Get Mic’d – Episode 2: Why Never Having A Plan B Is Key To Business Success With Matt Higgins, RSE Ventures – Transcript

Below is a transcription of Get Mic’d Podcast Episode 2, hosted by Katie Zeppieri and featuring Matt Higgins, Co-founder and CEO of RSE Ventures. Listen to the full episode here.

Matt Higgins is a serial entrepreneur and a growth equity investor. He is the CEO and co-founder of RSE Ventures and an executive fellow at Harvard Business School. Matt has recently published his bestselling book, Burn the Boats. He shares his rags-to-riches life story, his whirlwind career, and the lessons he learned to succeed. Matt was also the youngest mayoral press secretary in New York City. He managed the global media response to the 9/11 terrorist attacks. From politics, he moved to work in senior leadership positions with National Football League Teams. Connect with Matt on LinkedIn and learn more about his work.

Katie Zeppieri: Matt Higgins, welcome to Get Mic’d.

Matt: Thanks for having me. This will be a historic moment when we look back and you’re massive. I was early.

Katie: I love that spirit. So you have been involved in so many different industries, from politics to sports, to entertainment, to media and to tech. Plus, you also have a really strong personal brand. We’re looking at your book in the background there behind you that you just recently launched, “Burn the Boats”. How much has marketing and branding been a part of your career journey? And what is your approach to building brands across such diverse sectors?

Matt: That’s such a good question. With my range of experiences, people often wonder, “How does it all fit together?” Part of why I wrote the book was to explain how it all fits together, that there’s a method to this madness. And there’s an underlying formula, this “Burn the Boats,” unrelenting commitment, which we can get into. But marketing branding, and its cousin, communications, are huge.

On my desk is a typewriter from the turn of the century, because I feel like I owe so much to communications. When I was a kid growing up in poverty in fifth grade, in destitute circumstances, the first recognition I got from the outside world that maybe my skills were exceptional in one area was writing. I won a Stuart Hall essay scholarship. I still remember this because I was only in fifth grade and the scholarship was $1,000.

Being able to use my PR and communication branding skills was a turning point in my career because I thought, “Isn’t better to use those skills on my behalf than it is to use them on behalf of others?” So I am like an AI set. I got trained on these larger-than-life figures in different contexts. And then AI just ran amok and created all these crazy careers.

Katie: I think it’s interesting to learn about how you got started. You were a high school dropout. But this wasn’t just something that you woke up one day and decided to do. This was intentional. You thought about this and you had a plan about getting into the workforce. You talk about taking care of your mom and providing for your family, and when I was learning more about your journey, politics seemed to be one of the places where you got your start.

I’m wondering, how did you get into politics in the first place? How do you go from being a high school dropout to getting into politics?

Matt: Great question. I agree about politics so we can dive into that. But I grew up dirt poor. People throw these words around and they don’t mean anything but I always say I grew up on government cheese. I keep the box, not the cheese, but the box on my desk, courtesy of the US Department of Agriculture, a big block of cheese.

But I was destitute and doing odds-and-ends jobs selling flowers on street corners and whatever it would take because I didn’t have much. But we’re all given some gifts from the universe, nature versus nurture, I don’t know. For me, it was defiance. I always felt like I didn’t belong here—not in an arrogant way like I was better than my cohort in my neighbourhood—it was more just a sense of, it doesn’t have to be this way, and it won’t be this way. There was always a little bit of otherness about me and I didn’t feel like I needed to be shaped by these circumstances. I became an observer of my environment, maybe that’s somewhat of a trauma/protective response. As I was finding my way and scratching and crawling out of poverty, I discovered my writing skills and I started leveraging that. 

The first significant job I got was to work for a Congressman’s newspaper that he created. He went on to become a Congressman, but it was called the “Queens Tribune,” and they gave me this job as a muckraking reporter. People would send me clips about problems they were dealing with, they had to fill out a little coupon that told me, “I’ve got overgrown trees and they’re blocking the stop sign, somebody’s gonna die.” But within these little coupons, it was called the Trib Action Desk, were these incredible nuggets of real—not wrongdoing per se—but really sad stories where people’s complaints weren’t being listened to. I realized I had no power as a little reporter in a Queens newspaper. But if I could team up with a New York Times reporter, or one of the major newspapers, I could bring the heat. And so I would write all these articles. 

Eventually, I won a bunch of journalism awards and investigative journalism features, and I was profiled in this daily news supplement in New York. It was me on some weed whacker algae killer on a lake—Oakland Lake in Queens—and I got the attention of the mayor’s office, and they offered me a job in the research department. It’s the equivalent of shovelling coal on the Titanic. My job was to take newspaper clips and put them on an 8×11 piece of paper and walk them around to City Hall. Why that’s so important is because I leveraged the fact that I was on the inside to start doing ghostwriting for the Mayor of New York, which at the time was Mayor Giuliani version 1.0, by the way, America’s Mayor, not the version we currently know. 

So I leveraged it. And getting to the point of the story, what’s interesting about politics, and I tell anybody out there who’s listening to this, whatever side of the aisle you’re on, politics is equivalent to a tech startup. There are all these jobs to be done and there are not enough people willing to do it. There are not enough people willing to surrender their entire life. If you think the hours at a tech startup are bad, work at an executive level of government, they’re insane. But they look past age and background and I have to say in a lot of respects, it didn’t matter where I came from. It didn’t matter that I was living in squalor and that I had a GED. Nobody cared as long as I could write and as long as I would be willing to work with an inch of my life. And so I owe a lot to the political environment for giving me these jobs earlier than any other environment would have given them. I was Press Secretary for the Mayor of New York, I went from scraping gum at McDonald’s at 16 to Press Secretary by 26 years old.

Katie: That’s remarkable. What do you think—there are so many contributing factors—but what do you think helped you rise so quickly?

Matt: If I’m honest, I think the exigent circumstances of desperation were important. I can’t remove myself from the context. I felt so desperate while taking care of my mother, and so frustrated that the system didn’t care. She was obese and she had all these undefined health issues but no one ever did anything. I would spend nights at the ER sitting on the steps, reading my books, even in law school, and no one ever did anything.

So I will say I came to the point of not capitulation, but I’d say, “Okay, that avenue was closed to me. Nobody cares and the system is not set up to intervene.” I remember this conversation I had with my mother, I’ll never forget it. She was very depressed when I was growing up as a kid and felt very victimized, and she was in a lot of horrific ways, especially as a child. I would say to her, “I don’t want to see the world as if I’m a perpetual victim.” And she would always say, “You don’t know what it’s like, you’re a kid. It’s easy for you to say.” And I’d say “Well, maybe that’s the case.” And then she would say, “But I’m dying.” And I would always say “Well, we’re all dying.” And I remember this conversation I had with her and I said, “You know from now on, I’ve decided that I happen to things and things no longer happen to me.” And she would say that sounds naive. 

I have never wavered in that belief that I happen to things and things don’t happen to me. And I do think that we all get the last word. So, this book that I wrote, “Burn the Boats,” does try to encapsulate this idea that we have to take agency in our own rescue and that we should never abdicate responsibility, good or bad, for determining the outcome. So perhaps there’s a little 16-year-old sitting at the table and a mom who was grandiose, but as a 48-year-old, who’s written a book about his career, it doesn’t seem so crazy anymore.

Katie: I really liked that philosophy and I want to dive into “Burn the Boats” more in just a moment, but we have to hang on this Press Secretary for Mayor Giuliani during 911. I couldn’t even fathom the complications and unchartered territory of being in a time like that in a position like the one that you were in.

What did you learn about crisis communications and navigating a period like that?

Matt: Great question. I don’t get to talk about this as much as I want to. But everything in that 24-hour time frame, actually let’s zoom out 72 hours from the moment the attack occurs.

Number one, what I was doing between the first plane hitting the tower and the collapse, was standing on a corner, three blocks away on Church and Park alone with two aides with the building as the backdrop because we didn’t have a sense of the enormity. We all thought it was a Cessna, a small plane at first. You can’t perceive it, it was like a rotten apple core, and it’s black and you’re hearing sounds and you don’t realize until later that that’s the sounds of people dying—horrific. But you have a job to do. And the job to do is to represent strength and to set a press conference. That was always the mayor’s philosophy and I credit him for it. I’ve taken it with me in every context that the first rule of crisis management is to show up.

People often raise the bar unnecessarily high. They think that the standard they’re held to is to have answers. That’s not it. What’s more, the further you go from the catalyst or the epicentre of the disaster, the higher the expectation of the answers you’re going to have. In the early days, there’s zero reason not to communicate because all you have to communicate is: We don’t know, but we’re in the process of finding out. When we do find out we’re going to tell you, and here’s how you should feel and maybe think and do in the interim. That was always his philosophy. 

I’ve been to a plane crash, unfortunately twice. I’ve dealt with a West Nile virus, a disease outbreak. I’ve been to every kind of catastrophe, and violence, and the first rule was always to show up and communicate. So that morning, that’s where I was standing. But then it became clear as everyone evacuated, and I would see a column of firefighters going in, that this wasn’t any ordinary crisis. And so when the first tower collapsed, I was in the process of trying to find my way back to City Hall to find the mayor because that communication stopped working. And then the building collapsed.

The number one priority was to project strength and to do that first press conference. Those who may remember, but you’ve seen the documentaries, the mayor is asked, “Mayor, do you have any estimate of the number of casualties?” And he says, “We don’t know. But what we do know is it’ll be more than any of us can bear.” And when he said it was just so instinctive and primitive, like, that’s it. That’s the answer to what we need to hear and we need to acknowledge that this is unlike anything we’ve ever been through. 

And now compare that with President Bush—we all have these views of President Bush—I have a personal connection to him. I was around him at a very intimate moment, so I was always amazed by his incredible memory. Bush had a remarkable memory and was a very empathetic human being, whatever you think about his politics. So do you remember when he didn’t show up for four days? The plane was circling and he sort of fed into this narrative that he was aloof. It was my job to work with the Secret Service and the Vice President’s staff to arrange the first visit to ground zero. And I remember when we decided he would walk through the carnage and he spontaneously decided to climb up on top of a pile and put his arm around a firefighter and somebody in the crowd yelled, “Mr. President, we can’t hear you.” And he goes to the blowhorn, “Well, I can hear you and soon the people who did this will hear us too.”

I’m sharing this for anybody out there who’s a marketer or communicator, it really matters. Sometimes we tend to think communication or even marketing is an afterthought. But actually, oftentimes, it’s the main event. It’s actually the very thing we need and leaders who are not equipped to deal with it, don’t feel comfortable, resent it, tend to really suffer during a crisis. I just like those moments juxtaposed with Giuliani. He was instinctive that we needed to show up. We had to practice it for the President—maybe bad advice, or maybe he was the victim of circumstance—but it took too long. From that moment forward, when he projected strength, everything changed.

Katie: I also like that it sounds like he showed up and he showed up as a human, just like a person.

Matt: He did. I had to go with him to the Family Center, again, the surreal views. I remember I was in the car behind the car protecting him with a Gatling gun aimed at my car as I followed him down the West Side Highway and we went to the Family Center. He’s tearing up and he’s meeting with all the family. He spent the whole day, very, very sensitive again, forget about politics, he’s a very sensitive human being. But you’re right, he showed up as himself. Not as a character, not as a President of the United States, as a human consoling people. Again, most of us, unless you’re a sociopath, have a lot of empathy in us. We raise the bar during a crisis, when we should be lowering the bar and we should be connecting with our humanity. 

By the way, even if you are part of the perpetrator in some way, or your company screwed up, just show up as a human with empathy. Lawyers get in the way—sorry, lawyers, close your ears, but I’m a lawyer, never practiced, it’s just fancy wallpaper right there—and I know enough to know when to not listen to you, lovely people. We tend to overthink the consequences. “Well, if you say this, it’s admitting culpability.” How about the fact that we won’t have a company tomorrow? Or somebody was wrong, and they’re grieving? I’ll live with the consequences.

I didn’t mean to go on that tangent, I just remember all these times in my life when a lawyer would have told you what to do or not to do and then you missed that important moment when you’re acting on instinct and empathy and lawyers logically want you to act on reason and forecasting liability.

Katie: It’s sort of amusing to me that you are also a lawyer, and wrote a book called “Burn the Boats.” It’s like the opposite.

Matt: Yes, and no, as we’ll get it to you, because I am also a very paranoid risk taker, and you can’t work for the government all those years and be a lawyer without being one. But it is kind of funny. I never practiced a day in my life, which is also in the book.

But nothing is ever a waste. I have managed lawyers throughout my entire career at any moment of time and managed multiple different lawyers. The fact that I have that education has made me so much better at managing lawyers, I’ve just never wanted to be one.

Katie: Let’s flash forward. There are so many different chapters to your career thus far. How do we move from politics into the corporate world?

Matt: Yes. I love this topic. I go into this in the book as well—this idea of leverageable assets. We tend to put ourselves in our own box. When we meet our maker on the brink and we take inventory of our lives, I’m positive that for most of us, when we reconstruct we will ask: What happened? How did I end up here or there? You will find at the epicentre, not an oppressor, but you will find your inner voice that puts you in a box, subconsciously.

You always have to be intentional in defining your life the way you believe it’s played out. So, what do I mean by that? I could have been a government employee for the rest of my life. If I define my experience as a Press Secretary as being a government experience. But it wasn’t a government experience. It was dealing with the most combative press car in the country, except for the White House. It was managing complicated facts. It was a million things. It was crisis management. But the context of being in the government, getting in the government was very, very tertiary, and I could have defined it that way, and then next thing you know 20 years later I’m still in the government. 

I always zoom out. And I ask myself the following question, “What are the leverageable assets that I have by virtue of doing this job that I can now use to bring me closer to where I ultimately want to end up?” Not where I want to end up but where I ultimately want to end up, because I believe you just need to move in the general direction of your ultimate ambition. So being a government employee, I now know how to manage complicated dynamics. I was also one of the first employees rebuilding the Trade Center site and I helped oversee that for two years. I became the Chief Operating Officer and everything you see was planned out in the two years after the attacks.

But my leverageable asset was being able to bring together different constituencies. I used that to go to a sports team, the New York Jets, that needed to build a new stadium in the middle of Manhattan. In retrospect, not a great idea. But I knew how to navigate by virtue of the crisis. As we go into my career, if you look at well, what’s the connective tissue? It’s being intentional, identifying leverageable assets, and using them to bring me a little bit closer to where I want to end up to this very moment on this podcast.

Katie: It sounds like you actually thought a bit about your personal brand. I think people think personal brand means media interviews and speaking—of course that’s part of it—but personal branding is also just the impression that you leave on every single person that you meet, your network and what people say about you when you’re not in the room. It sounds like that was a thought that went through your mind even when you were just getting started.

Matt: It really has. To unpack that a bit, first of all, there are a lot of people who are intrinsically motivated by adulation or recognition. It makes them feel good and it enhances their self esteem. I am a total introvert. I just manifest with charisma and some good speaking skills. I can be alone in a room for 20 hours just to think.

So, what’s my why? Why would I be public? Or why would I build a brand? Building a brand gives you authority and the power to meet your objectives. I’m always amazed that you have to convince people of that. We can dive further into that…

For me, it started becoming clearer and clearer to me that my story was crazy. I dropped out of high school, ended up going to law school at night and working all these crazy jobs. But again, who cares? What’s the point? Who am I impressing? I realized that the most important thing I’ve ever seen in my life and experienced firsthand was the death of my mother. The powerless death of my mother in a world where no one cared to do anything about it. Because I can imagine how it would change the trajectory of that little boy’s life if somebody had cared. And two, she wouldn’t be dead. Especially in a world now with Mounjaro and Ozempic—the weight loss drugs—she would not be dead. I never want to lose hold of that. I wanted the authority to make people care in whatever context that moved me. So maybe that’s human rights because I care a lot about human subjugation, but people don’t listen to you unless you have authority. 

Along the way, the reason for developing my personal brand was so that I could accumulate authority, first to accomplish my objectives—we all have selfish objectives—but in a bigger way, to maybe end up not as Elon Musk. But I look at a guy like him who has got this incredible platform and he uses it to peddle Dogecoin. Imagine if you could use it to shine a light on the odd disease in Iraq. There are so many different situations where somebody can use their authority. My why, my meta-purpose, has always been that I’m going to accumulate authority through my crazy story so that I could shine a light on what powerlessness feels like, and that has motivated me all the time.

So to your question, I have been very calculated about my personal brand. I’ve been very calculated and aware that this is a crazy career. I wrote the book to tie it all together.

Katie: I think that speaks so much to the Shark Tank vignette of you. I was mentioning this to you before we even started this interview, there was something in those two minutes of capturing your life story that was powerful, like raising the hair on the back of your neck kind of powerful. And I think, to tie into your why, “Burn the Boats” really sounds like such a strong call to action that sort of summarizes how you’ve approached your life and your business.

I love in the beginning—the intro of your book—you talk about Generals and leaders within the army who would “Burn the Boats” so that there was no way back, right? As if we’re here and we’re fighting. We’re in it. We’re all in. I want to hear from you. How do you think that the “Burn the Boats” philosophy can relate to branding and relate to business?

Matt: Great. Maybe I could just give you a minute on why I picked that phrase and the logic of the book, back to the architect. That phrase “Burn the Boats,” for those who don’t know, people think it’s attributed to Cortes. He just had a marketing campaign. He was a very bad man, by the way, he’s a genocidal maniac, so you don’t want to emulate him.

But I was sort of fascinated that this phrase kept coming up throughout my career, and I’ve always loved it. So jingoistic, also simplistic too, right? There’s way more nuance than that. But I liked it as an umbrella. When I researched I found every culture, most of which have a similar story, the hero’s journey, where a fabled General was outnumbered and the way they overcame the enemy was by eliminating retreat optionality and by taking away their food provisions, creating manufacturing desperation. 

So I was like, well, there’s a great story. What’s fascinating about Cortes, obviously he was a Spaniard, but actually in 711. Maybe this was where 711 came from, but in 711 A.D., there was a General Tariq, who was Muslim, and he conquered Spain. So I imagined little Cortes, as a little boy learning about Tariq thinking, “I’m gonna use that tactic.” And then it goes back to Caesar, maybe in 49 A.D., and before him, there’s a story in China in 206 B.C. And then we go back to the first written appearance of “Burn the Boats,” in Sun Tzu in the Art of War, in which an army burns its boats.

So for me, I was like, this is already imbued with authority. It’s completely contradictory to everything our parents tell us. And so I wanted to pull that forward, and then actually appropriate it. Not for the self-possessed and the arrogant, those who don’t have impostor syndrome, but for the rest of us like myself who had to overcome anxiety, shame, and impostor syndrome. Actually, on the boat even though it looks like a little pagan symbol, this is actually meant as a child’s boat recreated and rendered over many, many iterations. It’s meant to be floating in my bathtub because that was the boat I needed to burn, the shame and the sadness of failing to save my mother.

So how does it all play into marketing and communications? The premise isn’t really about Plan B, as much as it’s about if you want to be successful—we can get to the science that you want to eliminate optionality—we are taught to hold two opposing thoughts simultaneously in our mind. Oh, I know you want to be the next Taylor Swift, but at the same time, let’s plan for you failing to be the next Taylor Swift, and we’re supposed to have them simultaneously. That doesn’t work.

So from a communications and marketing standpoint, when you actually aren’t fully committed to your plan A, it’s going to show up in your language. I see this at Harvard all the time. It’s going to show up in your willingness to represent your product publicly. There are always a couple of different types of students in the room. There are all sorts of founders—those who want to intellectualize their way to their business and solution and would prefer to stay behind the scenes like they don’t do social and just want their product to speak for itself—and then there are other ones who recognize that marketing branding is everything. 

I personally believe that the act of getting somebody to ingest your beverage is audacious. Like, are you kidding? You want me to drink that and not die? And you want me to believe it’s good? That’s an audacious act. So if you don’t represent that act, or your personal brand, and your willingness to communicate, what’s that telling me about it? So I would say to anybody listening, who has adopted a mindset of like, “I’m gonna let somebody else” or “My co-founder does that, I don’t do that.” I guarantee you, it’s showing up in sales, I guarantee it’s showing up in the success of your product, and I guarantee it’s showing up in the evangelicalism of your employees who think, “Well if you’re not willing to rep it, why should I rep it?”

That was a long answer but I love this topic because I talk about it all the time. People always want to make a choice, as if it’s a choice to rep your product for branding.

Katie: I like that you’ve added this sort of branding, marketing-specific angle to “Burn the Boats.” One of the principles you talk about in the book is a gut sandwich, as you call it, sort of trusting your gut, trusting your intuition.

In marketing and PR, there’s definitely a strong component of intuition. There’s also this push for numbers and measuring impressions and measuring all of these different aspects that help you analyze what’s working, what’s not, and how to continue. How would you sort of balance that idea of having a gut sandwich and trusting your gut, but also paying attention to data?

Matt: It’s so hard. For those who don’t know, the gut sandwich is basically me reconstructing some of these major developments saying, “Okay, they started with intuition, but there was no evidence for it, and the magnitude of an opportunity has an inverse relationship with the amount of evidence there is for it.”

Like when Steve Jobs creates the iPod. He had no reason to believe that we needed 40,000 songs in our pocket, but he wanted it, right? And then he looked for data and evidence. But data is not really data, it’s actually more evidence of traction, early traction, that you’re interpreting and applying some growth factor to it. Well, there are a few people who were doing this, and eventually it could come out. But the green light is intuition with most major decisions as it pertains to marketing and something I deal with all the time. 

I love data. I love science. I geek out on my studies. I would love to reduce the world to data. I would love to, even in selling the book, make it about CAC to LTV, right, like 1 to 3, perfect grade, 3 to 1 read the perfect ratio. But life doesn’t work that way. In fact, the book keeps teaching me this well, because I’m trying to make the process of selling the book, but really communicating about the book, efficient, so I could allocate bandwidth. And I’m like, “Damn, that tactic is the one that worked? That’s not supposed to work.” 

I’ll give you an example. Logic would dictate that I could spend digital marketing and I could figure out the perfect hack, and maybe Twitter will convert or Instagram Stories. Everyone’s talking about reels saying Facebook Reels will convert. I’ve been spending money there, right? All this stuff. And I had a moment of defeat as anybody who’s an author understands this, how many times have you nearly died and capitulated and said, “Okay, I’m done?” I had one of those moments. And then I was like, “No, I’m gonna do the thing that nobody else would do because that is the thing that will bring me closest to the thing that works in terms of getting it out.” I chose to do a radio interview at 1 AM, 1-3 am, two hours live in the middle of America coast to coast. I said, “I’m gonna stay up for three days straight and just do media until I figure out what it was.” Out of everything I’ve ever done around this book, every single major interview, every massive podcast—and I’ve been on some of the biggest ones—the most effective thing was the live radio interview between 1 and 3 am. And not a single person in the collective wisdom of the publishing industry told me to do that interview. So that’s marketing, right?

If I want to rely on data altogether, I eliminate serendipity and experimentation. Personally, my life is one big AB test. I’m doing this. I’m doing the opposite. The other thing as a CEO, I would advise to anybody listening: There’s a reason you’re the CEO or the Founder, you have a pretty high IQ. You have a lot of grit and gumption, whatever is your magic. If you don’t put yourself in the stream of data to get granular insights, you’re going to miss the opportunity to figure out what actually works. I am ridiculously tactical when it comes to marketing. You’d be shocked. It’s all day, it’s all night, it’s different times. I’m constantly experimenting because if I’m waiting for my team to tell me what to do, it’s too far removed. It’s not that I don’t take presentations and people don’t present their plans, but I am sitting there running Twitter ads, and LinkedIn ads myself and boosting Instagram Stories watching, all day and all night.

Katie: You’re connected. 

Matt: I’m crazy. But yes, connected would be another word. I deduce things and so I’m not going to deny it. Because there’s no precision to it, despite what everybody wants to say. The only reason we’re trying to make it precise is that it’s gut-wrenching otherwise, right?

But the truth is, you have to accept the fact that a lot of marketing is gut-wrenching. I don’t want to deny myself the benefit of spontaneous insights. The only way to do that is to be ridiculously tactical. As a result of being that tactical, I’ve come up with incredible things, especially around the marketing of the book, that people wouldn’t have expected.

I’m launching something actually tomorrow, that I’m so excited about that no one’s ever done and I wouldn’t have figured it out if it wasn’t tactical.

Katie: Amazing. What is one other story, lesson, or principle that you share in “Burn the Boats” that you feel exemplifies a lesson for people looking to build notable, recognized brands?

Matt: Okay, great question. So I speak more to the leaders and the people who are a little bit reluctant, or those who have naysayers around them and feel a little bit vulnerable.

When I went on Shark Tank, of course, you have to have a personal brand and you have to communicate. For a long time I was like dormant because I had my head down. And then out of nowhere, I shot out of a cannon and I started sharing my crazy story, and it was a change of behaviour. What was fascinating is a lot of people around me were put off by the change in behaviour, number one. So what I mean by that is embracing Instagram Stories, going live, doing whatever. So that’s the first act of stepping out and creating the brand that provoked people. And of course, you’re like, “What do you care? Get out of my face.” But that’s number one.

Number two, people ascribe motive to your behaviour when you step out, and start doing personal branding. They want to assume that you are an egomaniac. “Oh, you’re doing it for self-aggrandizement.” or “You’re being selfish, you’re not being a team player.” So that’s the second threshold that you sort of have to overcome, and you’ll have to block out.

And then third, you’re being very vulnerable, so that’s the backdrop. I had to go through this birthing of a brand that had been dormant while I kept my head down. And then when I successfully got on the show, which is equivalent to American Pie, the number one business show in the world that kids watch with their mom and dad—there’s nothing negative about Shark Tank—it provoked a lot of resentment and it was really hard to absorb.

And so my message to anybody out there, if you haven’t built a brand before, and you’re worried that people are going to judge you, you’re right, they are going to judge you. And the reason they’re judging you is one: They don’t feel comfortable doing it. Two: You’re breaking the mold and a lot of people feel like that’s very threatening because maybe they want to stay in place and they would like you to fail. So I’m saying that only to be a little bit of smelling salt for anyone listening. Damn right, it’s gonna be uncomfortable. And you have to block it out because you’re going to deny yourself your opportunity to excel.

When we use the word personal brand, so calculated, it can be a little cringy. It’s not really about personal brands, it’s about showing up in the world and showing up in 2023 or every year from now on. Showing up includes being heard, having the confidence to represent yourself and what you’re involved in, and being able to engage transparently. And if you can’t do those things, you may not be left behind in 2023, but you’ll be left behind in 2030 for sure. I’m giving you seven years to get your shit together.

Katie: You better get on it!

Matt: Better get on it. Exactly.

Katie: As a shark on Shark Tank and also, as the CEO of RSE Ventures, you invest in a lot of companies and you invest in a lot of entrepreneurs. Fundamentally, what is it that you look for in that company? And in that person?

Matt: Great question. I would say let’s talk about the person because I think the person is more interesting, even more than the company. As an investor, you realize every time you write a check, you’ve basically signed up for a job. So I’m always evaluating the opportunity cost even more than the opportunity, to be honest. I’m now more defensive like, “What are you going to screw up about my life?” Because now you have expectations about me and you’re also concealing how bad things really are.

A lot of it is sleuthing to figure out ultimately, what’s the opportunity cost. And the way to mitigate the opportunity cost is for me to back the right kind of people who have a balance of two seemingly opposing qualities, but they’re actually synergistic. One is confidence and the other is humility. And the reason why those two matter is because success is also ultimately determined by the pivots that you make along the way, as well as when you make the pivot.

I can predict a Founder or CEO’s success by the amount of time it takes for them to pivot or adapt from the moment that it became objectively necessary. Now, of course, that’s a subjective view, but I’m going to call it objective. For instance “No you’re going to die,” “If we don’t change the course…,” “Your product sucks”. The longer you wait, the harder it will be to avoid the iceberg, right? Extending the boat metaphor. So that’s number one. The way to ensure that a CEO or Founder will make those pivots is through confidence and humility. Confidence to go ahead and to look within and audit and be open and receptive to the possibility of failing, and humility to acknowledge that things do go wrong, and “I can go ahead, and I’m going to do something about it.” So I look for little signals and tells of those two qualities.

And then in terms of what do I choose to back? I look for things that can be outrageously large. That’s not always obvious, but at least I want to be able to connect the dots to say, “I think this could be huge.” To put it in a Shark Tank context, if you would do a deal on Shark Tank and all of America is watching in the world—let’s say 3 million people tune in to watch that episode,—but yet, it’s a brick-and-mortar location in New York. That means that of all those 3 million people, the only time they could experience it is if they happen to be watching. It’s a waste of impressions. So my view going into the show is scalable and available. Is it available to everybody watching? And can it be global? And that is generally the way I look at investing. Not nearly with as much precision as I’m making it sound. I focus way more on the two qualities. 

And my last point, I talked about this in the book: Italians have a great phrase, I’m not going to say it in Italian because I’ll ruin it. But in English, it’s “The fish rots from the head.” I think so many institutionalized investment firms, private equity—because it’s more scalable—focus on data and the numbers. When in reality, the CEO’s mindset, psychology, context, everything is going to have a way bigger impact on the business than the numbers.

Katie: I love your take on the importance of a founder’s personal brand. Let’s talk about startups, for instance. Startups are just trying to get their name out there, they’re figuring out product-market fit, and they’re doing all of these things.

Do you believe that it’s important for the founder to simultaneously be building and be intentional about their personal brand?

Matt: 1,000%. I know not everybody does. At a minimum, it’s a waste of a potential asset. Right? Let’s take two different products. Those of you who don’t know me, but don’t know this brand, Google it, you’ll see what I’m talking about. But let’s talk about Milk Bar. It’s run by Christina Tosi. Christina Tosi is brilliant, amazing, effervescent. She created this brand with David Chang, Momofuku. I’m the largest shareholder. She could show up anywhere on Instagram Live, Bay Club on a TV show, and she will light up the room, right? So now let’s AB test her and a nameless commoditized kick, right? Obviously, Christina will get an advantage because we connect with people, and we obviously love our brands. But when they’re led by somebody who reflects our values, or who’s aspirational, it makes it easier and makes us more evangelical. 

So of course, it should be that. But I think it’s even deeper than that. I think that the most successful companies and products are a natural expression of the person who created them. I just love backing things where it’s not that the founder intellectualized what I call a sleepy TAM. Like, “Oh, there’s no one addressing this large TAM (Total Addressable Market for those playing at home) and I’m going to create this company because I have an MBA from Harvard, but I could care less about the underlying sector,” right? 

Versus a founder: Lola, is a good example. They decided to address feminine care and they were very passionate about the things that we’re putting in their body and horrified by the ingredients. It’s a natural extension of who they are as human beings, but that’s business. And why it matters is not just philosophical. For me, it’s the structural integrity of the exercise. It was born from a good place. You have insights from your life and context, but also your motivation will be impacted because you are on a primal level and it’s not something that you put on a spreadsheet to get rich, it’s because you were put on this earth to do it. So not all of the checks I write fit that but the ones that I love the most are the ones where the founder was motivated because then we bleed together, we almost die together and we resurrect together.

Back to branding: You should be so excited and care so much about the brand that you represent. I have not always felt that way in my life, sometimes I’ve been tentative. This book is an expression of that to me. I would die to get this book out there. I don’t want to, but when I wake up and I get a DM from somebody around the country who feels like they were unseen, or they don’t have a dad who is supporting them, or a spouse is undercutting them, and like they read my book and they feel empowered. What’s that worth? And so that enables me to speak effortlessly in any context and take any incoming. You could try to cut me down to pieces, criticize the book, but because I care so much about it that it doesn’t matter. To me, those make the best founders.

Katie: Let’s talk about strategic partnerships. You have partnered with many people, companies, notable figures like Gary Vee, and invested in companies like Momofuku and REZI. How do you approach collaboration and strategic partnerships to help enhance overall brand value?

Matt: From a very calculated way, or how do I approach partnerships, would you say?

Katie: Let’s talk both.

Matt: Well, let’s talk about big picture partnerships. I talk a lot in the book about the fact that the first question that people fail to ask is, “Do I need a partner?” A lot of partnerships, I would say the majority of partnerships, are born of insecurity at a moment of time that’s fleeting. So I’ll give you the fact pattern. I’m the founder and I’m looking to disrupt a new industry but I’m not from this industry. So I feel a little nervous, because I don’t know what I don’t know. So I seek a co-founder. What do I do? I go to the industry that I’m looking to disrupt and I get a co-founder. So that makes me feel good in the formation phase and maybe it makes investors feel a little bit more confident to give me a check.

But then time goes by and you realize, “You are kind of annoying me, because you represent the very things I’m trying to destroy, and you keep trying to pull me back to convention.” So that’s one of many fact patterns of partnerships that were born with impure motive, or at least motive that wouldn’t endure through the duration of the partnership.

Second issue: Students are always fascinated in my Harvard class, to ask co-founders, how did you choose each other? And it’s my favorite part of the class because the answer they get is always the exact opposite of what they believe is the answer they need. They assume that people choose partners because of skill gaps, and you’re looking to backfill skills that you don’t possess. For example, I’m the marketing person and I need a numbers guy. And without question what the co-founders always say is that you choose a partner based on value overlap, not skill gap. Skill gaps are actually secondary. The reason why companies succeed or fail with how they weather crises, and when you have value overlap, you’re going to approach the crisis the same way. And I’ve pressure tested this, “But what if none of you can even do math, like if he’s an abacus,” and I’m like, “So one of us will learn math!” But the more important thing is that we agree how screwed we are that we don’t know, math. I love talking about partnerships because I’ve entered so many bad investments where I could sniff out that the partnership wasn’t great, or I benefited from it by buying one out, whatever it is. And then in general the kinds of people I look for are those who over-index on self-awareness.

Self-awareness is the greatest arbitrage entirely within our control because you can invest in it and work at it. The reason why self-awareness is important in a partnership—everybody knows what I’m about to say when I’m saying this—is you’ve all been in a situation where you know your partner is doing something that is either destructive to them or to the business but you can only deal with so much conflict because you’re dealing with other crap. And you don’t want to say it, but you wait longer and longer. I call these the missing conversations. I didn’t come up with that term, it’s from the Navy SEALs, but they’re missing conversations. Eventually, you expend your political capital and emotional capital and you confront your partner but if your partner is already over-indexed for self-awareness, they would be constantly auditing and all it would take would be a single trigger or comment. You’d be like, “Bob, just be clear, you seem like you’re not yourself, because you’re kind of an asshole.” And Bob’s like, “To be honest with you, I’m in the middle of going through divorce. And I’m taking it out on everybody, you’re right, I’m gonna go take a break.” You know what I mean? Self-aware people, one, create space for other people to be vulnerable by sharing their own vulnerabilities, but two, they’re not afraid to look within because they’re well constructed.

The single greatest problem I find is that I deal with founders, if you would ask me, what’s the number one challenge? It’s cultivating self-awareness and then convincing somebody that it’s missing and doing the hard work to do it because it scales better than any other attribute.

Katie: I really like that.

Matt: People make fun of me because I’m all about the industrial psychologist but it’s just the way I’m wired. I think that it could make a huge impact.

Katie: I want to move into our MicDrop lightning round. I’ve got a handful of quick questions for you here to really bring this home. All right, complete this sentence: To me building a notable brand means _____?

Matt: A brand that stands for something and it doesn’t take you ten sentences to explain it.

Katie: What has been a memorable MicDrop moment for your brand? This could be for a company that you’ve worked on, or personally.

Matt: When I dropped out of highschool. As much as I now tidy it all up in the book, it was one of those decisions where you say, “Well, this is very crazy and very lonely.” To be able to go through with it, I burned the boat by failing every single class except for typing as a little kid so that the system would write me off eventually. And they did because the interventions were exhausting and they were defeating my conviction.

Imagine a kid who had done well and is now a dropout, or about to be. So when the day came, it was the equivalent of the academic walk of shame. You have to take your book and walk in each room. For me, I remember walking into my science room and saying, “Hi, Mr. Rosenthal.” He doesn’t look away from the class. He’s like, “What’s this?” And I say, “It’s my textbook, it’s unopened.” I was a wise-ass, right? And without missing a beat, looks at the room and says, “Higgin’s, what a waste. I’ll see you at McDonald’s.” And everyone’s laughing at me and I’m Irish and I’m red and meanwhile, I’m thinking, “He’s right.” And as I’m about to walk out, no bullshit, this happened, I grab the door, and I stop and I say, “You know, Mr. Rosenthal, if you see me at McDonald’s, it’s because I bought it.”

Katie: Wow.

Matt: Yeah. That was my MicDrop moment. And I love it because the truth is, I kind of agreed with him, but I’m also thinking, “FU, I’m not gonna let that be the last thing I ever hear in this building.”

Katie: It’s funny how you burned the boats on your high school education. You just set it all on fire. You did nothing. You went from being a good student to just doing nothing. So you cut that option entirely from continuing.

Matt: Somebody wrote me the other day, a comment. I love the negative comments. They said there is hindsight behind this and so I’m like, “No, I lived it.” I deliberately set fire. The reason I share the full context of the story is because it would be easier for me to presume, “Oh, you’re a kid gone wrong, but you made good,” right? But that’s not a useful part of the story.

That’s not true. It was intentional. But the part that’s meaningful was the self-sabotage and how painful and how lonely it was. And here’s Mr. Rosenthal on the front line reconfirming that I’m a piece of crap. He was a nice guy by the way, but he’s saying, “You are a loser.” What would it take to overcome that? 

When I went back to my prom a year later, everybody listening to this, I had my sort of “them apples” moment from Goodwill Hunting, if you’ve ever seen the movie. I went back to my prom, I was now on the debate team, President of the debate team, had like a 3-4, 3-5, at college. I was still working two jobs but now I’m in college. I always had a supportive homeroom teacher, I would never forget her. She watched over the land of misfit toys, kids with a beeper, dealing drugs, all of us little misfits, me with my head down sleeping on the desk, and she was proud. And Mr. Rosenthal was, “Huh?”

Katie: Respect.

Matt: That’s what I’m saying. I love sharing the moment because then when I went to law school—my degree’s right there, fancy little $200,000 piece of wallpaper, right?—when I said, “I don’t want to go be a lawyer.” I had a conversation with the law firm as I was about to start the job and said, “So when I out-compete my colleagues…,” God bless them, love them, “But when I out-compete them, how long would it take for me to make partner?” And they said, “The typical partner tracks 11 years, but you can get there at seven or eight. If you do well.” And I was like, “So seven or eight years of looking over documents in a basement with a highlighter? But I already make more money than a starting lawyer.” And because I had gone through that “burn the boats” moment already was 16, it was effortless to walk away from law school. But more importantly, it wasn’t that I didn’t go and become a lawyer, it was that I never took the bar exam, even though I was on Law Review and top of the class because I was like, “I don’t even want to doubt this is the right move for me.” To this day. I’m like, “Damn, I wish I could have done that.” But there was a utility to giving myself no option to do that, and look how it all turned out, right? So some people will say, “This is you tidying up your life.” And they could say that but it’s not true.

Katie: That was just filled with MicDrop moments. I need to get you a mic so you can just drop it.

Matt: I mean you can edit it down so it was like a MicDrop moment.

Katie: I love all of those moments. Matt, what’s one brand that you admire and why?

Matt: I’m gonna say Apple because when Steve Jobs died I didn’t think Tim Cook had what it would take to continue that legacy. I thought it was more of a cult of personality. And here we are years and years later, and they continue to be Apple. They are disciplined, and they’ve rolled out new products, they just continue to be Apple.

Those who know the history know that Apple almost went under, right? And it took one person, Steve Jobs, to right the ship. So I presumed that with the absence of that person, it would enter into a period of decline, and it’s done the exact opposite. So I think Apple is the best brand on Earth, but probably the best-run company on earth of that magnitude.

Katie: What are three resources you’d recommend to someone looking to build their personal or corporate brand?

Matt: So number one, I think LinkedIn is incredibly powerful and still underestimated because it is the only platform where you can go viral. So LinkedIn is important for a number of reasons: One, to develop reach, and two, it’s to reach the people that you probably want to reach more than you even realize. You’re spending all your time on Instagram or other nonsense. I would make sure you’re on LinkedIn and also test out your confidence. Don’t just be on it, post on it at least once or twice a week. So that would be one.

Two, I think YouTube shorts are going to be huge. It will eventually inherit the landscape after TikTok runs its course. I think it is already running its course and I believe it will be prohibited within probably two years to three years. So I would say YouTube.

And then the last thing is less about personal brand. It’s more about understanding all the tools that are available to put yourself out there, and that’s Twitter threads. I love Twitter, I think Twitter is the land of hate otherwise, and vitriol and cortisol, but I love the threads. And so back to my point about me being incredibly tactical, I think the strategy is actually very overrated, I would stay very tactical around AI tools. I go deep into Midjourney and to Pictory and every kind of tool out there. I’m constantly playing with it because it’s real-time. A lot of those tools are really about enabling communication and your personal brand and how you show up. So anybody listening here who is like, “Well, I don’t have a marketing person, or I don’t have somebody to film me or make my videos.” And the reason why I’m landing here as my third point is that I would imagine anybody here who doesn’t have a brand, or believes they don’t have a brand is using the excuse that they don’t have the resources to have a brand, and in reality, that’s not true anymore and you’re doing yourself a disservice. The only way I could prove it to you is for you to read the Twitter AI threads about content creation, and you will realize that you 100% have the ability without a single employee to build a massive brand and to get it out there. 

Katie: What’s up and coming for you Matt? Where can people connect with you? Where can they get “Burn the Boats”?

Matt: Well, at any moment I’m doing a ton of things. I think what I’m excited about right now is that I have a new TV show that I worked hard on. If anyone out there saw the show “House Hunters,” it’s a cool show. I partnered up with Mark Burnett to create a similar version of that in a business context where I present people with three different options for a business to buy. 

I love the show, we shot it for 10 weeks, and I killed myself working on it, and then it never aired because CNBC went a different direction and cancelled their primetime slates. So what I always do when things don’t go right, I was like, “I’m gonna create my production studio.” So Gary Vee, Gary Vaynerchuk and I, and Eric Weinberg, launched our production studio so we can do reality programming. I’m going to be doing a lot of business programming. So if anybody hears this and you have a brilliant idea for a business show, DM me. In terms of where they can find “Burn the Boats,” it’s available on Amazon. I also speak about it, which I love, and I spend probably the most amount of my time on LinkedIn. So if you want to find me, DM me on LinkedIn.

Katie: I encourage all of our listeners to pick up a copy of “Burn the Boats.” It’s an inspiring call to action to take big risks with your life and with your business and I think it just leaves you so encouraged reading it.

Matt: Well, thank you. I’m so excited to watch you build your business, you’ve already built the most incredible studio look. I just know you’re gonna go to big, big places. As somebody who has built agencies from scratch and taken them to incredible places. I know you’re gonna do the same thing. So thanks for having me!

Katie: That means a lot, Matt, thanks so much for being here. I was energized by this conversation and I know our listeners will be as well. Thanks very much for your time.

Matt: Thank you, everybody.

Katie: Thank you for listening to Get Mic’d. If you enjoyed this episode, please be sure to subscribe to the podcast and leave a review. We’re excited about continuing to bring forward more conversations with thought leaders on what it takes to build a notable brand. We’ll see you next time.