I recently went one-on-one with Matt Higgins, co-founder and CEO of RSE Ventures.
Adam: You have a pretty unconventional background. You grew up in Queens, which is the home of many generations of the Mendler family. My dad, like you, is an alum of Queens College. You dropped out of school at a very young age and wound up working at McDonald’s. What were the best lessons from your early days?
Matt: Yeah, well, first of all, thanks for having me on. I love being with anyone from Queens. It always brings me back. For those who don’t know me, and for those who do, I’m sorry if this is a little redundant, but I do think sharing the story is helpful for someone out there who feels like the die is cast because of the circumstances they were born into or find themselves in. I grew up in Queens in a rent-stabilized apartment. The most important part of my story, and the thing that shaped my whole existence, was taking care of a mother who had a lot of health issues and some psychological issues stemming from a really tough life. Eventually, it was just her and me in this tiny little shoebox apartment, basically a little roach motel on Springfield Boulevard in Queens. My mother was fiercely intelligent, but she was also the product of abuse and never had the opportunity to get much education. She was very heavy, and as time went on, things just kept getting worse.
As I was growing up, everything became this desperate attempt to figure out how to take care of myself and how to take care of her. But when you’re a kid, you’re also inherently selfish, and you should be. So there was always this tension. I felt this pull, this guilt, this weight, maybe even this hero complex, but at the same time, I wanted to move on with my own life. I wanted to have friends over. We never had friends over because the apartment was embarrassing. There were just all these conflicting emotions as a kid. I started this treadmill very young, around nine or ten years old, where I would sell flowers on street corners, scalp tickets, which back then was illegal because we didn’t have StubHub, sell leather handbags at flea markets, whatever it took. I would stand on top of a van selling handbags for 10 bucks. That was my youth. It just became increasingly unsustainable trying to go to school while also taking care of my mother.
One of my darkest moments actually led to an epiphany, and it was inspired by my mother. I watched her, as an adult, go to Queensborough Community College and get her GED. That enabled her to pursue her dream of getting a college education. She eventually went to Queens College and started taking classes. I watched her experience dignity for the first time in her life while she was still working on her hands and knees, cleaning apartments for elderly people. That was her job, but college gave her something more. Around seventh grade, I had this realization. This is not hindsight bias. People always ask if I’m making this up, but I remember it very clearly. I thought, “I do not want to go to school anymore. Why can’t I do what my mother did?” But instead of doing it accidentally later in life, I could do it intentionally. I could drop out at 16, get my GED, and back then, there was a loophole where if you scored high enough, you could convert the GED into basically any GPA. I don’t think that loophole exists anymore.
So I came up with this whole plan. I remember going to my guidance counselor at Cardozo High School, and he was asking me why I kept getting picked up by the police at McDonald’s. I told him, “No, no, I have a plan. I’m going to get my GED and enroll in college.” My logic was simple. If I could start college at 16, then instead of making $3.75 an hour at McDonald’s, I could get an $8-an-hour job just by being a college student. To me, that was life-changing money. Everybody dismissed the idea. Everybody told me I was crazy and tried to talk me out of it. The biggest lesson from that period, and really the lesson I later wrote an entire book about, was that the way to pull off impossible things in life is to give yourself no escape route. To literally burn the boats. My first real act of burning the boats was making sure I failed every single class in high school for two straight years. I got left back twice. I technically never got past ninth grade. The only class I cared about was typing because I thought it was practical. Other than that, I intentionally failed until I finally executed the plan at 16 and enrolled at Queens College.
Adam: What a great lesson, and what a great personal example of that lesson. You wrote a bestselling book, Burn the Boats, and you shared your own personal example of the importance of burning the boats. How else have you seen that play out over the course of your life and career?
Matt: First of all, it’s a very muscular phrase, right? Burn the boats. For people who don’t know the origin, most people associate it with Cortés in 1519, although he’s probably not somebody you’d want to emulate because he was basically a homicidal maniac. But the idea was that he conquered the Aztecs after burning the boats so his men knew there was no way home except forward. What fascinates me about the principle is that it goes back to the beginning of recorded history. Every society has some version of this story where someone is deified because they sabotaged their own escape route in order to succeed. The reason I love the concept is because it’s deeply counterintuitive. There was actually a study at Wharton where professors thought students would perform better if they had a Plan B because it would reduce anxiety and help them feel calmer and more self-possessed. What they found was the exact opposite. Merely contemplating a Plan B was enough to sap motivation and weaken performance.
I think growing up in that roach motel, trying to save my mother’s life, I became so desperate that I stumbled onto what felt like a portal in the universe. The rules everybody else followed weren’t written for me. Those rules were written for kids with two parents and stability, not for a kid carrying a butterfly knife on Woodhaven Boulevard because he thought he might get jumped on the way home. They weren’t written for a kid helping his mother bathe. I realized there had to be another path. The key thing is that you’ll never discover those alternative paths unless you believe they exist, but you also won’t walk through them unless you feel like you have no other choice. That became a recurring theme throughout my career. What I’ve learned is that people often believe they need to fully identify the solution before accepting the problem, but I actually believe the opposite. Once you accept the problem, solutions emerge from it. But that requires faith.
I still remember sitting on the steps of Cardozo High School after officially dropping out. I had just handed in my textbook to my teacher, and he turned to the class and said, “Higgins, what a waste. I’ll see you at McDonald’s.” I remember telling him, “If you see me at McDonald’s, it’ll be because I own it.” Then I sat outside alone on those steps with my marble notebook and cigarettes. You could hear the blood rushing through your ears. It’s one thing to hang around outside school cutting class because you think it’s cool. It’s another thing entirely to sit there in the middle of the day, knowing everyone else is in class while you wonder whether you just destroyed your entire future.
But once I made that decision, I had no choice anymore. I was officially a high school dropout. So I peeled myself off those steps, whatever dignity I had left, took the GED within about 60 days, and within three months, I was at Queens College. By the end of that year, I was president of the debate team. That experience shaped the core philosophy of my life. If you accept the problem before you’ve fully mapped out the solution, and trust your own ability to figure it out, you can accomplish extraordinary things. That’s really who I wrote the book for: people who feel anxious, unsupported, risk-averse, or boxed in. I wanted to show how you take a phrase like “burn the boats” and actually make it actionable in your life.
Adam: I love it. And the whole concept of burn the boats really clashes against another principle that we think about constantly as leaders, which is creating optionality. You want to open as many doors as possible, but when you do that, you can create paralysis because suddenly, there are too many options. One of the most important things every leader has to do is make decisions. Sometimes it’s more important to simply make a decision than to make the perfect decision because if you make no decision at all, your entire team and organization can become paralyzed. Your thesis around burning the boats, getting rid of the Plan B, and going all in really speaks to that. You can spend all day creating options and planning for different scenarios, but if all your time goes into planning, none of your time goes into actually doing.
Matt: One of my favorite environments to give this talk to is a military context. I’m blessed to be able to spend a lot of time around our soldiers. I have a defense tech company that I’ve been working on for a decade, so it’s probably the thing that brings me the most joy, being in that environment. I gave a speech to the whole command infrastructure for USASOC, United States Special Operations Command. Talk about an intimidating room. One stars, two stars, three stars. I like a military context because that group is usually the most likely to reject this. The conversation usually goes, “This is the opposite of what we’re told. We’re always supposed to have a contingency plan.”
They’ll say, “During the bin Laden raid, there were two helicopters. Thankfully, one went down inside those walls, so the second one came.” They’ll say burn the boats is the opposite of what they’re trying to do. So I ask them a question. When an American hostage has been taken overseas, do you ever waver in the goal? Do you ever say, “Maybe we’ll rescue the hostage, maybe we won’t?” No. How you rescue the hostage is not what you burn the boats for. That you will rescue the hostage is what you burn the boats for. The principle of burn the boats is about goals. You burn the boats for goals, never tactics. By virtue of committing to the goal and being laser-focused on what you’re burning the boats for, you actually gain more freedom to jettison a tactic that isn’t working.
I remember on Shark Tank listening to entrepreneurs pitch businesses that clearly weren’t working, but they just wouldn’t give up. They were deriving self-worth from saying, “I’m tenacious. I never quit.” I would think, no, no, did you burn the boats to sell this widget? Or did you burn the boats for financial freedom for your baby? For your legacy? To prove your good name? Whatever it is, you burned the boats for a goal that was bigger than this tactic.
I think where a lot of people go wrong in business and life is they confuse tactics versus goals. I’m always meditating when I find myself doing the same thing over and over again and telling myself I’m just going to power through it. I stop and think, wait a second, that wasn’t my objective. My objective was to achieve this bigger purpose. It doesn’t always come easy for me. I have a big tattoo up my right arm. My wife thinks it’s cringey, but I don’t care. It says “Po Fu Chen Zhou” in Chinese, which effectively means burn the boats in that culture, dating back to 206 AD. It doesn’t come easy for me, but the way I reframe whatever I’m doing is by asking myself, “Is this a goal or is this a tactic?”
Adam: I love that, and even if it is a goal, is this the right goal? Is this the right goal for me to spend my time on? Is this the right goal for me to exert all of my energy, all of my focus on? Because if I’m going to be channeling my energy, my attention, my focus on this goal, there’s going to be another goal that I’m not going to be able to spend my time on.
Matt: Yeah, well, that’s such an important piece of advice. I talk about this in my book. I get asked this question all the time. Somebody out there is probably thinking about it right now. How do you know when it’s time to go all in? Or whether it’s worth going all in? Or when it’s time to abort? The most important question you have to ask before you fully commit to an epiphany or an excited idea is whether this idea or goal is going to sustain you three years from now, juxtaposed against the future version of yourself that will have grown and evolved. In order to figure that out, you have to ask yourself a few fundamental questions.
In pursuing this goal or business or idea, am I running from something or running to something? Most of the time when we’re in movement, we’re running away from something. Pain, divorce, a bad boss. Those negative emotions will not sustain you for three years.
The second question is, am I pursuing this because I’m afraid this is the only time I’m ever going to have a really great idea? Like, I had a good idea at three in the morning, and now I have to go all in. I find that some people are afraid to self-scrutinize the quality of an idea or the likelihood they’ll be successful because if they abandon it, they’re worried they won’t have another.
I always say ideas and dreams and epiphanies are like houses. When you’re house hunting, there will always be another one right around the corner. You have to have the confidence to kill your own ideas and trust that you’ll have another.When I dissect somebody’s journey and try to figure out what went wrong in their life or career, a lot of times it’s because they failed to ask those questions at the beginning. Is this going to sustain me three years from now? Am I afraid that I’m not going to have a better idea if I don’t pursue this one?
Adam: I love that framework, and it’s a great framework not only when it comes to deciding whether to start a business or what business to start, but in any move you make in your career: Asking yourself why. What’s motivating me? What’s driving me? Am I doing this out of a position of weakness? Am I doing this out of a position of strength? If you’re doing it out of a position of weakness, what can I do so that I can instead make a decision out of a position of strength?
Matt: That’s a great way to frame it, by the way. I’m always thinking about how to disinfect my logic, my corrupted thinking, so that I can make a stronger decision. A lot of it has to do with money. When you feel like you don’t have enough money to make a decision, money becomes incredibly powerful, not because of what it can buy, but because of the confidence it can give you to make better decisions from a position of strength.
The true measure of money is actually units of time. It enables you to buy optionality and explore what you really want. People ask me, “What’s your number?” I always say it’s not a number, it’s three years. What’s the amount of money that would allow you to strip down your life to the basics and still have enough joy to live for three years? Because you can reinvent your whole life in three years. You can get a master’s degree, learn a language, or start over completely.
For me, it’s always about units of time. But back to your point, it’s about stripping your mind of all those corrupting forces that make it hard to make good decisions, which is why everyone listening to this should meditate so they can center themselves every day.
Adam: What are the keys to making successful decisions?
Matt: I try to be spiritual as best I can, and for me, that means reading the same book over and over again, literally for many years. It’s a book called Buddhism Plain and Simple. I read that book to remind myself that at the end of the day, the only thing guaranteed is the present. So much of what we experience is just a fiction of our own mind and our own making. I also try to stay connected with the prospect of death, which sounds grim. I have an app on my phone called WeCroak that reminds me several times a day that I’m going to die. My wife is very well adjusted and perfectly regulated, so she doesn’t need an app reminding her she’s dying five times a day. I do because I tend to take things a little too intensely.
By reading this book and reflecting on Buddhist principles, especially the idea that so much of our pain and suffering comes from wanting things to be different than the way they are, I try to sit with that concept. So much of our internal struggle is, “Why does it have to be this way? Why can’t it be different?” Staying connected to the fact that life is temporary helps me zoom in on the present. It gives me peace, but more importantly, it helps me make better decisions.
When my decisions are driven by anxiety, fear, desperation, defensiveness, or feeling boxed in, those are not high-quality decisions. When my decisions are based on aspiration or helping someone else, when I remove some of the self-centeredness from my thinking and feel more connected to other people, I make better decisions. I think everybody has to figure out what works for them, but whatever helps you make better decisions is incredibly important. It’s also important to recognize, especially if you’re a manager or leader, that emotional fatigue is real. Decision fatigue is real too. We only have so much capacity as humans and leaders to take on emotional friction.
If you’re going through something painful in your personal life, especially something invisible to everyone else, that pain is probably consuming a huge amount of your emotional capacity. That matters because we need emotional capacity to do hard things as leaders. Terminating a toxic employee. Standing up to your boss. Killing a dead-end project. Having difficult conversations. When you’re going through something painful personally, you can either acknowledge it and create some space for yourself to heal, or you can ignore it and make really bad decisions. I’ve audited my own leadership at different points in my life and thought to myself, somebody should have taken the keys away from me. I had nothing left to give.
I remember difficult periods where I’d go sit on the bathroom floor with my head in my hands just trying to get through the day. In those moments, of course, you’re not going to have the emotional bandwidth to deal with difficult leadership decisions. That’s why I like surfacing this topic. As leaders, we tend to conceal more than is actually useful. Sometimes the healthier thing is to acknowledge, “I’m going through something difficult right now. I may not be fully on my game.” Whatever helps you put yourself in a position to make better decisions matters. I know for me personally, when I’m dealing with heavy incoming pressure on the personal front, my capacity for emotional friction becomes very limited.
Adam: What an important point, and it really starts with being honest with yourself, having the capacity and the desire to look inward.
Matt: Our greatest arbitrage is self-awareness. It’s the greatest arbitrage entirely within our control. I would say to anyone out there who has found themselves, either at different points or for long extended periods of time, being a caretaker, maybe not even by choice, you become so comfortable neglecting your own needs that you can lose your sense of self. Why that matters as a leader is that if you lose your sense of self and you’ve never been able to get in touch with it, then you don’t know how to optimize yourself either. You don’t know because it was never a question you were permitted to ask.
For years, I was taking care of my mother. I didn’t finish the story before, but I was on this race to escape poverty. I went from McDonald’s to college. I did seven years at Queens College at night and then four years of law school at night. In that one decade span, I went from being the kid cleaning tables at McDonald’s and scraping gum off the floor on my hands and knees to becoming the youngest press secretary to the Mayor of New York. I was still living in that same sad roach motel while my mother was deteriorating in front of me.
The first day as the mayor’s press secretary was supposed to be my moment. I was going to make $105,000 a year. I was finally going to move across the street. I had this whole plan. I wanted to be close enough to take care of my mother, but finally have my own place and my own life. I was 26 years old and felt like I was finally entering adulthood. Then, on my first day on the job, my mother called me and said the ambulance was there. We’d gone through this routine many times before, but this time, when I got to the hospital, she had died.
So I had this greatest professional achievement of my life at 26, and at the exact same moment, my mother died. I learned a lot of lessons from that. One of them is that the cavalry is not coming. My instincts were correct. I was on a race against time. But what took me decades to really realize is that if in those formative years you never cultivate the ability to understand what makes you happy, what makes you perform well, what allows you to function at your best, then you never really develop that muscle. You don’t know how to cultivate and optimize yourself.
I say that not as a victim narrative. I say it because I think a lot of people listening may have gone through something similar. Maybe they were caretakers. Maybe they were stuck in unhealthy dynamics at work or at home. Long periods where the self gets subjugated. Over time, you lose the ability to ask yourself, “What do I need? What helps me function effectively as a person and leader?”
So when somebody says, “I can’t meditate. I can’t stick to a gym routine. I keep stress eating late at night,” I think sometimes the deeper question is whether they’ve actually been allowed to figure out what makes them great, what helps them function well. A lot of people never had the space to ask those questions. I’m bringing this up because all of it spills into leadership. It affects how you function as a boss, a manager, and a leader.
Adam: How can anyone become a better leader?
Matt: I would say my first question is, why do you want to be a leader? Some people truly want to be part of a team. We’re in this culture where we’re deifying, maybe even fetishizing, being an entrepreneur or solo creator. There’s a lot of societal pressure to be the leader or the creator. So the first question is, is that really in your DNA? Or would you actually be happier as part of a team? If you do want to be a leader, what kind of leader do you want to be? There are a lot of subsets.
Some people are leaders by virtue of being operators. They’re process-driven. They don’t mind reports, org charts, HR issues, and all the mechanics that go into getting the best out of people. That’s a very specific skill set and honestly, a pretty rare one, even though many more people attempt it than probably should. Then there are leaders who are more catalysts. People who like to create something, set things in motion, and then maybe hand it off to somebody who is more of a professional operator. I think a lot of people in management or leadership positions haven’t really audited themselves honestly enough to ask, “Is this actually what I’m good at?”
There’s also pressure, especially among entrepreneurs, to prove that you’re an operator, to resist professionalizing the business because it somehow feels like weakness or inadequacy. I don’t know who told entrepreneurs that they have to be good at running large, complicated organizations. Personally, I have no interest in running a large operating organization ever again, and I don’t feel insecure about that at all. I prefer to create, solve problems, architect ideas, and give advice. I don’t want to run a giant org chart, and there’s no shame in that.
Adam: It really starts with know thyself. Understand who you are. Understand what makes you great, what makes you special, what you enjoy doing.
Matt: Exactly. To unpack why that resonates so much with me, the reason I don’t want to operate a giant organization is because what gives me joy and self-worth is the act of creation when something isn’t obvious yet. I enjoy having a thesis about how the world is going to evolve and then acting in that space before the evidence becomes obvious to everyone else. I use this lightning and thunder metaphor. Lightning is the flash of an opportunity or insight. Thunder is the confirmation. You have to train your mind to act on lightning, before the thunder, because by the time everybody hears the thunder, it’s already obvious.
For me, the thing I enjoy over and over again is saying, “I think drones are going to become critically important on the battlefield, and I think the United States is at a disadvantage.” Then, going and building a drone company before most people would even think about it. Going through what people call the valley of death, where there is no funding and no obvious validation.
That journey started for me around 2015. That’s what gives me satisfaction. I don’t fully know why. I think I just enjoy trying to discern patterns and then having the courage to act on them. Burn the boats. That is very different from running an operating business and doing HR reviews at the end of every quarter. That’s just not where I am naturally. So yes, know thyself. But not in a cliché way. There is actually tremendous relief in identifying what you’re not good at and no longer feeling ashamed of it. I don’t know how to use Excel. Nobody needs to anymore anyway. I was just early at being incompetent at Excel.
I would encourage people to identify something they’re bad at and stop feeling embarrassed about it. I find that founders and managers who cannot acknowledge weakness usually have some deeper psychological issue driving it. Maybe they’re still trying to prove something to a parent who never told them they were proud of them. There’s often some emotional force underneath that discomfort.
It’s fascinating how life has evolved because we’ve now commoditized execution, at least in certain domains. It’s the idea and the curation that are now becoming more valuable while execution itself is increasingly commoditized. I was writing articles for CNBC in 2023, saying that AI was going to become the great equalizer because it would enable people from very different backgrounds and skill levels to bridge gaps. English isn’t your first language? AI can help you communicate perfectly. You don’t have design skills? You can use Canva or Midjourney. You don’t know how to build a deck? That no longer matters the way it used to.
It’s pretty remarkable. Thankfully, we didn’t spend our whole lives mastering Excel because a lot of those execution skills are becoming commoditized. What’s extraordinary is that this is going to enable an entire generation of people to put their ideas into production in ways they never could before.
I’m actually a very good typist, but now I barely type anymore. I use an app called Whisper Flow. Anyone listening should check it out. You hit a button, and it translates your speech almost perfectly at the speed you’re talking. It makes me hate Siri even more because it shows how outdated so much of our technology already feels. But the larger point is that many of these execution skills are now being replaced or heavily augmented. That changes what becomes valuable.
Adam: What are the most important skills that have allowed you to get to where you are today? What are the most important skills that you believe everyone today should be developing?
Matt: I talk about this in my book. I have this concept called proprietary insights. One of the fun things about writing a book is you get to invent your own terminology. Proprietary insights are the observations and understandings that are unique to you because of the circumstances you were born into, the jobs you’ve worked, the experiences you’ve had, and the things you’ve seen that other people haven’t. Those insights can become the seeds of entirely new businesses or entirely new lives.
I had a TV show called Business Hunters, kind of like House Hunters but for businesses. I would mentor people trying to decide what businesses to buy. One woman on the show had created an Airbnb business that specifically catered to visiting nurses. I asked her, “Why visiting nurses?” She explained that they stayed longer, paid higher rates, and were more stable customers. I asked her how she figured that out. She said she had worked the front desk at a Holiday Inn and noticed that visiting nurses were always staying there for long periods of time. She simply paid attention. That became her proprietary insight. She turned that into a business worth hundreds of thousands of dollars in equity value.
Every person listening to this conversation has proprietary insights that come from their own life experiences. The problem is that most people dismiss them because they think success has to look like Shark Tank. They think they need to invent some revolutionary gadget. In reality, many successful businesses are simply evolutions of existing systems or observations about how something can be done better. So my advice is to ask yourself: what do I understand from my life and experiences that other people don’t? What patterns do I see that others overlook? Those insights can absolutely become the foundation for a better life or a business.
Adam: How can you figure that out?
Matt: I think it goes back a little bit to the old business school idea of vitamins versus painkillers. You want to solve real pain, not create something that’s just nice to have. So if you think you have a proprietary insight, the first question is whether there are enough people who actually have this problem. Let’s go back to the visiting nurse example. Okay, how many visiting nurses are there in this market? Is all the demand already being captured by hotels? How can I make my Airbnb more attractive? How do nurses make decisions? Is there a platform they use? Is there a way to market directly to them? You start pressure testing the idea.
Then, after you’ve thought through the mechanics, you have to ask yourself something deeper. If this works, is it enough to feed my family and satisfy my ambition? And if I pursue this for three to five years, which is how long it usually takes to make something work, will it still sustain me emotionally by then? Or will I have evolved past it? A lot of times, the answer is yes if the idea was born from genuine excitement and purpose. But if the idea was born from fear or desperation, if you’re running from something instead of toward something, then it probably won’t sustain you long term.
Right now, AI is creating a little bit of a dangerous mirage because people suddenly realize they can build things very quickly. They’re using Claude or other tools and thinking, “Oh my God, I can create anything.” But they’re skipping the meditation on whether they should create it. I’ve seen people spend weeks in this manic energy building something just because they can. The problem is that if you can build it quickly with AI, so can everybody else. The ability to execute is no longer the gating factor. The real question is whether the idea is fundamentally good, differentiated, and solving a meaningful problem. That used to be masked because execution itself was difficult. Now that execution is cheap and fast, people are bypassing the harder thinking around whether the underlying idea is actually strong.
I remember going through a period where I felt unmoored and was trying to figure out what to do next. I had a big job, but I wanted to be an entrepreneur. I wanted to create. So I was grabbing onto any idea that could act like a life raft and carry me somewhere better. This is almost embarrassing now, but I had an idea for a subscription mitten business for kids. The concept was that you’d put your child’s hand on an iPad, it would measure growth, and then automatically send you new mittens as your kid grew.
I went incredibly hard at this idea. Thank God we didn’t have AI tools then because I probably could have built the whole thing overnight and convinced myself it was going to become huge. Fortunately, the rabbit holes were shallower back then. That obsession only lasted about a week. Now, with these tools, people can disappear into those rabbit holes for months because the barrier to execution is so low.
Adam: You’re bringing up something so important, which is the danger of falling in love with your own ideas. We all have ideas. Some are going to be good. Some are going to be really bad. Given your experience not only pursuing your own ideas but evaluating the ideas of others, what advice would you have on how to assess whether you have a good idea or a bad idea?
Matt: There are a few principles I really believe deeply. One of the most important is that every crisis creates an equal and opposite opportunity. So even when you’re pursuing a bad idea, that experience can still create the conditions for something valuable if you stay open to it. I define success differently than a lot of people. To me, success is reducing the amount of time between when a decision becomes objectively inevitable and when you actually act on it.
If something is clearly not working, if a relationship is dead, if a project is failing, if a business model is broken, the question becomes how quickly are you willing to acknowledge reality and act? The longer you delay, the more damage compounds. But the faster you kill the bad idea, the more time the good idea has to compound. I constantly look around and think, “What decisions are objectively inevitable right now that I’m delaying because of emotional friction?” Everybody listening probably has a few.
I had another business idea years ago called Leap Seats. When I was running the Jets and Dolphins, it always bothered me that there were empty premium seats halfway through games because season ticket holders hadn’t shown up. I thought, why not dynamically resell those seats to people already in the stadium? We built the company. We raised money. We pursued it. The idea itself wasn’t terrible, but eventually I realized it wasn’t actually a standalone business. It was a feature that Ticketmaster or somebody else would eventually absorb.
One of the best moments in that whole journey was shutting it down. It felt courageous. It showed confidence. It showed I believed I would have another idea. And I was able to redeploy the people working on it toward more important opportunities. That goes back to the principle that every crisis creates an equal and opposite opportunity.
Adam: Having the courage to move on is incredibly important and something that we don’t talk about or think about enough. You shared a great lesson. Is this a business or is this a feature? Is this something that I think is a great idea and maybe would be really cool to bring into the world, or is this actually a business? There’s nothing wrong with saying this isn’t it. On the contrary, when you say this isn’t it, that gives you the freedom to move on to what ultimately is going to be it, whether that’s your next at bat, the at bat after that, or the at bat after that. You need to free yourself up so that you can step up to the plate and swing at the pitch that you’re ultimately going to knock out of the park.
Matt: Yeah. This is especially true now when you see all these AI businesses launching and generating phenomenal ARR with almost no investment. You look at it and think, wow, they’re doing $50 million with two employees. But then you have to ask yourself, how long is that going to last?
If the margins are that high, eventually competitors are going to flood the space. That means if you’re building one of these businesses, you have to think differently about it. Maybe this is an opportunity to generate meaningful cash flow and then move on, not build your identity around being the next giant platform company forever. There’s never been a better time to create a cash-flowing business using AI tools. But a lot of these businesses will probably have finite lifespans. That’s important to understand.
Adam: How can we best utilize technology today?
Matt: I don’t think of myself as a Luddite, somebody who wants to smash the machines, but I’ve never seen a period this disruptive where I genuinely have so little clarity on exactly how all of this plays out. We’re in the greatest period of college graduate unemployment in decades. The implications of AI are massive. Somebody recently asked me, “What are we supposed to do?” Honestly, my answer was: be the deployer. Be the person deploying the tools rather than the person consumed by them.
What does that mean practically? I think there has never been a greater gap between leaders and the actual art of the possible because most executives don’t have the time to tinker. They still carry old assumptions about what requires staff, time, or complexity because they haven’t sat down and actually played with these tools. So my advice is very simple. Whether you’re a CEO or a parent, go buy an Apple Mini, set up Claude or whatever tool you want to use, and spend time tinkering on weekends. Figure out what’s actually possible.
Every brilliant founder I met recently at Harvard Business School was doing exactly that. They weren’t watching Netflix. They were experimenting. Building things. Automating things. Learning through play and immersion. You cannot delegate understanding this technology. You can’t just assume your team understands it. Some people on your team will be curious. Others won’t. But if you’re leading an organization or trying to build a future for yourself, you need a firsthand understanding of what these tools can actually do. Honestly, it brings me a huge amount of joy. Ideas I had for years that once required entire teams can now be prototyped quickly. That changes everything.
What fascinates me most right now isn’t even the giant startup stories. It’s how leaders are using AI to organize the chaos of their lives. For me personally, email feels like tyranny. It feels reactive and defensive. I want to spend my time on offense. So using tools like Whisper Flow, where I can speak rapidly and process communication much faster, gives me more control over my time and energy.
What I’m seeing in this first wave of AI adoption is leaders using these systems to create order and clarity in their lives. They’re building personal systems that help them feel less overwhelmed. In a weird way, it’s similar to why people go to the gym. It creates a sense of order and self-mastery. These tools are giving people more capacity, and capacity matters. That’s the thing I’m most interested in right now.
Adam: Is there anything else you would like to share?
Matt: How do you survive this era when we honestly don’t know exactly how it’s all going to play out? We’re in a period of massive disruption, and there are going to be a lot of downstream consequences from that. My advice to this generation remains what it’s always been. If you make yourself indispensable at whatever job you’re given, you’ll always have another opportunity. You’ll always have value.
What surprises me is that I don’t actually see enough people becoming truly fluent with these new tools. Not just using ChatGPT to write a memo full of obvious AI phrasing, but really understanding how to deploy these systems in sophisticated ways. If I were entering the workforce right now, I would become the most agile AI operator imaginable because leaders still don’t fully understand these tools. That creates an enormous opportunity for younger people who are willing to immerse themselves in them.
The second thing is that we’re in an age where you really have to challenge assumptions you’ve made about how the world works. There’s never been a more important time to audit your assumptions and recognize that many things people assumed would always remain true are changing very quickly.
For younger people, especially, the greatest life hack still remains time and compounding. Take advantage of that. Invest early. Let time work for you. I know I sound like a boomer dad saying that, but it’s true. That’s still one of the most powerful advantages anyone can have. Those are the things on my mind because I’m constantly thinking about them with my own kids, too. I don’t try to outsmart the market. I think about time and compounding.
