Bill Gurley: 6 Out of 10 People Are Making This Mistake

Transcript from https://podmenti.com/t/7f0e36b8db93e1d7

If you're crafting your own personal career and you're high agency, AI is like a jackpack. We've taught children, young adults how to grind. We've taught them to persevere for the sake of perseverance.
And if you're stuck, you're stuck. In order to like do these exercises of finding your passion, you sort of have to be like a ruthless asshole, you think unless you're trying to find that edge, somebody else maybe. You have to understand the difference between risk and uncertainty.
I don't ever remember wanting to quit. Really? Really. What did the voice say when it was like I found my calling?
I feel like I can rule the world, I know I could be what I want to
I wanna talk about the book because there was this there's a bunch of crazy stuff in the book. I wanna talk about the Nobel Laureate thing.
That was interesting. But the craziest like one of the craziest things early in the book I think
Did you run this survey?
And it said that like six or seven out of ten people hate their job.
Yeah, so I had a co writer, co researcher on the book and we spent a ton of time
Together on Zoom calls and
Someone encouraged us to dive
into
A bunch of academic literature. We came across this Gallup poll that said fifty three percent of people aren't engaged at work.
And so
We had this idea to ask like a thousand people if you could start your career over again, would you do it differently and
And seven out of ten said yes.
And then
We w we took that.
to to warn people analytics to do the
official academic version, so you you make sure you get all the statistical data correct.
And their their number came back six out of ten, so still a really big number. And crazy.
There's a great book by Daniel Pink called The Power of Regrets, and he has a somewhat similar survey data of
longitudinal through people's lives. And as you get older
Y your regrets of inaction start to really weigh on you and ruminate in your brain. And
A regret of inaction is is
Actively
not doing something versus a regret of action is I made a mistake.
And humans are really good at
allowing themselves to make a mistake, but the path I never traveled, the door I never opened, is heavier in their mind. And it m the survey d might have been getting at that, like people thinking
Wow, what if I had done something differently?
Well, the reason I was asking is like I kinda want this whole like I'm kind of obsessed with this idea of finding your passion, not just because of your book, but like one of my favorite books is Mastery by Robert Green. Yes, which changed my life. Uh that changed my life.
But
The reason I'm I'm interested in it is because
Like um
I previously had a company that I sold and it was like very s successful, uh, and all the traditional measurements. I have a company now that's quite successful and I like what I do, but in the back of my mind, I think that it's normal
And maybe you could tell me if I'm wrong that like
Even grown ups like who are successful still are like do I am I'm am I following like the right path? Like am I following am I gonna be in that six out of ten or the four out of ten. Do you find that like even when you were
when you left Compact and then eventually got into V C, which I imagine that would be your calling
That you still questioned it?
Yeah, after the engineering
degree I went to Wall Street for three years. So I'm like a re in research? I was in a cell side research analyst, yeah. So I had two stops before
I made it to to venture.
And
Um
In both cases I had a moment of reflection.
And I it it's more clear to me now than it was then, but where I
I asked
Do I see myself doing this thirty years from now?
And in many businesses there's a lifer in the room, you know, that's
that's done it their whole life. And I I don't that sounds a little judgmental. I don't mean it to be
Like but it it gives you a way to reflect on whether that's the
the place you want to be in. Yeah. Because they did it. And and
Th in both cases it
after about two or three years I got to a no, even though I was doing well in those jobs.
But thinking do I want to be still be doing this thirty years from now was was
Clarifying for me. But you said something interesting. So like all right, I thought the book was amazing. The best chapter, the the best part was the early part about f finding your passion. And you're like, that's the hardest part. And like you said that uh
Just now you're like it didn't seem clear to me then, but it does seem clear to me now that I was questioning that. Well, I did do that exercise in my brain, and there's another exercise that Bezos is famous for.
c what he calls the regret minimization framework where he said, What would my eighty year old self
advise me to do in this situation, which is another way to get at
What I was doing and to get at
This uh
This notion of you know
You only have one life.
Like are you really thinking about this decision
With a reflection of the whole life.
And so your eighty year old self
It's probably more risk seeking than you are in that moment.
Because he's trying to minimize that.
Yeah, regret. What was the exercise you did then? How old were you?
I w I the the thing I did is what I already said. I asked myself, Do I still want to be doing this thirty years from now?
And I did it once when I was an engineer, so I was
twenty
Three, twenty four.
But was that voice loud?
I think it was loud.
I had no inhibitions whatsoever about walking away.
Like it didn't bother me. And I
I may have benefited.
In the back of my brain.
Uh from the fact that my father
Went across the country. He he took a flyer and a job.
He got recruit from uh
Virginia to Houston.
To be one of the first employees in Nassau. That's cool.
And and I knew he had done that.
And and
So I d I didn't come from I think if you come from a family where multiple generations have stayed in the same town
It may feel really wild to just
Take flyers.
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Yeah, I was um
Twenty one years old.
I'm from Missouri. I went to school in Nashville, Tennessee.
I had a hot dog stand and that's how I paid my way to college. It was called Southern Sam's Wiener's As Big as a Baby's Arm.
And we had a bunch of locations at these hot dog stands. It was really fun.
And I was like
This is so hard to be out in Tennessee whether it's on hot dogs. It was so hard.
And so I Googled like
Where do internet companies live?'Cause I didn't even know'cause I was obsessed with the internet.
And it said San Francisco. And I was like, What internet companies are cool? Or like I don't know, what like what's like the hot thing.
Well, at the time it was Uber at the time it was called Uber Cab still and Air Bed and Breakfast. Yes.
And so I started looking at this thing called Air Bad and Brefus.
And I called email.
This guy named Brian, the CEO.
And he didn't reply to me, but then I found like another employee to email named Justin and I emailed him and I was like, I'm gonna be there on Monday, can I interview for this company? Obviously Air Ben Bref was called Airbnb.
And uh
They're like, Yeah, you live in the Bay Area and I was like, Yeah, yeah, I live there, which of course I didn't. I was in college in Tennessee.
And so I flew out there the next day, got the interview, got the job, went back to Tennessee, dropped out of college, sold everything I had.
But my parents are entrepreneurs in Missouri, they started their entrepreneurial career owning a fruit stand.
And I remember when I told them, I was like, I'm gonna leave school, I'm gonna join this thing and they're like
What's a startup?
And does it have health insurance? I was like, it has health insurance and it's paying like twenty two dollars an hour. I think it's gonna be fine. And they're like, Okay, cool, we'll come pack up your stuff.
And I remember at that moment, like
that emotional support what's is one of the biggest things that separates what allows people to win versus allow people to lose, because I have met so many people, a lot of my friends are immigrants.
And like the immigrant experience is interesting because a lot of the immigrants it seems like they fall in two categories. One category is like they came here with nothing, so there's
they ha they're willing to do anything to to win and they go down one path. And then the other path is I came here to create a big life. Don't screw this up. Take the safe path.
Right. And my parents were not the safe path. And that was like the most support that they could have for me. And it was so amazing. I'm glad I'm so glad you told that story because
Um
Even though
The
person this book is written towards is the the person on the career path.
And it and I mean that we don't have a chapter on how to advise people. Like it's not written for the advisor, but I think
It will be particularly interesting to parents and advisors to
test whether or not they're willing to help support people in a way that your parents did. Well I think that's a big deal because like for example, you go to the doctor to get like your basic stuff checked.
I go to cow I go to school to get good grades.
But at no point do they ask like are you asked like
Are you happy doing this? And I think that that's like
I think that's why I'm still ups. I don't think I've ever formally I don't think we've ever formally learned how do you find I call it Ikigai, which I'm sure you're very familiar with. It's this Japanese term where imagine like a Venn diagram, but there's four. It's what the world wants.
What the world wants to pay for.
what you're good at and what you're passionate about. The goal is to find something right in the middle.
But no one teaches that, right? It's y and so it's interesting. I the reason I like your book is because that's what it's about. In the yeah, and in in the uh
Chapter titled Chase Your Curiosity. I tried to borrow as many of those type of exercises as possible.
pathways as possible,'cause I think the very hardest part is to figure out actually what it is that drives you
In this way that's gonna make a very
Easy for you to differentiate yourself.
And um it's funny, y you know, you you
You mentioned that one.
There's a
Story in the book about this guy Burt Beverage in Austin, Texas, who's forty.
Years old.
And he's watching a PBS show.
And they say to take
A sheet of paper.
Put it horizontal, draw a line down the middle.
Right on the left what you love to do and on the right what you're good at and try and find something in the middle.
And through that exercise.
He quit being a mortgage broker. He had been a seismologist before that.
And launched a vodka company called Tito's.
Um at the age at the age of forty.
I think there's this like famous Mozart quote.
Where someone was like asking Mozart, like how do I find my way? Or how do I like Do I have what it takes to be the man? And Mozart was like, dude, if you're asking that question, the answer's no because the conquerors just conquer.
And I o I hated his reply to that because I'm
But I'm curious. So
I don't even know all of the companies you've invested in because you've been doing it for so long, you've like I don't know how many unicorns have you invested in. I don't know. I don't know. D dozens? Sure.
A lot.
Yeah.
And you've been around all the movers and shakers.
um whether you invested in or you pass or not, you are somehow like touched all these amazing people. Did they follow a similar path?
Um, for the founders, I think you'd find a lot of different stories and different pathways that got'em to where they are. I mean if you
The like the Zuckerberg story's pretty famous. He's at Harvard doing messing around.
And and that's very different from the path, say a Gates took, or or even uh Bezos. So I don't know that there is a pathway to that place.
Um
I'll tell you, I I once asked Jeff Bezos
How he could possibly be good at angel investing wise running this company.
Oh, he did uh Google Uber.
But murderers road. He was on the uh he was in the seed round of Google. Yes.
Oh d wow, that's amazing. What was the evaluation then?
I I think that first round was a ten poster. But but but to get to the point, he said
The only thing he looks for is this
Insane determinism.
He he wanted to believe the person was gonna go do this no matter what, come hell or high water.
And I think that may be a common trait.
A lot of the founders. They're just
Really, really determined.
Um and pushing against this thing. The other thing
That's true of any
Tech founder.
Is they're hyper curious about the edge of what the technology can do.
And
Any time there's a big disruption, AI being the most recent, but before that
There was social media and the mobile wave and the SaaS wave and
All these waves.
And they create opportunity because incumbents are usually slow to embrace them and so you can run at these things fast. But that requires
you to be hyper curious about where the world's going and what's changing.
So that you can master it before anyone else does.
You uh there's this cool book called Grit. We talked about it a ton here on this podcast and you cite it a bunch. Yeah. It's awesome.
I forget the exact equation, but it's basically like she Angela Duckworth, she's like
I think she started um the original book with fifty percent.
Passionate fifty percent perseverance. And
Um one thing we highlight we actually had a chance to talk to her, which I'm super grateful for.
But we found this podcast she had done ten years later where she said it probably shouldn't have been fifty fifty that it needed to put more weight on passion and her
Her fear is that we've talked
Children, young adults how to grind.
So the we've taught'em to persevere for the sake of perseverance.
And she believes that now that now she believes that leads to burnout.
And so if you have
Like
All this effort without the love for it.
It it feels more like work.
And one of the things
You know, my the second principle here after you chase your curiosity is to hone your craft. And that's a lifelong journey, always learning.
And
For people that are in the right space.
That comes free.
Like you just do it naturally. You wake up and wanna do it. Like you're drawn to knowing more about
The craft.
And
And I think that that correlates nicely with where sh where she came out, which is
You it's hard to do all the things I recommend in this book if you don't truly love it.
I didn't realise it, but passion I think is
Probably I think passion's kind of a bad word.
Because like passion
kind of implies that I'm gonna like everything I do. And if you like talk to like
a lot of athletes, they're like, Well, I love competing. I do like practicing, but there's definitely days that I hate doing it, but I'm a pro and I'm gonna do it no matter what. And like I love winning.
W we highlight in the book that that word's kinda cliched and overuse. Uh uh Seinfeld gave a talk at Duke where he said fascination was a better word. I think obsession's a good word
Um
We titled the chapter Chase Your Curiosity. Like what just what is it that you
You can't ignore. Like what is this thing that you love so much that you always want to know more?
About it.
Yeah.
What was your uh
You did a good job of like listening to all these exercises to like find it. What was the uh most productive one that you found?
Well, I mentioned the one that Tito had used. Um the the team that wrote Designing Your Life has has one that they say is most popular, which is is battle carding. So
Like come up with three to five potential career paths, not just one. And let your brain roll around in'em for a while. So you you could do that. Especially with AI today, you could
Imagine I'm gonna do this. What does it look like two years from now? Like who are you know, what might I like, what might I not like? You can
You ca and then you know, you could say, Well what if it were this or this?
So that's an exercise.
Um
I think having the mental
relaxation to not feel like some path you've been down at some cost. Like I'm gonna go try this. And if it works, great. If not, I'll do something else.
Just as your parents.
Said it's okay to quit college and go work there.
Um, it's okay to quit the job you're in as well.
And I just fear
We put so much weight.
On
Economic stability, you know, you mentioned some of those immigrant families and what they they push the the the there's this burden
Two
Do that.
above and beyond
What might be fulfilling.
in your life. And
I I think it'd be better if we got out of that. And and or or at least this way.
Think of it as a a you know
A gate. We've gone.
pretty damn far to one side. Let's let's bring it back a little bit.
Have you messed up?
With your like have you had to pull yourself back with your kids? Yeah, yeah, yeah. I think there's a and having
Um, they're all in their early twenties, so they're all trying to find it. Like I don't know if they're all even there yet, but
There is this intuition as a parent and I
I think it's well intentioned.
Two
Two.
Worry to feel like they're on a safe path.
And safe is usually economic, but it's also
Uh it's just
Risk feels like your risk. Like it like and and
I I love the story what your parents did and I've got a few anecdotes I found
Since we finished the book that are great on that are very similar to what your parents did. But I think it's
the exception. I don't think it's the rule. I think a lot of parents would have
tried to convince you to finish out and get your degree.
I think that's built into to most uh parents and and so there are other people other than myself that
That have highlighted that
The
I'd call it like this industrial college matriculation path has gotten
Very rigid and
And it's competitive and it's grindy.
That the the c like getting into college now is significantly harder. Yeah, they've not expanded they've not expanded the uh enrollment at these schools, but the number of
people that want to go to college has gone way up. It's crazy. And
And starting around sixth grade, once again, well intentioned parents start building the resume to get into college. And so we over schedule children today compared to when I was young. For sure.
And so they're they're scheduled from when they wake up to when they go to bed.
There's actually a chapter in Jonathan Heights book, Calling in the American Mind, called The Decline of Play.
Where we've just got to be a little bit more.
We we
It's harder, I think, for a child to explore and try on different
Ideas.
Um because they're caught up in this.
Game to try and get into college. You had this crazy stat. You said um
I think the it was uh the people who won a Nobel Prize in science. The scientists who won Nobel Prizes.
Correct me if I'm wrong, but they were twenty two times more likely to participate in things like acting or dance class and things like that. What was that stat? So this was work that Keith Holyoke had done at U CLA. And it relates to a lot of the concepts in the back of range, the book by David Epstein, but
Yeah, it was
Th the people at the top of their field
Um
Are like h much more likely to have
A a breadth of hobbies.
Um, speak more languages, do more things.
Um
And and
Almost I think have a lens on the world that's broader because they were able to try so many different things.
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So
I read this book, uh, Mastery and like the premise is like being a generalist is kinda nonsense. You have to specialise in something, but once you specialise then you become a generalist. I think that's the right pathway. Like I I do I do think you wanna
get started in an area where you can differentiate yourself and then and in in
Many
In both the principal chapter on mentors and peers.
In here and even in the learning.
Uh principal I recommend
You know, as a more advanced level, once you get
You know, up to this level, then go broader. Like start to learn outside your field, find mentors and peers outside your field, and you'll get pulled in more innovative ways. So tell tell me more about that. That like just blink kind of blew my mind. Well I think
What Keith's work
Um
Highlighted was that
Some of the people that are able to reach the top of their field.
are able to draw on mental models from
Much.
from a variety of different places and
Where a hyper specialist
And and
David Epstein's book Rains is all about this specialist versus broad thing. Like that's the really the
The whole
point of the book and he quotes Holyoke as well, but m many different innovations in science have come from people who repotted from one place to another, chemist who becomes a physicist. The person who's a lifelong
Physicist has
Mental models that are pretty rigid at that point in time,'cause that's all they know.
And so
Once again, I think this is an advanced skill. I don't I think after you're succeeding you start to do this. I don't think it's the pathway to the beginning of success,'cause I think you just be too broad.
But some of the smartest people I know
Like like one person profiling the book is Danny Meyer, the Gras Great Restaurant Tour. We're asking him about his mentors and one of the mentors that influenced him the most isn't from the restaurant industry.
Yeah, and so it's uh
It it is a more advanced skill, but it is where you will look the whole goal, I think, is to differentiate yourself along the pathway.
And that is a great way.
More advanced way, but a great way to
To take yourself places you wouldn't have thought of.
Yeah, this cool line. He said.
There's if there's one takeaway that you should have from this book.
peer groups more so than coaching, consulting courses, whatever, is probably the most
powerful thing that you could use and it's under discuss because it doesn't feel intuitive.
to like wanna be peers with someone who might take the same job as you. But it's really powerful.
I think the way you describe it is right. Like everyone talks about mentors and no one talks about peers. So I do have a
A chapter on mentors and I
offer a ton of very practical advice about how to
Play that correctly.
But the peer thing.
The idea is that
When you get on that first rung of the ladder and you're trying climb it.

A friend group.
It might be four, it might be six.
That are also on that same journey and hopefully
I think outside your organization. I think you could start maybe with one person in your org, but for all the reasons we just talked about how breadth of knowledge might give you insights you wouldn't have.
If they're outside your org.
They're gonna see different cultures, they're gonna see different management structures, they're gonna bring a different
viewpoint to you that you wouldn't have had
If they were inside.
Um and then with today's modern tools, you know
Create a create if you're adventurous, create a Slack channel. If you're
If you just want to do a WhatsApp group or a signal group.
And
Share.
You know, share your learnings along the way. When I moved to San Francisco
For Airbnb.
It um
I didn't actually end up getting the job, by the way. They offered me a job and I got it. And then when I was in college, I was like kinda crazy.
And I got arrested. I got D U I.
And I'm sober now. I don't do any drugs or alcohol. I'm completely clean and and by the book.
But they're like, You lied on your resume. You said you didn't have a uh criminal record. And so I didn't end up h getting to start. And so I was stuck out in San Francisco. I was like
What the hell am I gonna do? So I ended up starting a company and it worked out well. But it was like super low point in my life. And when I got there
I created this thing called the anti MBA.
It was my version of a book club and we met once a week.
And we would get a book.
And we would read a book a month and talk about
a quarter of the book every single week.
And it changed my life.
like having those group of guys to like sick and I think that like
You need a few things to make a group like that work. I think you need like rules. You need like some rituals and you need to like take it serious. Yeah, and I think if there are people that are sharp elbowed or climbers that that step on other people, you kick'em out. Like I I I think you need like minded people who are
Equally gracious to one another.
Who is in your group now that's like uh big shot now.
Well, we one thing I've I've I've discovered lately is setting up different
Like what's up for signal groups for different topics.
I think for someone coming in early into a career it's better to have people that are on that exact journey and I'm not in that place anymore.
I have a company called Hampton, that's my main company.
Are you familiar with the YPO?
Sure.
It's like YPOs. We have thousands of members all over the country and you
It's Chris Pier Group.
And then we have executive coaches who like lead the conversation.
It's for CEO, so you have to like
The average person has like thirty million, twenty million in revenue or so.
And it's been really cool to like watch these members like team and I'm in a uh a
Pure uh core we come core groups. I'm in one as well. And it like
You have this uh a bunch of lines in there about
peer groups and I'm like, Oh, you're writing my ads for me. Yeah, but but but and those things exist with YPO and and your thing for CEOs, but it could be done by anybody. I mean like m my wife, when she was pregnant, she had one for moms.
Uh I've got a a
buddy of mine has one for Jewish dads. Like like it it could be anything, you know what I mean? But like it really does like change things.
It does. I really does.
I think it can uh
And and
Almost all of the
Other principles are accelerated. So
Your learning is accelerated. There's a great
story in the book about Mr Beast that ties to that. There's uh
Your your your network is accelerated. So your network isn't just your network, it's now the network of the group if people are willing to share introductions and that kind of thing.
You know, both for mentors and other peers. And and then the group I think can be really helpful on bad days and everyone's gonna have bad days.
And
There's a support element that comes in into play that I think is really useful. And then also
You you may be at a shitty company. Like your your dream job may be the one you're in and you might be at a shitty company. And if you're alone
You have no way of knowing if that's normal or not, like the the stuff you're exposed to. Whereas if you had a group of eight people that were all doing this in different companies, you'd get different perspectives on that.
What did the voice to you say when
It was like I found my calling.
There was a lack of that voice that kept asking.
Is that what you want to be doing thirty years from now?
Like that.
That worry was gone. Like I I I wasn't
having those negative thoughts, if you will. And what was the thing that you were doing? Investing?
Yeah, once I became a V C, I just adored every minute of the job.
It um but but a lot of that's fitting my individual personality, you know? There are people who
You know, are kind of
They go, Oh, you can't be a V C because you're not the one actually doing the work.
That never bothered me, you know. I I'm someone who's really drawn to intellectual breath.
And so a service job whether it's
working in banking or working as a B C gives me a window
Across way more companies than if I were working in one.
And I also I'm fairly certain I have A D D
And like focusing on details is not something I'm good at. No, you said when people I've heard deaf
Bezo or someone was like I tap dance to work every day and then you're you're saying you adored every minute of it.
It's like I think I found my
Passion, but like
I probably like running a company, it sucks like eighty five percent of the time. And like my last company that saw that it was great, like
If you talk to my wife, she was like you laid on the floor like all the time saying I can't do this, I wanna quit, this sucks.
Like is a door every second of it the right
Is that really I I'm I'm telling you the ex post kinda
Um
But like how many times when you were doing it did you want to quit?
I don't ever remember wanting to quit. Really? Really. That makes me feel horrible.
I think the CEO job's the loneliest job in America. I've said that many, many times before. It's hard.
And one of the things that makes it particularly hard
You need to run
Culturally opposite.
What's happening at the company. So if the company's doing poorly, you have to bring
the positive energy and make people believe it's possible. And if the company's running hot
You wanna bring'em down to earth.
And
This is my
This is my theory on why the CO job so hard. So
Running.
Counter
Emotionally to
What everybody else in the organization feels is exhausting. It's exhausting.
In a world where like
I I've all I've grown to dislike the word and the idea of authenticity.
It's sort of like when you're a young kid and you're trying to meet girls, people say, Just be yourself and I'm like
Girls don't like myself. Like I need to change to be better. And then people are like
Be authentic. And I'm like
But I'm not a good leader. I need to be better. You know what I mean? And so there'll be like be authentic. Like be transparent with your team. Tell them that you're not feeling great. I'm like
No, line. Like you have to like
Convince them that like we're gonna figure this out and somehow you w you know you know what I mean? I do. I leadership's really, really hard. I think one of the things that
Um is often
Not talked about enough.
in the the whole
Both Silicon Valley and just the the uh celebration of the founder
Is that
Did
If you're successful and your company grows, you're gonna go from
Ten employees to a hundred employees to a thousand employees. And eventually leadership's gonna be required and matter.
And
You don't have a place
To learn that.
You know.
It's not
There's no book that he teaches Oh here you're a
founder, you wanna learn to lead people like
And it's not discussed much, but
But the Zuckerberg of the World I know
For a fact that Larry and Sergey
There's this gentleman named Bill Campbell who's unfortunately passed. Trillion dollar coach. Yes. Campbell was there
Ten years after the IPO he was still running the weekly
Team meetings with Larry and Curse.
Bad leaders? I mean what
But I don't know. Steve Jobs used Bill also, so I d I don't know that that makes him bad. I I'm just highlighting the fact that there's no reason
From a DNA standpoint that a founder should naturally be able to lead a thousand people.
Because there's a skill set required to lead a thousand people and no one's taught it to you.
Can you learn it?
Yeah, I think you can learn it. I think certain people have. I think Zuckerberg learned it. I think
Bezos didn't have any
Leadership skills going in. Like he had never run a large team before. What do you suggest to someone to learn how to be a better leader?
Get to know Bill Campbell, but that's no longer with us. So um
You know
I've I've often said
Um
Get two or three mentors that have ran large groups. They will all have
their leadership philosophy and patterns.
And try those on and see which one fits you the best.
So maybe th that's maybe in the middle between
Between the authentic and uh like you
Having a
Programming philosophy is better than none. I can't tell you how many
Found to like two hundred employees and they're not running a weekly meeting. Like
They don't know
To do it.
So some structure.
is better than no structure. And therefore
Rather than say
One of those CEOs you talked to is absolutely right.
Find out what they're doing and see which one feels best for you and your org.
Well you talked about that with
the Danny Meyer.
Uh Daddy Meyer, I think probably most known outside of New York for finding Shake Shack.
You said that um
I think he was gonna be a lawyer or something and he and he and he hated it. But he went and toured a bun his uncle was like, Dude, what are you doing? You gotta be you gotta get in the restaurant business. And so what he did was he did like a field trip to like tour restaurants and then eventually got a part time job
as uh working at a restaurant before starting his restaurant.
Yeah, he also did a tour through Europe as a stage, which is a fancy word for work for free. But you
in the book, you're like he still does that. So like whenever like they're opening up a new restaurant, he goes and like
Uh field trips.
And then you're like when he opened up I think a barbecue place, he like went back to Saint Louis and like tests stuff.
Is there a world where like a white collar job
Uh
I think so.
Like pound the table in in the learning chapter is that most
people don't think about continuous learning in their job.
Yeah. They they founders do because th they're learning these new technologies and maybe doctors do because it's required by law.
But most people that get in into a field I think
I think the college experience in the
high school experience were so exhausting, they're like worn out and they're like
I'm glad I'm done learning and then they're gonna go to work.
But whatever you do, I guarantee you, especially with AI out there.
There's some nuance of what you could be doing that's new.
And and unless you're
Trying to find that edge.
Somebody else may be.
And
Th I think the people most that threat by AI are the ones that aren't continuously learning that are just kind of
doing the same thing they did ten years ago because they're they're kind of a widget.
You know.
And that could be automated. And the people that
Did
Are curious about what's possible.
They're naturally gonna see this AI thing pop up and go, Wow, that's a new tool. I better figure out what it can do and
For me.
And those are the people that are hardest to replace.
Like if you're if your company's trying to figure out AI and one of your employees is spending more time on it than everybody else.
They're the last person you're gonna fire.
I think that like
What I've been trying to tell a lot of like we have a lot of young people listen, particularly a lot of young men, and I'm like
You have to understand the difference between
Risk?
And uncertainty.
And that
Risk is oftentimes a lot less than people think.
But uncertainty will always exist no matter what, and you just have to get comfortable with that. And I think that
In order to reduce risk. I don't think people realize how
Many things in life.
They can try before they buy.
For example
I moved from Texas up here. Yeah. I rented an Airbnb for two weeks in a neighborhood that I wanted to see and like I tested it out and I actually realized I hated that neighborhood, but I like this other area. Yeah.
Or like you could do that. I remember before I wanted the I one time I wanted to buy a fancy car, I tested it on Toro
And I was like, Oh, I don't wanna own this car. This is a pain in the ass. Yep.
And like you can
email someone. You gotta email probably fifty. And you could like actually shadow them from I mean
Most decisions are reversible and there are ways to like reduce risk. No doubt. And like like um
When I was an engineer and before I went to Wall Street, it turns out I I had read Peter Lentz's one up on Wall Street. I was trading stocks in my spare time. So unconsciously I was testing
that in this field that I would eventually go towards. And so yes.
Like don't quit your job tomorrow just because you're unhappy.
Start figuring out
That you what direction is the right direction to move towards. Some of the people that you've you talk about, like for example in the book, you talk about Robert Zimmerman, aka Bob Dylan.
And you're like he um
Fo found his fascination.
And he like followed that route like pretty ruthlessly and and and became Bob Dylan and
But then you also are like
He's also like you barely mentioned this, but you're like he's notoriously prickly, like he's hard to like get close to
But then like I know you've worked with Travis Kalinick, who's like um a pretty wild guy.
The people who
In order to like do these exercises of finding your passion
Do you sort of have to be like a ruthless asshole, you think? I don't think so.
I mean
Right.
Danny's one of the nicest humans I've ever met in my entire life.
Um
Even though
Um someone like
Bobby Knight, who we have in the book, is known as being that way.
He's probably got the biggest coaching tree in the history of the sport, which means
People have developed underneath him.
And
both as coaches and players and become coaches. So
Even if
You know, this
prickly guy you see throwing the chair is is not the one that developed all these humans.
You know, and put'em on their way and on their path.
And
One of the things I love about a lot of the
Stories in the
in the book is that these people reach a place where they're touching so many people in their field.
I think that's a more fulfilling test of were you successful.
Then did you hit some milestone?
Yeah, but it's a lot easier to do a bunch of stuff.
Like following your passion when you have hit milestones like
Sometimes when people people say follow your passion
What I really want to tell people, I'm like basically this sounds like crew, but I'm like if you can get rich fast, do that.
Some people get in a position where they spend right up to what they earn and then they don't have they don't have flexibility. And so
You move from one town to another.
Um, a lot of the people in the book do that.
And if you're stuck.
You're stuck.
Yeah, you might be have to stay in a job because you've built a
Expense burden.
It goes right up against the top of it. I saw it.
A ton of those people when I came to New York. What did you see?
I mean, we were getting paid decent money, like for this was when you're a researcher? Yeah, yeah, for entry level jobs. But they would run and get
They'd go get the place in the Hamptons and they'd join the private club and they'd
Run their budget right up to the top, sometimes above it.
Where if they don't get the bonus, they're underwater. I know people that make seven tickers a year, one million dollars a year, and will literally have zero dollars in savings. I understand.
When I early on m uh I used to use this app called My Weekly Budget and I created a a budget.
And uh
I had a spreadsheet that would track how much cash I had saved, so ten thousand to twenty thousand. It was like
This is how long you could live without any income. So they the name of the game was said
score away as much cash while keeping expenses low.
And it was like
Want anything above six months.
That's like your F U number. Meaning y you could like go and like try and experiment. Yeah, it gives you flexibility.
Yeah. And it was like but it was like ruthlessly disciplined to make that number bigger, even though I didn't make a lot of money, but I was
like living very frugally. And I don't think people understand that. And like things like college debt, which I'm very privileged I didn't have, r completely ruins it. And so like there's a bunch of these like irreversible decisions that can really screw you up when it comes to like being able to like chase down some of these things. I agree with it.
What do you do with the money once you've already made it?
This is a question Sean and I ask our successful guests all the time. And the reason we ask it is because if you are successful, if you do have a little bit of money, information on how to spend or invest your money, it's actually really hard to come by.
And I know this because inside of Hampton, which is my community of founders, people ask this question all the time. People have made ten or fifty million dollars. How do you spend it? How do you invest it? And so to help solve this problem and answer this question, I actually interviewed eighty plus founders, guys like Scott Galloway, Alex Ramosi, Brian Johnson, people who are worth
fifty, a hundred, even billions of dollars. And we got them to reveal everything. So their net worth, how much they pay themselves, their monthly expenses, their portfolio, things like that. And we turn these eighty interviews into one document. And I don't think you can find this type of information literally anywhere on the internet. And it's completely free.
So if you want to see behind the net worth of people who are worth billions of dollars and their portfolios, their expenses, everything, you go to joinhampton.com slash reveal. Again.
Joinhampton.com slash reveal. Check it out.

The last night was special because I sat across from Jim Cramer.
And then next to him with Henry Bledgett, who founded a business insider, just a lot of like
crazy people.
When you knew these guys when they were younger, was it clear that you guys were all going to uh succeed, or have you been surprised that someone has been as successful as they are?
Well, I think he I think it goes back to our discussion on peer groups. Like like connecting with
I've just always found
Um, and I and I think I got more attuned to this the older I got.
Like
Haven't have a big tent mentality.
Like
Have as have as many friends as you can. Try not to judge people too much.
root for people to be successful when you can and
And it'll come back to you in spades, you know? And
I guess I've never been surprised that
The people that end up
You know
In Sam in in Silicon Valley in the middle of it all.
continue to move forward just because it attracts so many ambitious people.
Yeah.
And so
Oh no, I I I haven't I haven't been
radically surprised by anybody's staying power.
Keep in mind I'm fifty nine years old, so I have the benefit of time.
To build that network.
I had twenty five years as a venture capitalist. But I think you were on the board of uh
What's the moment you and Danny Meyer, you're on the board together? Copen table. That was like twenty years ago. I mean. It seems like you you kinda like hit up pretty early into investing, right?
That's kinda key in venture.
What he mean?
Oh, just to be in front of the the the wave or whatever rolls out.
Like you can't
Can't be late.
With AI going on right now, is this re does this remind you of a different period in venture?
I've never seen it quite like this. Really? Really. I w one thing I think throughout my career ventures only gotten more competitive and now today
It's
You know, as I've um hanging up my boots and watching the next generation, it's m even more competitive.
And
The um
The burn rates.
Yeah.
the V Cs are comfortable experimenting with are bigger and bigger than ever. Like I thought
Our two billion a year burn rated Uber was pretty frightening.
Open AI is burning way more than that. How much are they burning? I I don't know. I've seen different number I don't have access to their financials, but like Uber was losing two billion a year? Yeah, but open AI is at like eight or ten.
What did uh what does it make you feel when your company's losing two billion dollars a year? Scared shitless. Really? Yeah. Oh yeah.
Well how did you map that out? Like how do you go to bed at night knowing that like are you like what do you tell? You're like Well I didn't sleep much there was a piece of it that was
The the I think as as the venture industry gets more industrialized was a problem which was
I think
The lift investors.
New
That they had to keep
Funding.
Liquidity.
And and for all a bunch of reasons that relate to network effects. Th it was always supposed to be kind of a single marketplace that would win.
And
But you if you don't have the constraint of
financial viability you can lose money to create the
to the perception of liquidity. You can pay drivers to be present when
They wouldn't naturally be that. Yeah, I used to joke my last company in San Francisco, we didn't take
Venture capital, but we used to say we're still V C funded because uh
Uber and all these companies would give like the craziest referrals. So like I remember like giving my referral to everyone. I'm like, Oh, I drive on Uber for f or I ride on Uber for free. I get it. And and and and it wasn't until Lyft went public first, which is probably the best thing that could have ever happened to Uber.
Where Wall Street held them accountable for being profitable.
And and it's it's at that point when things really
Tipped and and where Uber was able to then take advantage of the network effect and being larger and and now spits off well north of ten billion a year in free cash flow. That's how big it is now?
That's insane. Did you did is that bigger than your prediction?
On I made a prediction about the the uh market cap. It had a bunch of ranges.
I I don't have it in front of me, but
Dar got it to two hundred billion market cap, and I don't know if that was in I I assume you're referring to the blog post I wrote. No, I haven't Oh, okay. Yeah.
What did you say?
Or what was the other thing? U that wrote a blog post that said it would only be worth four billion and I
Pushed back. I remember that. We did talk about that. Yeah.
Did you did you see the blog post the other day about on Substack where they're like AI is gonna make uh the economy worse?
You see how one blog post like brought down It's pretty amazing. That's crazy, right? Yes.
Did your blog ever do that?
Not not at that scale, no.
Yeah, that was that was insane.
Insane.
There's a lot of fear out there. Just remember
Uh Warren Buffett said be
Be greedy when others are fearful.
And fair for when others are greedy. So the first
Wave of AI.
was a lot of people being greedy and now all of a sudden there's fear for the first time. So if you're a net buyer of stocks
This is when you
It's when you sharpen your pencil.
You see all these interesting founders other than like I mean, I don't want to hear like Travis or like some of the big name ones who kinda have stuck out as like being like particularly sticky and uh formidable.
Well, one of the most impressive people I know is a guy named Rich Barton. He founded Expedia and then Zillow.
Expedia was
Acquired by Diller, so he knows Barry and all that, but
But rich.
Has
this remarkable ability to
B
Top one percentile as a
Product technology disruptor.
But also as a leader, that thing we're talking about.
before and I
I usually see people tilt
One degree or the other, and not both.
And he's this rare person that that does it on both.
Um
And so I
frequently lean on him for advice.
Do you have an example of like a story of like where
Good leadership.
Changed.
Getting companies to pivot fast when they need to. I mean, right now with AI
Any companies out there, you mentioned what happened with this report.
Like that that DoorDash is down five percent'cause the report said you could build DoorDash for free, which I don't believe, but you know, whatever. Yeah, and that report, by the way, for the listener, it was basically like what happens in the world if AI is so efficient that we don't have jobs and if we don't have jobs and we're not buying stuff.
And it was just like
A story. It was it was an idea.
But how do you get
So the the thing that I was gonna mention is just how do you make sure your company is properly aware of this new wave.
And how do you get everyone super excited about
Figuring out.
what it's gonna mean for your company. And that
That's not easy to do and I you know, I'm I'm back on the border Zillow, so I watched him do that recently.
And it requires
having both the conviction to
Make that kind of pivot and move and then the ability to get the people to follow you.
That's funny that you said it was like
being good at product and being a good leader I think you also said
Do you also say that like Jeff Bezos is one of those guys who does two things really well?
It would be a good exercise to s for someone to kind of
Write down the leadership.
techniques of Jeff Bezos because Amazon
remained innovative after it got to like a hundred thousand employees. And that's very hard to do. It's not
one human. It's one human creating a system
That reinforces whatever he thought.
You see what I'm saying? And like
How do you make that system keep doing that even after you you know, on days you're not there?
And him and Elon, I just don't think people
Fully grok how they're able to lead.
A lot of these people who are these tit like kind of the titans of industry that you know
Do you think that there's any correlation or reverse correlation?
uh of uh happiness.
I don't know anyone that laughs louder than Jeff Bezos. If you've been around him when he lets go one of his
is a guarantee man. I I and I think he really loves life. Um
Uh.
I'm just saying there I don't think there's a correlation. I mean I
I
Every chance I get
If Toby from Shopify does a podcast or something, I'm
Eating it up. And I find
His
Attitude on
Leadership in life to be
Lighthearted. He seems like a m another one of these product leadership guys. He's got a very unique flavor of leadership.
He has a very wise
Yeah, there's something wise about him.
Do you see where he's took screenshots of his computer screen?
Every ten minutes for the last twenty years.
And uh because he was just he's like I'm a nerd and I just love like having this diary of like what what was on my like he was tracking all of this and uh he's like I didn't know what I was gonna do with this. Now that AI exists, I can like upload this and like it can like teach me about myself. But he's got this like really cool
I call it like nerd wisdom. Like um you know Darmash at HubSpot?
I have men, but I don't know as kinda the same thing where there's like there's these groups of
group of guys who are like very like when you think of a leader, sometimes you think of like a Napoleon, like rah rah, like rile people up, but there's this other group of like fairly introverted people
And they're quiet and when they talk you listen.
But I think they're they're both useful. Um
For someone who's like
eighteenth, nineteen twenty.
They're listening to this.
You did all this research for this book. Are there what biographies do you suggest they go read?
I mean i I think it would be heavily dependent on what interests them.
Or rather, what made the biggest impact on you?
I don't know if I was reading biographies at seventeen.
I really got into reading when I got to business school and
I uh they're all listed in here. There's thirty five books listed at the back of the book.
So I
But it
I think the key is just to and it it I don't even know that it has to be reading. There's there's so many podcasts like the ones you do and
And
YouTube interviews with people, like it's so easy to go learn about something. So I'm just like
Whatever interests you
Go learn more about it and see if that takes you somewhere. See if that
Makes you excited. See if it makes you want to pick up the next one. And if it is
I think you're probably in the right lane. If not
Just pay attention to what fascinates you, you know, pay attention to what interests you.
I'm
Uh
A big believer that more people can chase careers in their hobby than
Someone else might say.
Like
Like if if if there's something you're just super passionate about
Even if it's a hobby.
You might be surprised. There might be there might be a way to make a career around it.
Well it's a lot easier now with the internet.
It's the this is but by the way, I would love to close with this point that you just made.
Um
If you're
A
What like I said, if you're someone who's disengaged at work that went through some process you didn't care about that much.
I can understand why this AI thing would feel threatening to you.
If you're
crafting your own personal career and your high agency. I think that's a word you used earlier.
AI is like a jackpack.
Like you can do more stuff than you ever could before. You can learn faster.
Then you
Ever could before in in the history of time.
You can find
people to connect with. You can network faster than than you ever could before. And so if you have agency and and of direction you're headed in,
AI's gonna make things way better. So I think it's just this interesting paradox.
Did they
Or people out there who fear that it's gonna
dismantle'em and there's people out there who are like, Oh my God, I can't I've met so many
What I would call
Like S and B founders or regional founders running
You know
businesses they're laundromats or storage facilities and and they've discovered all the things they can do with AI and now they they feel superhuman so I'll I'll I'll wrap up with the story. You'll you'll dig this so my mother in law, her name's Smithy, she came here uh to to America from Haiti at like fourteen or years old.
Didn't speak English.
um married my father in law Jeff.
Jeff owned a moving company.
Smithy was a stay at home mom for a long time. The kids grew up and she was like
I'm kinda lost. I need to do something. What's going on?
So about five years ago she says to me, she goes, Sam, I think I'm gonna start an online store that sells pillows.
The kills and
Or whatever. Sounds good. And I like sh I was like there's this thing called Shopify just start just start there.
It's been five years since that.
She now has a pillow company that sells over a million dollars a year in pillows.
She has a warehouse in New Jersey with five full time employees selling pillows. She was just on the pod.
And she uses AI like all day to like
She's like, How do I buy an ad? And like, you know, Chad GPT like teaches her or she's like
Uh how do I
Whatever.
Like it's YouTube and chat G B T like telling her what to do and she didn't know a she didn't know the word e commerce. She didn't know what that meant.
She basically just
knew what Google was, that that was it. And now she in her late fifties started a e commerce business that does millions of dollars a year. That's amazing. Crazy, right? Yeah, no, but there's never been a better time
Two
Propel yourself forward. If that's
If that's what you're prepared to do.
Well thank you for doing this, brother. All right. All right, God bless you.
I feel like I can rule the world, I know I can be what I want to
I put my law in it like my days off On a road less travel never looking back
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