Why Having a Backup Plan Is Making You Fail - Burn the boats with Matt Higgins

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A long time ago in 1519, Henaz Cortez landed on the foreign shores of South America. His mission was to capture local treasures. which had been defended for over six hundred years by very large local armies. As they disembarked onto the shores and their men stood ready for their mission, Cortez ordered them to burn their boats that they had sailed thereon. He promised them that they would sail their enemies' boats after the mission had succeeded.

It was this decision that led to Cortes's overwhelming military success and the actual downfall of the Aztec Empire at large. It also led to the coining of the phrase burn the boat. This action actually was not new. It had been a military tactic for a long time with generals ordering their armies to break the cooking pots that they used under the promise that they would eat their enemies' food that night if they won, or die of starvation.

In fact, this was even used by Julius Caesar, long, long before Cortes. Back here in the modern day, we will hopefully not need to invade entire continents. But psychology has shown that having a backup plan can genuinely increase the likelihood of us failing in our primary objective. And we are going to dig into that in depth this episode. So, firstly, I am delighted to say that I have Matt Higgins on the show to talk about the concept of burning the boats. He is the author of the book.

Burn the boats, so he should have something useful to say here. He was also a shark on Shark Tank for two seasons, Which is the American equivalent of Dragon's Den for anyone who doesn't know. Despite being wildly successful, blah blah blah, he started life in poverty looking after his disabled mother and hustling in any way that he could to keep things afloat.

He realised as a teenager who was stuck on minimum wage that there was a crazy hack that if you were a college student, regardless of your age, you could be eligible for a higher minimum wage. Sadly though, he wasn't at the level of genius to be sent to college three years early. But

He realized that there is a college entrance test for people who aren't in school that you can take and be let into college. So, crazily, he failed every single class he had in school deliberately so that he could flank out. and that way could be someone not in school eligible to take the college entrance test, and hopefully quickly raise his wage and his family's survival.

And he did it and it worked despite everyone telling him he was a complete idiot and that he was just going to ruin his life. That said, it's hardly been smooth sailing for him since. When he finished college and on the first day of starting his job, his mother died. Later, he had testicular cancer and went from being a healthy male to rushing into hospital to have a testicle removed within 24 hours of finding out about it.

So let's say he knows a thing or two about living with anxiety and the concept that things can just come crashing down around you.

He has also started several successful businesses. He runs a VC firm called RSE Ventures along with his business partner, Steve Ross, the owner of the Miami Dolphins. He has been an early investor in Resi and the Drone Racing League and even Vayner Media, which you might know as Gary Vaynerchuk's media business.

Matt has been so good at business that he's now been lecturing at Harvard Business School for over five years, so he has learned a thing or two about teaching people concepts they need to learn to get where they need to go. So back to burning the boat. His book Burning the Boats is a fascinating look at the mental models that most people find really hard to understand but are worth knowing if they want to succeed, so it was a delight to dig into the details with him.

Now to start with, burning the boats and not having a backup plan. A part of me is like, this is brilliant, and the other part of me is like, this is so stupid and dumb. I genuinely feel some cognitive dissonance in my brain, and so the first thing I want to find out from you, Matt, was Did you have much cognitive dissonance going on with you? When you failed out of school to go all in on your plan to try and raise your wage.

I love that you said that by the way,'cause at the same time it is so powerful and it's also so stupid and sophomore and simplistic and hard to apply, yet we're it's meant to trigger a debate and there's already raging inside you anyway.

So the whole cover decided to like piss you off. And the cover is a little bit of an inside joke'cause a lot of people who use that phrase use it in a very bombastic like burn the boats to hell with anyone. And I actually thought I was the one to write this book. because it doesn't come naturally to me. I'm not the perfectly self possessed person. I am the anxiety laden, angst ridden who burns the boat anyway.

And so the the whole book is a little bit of a parody on the idea while at the same time recognizing that it is true. and figure out how to do it. So to answer your question,

was I reconciled to doing it was no. And I did it in spite of when you were going through something terrible and you could hear the blood rushing through your ears. Like when I look back, you ask me, what's the first thing that comes to mind when you think back that era? I think about blood rushing through my ears. In a way that I almost want to pass out on the steps of that high school. Like that's what I think about. So this was not some like self-possessed kid who the universe opened up to.

This was a really hard, lonely, sad, isolating, difficult decision, but I knew instinctively it was the right one to make. I wrote this book because it doesn't come easy for me. And perhaps because it doesn't, maybe I can break through to those because I believe

Tons of people put a ceiling on their ambition because they self select out of risk, because others have told them they're not a risk taker or they believe they're not a risk taker. And no one's ever tried to mentor them along the journey. So I was like, Well, let me write a book about what it really looks like, the nonsense Instagram posts and show you like

What going forward, what going back looks when you've like got through the other side and it's done, it seems sensible. But we obviously heard all about people that drop out of college and start these huge businesses, but dropping out of like high school because you've completely failed everything is

like a much bigger risk, especially if you've got into like a college'cause you've got straight A's and you're just too busy building some epic business whilst you're there, it makes sense to drop out. But if you haven't got anything to date other than selling flowers and you then fail everything, that's like a much bigger level of risk, I feel. So kudos to you. Um the words around this idea do matter a lot in terms of

one on one burn the boats. The boat I'm obviously using as a metaphor for anything that holds you back. So for me it was some of those patterns and shame. A lot of it had to do with shame of concealment. But the boat is the metaphor for things that are holding you back, that are beckoning you to retreat.

And then the idea of what are you burning the boats for is a really important question. And I have been on Chart Tank before. I've looked at a tons of deals and I've mentored people whose lives are just going in the wrong direction and they're on a loop. And when you realize the problem, it's because they burn the boat for a tactic and not the objective. And what I mean by that is when most people start a business, let's just say they invented some random widget, whatever.

They liked the widget, but the widget was a means to an end, usually freedom and autonomy. And so when I say burn the boats, it's important to first say, what am I really burning the boats for? And I would argue most people who are like you were saying, I I'm segueing off what you were asking, when life isn't working out and they got nothing going for them and they're on repeat, it's because

They haven't meditated on like, wait, what am I really burning the boats for? And when you level up and zoom out to the big objective, it gives you the freedom to iterate within your tactics. And you'd be like, all right, that product sucks. All I care about is freedom. All I care about is saying my my care of my little baby girl. And so people become much more nimble. Jeff Babe Bezos uses language around this. I actually think that's the whole reason for Amazon's existence.

He basically says be rigid in your vision but flexible in your execution. And it's another way of saying burn the boats for the vision, for the goal, but be really nimble on the execution. Now that might have been a nonsense, what I just did. I wanted to share it. And I do really like the way you've spoken about this in terms of

the image and idea that people have when they say burn the boats'cause I think a lot of terms get hijacked these days or in psychology people talk about narcissism or gaslighting all the time now. Like it's just such a common thing. And they're really using it incorrectly. And I really like the way you then explain Burn the Boats is like it's more of a

like our own retreat plan, while the people generally just talk about is like, Oh, that's just a go all in on attacking something. But you can still go all in but still have a way to retreat out. Yeah, that's actually I love this conversation. I feel like we're breaking a little bit of new ground on this topic for me. I haven't talked about this. That you're right. I'm putting the emphasis on the thing that was c beckoning retreat, not on the thing that you're actually going all in on. In fact,

mentally I don't even think that much about that. I actually am much more focused on the thing that's undermining rather than the thing you're doing. To me, that is always the unlock, right? Not like less the fully commit, more the what is this thing that's beckoning you?

And in my head, when you first hear Burn the Boats as like a business lead, you imagine someone trying to be like brave heart and saying a big speech and like leading people into battle rather than the and taking away all the ways that you should have Terima kasih. Let's use it as a very practical example for those who are listening, anybody struggling with this. So think about all the things that you want to do or might do that are pretty bold.

And now audit the reasons why you haven't acted. And I'm sure within those reasons will be anticipated social appropriate from somewhere. It could be from your partner judging you. Maybe you have a partner who's a little bit subversive and is like, oh, there you go again, thinking that you can do this.

Or maybe it's anticipated about how your boss is going to react. So we're often preempting our own ambition in anticipation of being censored by someone else. And so that's not a going all in. That is a burning the boat. And the boat in that case is those that you imagine will undermine you and then self-censoring your ambition and anticipation of

I'm trying to now to say that in a textbook way is very boring. So the book is illustrates like even that little sub point in a very subtle way through storytelling because peop that's how people assimilate it, but I love what you're zeroing in on because that is exactly what I'm trying to focus on much more than like we're gonna hit our sales targets. Like that's not interesting.

'Cause you might not hit your sales target target. This is not an if then. If you burn the boats, then you will hit your s our sales target. It's if you don't burn the boats, you definitely won't hit your sales target. Do you know what kills business security besides hackers? Complexity Companies buy five different tools, none of them talk to each other.

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I do think that there's a big other area that I was also confused on around the concept of it can be really useful for people to have a way to retreat or depending on your levels of anxiety and risk taking, as in some people that's when they perform their best and if they really come out their shell and grow in these things and other people definitely shrink and have problems when they are put in a more risky situation without any boat.

So how do you manage your own risk levels and increase them in terms of like whole growth mindset, get out of your comfort zone? Now let's reconcile this because it's an important point because that's where the cognitive dissonance comes in. Like so if you don't break down the nuance of this idea, you'll reject it intellectually, be like, well, that doesn't make sense. Like I gotta pay the rent.

It's not what I'm saying. I am saying though, is that if you're trying to do something that is a by definition a breakthrough or a breakout, something slightly beyond your reach to achieve that, you probably need a hundred and ten percent.

of your ability, your energy, everything, of course, because it's beyond your reach. And so the what the studies show, which is fascinating, is there's a great study out of twenty fourteen out of Wharton, where they set out to demonstrate what you just said, which is that actually having a backup plan would make you perform better because you're more at ease, because you're you know that everything's gonna be okay if things don't work out.

So without going too much into the study mechanics, what was fascinating is no matter how much they tried to undermine the result of the study, and they tried, they couldn't undermine two points that came out. One, merely having a backup plan actually reduces the likelihood that you'll be successful against the control group dramatically, statistically. And number two,

It actually measurably reduces your intrinsic motivation to achieve what you always thought you wanted to achieve as measured right before the test. And in other words, you care a lot less. And what the study found and what other studies support is that actually the reason we tell ourselves we create a backup plan is very different from the true reason we do. We tell ourselves it's prudent. We've been conditioned that it's prudent.

logically resonates that it's like prudent. And actually the reason we're doing is to ameliorate the suffering and the pain of anguish of wanting something so bad you feel like you could die. But the problem is the pain is the very thing that propels you. And the pain is the thing that actually makes you pursue it. So how do you reconcile that though with the pragmatic reality of managing risk? And so for me, I have a

simple kind of four step process. This is not rocket science. It's what I use. One. I embrace my inner catastrophizer before I do anything hard. I'm very creative in all the ways like we talked, we start this conversation that I'm one step away from ruining my entire life. I I let that thing roam free. Like if I try to go on Shark Tank and I screw up

What's the worst gonna happen? Everyone's gonna laugh at you, you're gonna lose your job, you're gonna get canceled. Okay, all that good stuff. Number two, all right, if that were to happen, what would I do? And the reason why that's so important, we have hardwired into our factory settings, our back. We know how to feed ourselves. It's very primitive. Mine's on my wall right there. It's a law degree I hope to never have to use, but it's hanging up right there, wallpaper.

Number three, what's the probability that the worst thing I imagine is going to happen will happen? And the answer is very low. We're very bad at predicting the bad things that are going to happen, even though we're very creative. And that's important to confront. the absurdity of the things we imagine in our inner catastrophizer. And then four, my last part of my process. It's like what would I not be willing to do to give up? What pain would I not willing to subject myself to achieve?

my goals. Like I teach at Harvard Business School. It's my fifth year. Imagine going from a kid who dropped out of high school, sold flowers, and watched my mother die in a bed of urine, like giving her sponge bass, as a twenty-six year old man who never had a friend over that house.

and true like hellhole of despair and then to end up teaching in Harvard Business School. Like, I would come within an inch of my life to pull that off. And so the reason why that four step process is so important. When I started pursuing, and this is just one example, this actually happened. I was like, Oh, I'm gonna suck in the classroom. End trip's terrible. Everyone's gonna know I'm a fraud.

I was like, no, no, I already went through that four step process. Like I'm all in now. When you process risk at the beginning of your journey at the inception, it changes your entire outlook. So what I'm trying to say is burn the boats doesn't mean ignoring your risk profile. It means synthesizing. Your risk tolerance before you begin so that you can be all in when you're underway and don't look over your shoulder. Yes, definitely.

a lot that you can do to learn to understand what sort of crises are gonna come and whether they're actually worth paying attention to and then. I find there's a lot of benefit in realizing that most of these things that you're panicking about and be like, Well, if that actually does happen, it's not that bad as in

you're here now and you you've been through divorce, like it was probably terrible, but you're still having a pretty good life. It's it still didn't ruin your overall life kind of thing. And there's the concept of post traumatic growth and if you start to kind of Embrace that area, you realise like, okay, adversity is just gonna push me forwards anyway. And then you still shouldn't

right into the terrible things, but it does make it easier to be less afraid of them. It's funny with this perpetual dialogue now on social media commiserating about the things we're going through, but it's so superficial. So one of the ones I hate is like failure's great. I was like, Well that doesn't that rings not true. Failure is terrible and should be avoided at all costs. That's different than saying, and I believe this personally and I found this to be a hundred percent true.

that for every crisis I have ever been through, I have approached it with the mindset that I'm going to extract more value than was just taken from me. And I usually I do set it up as a battle of something taken and something taken back. If you approach every crisis, every failure, every setback with the mindset that I'm gonna extract more value

than what was taken from me, it always ends up being true. But if you actually don't have that mindset, it never is true. It's a long way of saying there's a ton of value not only in meditating on it's probably going to be okay. It's actually more than that. It's probably going to be better. Some people say, well, Matt, that doesn't hold up in the context of uh cancer. Like you had cancer, you have one testicle. And I was like, are you kidding? 100%.

True. Like I have people's attention now. I've been through adversity. I would gladly give up my right testicle to have moral authority to reach people about adversity. Infinitely exponentially more important than I had cancer in terms of what I do with it. My mother's death. As horrible as it is, and wherever my mother is right now, looking down, she's like, All right, I wish I had lived longer. That is true. But you have now written dozens of scholarships for single mother.

that you never would have written if you hadn't witnessed what I went through. And that the trajectory changing impact I've had on their lives could arguably be more important than what my mother's like. Maybe my mother would feel that way. And if she doesn't yet, she will in the end. You know what I mean? Like that is how I approach every kind of crisis and bad situation. Yeah, that's a really nice lighting.

Yeah, have you f found that people's perception of you has changed a lot since doing Shark Tank?'Cause I've feel like just even when you get introduced to someone as a VC, it already has people's kind of expectations around like who you are and what you can do. Yeah, I wonder if you felt like there's been a public difference now that you've sort of been on Charlie Tank where they're making this person is just makes dreams come true and stuff.

Yeah, that's such a great question. It was c one partly was calculated, right? It's a great proxy for communicating that you're the best or among the best. But actually two, then I began to feel very alienated. It's the re it's the reason that pr finally prompted me to write the book.

I remember going to talk to kids who were getting a G D. They were living in a homeless shelter and these kids were like struggling a lot of the men were been rejected by their parents were gay or there were lots of reasons And yet even still they were in a homeless shelter trying to get their GD. And I remember I went to talk to them in the room.

And I was like, Well, what do you think about me? Or I forgot how I framed it. And they're like, Oh, you're mad rich. And like you got custom suits and Shark Tank gave them a certain impression of who I am. And when I started sharing my story about, G D and my mother and d details that I don't even share publicly. One girl in the back was sobbing, sobbing, and I realized, huh? The authority of being on Shark Tank is not the kind of authority I wished you have in this world.

I want to use the authority that I now have on Shartang because it's now giving me credentials. along with Harvard to get people's attention. And then the question is, what am I going to do with the authority? And I made a decision when I wrote that book. I'm going to use that authority to actually pull back the curtain on how ugly it really is. Because I think at the service that we do,

This is a complicated thought. But like if you look at every an Instagram post is like a narrative arc with all these self-anointed gurus, it's like I once had a problem, but I overcame it. And now I'm gonna share with you what it looks like.

particularly well adjusted. And that's a lie. And what that lie perpetuates in someone's mind, because this is not how the rhythm of people work, it actually says that you're going to arrive at a destination and everything's going to be okay. And so a long way of saying back to Shark Tank in your question.

I was like, oh, this is actually a tool to get people's attention to use my authority. And when I look at people like Elon Musk, I'm always saying like, how do you use your authority? Like why would you not be using yours rather than do shit coins and doge? Why not use your authority to like shine a light on this topic? Long way of saying it did change. Uh, I didn't like it actually, but I've chosen to use it as a proxy for authority to then redirect attention back to this idea.

What does it look like to break through the ugly and be successful in spite of, not because of? your gifts. And I think most people are actually successful in spite of working against that which holds them back rather than working with whatever their God given gifts are. Yeah, it's a hard one working out where to pay attention of amplifying your strengths or working out your weaknesses. That is a hard one. What do you think on that one?

I certainly feel like I'm doing way better like running my podcast. without having so many distractions going on'cause I have ADHD and so if I try and do five million things, like I can really like suck of myself into stuff and not get things done. So it's really nice to be

focused and just know that I'm either working or I'm not working. Whereas when you have ten different things going on, you can fool yourself into being working all the time. And working out how to iron out the biggest flaw is essential. But then

Also, how can I use that to unlock all my strengths, which is okay, I do like geeking out, I do like researching loads of different topics and reading too many books and listening to all the podcasts. You also like running excessively amounts of long time every day and

I can do that to do more research. So how do you put them all together into one package? Just like work out where your strengths are and amplify them and the things that really just cut you off that stop you. Because I I used to be really inarticulate when I was young, which is another thing I've worked on a lot.

is to be able to talk'cause I was really shy and I had a lisp and I basically just muddled all my words and used any excuse to not talk. But now I'd have had no idea if you told me that I was gonna run a podcast like how I would have even got there like twenty years ago or something. It was be the last thing I'd have thought of. But

I started forcing myself to do more speaking'cause I wanted to be better at running a business, but now I'm not so bothered about running a business because it's actually quite a lot of stress and I quite like running a podcast. I love this topic because I think that where you just ended up is where I end up and that's why I don't like the cliche of like lean into your strengths or whatever. A few things.

I think it's exhausting to constantly try to correct yourself and to overcome whatever it is that you've been through. also think certain things that have been set in motion would take way too much energy to reverse. So let's just say like my version of A D D, was that because of the hyper vigilance? or whatever the reason is, like I don't think I wanna put in the energy it would take to become more adjusted.

And rather I've decided that particular attribute does not interfere with my general direction of my ambition or my life, my worldview. So I put the things that are now in the buckets that don't really interfere with my worldview and now I press those and don't try to fix it. So to give you an example, like My mind is racing all the time. I don't sleep well.

And I am lost in my head. I need a lot of introverted time. I'm the person who leaves that and goes to the bathroom so I can sit there and think or Google things. Like it's just it is the way it is. I really am. And so what I do now is like, you know what? I'm sick of trying to

meditate all the time. And I still do that too. But I'm sick of trying to extinguish that attribute. And instead I'm going to turn it into a positive in a way that satisfies me, even if it seems crazy to the outside world. So I trade derivatives all the time. because it enables me to have a little microcosm of pattern recognition and it's little hits of endorphins and self esteem. So Constantly. I'm looking for a pattern and then I play it.

And that is where my frantic energy goes and that makes me happy. And if you had talked to me a few years ago, I would have been like, that would have been a sign of me failing, of a regressing, not discipline of you. You're doing this is a distraction. That's useless to trade options in the middle of the day. And now I'm like, nope, it's what I need. So I think the answer to what you is what you said before. It's both, but there comes a point in your life where it's okay to accept I am damaged.

in this way. I don't know if there's much I can do about it, but I'm tired of trying and I'm gonna work around it. And I think that's actually important. We don't talk enough about that. We instead lean way too much on therapy, I think. And I think there comes a point where it's like, you know what, leave me alone. Like I'm okay with that this area. I'm all right. I'm not gonna try to fix it.

Definitely. It's a nice concept well around space sort of embracing your flaws or some of them and working out to like work with them might necessarily make them a strength, but make them something that's fine. As in terms of psychology, like we're all on a different spectrum of like introverted, extroverted, narcissism or not. And there's still strengths in each level of wherever you are with those things. They're still

assets that you can still run with, even though they're a weakness for one form of action, but they're still a strength for something else. So like where can it be applied and where there is more of a strength? Then also there's another thing around distraction of how you're using your general brain's capacity in where it gets energy from because of it's really hard say I used to do like engineering and be

storing out some systems on oil rigs, for example, and it would be so boring to go through like two hours worth of just like fault checking like a million different signals. But if I had an audio bo book on at the same time, I could just sit and concentrate for the whole hours'cause most of my brain was in an audiobook world.

And like I only needed enough capacity to just be checking these different signals and running these stupid algorithms and that was fine. But like how do you optimise the level of what your brain wants to do and where it's struggling to like be used is interesting. Well, also back to pattern recognition, right? Like pattern recognition is the greatest unlock of well, whatever's your tapestry for pattern recognition is valuable.

So for me, the reason why I do derivatives as silly as it is in public markets is because it's a contained, controlled universe where I could then

reaffirm my belief in my own pattern recognition, right? Oh, I spotted that. I knew what that movement was going to look like. I knew that Bitcoin post DTF would do X. Those things actually reaffirm pattern recognition. And so there's something to be said for the these little maybe a canvas that we paint on that enables us to use our pattern recognition skills and make us feel confident in our ability and then we use it writ large in a context that maybe

matters more. So that's how I have reconciled myself. Like I need that because I'm doing really hard stuff where you know, and any given day I feel defeated on some battlefield and I'm getting defeated and I need to go to return to something that I can control. That's frenetic unless my mind wander and then I feel better and I'm like, okay, right. I'm good at that. I can go back to there.

Another point, really important point we were talking about where to put your energy In terms of directing towards where you're weak or leaning to your strengths. What is fascinating, one of the benefits about getting older, it's so remarkable to watch. I'm obsessed with compounding, right? It's the most important principle in the universe, financially at least. And it's the greatest asset that a young person has, right? You're younger than I am. I'm forty-nine now, right?

What's fascinating about compounding is bad decisions compound just as effectively as good decisions. And so if you're trying to figure out whether or not something needs to be mitigated or eliminated, extinguished from your life. It's is that thing compounding negatively? and actually pulling you further behind from your ultimate goal.

And I do now, and it's sad but predictable, I'm starting to see people's lives play out. I'm like, oh wow, that was that negative thing that compounded that you didn't address and you leaned into the negative. And you didn't interrupt the pattern. And so that's how I draw a distinction. I say to myself, Okay, if I continue to act frenetically with derivatives, what's the like consequence of that? Is it more b is bad? Is it neutral? Is it or is it good? And so when I conclude that like it's fine.

Then I allow it to flourish. And if I conclude that it's compound negatively adverse to my ambition, then I address. When you look at other people it you're usually not surprised when you see them in ten years time where they've ended up.

'Cause you kind of like all the signs are there and it's the same thing. If you write a book about a character and that character's doing exactly what you're doing right now, where are they gonna be in ten years' time if they're eating too much food or just like their habits?

Like if they're gonna be the same for ten years, is that where you actually wanna end up? And it's it's quite obvious when you step a little bit out of just your day to day okay. I would say for people in their twenties that I think there's sometimes too much advice to like

optimized for your retirement pension and but you don't making savings in terms of it's also you're never twenty again and it's also maybe the time to discover the world and do different things. As in a lot of people get to forty and have a midlife crisis'cause they didn't do an something interesting when they were younger.

And that also impacts your long term things. But let's break that down. I wanna put that in buckets, which one I see more of. So as somebody who's now the other So I'll tell you the more likely pattern. is the one who regrets they didn't lay the foundation and let the foundation compound and the one who's like, Damn, I really didn't get to go to like Bali. I do not encounter the longing. I actually encounter the regret. Isn't that interesting?

I mean I oh now that's different than a different idea of settling. I don't think that's mutually exclusive. I think settling is its own category. I do encounter the settling regret more than any of those other two categories. Like I didn't get to do this or I wish I had been smarter with my decisions. I I encounter the predominant regret I think is actually something. So maybe that's what you're zeroing in on a little bit, like you did not Certainly in like the hierarchy of needs.

Like it's just so much money doesn't make you happy, but it definitely lets you remove a lot of the biggest causes. You know, the money is just a proxy for autonomy and autonomy is a maze. You know, the other thing is anyone who's not had money I always say money doesn't solve all problems except for the problems are created by ha not having money and that's a majority of problems. So

It does matter. But anyway, I think it all boils down to being intentional. Like you're living a very intentional life, right? You're moving. You love being a podcast. You really something very early about yourself, which I don't feel like running lots of businesses. That's honestly gold. Now you're thirty three and that you can curate your life.

I just think the biggest regret I found people later, one, they didn't live intentionally. They didn't curate around that intention because they didn't set the intention. And then they settled because they never set the intention and curated their life around the intention. And it ended up in a life of mediocrity and settling for less than what they could have had.

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I have a few things I still want to talk about. One that was So the book Burn the Boat is about not having backup plans, but then you did talk about the resilience of having backup plans. But I think there's also a concept around just other forms of like strength. So I think one of the problems with entrepreneurship and burnout is that when all your eggs are in one basket, when it doesn't go to plan, Like your whole life can implode. Whereas if you are someone that

has other hobbies, like you go to CrossFit or you exercise a lot, like you still have something that's like nice or you have a good relationship. If you have a few other like pillars of your life, if only one implodes, it's still nice, even though you are putting all the effort into making it happen. So I just interested in on if you've addressed that in the book. Bird of the boats is a recipe for commitment.

not for a unilateral focus and to the exclusion of all other things. It's like, how do you engender full commitment? And you begin by extinguishing the votes that beckon you to retreat from that commitment or undermine that commitment. it is definitely not screed for just like not doing anything else and being one dimensional. I think that's actually very unfulfilling and not necessary. Now what is necessary

is setting boundaries and setting intentions. Like my children are my are everything. My family is my everything. But so is my business and my life. So what did I do? I I don't have a a lot of friends and I don't socialize very much.

I created a self-contained social universe with my wife because something had to give, to be honest. And it's actually not an area that I have a deep need. I don't have a need a lot of like social interaction. I don't need a lot of deep friends. And so I married my best friend. So my point is

Everything comes with a cost. But when you're intentional, you don't mind the trade-offs, right? I go to the gym every day. Get up at six. I go to the gym. I don't turn my phone on. So I make sure I focus on like I have these little boundaries, but that's different than being one dimensional. Yeah, and I do like the concept of choosing the hard thing that you do is in

Easy decisions make for a hard life, hard decisions make for an easy life kind of thing. I guess you spoke to a bit there. The one question I really wanted to ask you around was gender. And I have realized that like two white guys talking about women might not be the best formula, but

Women like at least I've seen have a less of a risk appetite and maybe need some more assurance around doing things as then they're less like to start a business unless someone's told them that it's a good idea, whereas men will just do it or like they'll apply for a job even though they haven't got half the qualifications, whereas women want all of them before they'll apply. So in terms of burning the boats and making something riskier, if a woman doesn't like risk, would they have a different

concept when they read this book? To be honest, the book was written for women. I think it's very preachy to be like, I'm gonna write a book for women. I'd say it is engineered more, to be honest. And the with engineering is in the following. It's illustrating. incredible women who I've had uh privilege of being around who have synthesized wrists and have broken out because I do think most business books celebrate men.

And so if you uh it's so funny we're talking about this. I don't think I've ever had this cover. The first case study in the book is a woman. The last case study in the book is a woman and the end of the book ends with a woman who rejected a job offer for me and created a competing business effectively or an ancillary business.

and created a company that only had female employees because she decided to I hate we're using a word, manifest an environment that we catered to her needs of raising her daughter. So I love that you're asking this question. The greatest triumph of this book for me And I guess it's because women have such a huge impact on my life, my partner, my wife, and I've seen tremendous female entrepreneurs. is the most DMs I get are from women around the world. Saying the book.

held up a mirror to what they suspected they were capable of, not in a condescending way, in a commiserating way. And so to give you a quick story, I got a DM from

a woman named Isabella and she said, Hey, I just read your book. I just want you to know that I quit my job today. Thanks. And I was like, wait, what? I always get nervous. I get at least one message a day from somebody who said that they quit their job or burn their boats and I always feel anxious, excited, but nervous. And anyway, long story short,

She says, I'm gonna I I was uh I'm an investment banker, I'm twenty five years old, I'm gonna go create this company. But your book really gave me the courage and do you mind if I circle back and let you know what I created? I'm like, Yeah, sure. Great. And then three months later, circles back sends me a deck. And I'm like, oh, this is the one, right? Like I wrote this for you. And she sent me the deck. She recruited two female co founders.

This business was meant to be created. And I said, I gotta talk to you so I can understand your journey. I call her and I'm like, How did this all happen? She's like, I had this idea for a business. And every time I would bring it up in the workplace or brown, people would be like, Well, but you're an investment banker. What do you know about this? And it would always put me back. It always like push me down. And my mom, I was talking to her one day and like, mom, like

I don't know, I really wanna do this and she's first generation immigrant from Columbia and she was like baby like I don't know, I'm not an entrepreneur, but I think this book might have the answer. And she gave her the book.

And the book is the thing that got her to quit. Anyway, long story short, I'm an investor in her business. I'm an advisor. And so I love that you asked me that question because I do think I'm always amazed when I go to Harvard Business School and I meet with some of my students, some female students, right? And they're

processing risk and mentube and I'm thinking, wow, from afar, I think anyone who goes to Harvard Business School has de risk their entire life. You're gonna make six fingers. And that's not how people feel. So I really wanted to write a book.

that hopefully cross the divide from like a forty something white guy who you think is now wealthy and and actually pull back the curtain about where I came from so I could connect with people. But the response has been great from women. So long way of saying You'll notice if you read the book again, like, Oh, I see what you did.

Super rewarding, I'm sure, to like get things like that. I've hit it can be really concerning. I especially during the relationship season when I had people being like, Oh, I've made this decision. Like, oh God. It's funny you said that because think about it. Imagine the hit rate is still gonna be low, right? We all make snap judgments and I'll see

post something. And then after I wrote the book, I was like, what's my job here? What's my role now as being a because I'm never the genesis, but I'm sometimes the catalyst, right? For somebody to take this step. But I didn't plant the idea. And I decided my role was love and affirmation. You know what I mean? Was like, good for you. My role is not to render judgment, my role is to just be a kind voice that holds up a mirror.

'Cause again, the point is burning the boast doesn't guarantee you're gonna be successful. It's just not doing it guarantees you won't if it's a hard thing, if it's a breakthrough. So anyway, I love what you just said because it took me a bit to litigate. I'm like, wait, do I have am I now responsible? And I realized, no, what like I'm failing all the time. And if you read my book, it it's like I don't purport to be. The book starts with two very pathetic, stunning failures that broke my heart.

for a reason,'cause I wanted to set the stage, right? Like that this is gonna be painful. So anyway, but uh nonetheless every day I wake up and it is very rewarding and I do love the idea that I'm connecting with people about this anguishing journey of going for it. Nice. I have two questions that I then like to end with that are a bit more oddball. The first one is what is one of your earliest memories?

I'm gonna give you the first one that snaps into my mind. I was on an express bus with my mother taking a blast into the city and I had my head on her shoulder and m my mother would always have me miss school all the time. And I didn't understand that as a kid, what that meant. You know what I mean? And I don't have many childhood memories. I probably only have like five.

from the time before I was eighteen years old. But that is one memory and it's the first time I've recalled back to that of being like, Oh, that actually was dysfunctional because why are we taking a bus in the middle of a school day and we would take buses everywhere. So that's my earliest memory. That's very interesting. Thanks. Then what is one of it doesn't have to be the kindest thing, but one of the kindest things that springs to memory that someone has done for you.

I would honestly say my wife giving me complete understanding for how I show up in the world and compassion, as opposed to trying to squash this part of my personality or condemn it. She has been the greatest force multiplier, like known to the universe. And I'd say that as been the greatest act of kindness. If you ask me what am I most grateful for, it's for to show up in the world and be allowed. to be who you are and be understood has probably been

I'm just giving you what comes to mind right away. I love these questions. I'm not giving you a polished answer. That is the kindest thing. Thank you so much. And yeah, it doesn't need to be a polished answer at all. It's nice to just have what is in your head.

That's the whole point. So thank you for coming on the show. Thank you for having me. That was amazing. And uh check out Burn the Boats. Let me know what you think on Amazon. Operators are standing to DM me. Tell me if you liked it. If you didn't like it, just lie. Well. Thank you so much for Matt coming on the show to discuss some of his many ideas.

I wish we'd had some more time to share some of his personal story because it's absolutely nuts some of the things he'd been through. To be honest, he could write a whole book on just his personal story, and we definitely couldn't fit it all in.

Anyway, we did have some further conversation that wasn't released on this episode, and we will get back to you on a future episode around the concept of burning the boats in relationships and the important different dynamics you have in communication and shared values that make relationships work, whether in romance or in business partnerships.

So some things to look forward to. Otherwise, I would say that risk taking for personal growth is just a really fascinating topic, so it was a delight to have Matt on the show to discuss this all with him. If you want to learn more about this on the business success side, I can really recommend his book, Burn the Boats, for providing a new set of mental models that you really don't hear about that often.

Matt is clearly a super smart guy and he has a new TV show launching soon and I can see it doing really well and I'm sure you're gonna hear a lot more about him. They say that compounding is the eighth wonder of the world. And you talk to some people and it just feels like they're only just getting going. They're at the bottom of the big ramp up curve. Even though they maybe have already come so far like he has. But I am genuine but I am genuinely fascinated to see where he goes next.

On that, I'm of course excited to see where you go next, having heard this episode, and hope that you maybe embrace some more risk in your life and cut out some of those backup plans that are sabotaging your attention and your commitment. If any ideas hit you or resonated, please do share the episode with a friend, as that is by far the largest impact on how the show grows.

You could also be wonderfully kind by hitting us up with a good review if you are feeling generous. And finally, remember that life is very short. There is no backup life to do it all over again, so perhaps life is also too short to have too many of those backup plans getting in the way of you just doing your thing. Regardless of all of that, be kind to yourself and be kind to everyone else too. Thank you so much. Your consistency to reach the end of an episode is legendary.

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