tune in wherever you get your podcast. Today my guest is Matt Higgins, an American businessman, author, and the co-founder and CEO of RSC Ventures, a private investment firm that focuses on sports and entertainment, media and marketing, food and lifestyle and technology. In 2012 Higgins co-founded RSC with Steven M. Ross, the founder of related companies and the owner of Miami Dolphins. Higgins served as vice chairman of the Dolphins from 2012-2021, having previously been a high-level executive within New York Jets. Now he spoke about the burn the boats philosophy the title of his new book, why trusting our instincts is so important, how we can predict CEO failure based on one particular trait, optimizing anxiety, how we got on Shark Tank, his first investment, what he looks for in founders and why he reminds himself that he's going to die five times a day. Well I'm going to bet to piss off every parent who's listening to this right now, but the life event that said it all in motion from honest is dropping at a high school. It's actually the single greatest decision I made throughout the course of my life and it said everything in motion. I can tape you deeper into it if you want to go back in time. I would actually love to because that's obviously a very unpopular view, even though I have my own opinions about whether or not college university is worth it and MBAs are worth it. I've never made an argument for high school so why is that? Okay so a little bit of context when I grew up in place called Queen's New York and being taken care of by a single mother, living in a shoebox apartment. These words tend to lose meaning, abject poverty, it sort of loses its emotional resonance, but what does that really mean to say those words? For me it meant not sure what I was going to eat for dinner, it meant getting government cheese literally from the US Department of Agriculture, a big block of cheddar cheese, by the way, of which I keep the empty box on my desk to this day years later to remind me where I came from. It meant selling flowers on three corners, that little kid who would knock on your windows, excuse me sir, would you like to buy some roses for your wife or on Mother's Day? It just meant surviving. It meant becoming a parent of another parent at a very young age, right? Because my mother had all sorts of health disabilities and so that was the context I was born into and around 10, 11 years old, I was having all these odd jobs by the time I was 13, I got my first big, big boy job working in McDonald's and my job was to get on my hands and knees and scrape the gum underneath the tables in the party room because if the gum were to land on somebody's dress, you know, ruined the party. I can tell you everything about dry gum if you're interested, but that's the context, right? And so I spent a lot of my early years desperate like any little kid when they see their parents suffering and they also want to be selfish, right? I was always juggling the idea of feeling like I was going to be a hero and save my mom and then being selfish and wanting to have a typical wife, right? So those two things were happening in peril and a lot of my early years were spent just hoping a white night would come that there'd be some cavalry, you know, and I'd remember taking my mother to the ER because we didn't have insurance and just sitting there thinking like, can anyone intervene? And my mother's health issues were very generic, but they were compounding. She had obesity and thyroid gland disorder. So that's the context. And eventually I got to the point of saying if I don't have a trajectory changing event, we're facing imminent disaster. My mother's going to die. I'm unhappy with my life and I can't keep up school at this pace anyway. And I had an epiphany, which is the following. My mother actually went back to school. She was a high school dropout, but she was brilliant, born into her own dysfunction. And I watched her go get a GD and as a nine-year-old boy, she would take me to classes at Queen's College on the weekends. And I was probably around 13, 14. I had an epiphany like, wait, and I had it because I was looking through a penny saver, a free newspaper in Queens. I was looking at the job section and it said, you know, $9 an hour, delivering flyers, college students only. And I was like, college students only. How do I become a college student faster? And I had this idea, well, what if I dropped out of high school at 16, got a GD and got into college because my mother got into a GD. And I remember going to college night at high school once I enrolled in high school. And I was like, excuse me, sir, you know, if I were to, if somebody would have a GD and they did really well, you know, could they get admitted to your August institution? And I talk about this in a book. It's like a degree of no bless oblige. You're like, yes, young man. We believe in second chances, you know, very remote scenario, obviously, right? And so that set in motion, like, I'm going to do something radical because that's what the situation calls for is a radical change. I'm going to drop out. But I also knew that every time I surfaced this idea to any adult, I said, you're absolutely crazy, including the guidance counselor that I was going to ruin my future because of the stigma of being a high school dropout, that if I didn't actually make it impossible for me to do anything else, I was going to back out. Like in other words, if there was any possibility of salvaging high school, I wouldn't go through it. So I decided I was going to fail every single class and get left back. And so I spent over two and a half years in a, in the same home room with the, I called it the land of misfit toys. Some of the kids would beepers on, taking very different career choices, equally ambitious, but just different. And then the, and then the moment of truth came. So I had my reason why I slate that decision is I, number one, people didn't have the context for why I was making it. Because when you're growing up poor, you're doing everything you can to hide it. We all carry around a degree of shame. So you have to be careful about the advice you get, unless you've been fully transparent with, with the context. So my guidance counselor didn't have the context of my mother was degrading in the room next door. Number two, when you're back as against the wall, you tend to make the best decisions, right? The lot of clarity came with the poverty and with the desperation of taking care of a parent, right? And number three, when you see an angle, don't wait for validation, right? You don't need validation. If, if your instincts are telling you, this is the right plan for me, even though no one's ever gone in this direction before, nobody would affirmatively torpedo high school, to be a high school dropout. But it actually made a lot of sense to go from making $375 in McDonald's or $5 at the, at the, at the, at Delay on Woodhaven, Mulvard to nine bucks as a college student. That's crazy. That sounds because the most important thing was I needed to get out of this situation. So I dropped out of high school and a year later, I went to my prom as president of the debate team. And I remember seeing my guidance counselor, my teachers, and the look of pity, because it was pity when I dropped out, like what a shame, what a waste, to one of respect, with one chest move. So that single burn the boats move is the reason why I wrote this book. It's the reason why I was on Shark Tank and we can get into everything else, but you asked me. So I gave you an unpopular answer. I'm sorry, moms and dads out there, but now that you have the context, it's not as simple as telling everybody to just drop out of high school. No, but you were very clear on your vision. And you know what? The one thing that I see emulated in a lot of successful individuals, it's always a chip on the shoulder. It's always the, we got to, there's a reason why you're so clear on your vision and there's a reason, like you didn't just drop out of high school. And again, like a lot of other kids who dropped out of high school, maybe they had, maybe they had alternative career choices. You're very purposeful and strategic, but that chip on your shoulder, I always, the burn, burn the boats is a great, is a great concept, but the chip on the shoulder makes it possible. And you had this environment that forced you to not have an anger, but just have a little bit of unhappiness with the situation that you were in. So I always like to pull out that origin story, but then I also like to ask you, how does somebody manufacture that feeling? Because that's what it takes to be successful. I love this question, by the way. I talk about it in the book, you know, the burn the boats. When I break down these common patterns of successful individuals, successful leaders, and you isolated one of them, which is defiance. I actually, I use an industrial psychologist way too much, everybody's always you and the psychologist, but I think the fish rods from the head, right? So I always try to get the head right and look under the hood when I'm making writing a check. But one of the qualities that she identified that repeats over and over again is defiance. That when you're overly, overly deferential to the status quo or to others, you can't have breakout success. So while, you know, I like the way you distinguish it. I don't really have a chip on my shoulder, I'm not bitter. I left that experience incredibly empathetic and I retain that empathy, but I am defiant. And I have found the worst decisions I've made of when I've tried to outsource my judgment to suppose it experts, because a exceptional generalist will have much better judgment than a mediocre specialist, specialist all day long. And so defiance is a critical thing. So how do you manufacture it a bit? One, you had to believe it that it's necessary. And two, honestly, it stems from self, from self worth. Like if you really believe in yourself and believe in your destiny and believe that there's better for you and you're not entitled to better for, but deserving of better for you will seek it out and you will be defiant when somebody's trying to force you to accept mediocrity. We see it manifest all the time in the relationship context. When I see somebody tolerating a partner who's putting them down, putting them in their place, you know, or is just unhappy, it's usually for one of two reasons. One, you don't believe you deserve better or two, you don't believe better exists, right? And they're very, they're nuance and they're different. But if you approach every situation with a degree of defiance, where your base case is, what's the best I can have in this situation? You will always be a little bit wary of accepting mediocrity for yourself. That's a great, that's a great answer. I love that. And I've never heard Chip on the show that reframed his defiance, but it's a much more positive way to look at it. I've never. Yeah, because people say to me, I still got a chip. I'm like, I actually don't have a chip. I like crying like a heartbeat when somebody, when I encounter somebody else's pain. I have the opposite of the chip. You know, I have defiance and insistence and an unrelenting energy, but, but I'm not bitter. So, okay, so now, now you've moved yourself out of this really destitute situation that you're in. Burn the boats at later stages in your career. What does that actually look like for you? So, and I think it's good to frame a little bit what the phrase mean. Why? I became obsessed with this idea. Actually, because I think we've heard some of us have heard this before, but I've never heard somebody go so into the weeds on it, yeah. Yeah, no, it's funny. I remember I was with Mark Cuban at an event, and I made this burn, you know, burn the boats reference, and he's like, burn the boats. What are you talking about? And I was like, oh, I thought, I thought this is sort of like in the vernacular, and I realized it's not entirely. So, what, where's the phrase come from? Throughout recorded history, from time immemorial, you'll see military strategists will invoke this idea that they weigh the way they got their army to overcome improbable odds. They were outnumbered 10 to 1, whatever the cases, that they literally burned the boats. They eliminated their escape out, their escape hatch, art of war, they referred to burn the boats and the cooking pots. And the reason why is that humans perform better when they have no plan B. They have no, you know, escape route. Now, these tend to be some pretty nasty people in history. So, I have appropriated this military doctrine and decided to use it for the rest of us in peacetime. So, let's forget Caesar, you know, Sunzu and Cortez, and pull it forward for our own life. So, I got obsessed with this idea, and then when I work for the New York Jets, for those who don't know, I used to oversee the business of the New York Jets back in the day, and I work with Rex Ryan as a coach, and, you know, Rex is an animated individual, wears his heart on his sleeve and can fire anybody up, and we were playing the Pittsburgh Steelers in the playoffs and the underdog, and Rex gave a speech about this idea of burn the boats. I'm just asking you to go all in for one day, and don't worry about what happens if we fail. Don't worry about the consequences. Just give me everything you got for one quarter or one half. It was, I think it was a halftime speech. No, it was the night before, for one day, and the team won, and you could feel it was palpable in the room how catalytic this idea just surrendered to the goal, submit, let it go. And so, I said, okay, that, I want to prove to end up to people that humans perform better without a safety net, and I want to approach it from two different angles. One, I want to approach it empirically. So, I want to survey history, psychology, and science to prove that humans actually perform better without a plan B, and the reason why is when they, when a lot of folks hear the title of this book, they reflexively say, well, I can't take on risk. This is irresponsible. It's called burn the boats, not burn the boats with you in it, and it's not called blow up the bridges, right? So, the idea is eliminate your plan B that doesn't part of the process of doing so is actually processing the worst case scenario. One of the, I talk about this in a book, one of the first steps is to synthesize and recognize what's the worst that can happen if this big move I'm about to make goes wrong. And by doing that, you can now can peacefully accept the risk because you've already processed, you know, the downside. So, one, I want to approach it from science and history and psychology, but the other is I want to provide actionable case studies, illustrations so that you wouldn't distance yourself from the individual. What I mean by that? Like, I'm on Shark Tank. If you met me and I look well dressed, you can make lots of assumptions about me. I teach at Harvard Business School. You could assume that I was born on third base, right? I want to deconstruct who I am so you see the origin and the journey, and you could say, oh, you were a high school dropout. Oh, you have imposter syndrome. You were divorced and you're embarrassed by it. You went through a lot of pain. You suffer from anxiety. You have a degree of lingering PTSD. You're not over your stuff, right? Like, I very important to be to manifest in this world as a representation of how I got there, not where I am. And I then broke down 50 different individuals that from every different angle, founders, billionaires, actresses, Scarlett Johansson as a friend of mine, an Olympian who became a paraplegic at 14 and thinks her life is better off for it. An activist who is the victim of sexual abuse when she was a child from her nanny. Every angle so that those who reflexively say, I can't afford to burn the boats and I can't afford to let go of my plan B. And those people are different from me. I want to offer so many different case studies that it would be hard not to identify with something. And the second part, Instagram is full of so many, you know, empty platitudes, you know, sunny, sunny advice like, burn the boats, you know, get out there. Like, that stuff is useless. It doesn't last more than 30 seconds, a little adrenaline hit. I hope what I've done with a book is provide an actionable blueprint to to embrace a growth mindset and to just let go. Like, shed your shame, shed the things that are holding you back and move beyond the rhetoric into actually actionable advice. And okay, so let's lay out like a little bit of this framework so people can understand it. So what is the framework that you actually teach over? Because obviously this is probably something that you've seen again across all those leaders that you just mentioned, you've probably seen it with. I'm assuming some of the successful investments you made on Shark Tank, obviously in your own life as well. So what are the main points of that framework? Okay, great. Well, one number one, the whole concept is promised on the idea that the true joy of living is in the striving. And when you go to the top of the mountain top and you look around, you realize there's nothing to see. That the joy was declining when you were looking up, trying to get there, not looking down and looking around. So that's number one. So I think that's true for like 99% of the population. So we begin there. So how do you live a life of perpetual growth and how do you? And the things that stand in our way are either internal obstacles and external obstacles. So I say any journey of transcendence across an authority to make that bull move begins by unlocking the greatest arbitrage entirely within our control, which is self-awareness, right? It's figuring out what is it in me that's preventing me from making that bull move. You know, it's in whether it's imposter syndrome. And I talk about how to overcome it, whether it's shame. I think a lot of the reasons why leaders underperform is because they haven't gone through the exercise of shedding shame. So how do you create a place and space for you to go ahead and let go of your vulnerability? It's how do you retrain the voice in your head to be your greatest ally rather than your greatest enemy? I talk a lot about sabotage. And so with it's a little bit similar to what I do when I'm assessing an investment is I analyze and look under the hood because the fish rods from the head is the Italian side. So you need to undertake that own exercise for yourself. My book takes you to the journey of how I did it myself and how other leaders have reflected upon what's holding them back and overcome those internal obstacles. And then they're the external obstacles that stand in your way. I go through the corporate saboteurs. And I tried to put into words things we all feel and I'll make it a little abstract. They are these archetypes that manifest in a corporate setting as leaders, CEOs, managers, and they're either victims, they're martyrs, they're corporate gaslighters. The one that I think a lot of people can relate to is this idea of a withholder. So what's a withholder? A withholder is someone who recognizes that an employee or a partner in a relationship context is a pleaser and is dependent upon validation and affirmation in order to sustain themselves. And they understand that if they withhold that recognition, that praise, they destabilize that individual, that pleaser, and they'll work that much harder to go ahead and over and get that approval. So I tried to in the book deconstruct these unsaid things that operate upon us that hold us back that prevent us from going that destabilize us so that if you can identify it, you can deal with it. And I love the withholder one because when I mention this to people, oh, I feel that I feel like somebody has denied me the praise that I need and one, I'm sad that I can't get it and two, I'm sad that I need it. And so I think when you find when you read the book, again, that's pretty abstract stuff we're talking about, but you know, you can reduce these things that are operating on us that are holding us back into words, articulate them and then manage them. And so for each of these ideas, I come up with strategies for how to how to move beyond them and talk about how I did it in my own personal life. And one thing you mentioned, you mentioned perpetual growth and then when you adopt this mindset, it's as almost a forever mindset that you apply to your life. So for people listening, this could be very stressful because now they're thinking, oh, if I really want to make it, I always have to be uncomfortable. I always have to be growing. I always have to, you know, I got the next career advancement or I launched the side hustle, turned it into a company and now what do I have to burn next so that I take it to the next level. So I get that you have to enjoy the journey, but does this not turn into perpetual stress, perpetual discontent? How do you mitigate that so that you still enjoy what you're doing if you're always putting yourself into this position of high stress, high growth? Such a great question. I talk about this in a book too because if position the wrong way, you'd be like, stop, like, I'm good. So, so a couple of thoughts on that. It is only stressful if you live in a perpetual place of anticipation, if you're never present, if you're always worried and thinking about, you know, what's going to happen to downside. I talk a lot in my book about how to retain your group grip on the moment and how much contemplating my own mortality factors into this philosophy. I have an app in my phone call, five times a day, this sounds actually crazy, but five times a day in different ways it reminds me that I'm going to die. It's a different philosophical message from Socrates or somebody else. It's a little bit of stoicism built into that. That's right, a little bit of a lot of bit of stoicism, right? On the simple idea that when you're reminded of your mortality, the number one thing that we all fear, it actually does the opposite of what we're afraid. It makes us peacefully locked in on the moment. So number one, in order to have a joyful life of perpetual pursuit, you actually have to stay present, which is, you know, counterintuitive. The second thing is it's okay to take a break. It's okay. I talk in the book about consolidating gains. You achieve a new milestone, you consolidate it, you go ahead and you lock it in. You don't want to be a grasshopper where you're jumping from one team to the next. The point is sooner or later, if you're like most people, Mel and Collie will set in because you don't feel challenged. So Mike, the point of the book is not you have to perpetually jump in a frantic way from one thing to the next. The sequence is burn the boats, achieve what you previously thought was unachievable, consolidate your gains. Because what's the point of achieving things and then the accomplishment is eroded because you didn't focus enough to make it scale. Scale yourself, right? So that it works in your absence or with less energy, right? I talk in the book how I taught at Harvard Business School was really, really hard the first time. The second time, less hard. Third time, every time you repeat something through habituation, you unlock more energy for you to allocate to something else. So again, I want to make very clear to be listening. I'm not arguing that you have to live a life of perpetual discontent. I'm asserting that eventually you will feel Mel and Collie like every Olympian, a marathon runner who finishes the race and you will want another race. And so the thing that holds us back are these internal and external obstacles. I try to deconstruct them so that you can figure out how to one burn the boats to consolidate the gains and then three continue on. One of the concepts in the book is backing the jockey, not just the horse. What does that mean? Yeah, so a bit of a cliche, but there's reasons for these cliches, right? It's just that though some of the worst deals I've ever done in my life have been when I draft behind a private equity firm that has supposed dreams of data and diligence and excel sheets, like it's just all nonsense. The answers are always about the individual, but that's, it feels inaccessible, borderline mystical. And so the folks who under index on EQ wanted to be about the numbers and it isn't about the numbers. It's about the jockey. So it's just something I strongly believe in and I put a lot of energy into like I said before looking under the hood and figuring out what makes people tick. I'm actually curious because obviously we're speaking more generalized, but a lot of the audience here is founders entrepreneurs and obviously very interested in your opinion on that because you work with a lot of them. So I want to pull some lessons out from what you've seen with all the companies that you've invested as a, you know, building a private equity firm also as an actual angel venture capitalist. But let's talk about Shark Tank that's always a fun topic. So I'm actually curious. Why, because you have great business ideas, experience, but why do they choose you? What's the what's the differentiator with you that allows you to be on that show? What's the value at? I mean also a great question. One that I asked myself when the lights went on saying, wait, wait, what? That's Cuban looked at me like, who invited this guy? Why did they choose me? I if I'm honest, I chose myself and then I manifested it. If you held me up against the consolidation, yeah, I mean, let's just be honest. If you held me up against the constellation of people who've tried to be on that show or want to be on that show or pretend like they don't want to be, you know, there are some serious huge CEOs out there. The difference is I thought it was possible. I thought I belonged on that set and I worked for a year of my life to put myself in a position to do it. And the end, why did they choose it is because they thought the origin story was compelling and I had something to share. They thought the way, you know, I approach business was intelligent, you know, probably wanted a New Yorker, you know, kind of like there was a whole range of things. But I think that's the end of the story is less interesting than the beginning that somebody like myself who, you know, objectively didn't have any business being on the set at the time, reached out to some random producer and said, would you give me a minute? And I met him on his name is Clay Newbill. My agent got me a meeting. I'd never been on a Hollywood set period. And the sun was setting. He said he'd meet me for coffee was supposed to be 15 minutes. You know, hour and a half later, we're talking about what we're talking about right now. So it began with the belief that I belong there and that I was willing to put in the work and the uncomfortable energy and the honestly the embarrassment and ridicule and the audacity to put myself on that set. I just want to take a second to thank the sponsor of today's episode HubSpot. It's time to get out of your spreadsheets. With HubSpot CRM, you get real time data at your fingertips so your team stay in sync across the customer journey. You track your contacts and customers and personalize emails and bulk and get the contacts you need to create amazing experiences for your teams and customers at scale all from one powerful platform. It's why more than 150,000 companies already use HubSpot CRM to run their business better. Plus HubSpots user friendly interface sets you up for success from day one so you can spend less time managing software and more time on what matters your customers. There's no better time to get organized. Learn how HubSpot can help your business grow better and get a special offer of 20% off on eligible plans at HubSpot.com slash success pod. And now I love the answer because I'm sure a lot of people ask you and I will ask you, you know, like what makes a great investment and what what a great founder looks like but I love the lessons that you pull out from your own story to be quite honest. Like you're very self-aware and just totally because we're talking right now and it's hard for me because sometimes people be like, you don't have to tell all that. I just say it's because you're one of the biggest investors in a country, whatever nonsense and I'm like, well, it's not true. Like it could be true and it's sort of true on one point. It is sort of true. But I don't think that's the accurate truth. And if I say that, the reason why it's important to me to be transparent about this, I want somebody listening this to not separate yourself from me, right? And think, oh, well, you're that's why you are. No, no, no, no, no, I like, I worked hard on it. And I also don't want to perpetuate this idea that they chose me, right? Because that's another thing. Well, of course, right? Like they chose me. It may look that way now because of my credentials, right? But I don't know. We do a disservice when we don't pull back to Kurt in my opinion and we perpetuate the myth and then people feel like the myth is not for them, right? So when you when you work with all these different founders and you work with all these different entrepreneurs, what do you look for in because I'm a founder, centric investor. I'm very bullish on the person. Like you just mentioned, you know, it's great to go into the spreadsheets and the data, but you can sell everything with a great spreadsheet and a great PowerPoint. Like it really, it really depends on the person who's running the company. So what do you look for? What is what is the characteristics of a business leader? I'm sure some of them are actually disgusting your book because that's what you look for to invest in, but just quantify for me a little bit. Yeah. So let's let's eliminate intellect, table stakes, right? Do you have intelligence? Just to go to the, you know, the core issues, right? Number one, I want to feel like the universe or God put this person on this earth to pursue this business. So I want to see a connective tissue to something in the person's life or their values that led to decorate this specific business because that connective tissue is going to be the thing that sustains them in the dark hours, right? When nothing is manifesting or playing out as as that PowerPoint. So I want to make sure that the Y is strong enough to sustain someone because that helps de-risk my check, right? So those are just like two specific, you know, examples. And then in terms of the person, I am above all else back to what I said before. I'm looking for proxies of self-awareness because, and again, this, I love that I'm talking to you and founders who are listening to it. They can understand what I'm about to say, right? Why is, why is that so important? Every single CEO founder listening to this is going to have to pivot their business at some point, right? And I believe that every one of us has given us, given an opportunity to avoid disaster before it's too late, right? The universe is benevolent fundamentally, in my opinion. And if you look back to some of the worst decisions you've ever made in your life, you can identify the moments where like, oh, if only I just had, you know, like we all have them, if we're honest. And so the ones who make the pivots and the course corrections before it's too late are the ones who don't need to see the iceberg port side in order to steer clear, right? Like the ones who could, and I always say, I can determine and predict the few, the success of a CEO by how much data they have to have in order to make a decision that is objectively inevitable. Like you were going to hit that iceberg, do you really need it to be 10 feet away or can you forecast? And so, so self-awareness will enable you to look for those icebergs to be intellectually curious about them so you can find them. And then a degree of confidence and humility will be the reason why you act upon that insight. So why those two together confidence gives you the willingness to look within, the willingness to sort of ask the questions about why might I be wrong? Humility gives you the comfort to acknowledge it publicly and not worry about judgment, right? To recognize that, you know, they're about by the grace of God go I and we all make mistakes. So that's a lot to like unpack, but I'm telling you 100% when I'm talking to somebody, I'm looking for that. So what was interesting about Shark Tag, you have 40 minutes to figure all those things out, you know, consistent with my philosophy. So I'm looking for little tells signals, right? That are parts. So I'll give you an example on the set of Shark Tag. You know when you have an investor come on and one of the more assertive sharks will say like a Mark Cuban or Kevin only be like, you know, this business is dumb. You should change the name and you should no longer sell widgets. You should open a brick and mortar. And the person is like, create an idea Mark Cuban. I will abandon my business and I will open it. If only you'll go ahead and, you know, become my investor, right? And like write that little microcosm of an exchange tells you a lot about the person. It tells me you don't really have conviction in your vision. It tells me you're willing to do anything you, you know, you want to go ahead and, you know, get the check, etc, etc. So I stay very closely to my core philosophy that it's about self-awareness, manifesting his confidence in humility, and I have a bunch of signals that I'll look for. And that's why I use industrial psychologists a lot when I'm writing a large check because I want to efficiently get under the hood and see if I can identify it. Now, if I see somebody under indexing for any of that, it doesn't mean I don't write the checker or I dismiss them. It means I have an honest conversation about the things that I pick up and say, Hey, I'm picking up that you're somebody who won't take feedback or I'm picking up, you're using the word I a lot, but this was clearly a wee situation, but you say I, right? And so I'll give somebody the data. And by the way, as you could see as we're doing on this podcast, I'll also create space for vulnerability by sharing, you know, my story to see how people respond to it. And how do you wake? That's a great, that's a great problem to solve for because you just mentioned that if somebody is so, so passionate about what they're building, that's great, but then you don't want them to waver too much if somebody who's influential offers a new idea, but how do you gauge whether or not they're coachable and they're willing to learn versus their mission-oriented and their steadfast and their idea, which could be a benefit, but it could be a detriment of taking to the extreme because then they won't listen to any outside advice. So how do you balance that out? Well, Jeff Bezos has this great quote, right? You want to be rigid in your vision and flexible in your execution. So I do look for a degree of steadfast-ness in the vision, but that is not, that is not in opposition to being intellectually curious about where your execution is wrong, or intellectually curious about other people's opinions, right? Those two are not. I to a detriment sometimes, I take all these inputs, right? I'm not one of those people. Like Gary Vaynerchuk is amazing. Like he blocks out all the criticism and I don't block it out because I want to sift through for nuggets of truth. Sometimes I relate, like, as a point. So I'm looking for the rigidity in the conviction on the vision, but I'm looking for flexibility in the inputs and intellectual curiosity. And so now you obviously don't want to be destabilized by those, right? So if I see somebody who, you know, can't handle it or, you know, the shoulders are all slouched because they're criticized once. Like that's, that's, that, you know, we need to do a reset. But I don't, I don't think it's that hard to reconcile those two because I don't think they're incompatible. And, and in all the investments that you've made, let's take it back to even when you first started investing. So you're, you're investing career commenced. What was that first investment? What did it look like? Was it a success? Was it a massive failure? Do you even want to talk about it? It's not that's okay to know that's great. I will say when I first partner with Steve Ross, who's amazing, one of the greatest entrepreneurs, you know, most of his career is in real estate. He's known for that, but actually incredibly dynamic and delightful and curious. Always trying to shake things up. But when I first presented this idea, I will partner with you on the dolphins and help oversee the team. But my real passion is to creating things from inception and, and backing great people and helping unlock their potential. I had some specific ideas that I talked to him about. And one of them was this crazy guy who sells wine named Gary Vaynerchuk and, and, you know, this firm that he was building in social media, and we're trying to sell them jets tickets from what I, I understand you guys like that. Yeah, so, so I had Gary was on, it was on my, it was our original conversation, believe it or not. And then another one was a guy named Jesse Derris. So I'll use that as the case study because that was in fact the first deal that we did. There was a young man named Jesse and I had hired him to do public relations at different points in my career. And I think it was 27 at the time. And he's one of those people that is able to identify the patterns of the universe in a way that is almost mystical and makes you a little bit uncomfortable and feel violated. Like, how do you know how this is going to play out, right? I always say the practitioner of the dark arts, you know, but I, but I had a conversation with him all the time you will own your own firm one day. And by the way, just FYI, if you don't end up owning your own firm, you made a big mistake in your future. But we'll just leave it at that. Those were the coach exceptions we'd have. And then when I partnered up, I said, I want to try to put him in business and help create his own firm. And I, and I talk about this in a book about how I call Jesse out, we went for a walk. And I painted a picture of the way sliding doors of how his life could play out. On the one hand, you know, continue to work. Hope that your name ends up on the door one day. You know, you think you'll launch your firm when you're when you're 40. But at that point, you'll have kids and 529 plans to worry about. And you're actually your risk tolerance will go down, not increase. Or you can quit. And we'll backstop it. We'll build a firm together. And we'll get it going. And like he did it, he quit. And just a few months ago, he sold that firm for tens of millions of dollars. He is fantastically, well, think not that that's the object or the exercise, but it's one, it's one way we keep score. And, and, and I, and the, the money part is, is great. But what would, what would, what would feel so magical is going from an idea, a conversation, a walk in a park, you know, us trying to figure out how do we get email addresses, like how does, you know, where do we, where do we, where do we, where do we have the whole cloud thing work, right? And then walking into a room and seeing, you know, 80 people work for us. Like it actually makes me emotional. Like that is incredible. So that, that was the first deal I ever did. And, and then the second deal we get aside on him. What, what, what make you decide on, what make you decide on him? I just, number one, the product was so great. The quality of his advice was fantastic. Two, I love him. He's like a brother, but man, he could be a pain in the ass. And he just is really convicted, you know, and like, that's why I said he would speak truth to power. I'd watch him in these situations. Like you didn't just say that. Like you like, you just told that CEO, by the way, why did you tell me that? You know, and so at first I would look at, I'd call him like a punk, like, well, I can't believe you're giving me this advice. And I'm like, I can't believe you're giving me this advice. Your advice is probably right. I think I needed to hear it. So, you know, he's so the product was great. Then, but then running a company is a lot more than a product. It's like, do you have, and, and because he had such strong conviction about principles about how he would like to run something if he was in charge, you know, when you see somebody with very strong principles about what they would do if they were the boss, that's a pretty big part of the foundation of one day being a boss, right? And when I would talk to him, this is how I would do it. This is who I would hire. This is, I knew, okay, what he was missing was the capacity to burn boats. He had all these reasons, you know, to hedge, hesitate. This is what happens when I talk to folks a lot. I talk about this in a book. I love this idea. I think most people, when presented with an opportunity to grow reflexively or instinctively choose incrementalism over step change. So, what I mean by that is they presume that in order for me to get to where I really want to go, I got to make all these little stops along the way. Well, I want to, I want to own a lemonade, you know, conglomerate, but I got to make a lemonade stand first, you know, outside of my house. Like, so Jesse at the time felt like, you know, maybe I need to do this, maybe, you know, I need more seasoning and I love challenging that because 90% of the time we are manufacturing reasons to delay getting to our ultimate destination. 90% of the time we are overestimating the value of experience because you already have the experience. You just don't have the title. You just don't have the recognition from society. So, that was Jesse's case. That was the one thing we had to overcome and again, also talk about that and he overcame it and he ended up reaping the rewards. And what advice do you have for people that are in that mindset that are playing small? I would say, take a step back and audit all the reasons why you think you need to do X before you could do Z, right? Ask yourself. And here's what oftentimes is the origin. You feel like you need to do X because you're embarrassed that somebody's going to believe you're not ready to do the thing you really want to do. Or you believe that, well, dad, my dad feels like first I should get an accounting degree before I do whatever it is I really wanted to. There's usually an external voice of approval that is telling you you shouldn't be allowed to do it yet. Or there's a partner because you're in a bad relationship who keeps cutting you down every time you have an audacious goal who keeps finding ways to undercut your ambition. It's true. I talk about this, like we are all partnering often with frenemies of some sort or another and sometimes we end up, you know, married to them. And so there's usually something that is telling a person and contradicting their instincts. So I say, all right, isolate the reasons why you're choosing incrementalism over a step change. And then to ask yourself what the step change looks like and start looking, can I pull it off? I have a great start. I teach at, you know, HBS, right? And I had a student come to my office once and he worked, he was a military special forces guy, special operations and just brilliant and had an idea for his own fund. He had the deal flow to do it. He had the experience of my opinion to do, he had everything. But he came to meet with me and he said, hey, I'm in New York because I'm about to take a job with a big private equity firm. I'm like, well, you don't look too happy. He's like, it's not my first choice. And so what do you want to do? He's like, well, I really want to have a fund. I have all this deal flow. And I'm like, well, why won't you do it? And you go, well, who's going to write me a check? I said, nobody. Until somebody writes to the check. So, you know, I don't get it. We have a great conversation. I assume he takes a job, calls me up a few months later and he said, hey, I want to get your address. So for what? To send you some swag, swag from what? The firm that I created when I walked out of your office. I was like, stop. He's like, yeah, I raised $10 million now. I'm raising $50 million. Like, I love it. So anybody listening, who's making small moves, just like when I sat on the steps of Cardinals High School and dropped out and said, why do I need high school? That single decision compounded my success dramatically. I would urge you just to consider whether you're manufacturing reasons for why you can't make that big move. And another concept, again, another concept, I love how, by the way, this book actually walks through the whole cycle of a founder journey. So it gets them off the ground. But then it walks you through all the different things you're going to have to basically overcome as you're building out literally anything, any category, any industry. One of the concepts, by the way, thank you. Thank you for reading the book. I mean, did you find it helpful? Now I have to ask you. Like, no, it was actually, so I actually, I actually really enjoyed it because it does walk through everything that I've dealt with myself personally. And I find that it doesn't leave a lot lacking. So there's actually, there's two more points that I want to pull out that I found in the book that are helpful for the founder because I've hit these at various stages in my own career. But yes, it's, it's exceptional. And I actually appreciate that it speaks from a place of experience. So no, my pleasure. It's well done. Is your first book, by the way? Yeah, my first book. Yeah, I like, I worked for it. Thank you. No, I worked like, well, I mean, it's, it's, I was, I used the word extra in a positive context. It's definitely a little extra interviewing 50 people was quite an undertaking. But I find a lot of these books, when somebody's in a position of authority or prominence, we write a book because they have permission from society to write a book. And they don't worry whether the book is useful. I really tried to not make it an autobiography because I don't really care. And I just, what people, people, I wanted to provide value to the reader. And I tried to keep you Scott at the center of the journey and not me mad, you know, and hopefully I totally get it. I totally get it. A concept that you, you discuss optimizing anxiety. I want to, I want you to explain that concept, how to do it. Obviously, if you've built anything, sometimes you're like in a perpetual state of anxiety. And then there's one last point that I want to go into and then, and then we'll close it out and we'll tell people where to go to get this and connect with you. But optimizing anxiety, what does that mean? How do we, how do we do it? Yeah. So great question. I talk openly in the book about anxiety. I think anybody who's, you know, who were successful doing hard things probably has a degree of anxiety propelling them either. And then, and then there is a good degree of science around this idea of optimal anxiety, right? Which is the balance between a certain amount of anxiety is actually needed to produce exceptional effort. So you don't want to walk away from that. And too much anxiety can obviously render you paralyzed. And so how do you constantly strike a balance between those two situations? So number one, to put it yourself in a position of anxiety, you need to be doing things that are a bit uncomfortable. That's a fact. And you need to look at the feeling of being uncomfortable as a feedback loop, as actual confirmation that you are engaging in a perpetual growth mindset. And again, those sound like words, but it's sort of true. It's very peaceful when you say, I feel uncomfortable and distressed. I feel a degree of imposter syndrome. I'm like, okay, good. Will you put yourself in the arena? That's number one. I'm a huge believer in self-talk in the third person. Lots of science shows that self-talk within the third person is creates this super ego that you defer to as an authority that can calm you down. So I go through lots of different ways to bring it into balance and talk about ways in which I have been completely crushed by anxiety. And they, you know, can deal real to real the outcome. I think the first important part is that we all have an open conversation that anxiety is not a proxy for necessarily illness and not a proxy for necessarily things are wrong. It's potentially a feedback loop. You just need to keep the two, you know, in equilibrium. And last question to pull out of this. So now we're still going along the founders journey, or anyone's journey, really. But what happens when you go all in and you fail? Well, it will. And 100% it will. So first I have to say that I am not one of those people that, you know, fetishizes failure. Some of this, the rhetoric we use just feels so dishonest and inauthentic. Like failure is amazing. You know, I'm so glad I felt today. Like that's not true. I hate failure. And I do everything I can to avoid it and it rocks my world when I do. But I do think that if you can adopt a mindset, a process, it can make it manageable. So one of the things I found that with some of the most widely, wildly successful people, let's just start with some billionaires that I've talked to, a friend's in a book, Mark, Michael Rubin is a great example as a CEO of Fanatics, right? What I found with him and many other really successful people is that anytime they encounter a specific incident of failure, right? They simply widen the definition of success to accommodate that failure on the road to success. It's amazing. It's like, it's almost instinctive. Sometime from afar, it looks delusional. Like, no, that was like a big mess. Nope. As a result of doing that, now I'm not I'm able to, you know, et cetera, do whatever. So my overall advice is, number one, never allow your identity to be enmeshed with a specific failure. So I never use a language. I am a failure. I never allow myself to believe that, but I do use the words I have failed. That's number one. To remain intellectually curious about that failure, dissect exactly what happened, what can you extract from it? What value can create? Three, I buried in the desert. I never pay my respects again to it. So I just, you know, move on. But I, I'm sharing the first part about the billionaires because it contradicts what I just said. They have a unique ability to reflect the losses, repel them, and absorb the wins. In what almost appears delusional, I do not have that capacity. If you wish to be an incredible multi-billionaire, work on the degree of delusion that any time you fail, you're like, no, no big deal. I really meant to do that, actually, and just widen. That, that is the common thread. And I talk about in the book, but for the rest of us mere mortals like myself, we need a process to ensure that we never allow our identity to be enmeshed with a single act of failure. And that's how I do it. So I'll talk to some other folks, and they're not even intellectually curious about why they failed. And those, those people do tend to be extremely, extremely successful and weirdly resilient. I unfortunately don't have that thick skin, and I need to process failure. Okay, so where should people go to connect with you to when, when is the book coming out? Where can they get it? I'm assuming all the regular places, but still drop me all the links. Okay, great. So the book is available now. You can go to Amazon. It's Burn the Boats. You can go to my website, Burn the Boats book. I tend to spend a lot of time on LinkedIn. I like LinkedIn, a little more civilized and thoughtful. So the best way to probably get in touch with me is to go to LinkedIn and look for Matt Higgins there, and I'm on Instagram as well. But I'm so excited for people out there to read it. It means a world to me. If this in some way affects you, changes your life, gets you, changes your relationship with risk. This is why I am doing it. So if you could let me know, I'm a vulnerable human being, just like you, that feedback, you know, makes it all worthwhile. Last question, I ask everyone before we close this out after all the things you've accomplished. What does success mean to you? What does success mean to me? So I went through a lot of people, a lot of trauma when I was young that sort of shaped the future, and I do believe that the reason why it happened to me, because I witnessed something at 16 that I have not been able to unsee, and that is the power of human intervention when someone is suffering or dealing with subjugation. In other words, if somebody had come along and taken an interest in my mother, and our situation, she would not, she would be alive now, probably. So I believe that the highest and best use of your power, money, platform is to ameliorate suffering in another. So the more time I spent and allocate to ameliorating suffering, either through sharing the wisdom of this book, or the work I'm doing with migrants and refugees, I've had two private audiences with Pope Francis in the last year, which is amazing. To me, success looks like an increasing amount of my life devoted to ameliorating suffering and then seeing the impact. The impact makes me feel good. Maybe that's selfish, but it feels like living.