Adam Outland: Welcome back to the Action Catalyst.
This is Adam Outland, and we're continuing the discussion.
We began in episode four 15 with Matt Higgins, co-founder and c e o of private investment firm, R s E Ventures, executive Fellow at Harvard Business School Guest Shark on a b C Shark Tank and author of Burn the Boats, A Guide to Casting Away Your Safety Nets and Overcoming Your.
there's a, a paraphrasing of a, of a quote that I'm gonna butcher right now, but it says something to the fact of, it's important for a man to be ready for when his time comes.
Right?
Yeah.
And I feel that even if you hadn't had that clear picture in your path, you were constantly preparing yourself for a bigger
Matt Higgins: play.
Yeah.
I real, I realized very early, like, okay, if I'm gonna have what's, and again, another question I always ask myself, what's the highest and best use of my time, energy, and resource?
What's the highest and best use of my skills if I know how to communicate and I understand how press works is the best use of that.
Deploying it on behalf of somebody else or on behalf of myself.
Hmm.
So let me put myself in a position to be somebody who needs those skills and not somebody who is rented for those skills.
The kind of a key decision.
And I want to tee off of something you said about about timing and life too and opportunity.
One of the hardest decisions I ever made was taking the job, the press secretary job, because if you look at my life, uh, I'm going to law school at night, I'm trying to get through law school.
Anybody went through law school knows.
It's not like, it's sounded like a, a walk in the park.
Right.
And I'm gonna law school at night, working during the day.
Uh, and then I get a call in April of, uh, you know, of uh, March inviting me to come back at the last year of the mayor's office.
Right.
And, you know, the last year of any administration, you're like a lame duck.
So it was like, and I was stressed like, oh God, I have law school, I'm taking care of.
Like, don't worry, it won't be like, it's the last year we'll coast.
I'm like, I don't think you can coast like City of New York, but Okay.
And then my mom had been deteriorating incre increasingly, but at the same time we, with the money was drained.
We had a home health paid.
I couldn't afford to pay her anymore.
Uh, my mother couldn't even use the shower anymore and my mother was at that point using oxygen.
And I remember she was saying like, you know, don't go to work.
Like, I don't feel good.
And I, and I would say like, I like, what do you mean?
Like we have no money?
I have to, I'm the press secretary of the mayor of new.
, like I have to go.
And so think of the juxtaposition.
You're walking out of this house, which is a source of shame for me that nobody ever comes over.
But this is the day, you know what I mean?
Like, this is the day I am going to achieve my destiny.
I'm gonna make, and I would say like everything changes from here on.
What I really meant is like I can finally break free if I'm honest.
And she asked me not, she asked me not to go, you know, I go to work, you do what you gotta do, you know?
And I get a call that day at 10 o'clock, she had called an ambulance, but she had never done before.
And I was actually relieved, you know, that she was gonna go to the hospital.
And I remember somebody in the office like, Hey, do you want us to send somebody with you?
I mean, you know, we can, we can help.
. I went to the hospital after stopping off and, and she had died, you know, half an hour earlier.
Yeah.
For me to spent all this time in my life, and then she passes away that day.
You know, like it just, I, and I don't know, the moral of that story is like, what was the purpose of all of this?
Like, I was doing all this work to try to get there.
And I guess the, the takeaway for me was that, Um, there are no happy endings guaranteed in life, right?
I like as harsh as that is.
The day before she had died, number one, she had committed that she would eat applesauce from now on because she was 400 pounds.
And she was con like, I'm ready to, you know, you, we all know when, when life is being squeezed out from us.
And two, she said, I just want to take an airplane before I die, cuz she had never taken an airplane.
It's hard for me to, sometimes I have to like disassociate myself.
I talk about it because we should be reminded that there are no guaranteed happy endings and that mortality.
, it's a real thing.
And, and use that time.
Uh, like people, when I hear the story of my mom, they're waiting for the happy ending, like it's a movie.
I was like, no, it ends horrifically , right?
It's just like, it ends terribly, you know?
And.
, there's something
Adam Outland: that I feel like you possess that I wanna pull out of you from all this time that is some ability or something that you do to decompress.
I dunno if it's like a tool or a mental process or, because the amount of stress when you layer in everything would cause some people to just shut down.
You're talking about mentally.
Exhaustion from law school to press secretary to one of the most intense situations that city's ever encountered with, you know, the passing of your mom and the health issues prior to that.
How do you do that then and, and now, like how do you deal with such high extreme amounts of stress and
Matt Higgins: pressure?
It's a great question.
I don't have perfectly great coping mechanisms.
Honestly.
I know what brings me joy.
I marvel at human capacity and I love when I have interactions with somebody.
Is trying to break through, and I could change the trajectory of their life by holding up a mirror.
Hmm.
That's a convoluted thought, but that does make me almost manic.
Like, this is amazing.
Like I, I was able to use my story to inspire you, and you asked me for advice and I was able to distill what's going on in your mind, and we made progress, right?
So that, that, that excites me.
And the reason why I'm pulling that out is if I don't have that in a given.
The stress starts to really get to me.
Yeah.
If, like, if my day is full of, you know, nonsense, small talk, I end up hiding in the bathroom.
You know, like really, like, I'm, I'm, I'm not actually an extrovert.
I'm very introverted.
And so, uh, the way I decompress is to make sure it all matters by having these moments of, of intervention with other people.
Cuz if I've had a lifer of stress and constantly breaking, And the payoff is that I can model what it looks like to somebody else, right?
What I love is that I have authority.
That's why I always start with the g e d because what happens is when you're me and you're, you know, look, I'm, I'm white male in my late forties.
You can make all sorts of assumptions about me.
Like, I don't wanna be denied my origin story because then I lose the opportunity to inspire somebody else who's in the same spot, right?
So I don't wanna be typecast.
And so, as a.
Because I put in the work of the stress.
If I share it, I can.
I have authority and then I have, and then I can make progress faster.
Does that make sense?
Somebody's not rejecting Well, you don't know.
It's like, what Don't I know.
I just told you that I grew up on government cheese and my mom died after 10 years of agony.
Do I have authority now?
You know?
And then I ended up on Shark Tank.
Will you listen to me now?
And so a lot of the things I've done, if I'm being perfectly honest, were to accumulate authority so that I could do what I really wanna do.
Yeah.
Which is share the lessons I learned when I was 16, that the highest and best use of anybody's life is to ameliorate suffering.
Right.
Like if somebody had like reached out when I was a kid and said like, can I help your mom?
She wouldn't have died.
My mother didn't die cuz she needed to die.
She died because that's how society.
Yeah.
You know, that's the real reality.
So what long way of saying, I guess I don't have decompression mechanisms.
I have things that that excite me and, and sustain me through the pressure that this
Adam Outland: is where, this is the outcome
Matt Higgins: it, right?
Yeah.
I mean like it's probably less well adjusted.
My wife is like the source of everything for me.
Instability.
I married the most amazing person, so she is truly my partner and everything.
She's brilliant, but she's also very well regulat.
And so, so I draw strength from that rock.
Probably the single greatest decision I've ever made.
But like, all kidding aside, everyone should have a partner in the Fox, so helps them get through and she is my rock and that does help me, you know, decompress.
Lesson number four, Mary.
Adam Outland: Well, I like it, you know,
. Matt Higgins: Exactly.
It's so, by the way, lesson number one, number two, and number three, . Right, exactly.
Like I, you know, I don't know if you meet, I meet people, anybody out there listening, I always look for these little signals when I'm doing a deal because it important, it's important who you partnered with.
And when I see these little proxies for contempt and resentment, when a couple is together, I'm like, oh, that's not good.
Why are you trying to cut them down?
Or when somebody says to me like, oh, you know, I really like, uh, him because like, you know, they put me in my place.
You know, when my ego gets too big, I'm like, are you, did you go shopping for somebody to put you in your pla?
I don't know about you, but I'm trying to overcome the imposter syndrome.
I guess you must be an egomaniac.
You know, and they're like, well, I'm not, but like, you know, I have these like, grandiose thoughts.
I'm like, , like, like why are you what?
You know?
And then, and then you realize, I, I get this epiphany.
What I kept hearing people say this word in these questionable relationships.
Like, well, I like, I, you know, they helped me keep grounded.
I'm like, God, like grounded is for planes.
Like, that's not a good word.
You know what I, you know, anyway.
Yeah.
My point being lessons number one, two, and three people out there listening merry Well, you know, like
Adam Outland: Yeah, and, and I like what you just said, that how you see other people interacting with their committed partner tunes you in to maybe some underlying behavior that you want to either invest in or you don't wanna invest in.
I think that's a, when you read some literature about Andrew Carnegie and some of the old heavyweights in business, and they actually would.
Spouses out on dates, uh, with their, with their couple they would take out so they could see the interaction
Matt Higgins: of the family.
And I, I do it all the time.
You know, it's funny in private equity, well, obviously everyone's heard about, you know, s B F what happened with ftx, right?
And, and, and the unspectacular, yet unsophisticated fraud that was allegedly per perpetuated.
But what I find most interesting about that, it's a proxy.
Private equity and, and venture that here's a guy who could basically run his business on Excel, you know, and refuse any sort of oversight and accountability and whatnot like, but what that triggered in me is how some of the worst deals I've ever done are when I defer to the judgment of supposedly a sophisticated, massive firm.
You know?
And then you see all this motion, all these experts, all this diligence.
and then I'd meet the founder after writing the check.
I'm like, he has no color stays.
It's like shirts, a skew.
Looks like he's outta his mind.
Anybody notice he's not in a good place?
Like I always say, there's a great word phrase in Italian, but I won't mess it up by doing it in Italian, doing it in English.
The phish rots from the head.
And so you always wanna understand what's going on in somebody's mind.
What are the choices they made around them?
What's their dynamic with their partner?
Not because you want to judge them for it, because you want to know the areas that you need to unlock and, and get through.
And so a lot of times when you see somebody with a, a partner, That the dynamic just seems to offer, there's an under undercurrent of resentment.
It's one of two reasons.
It's it's, or many reasons, but a couple that kind of rise to the top that the person didn't believe they were good enough at, at a moment in time, right, and or they didn't believe there was better out there.
So they're sort of settling.
So I just think a lot, a lot can be said, but the reason why I care the most is because that's gonna be an extra layer of stress that I'm gonna have to manage if there's a partner dynamic.
Yeah, so good
Adam Outland: for our listenership.
What are some key qualities to expand on what you just said, that you find to be some of the most important attributes to what you look for in someone
Matt Higgins: who's building something?
Let's talk about it from the individual's perspective.
Who's writing the check or backing the business or deciding whether to get involved and from the perspective of evaluating the person who's running the business.
Right?
So from your perspective, I find that people are so afraid of the, the, the idea that they just had or the, you know, or the, or the idea they just stumbled upon that somebody else had.
Is going to be somehow torn apart, that they'll never have a better one.
And so people are, are, talk themselves into it as opposed to scrutinizing, right?
Like it's that spontaneous insight at two in the morning, like, I got a knife for an idea for a business.
And you don't wanna one talk yourself out of it, but two, you don't want to ask yourself the following question, if I pursue this at what cost three years down the road, what, what better thing could I have?
In lieu of doing this, right, and so I spend a lot of energy on opportunity cost.
I'm always pulling forward opportunity, cost, and always assuming I can do the impossible so that I can hold up future met.
Against this Matt, that's gonna have to spend the next three to five years working on this project, business, whatever.
So I do a lot of coaching when somebody tells me they have an idea and you, you've experienced this and you have to deliver the bad news, like this is just not worth your time.
Or you know, more specifically, What you have come up with is a feature, not a, not a business, right?
And whatever the bad news you have to deliver to somebody, that they're on the wrong path.
I always say when I construct when things go wrong or people are unhappy for three, four years down the road, it's because they failed to ask themselves the the right question.
Not that they went down the wrong path.
The question is just because I can do something doesn't mean I should do something right?
Just because I had a good idea at two in the morning doesn't mean it's the best idea and ideas are.
In real estate, there's always a better house on the corner when you lose that house.
Like the same thing with ideas.
So, so I think from, from a, from an investor's standpoint, ask yourself the critical question like about opportunity costs in terms of evaluating who to back, and it, it really is always about people.
Again, cliche, but cliches exist for a reason, like, So I spend a lot of time trying to figure out what makes the person tick and do they have what it takes.
So if I was to boil it down to one thing that I'm always looking for, aside from intellect, those are table stakes.
Fried from general competency.
It's self-awareness.
I think self-awareness is the single greatest arbitrage entirely within someone's control.
Like we spend so much time looking for a hack.
We go to Barnes and Noble and we look at business books.
My book, we listen to podcasts.
We spend so much, we spend more hours now than we ever have before seeking out.
Expertise, all in attempt to outsource our instincts and judgment to another.
Mm-hmm.
, it's all the same underlying exercise, right?
Let me outsource my judgment to Matt at the bookstore or to a podcast as opposed to saying, well, let me begin by seeing what I can unlock myself and that journey of unlocking.
Where the arbitrary arbitrar is self-awareness.
So how do I spot self-awareness?
I look for signals tells for a blend of confidence and humility.
Confidence in humility, while they may seem in opposition, are actually inextricably linked because you have to have the confidence to look within and, and face the reality that you're wrong and you have to have the humility to, to acknowledge it publicly.
That's where the course corrections will be made when those things work together, and I can generally predict the outcome of A C E O by the amount of time it takes for them to implement.
A decision that is objectively inevitable.
In other words, you're so screwed and if you don't change product lines, you are gonna fail.
And I, and I find a lot of times people are so afraid to deal with that reality where what they don't realize is the universe gave all of us.
Cuz I do think the universe is benevolent, gave all of us the capacity to iterate and pivot before it's too late.
If you ask yourself how many, when you made the dumbest decisions in your life, how many second chances did the universe present to you before you made that stupid decision?
Like you married the wrong person.
You're like, you kind of knew, but like, and then you broke up seven times.
You know what I mean?
Like yeah.
You have a crappy boss.
You know, they treat you like not, you know what I mean?
Like, you know, self-awareness, confidence, humility will mean that you'll take one of those opportunities sooner out later.
Mm-hmm.
Adam Outland: That's good.
Yeah, and I could even extend on that, that going with your gut is something a lot of managers and leaders sometimes fail to do because we often have to coach them on.
When it's time to let someone go, cuz they're so emotionally tied to someone they know in their gut it's not a right fit, but they'll wait six months to a year to to, to actually pull the trigger because the, maybe the emotional attachment to that person.
So there's so many examples I think of what you just shared.
Matt Higgins: Well, well, what to say with what you said.
It's like, I, I think the, the letting somebody go is an emotional decision full of friction.
We as leaders and as people only have a finite capacity to make hard emotional decisions, they are more draining than other kinds of decisions, right?
So what I, what, when I find this is convoluted, so bear with me, but I really feel so passionate about it.
When somebody's taking on water and they're going through duress, um, particularly in a divorce or, um, bereavement, you know, or depression, your capacity to make hard emotional decisions is severely limited.
And so you can't, you don't wanna face conflict like that.
You just, cuz you're dealing with so much emotional leakage, which is why if you don't create space for your managers or your people to be vulnerable about the incoming, the water they're taking.
They're going to hide that and make really bad decisions to cover it up.
They're gonna rationalize, I need to keep Bill because Bill is a real producer.
It's like, no, no.
Bill is tanking the company when the reality is you don't wanna make it because you're, you're so bogged down with the emo emotional weight, so, Again, so convoluted, and I don't know how you'd put this even in a manual, but I know it to be true, how bad the quality of your decisions were when you were taking on water and how much you wish to avoid emotional conflict because you were already in pain.
So when I, I always think back when I was going through divorce, I made some of the worst decisions I've ever made.
and, but I also was like, there's no room here for this pain.
Like if I had just told everyone I, somebody died in my family, everybody would be consoling me.
But when it comes to that, it's like, uh, nobody cares.
This is the worst thing that I've ever gone through.
Everybody was nice when I had cancer too, and I was like, everybody's really nice when I had cancer.
But with divorce, it's like, No big deal.
And so I learned a lot about myself, about how prior to that I, I didn't have a lot of room for empathy around things that were not objectively cataclysmic.
Mm-hmm.
that I, you know what, but otherwise get over it.
And that's because when I had cancer, I wanted to show everybody.
I was so tough cuz I was so insecure.
I went, I went to work the next day after getting my, you know, testicle removed.
Went to work with a bag of ice and I was like, check me out.
I had a dog tag.
Uh, I said Half the balls twice the man, sorry, many close your ears, children, you know, any, but like all in attempt to show that I was so tough.
And, uh, that's the last thing a manager should do because then people start modeling that behavior and then they hide their.
Yeah.
And packing
Adam Outland: the emotions.
Yeah.
I such a good lesson in that you, you've been so vulnerable about the, the learning paths that you've experienced and I think, you know, listeners really appreciate that cuz so often we look at our models in life, and this is a, a meta example of what you just said, and by listening to a podcast we hear all the perfection.
And we don't get the, the procedure they had to go through and the peeling back the onion and the heartache and the mistakes.
And so just even getting a, a gleam at some of your own personal lessons that you've been through in your journey, I think makes you human to a lot of people.
It also gives people hope they can have the success and, and build something
Matt Higgins: similar.
No, I appreciate you saying that cuz I, I do think we, we're now in a world where people embrace vulnerability.
Everyone knows that you now you need to have a vulnerability.
Like you need to have struggled.
Have struggled and overcame it.
What I think is inauthentic about the universe still and what we see on social media is that everything has an arc.
I was doing great and then I stumbled and then I was humbled and then I rose again and now I'm still here.
Whereas that's not how life is.
Like we all regress to regress as human and so I'm always trying to.
The best I can.
The hu The reality of it, which does ring true.
I mean, I, I I hope people hearing this be like, oh, I can relate to that.
Mm-hmm.
like, and so I don't, I don't like the way the, we manifest on social as if people are now a finished product.
Cuz I think that actually hurts people because It does, it does.
They can't recognize themselves in this because you know that our lives aren't tiny little narrative arcs where we stumbled and we came back and now we're, now we're good again.
We are, our lives are about regression and progress.
In constant seesaw with each other.
And so I work really hard to asterisk the outta my life.
like, you know what I mean?
Like other people try to get rid of the Astor.
I'm trying to put them in because I don't want to do disservice to anybody listening.
Yeah.
Feeling like, think about Shark Tank.
I talk a lot about imposter syndrome on Shark Tank instead of Shark Tank.
And the reason why I feel it's so important, if you watch my first episode, people would objectively say I was very good at it, and the other sharks said, you were great at it.
Right?
Well, if I let the story lie there, then I haven't made a gift of my appearance.
The bigger gift is to say I was shaking like a rabbit . You know what I mean?
And I felt like a kid from Queens.
Adam Outland: Yeah.
What a big thing.
Um, this has been excellent.
In, in lightning round.
These are real quick responses.
Sure.
Tools, apps that you've used recently.
Anything that you
Matt Higgins: feel like has been.
I really, really believe in the power of, of contemplating mortality multiple times a day.
So I have an app that reminds me I'm gonna die five times a day.
Five times a day.
A quote will pop up my phone in new eloquent ways from different philosophers telling me you're about you're gonna die . And the re the, the reason why I hopped into it when I had testicular cancer is like, When, when you, when we're afraid of dying more than we are, anything, I think it's a source of a lot of our grief, but actually, when you contemplate mortality, what it does, it zooms you into the present.
And in the present you have very little pain.
Hmm.
All the things that you anticipate going wrong don't exist in the present.
And then you realize the truth of life is that it is the only thing you're guaranteed.
But we don't connect with that thought.
We say it in a, in a way that's, you know, that we don't really.
And so I have this app on my phone that I use constantly.
It is called We Croak.
We Croak.
Okay.
. I'm actually gonna look into that.
Cause we talk about that.
I really do.
I wonder if the people out there are on this app, like who's that guy?
Keeps talking about our app.
But yeah, that's great.
Uh, and
Adam Outland: then either a book mentor, someone that you
Matt Higgins: follow.
Oh, that, okay.
I'm a huge Emerson fan, right?
Mm-hmm.
I mean, like a lot of my life has lived around Ralph Walder, Emerson, and, and I probably read Self-Reliance every week.
I think it's one of the greatest pieces of writing ever written, and it touches upon themes we talked about in this podcast.
In fact, I think I just basically plagiarized him with my, my thoughts, but basically this idea that, and everyone can relate to this, when you have a spontaneous insight that you feel like you're right.
But you reject it because it's not being validated by the by someone else, and you wait for it to be validated, and now you're forced to take your own idea from another.
And the essay talks about how demoralizing that idea is, which is why, and I coined my own phrase for this, but that OPP opportunity arises before the tipping point of evidence.
And I like to think of it like lightning and thunder.
Opportunity is the flash of lightning.
And then there's the five second time delay before thunder.
If you wait to operate on thunder.
Everybody saw it, but not everybody saw the flash of light.
So Emerson, the, those thoughts came to me as a kid.
I first read it when I was a little boy, and that changed the course of my life.
So self-reliance.
Adam Outland: So good.
Everybody listening?
Uh, go check out the book.
Matt Higgins: Burn the Boats.
Yeah.
Can I give you a minute on the book?
Can I tell you the book?
Yeah, please.
So, burn the Boats.
Why is it called that?
Um, I have basically, uh, appropriated a term that has been used throughout military history by some very bad actors from time to time.
But the common thread of all them, and it goes back to since the beginning of recorded.
The phrasing sometimes slightly different about burn the boats.
Meaning when you are in a, in a position, when you are outnumbered and your back is against the wall, the best way to to channel, um, the best of you is to eliminate your escape route and literally burn the boat.
So it's an art of war.
, it shows up with Caesar and uh, uh, and the ancient Israelites like, it, it it, the simple common.
So my, my thought was, how do I take this idea of giving yourself no plan B uh, and demonstrate that science history, psychology all shows that humans perform better when they don't have a safety net.
Humans, humans are, and that's counterintuitive, cuz when I say this, people like, well, that's easy for you to say, you know, you have money or you, I can't take risk.
I said, I didn't say burn the boats with you.
. Now, I didn't say blow up the bridges.
That's not what the book is called.
. You know what I, I said Burn the boats because what it means is to eliminate the plan B.
And the way you do that is to first by contemplate the worst case scenario.
So to work backwards, right?
So that you can comfortably assume the risk.
And so I decided, let me write a book about what does it truly take.
So it's not Instagram posts and platitudes, like put real thinking behind how do we overcome the.
and the external obstacles that prevent us from fully committing to plan A, because everybody listening to me right now wants to do that.
We all want, I want to do that.
And so I used my story only as a vessel to transmit what does it look like as one case study.
And then I interviewed 50 different celebrities, athletes, artists, people that I have mentored or advised or touched throughout my life.
To show their journey of transcendence because we sometimes like to think, yeah, but I can't, so I wanted to show different manifestations of you or versions of you.
So I have billionaires from Mark Lori, um, and I have Scarlet Johansen.
I'm a partner with her, and then I have a paraplegic gymnast from Connecticut who I'm from Canada rather, who believes her life was better after the accident happened.
Showing how people crossed a threshold of commitment.
And I, I, I, I believe what I did, I hope I did, because this, I feel like this is my life's work.
I tried to create a blueprint for how do you live a life of perpetual growth where you can let go, where you can shed your shame, you can shed the things hold you back and you could fully commit to planning.
Hmm.
Uh, and that
Adam Outland: kind of leads to your, your theme in life of freedom, which I love.
So
Matt Higgins: freedom.
Yeah.
When doesn't have to be your why, but you have to have a.
Adam Outland: Thank you so much for this interview.
Appreciate you being generous with your time.
So this has been wonderful.
Matt Higgins: No, thank you.
I, I love, I love talking, I love talking about these themes.
Take care.
Your hair is amazing, by the way.
I didn't get a cast compliment you on your beautiful hair, right back at you.
Well,