The Career Advice That Ruins Lives (And What Actually Works) - Bill Gurley

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What time is it, Ben?

It's Barbara Dye!

Life is a use that are lose of proposition.

Young people don't see the end of times, but older people really.

By the time you're 40 or 50, I think it weighs on you.

And so my argument is, you're going to end up working 80,000 hours in your life.

Why not do what you love?

And I fear that our society has been steering people towards, quote, safe jobs, which in a day

of AI may not even be that safe anymore.

And I would argue, the safest thing you can possibly do is find a career in something

that you're totally fascinated with.

And the reason is, all the techniques that tell you how to be the most successful thing

you can possibly be, they're all 10-time easier if you're fascinated and in love with

the subject matter.

Everything gets easier, and you get energy rather than it costing you.

Welcome to Open Book.

I am your host, Anthony Scaramucci, joining us today's Bill Gurley.

The book is phenomenal.

Running down a dream had a thrive in a career you actually love.

Don't all of us want to do that.

But Bill, I've been following your career from a distance.

It's a real pleasure for me to have you on our podcast.

Thanks for having me on.

Yeah, there.

And I'm a big book lover, and this is going to be on my recommended list going forward

for young people.

I appreciate that.

There's so much in the book.

I want to go to something that I love, which is getting a book published.

Let's start right there.

How does it feel to have it this published now?

It's a bit overwhelming.

This was a passion project on the side for me, not my day job.

And it was born out of a presentation I gave eight years ago at the University of Texas.

Once it began to take life as a book, for reasons that we could dive into, I took it

very seriously, and did a ton of academic research talk to a ton of experts.

I really wanted it to be great.

And so it took about five years, literally, not full-time, like in the background, to

get it burnt.

And then, the thing I had no idea, promoting the book is quite tedious.

Yeah, it's hard.

Now, I've got to go forward with it.

You've got to get out, you've got to get your personality out there, but you're doing

a hell of a job.

I've seen you on a different, a couple of different podcasts.

I've listened to you.

I think the story about James Clear observing you when you were at the University of Texas

at the McCoy's.

He found the video on the YouTube and reposted it, which gave me some confidence.

He perhaps the best-selling author in the self-help categories, or him in Mel Robinson.

He's written a phenomenal book about habits.

But you have recognized something through pattern recognition, but there's also something

else that you're doing, which is evident in your book.

You have a tremendous amount of self-awareness, which is, if you don't mind me saying this,

because I've worked on Wall Street for 40 years, venture capitalists, and Wall Streeters

typically don't have a lot of self-awareness, though, girl, okay?

So this is something that you have, which I give you an enormous amount of credit for.

So tell us about your insights from your own self, and tell us how you saw these patterns,

and that's why the book is so good, by the way, so tell us about that.

Yes, so I was, there was a period in my life, I'm a big book fan as well, where I was reading

a ton of biographies, and I finished this third biography and saw a through line between

it and two others in completely different fields, and these were all people that started

on the very bottom, wrong of the ladder, but had high intent.

So they wanted to be successful in the category, starting at the very bottom, and I noticed

that they all did very similar things, and some of these things are things that aren't

generally recommended to young people.

I think we also live in a world, at least in North America, where our path to and through

college has gotten super intense, and kids are just way over-scheduled, and they don't

really have the opportunity.

And others have written about this, heights written about this, Rick Rubens talked about.

They're so over-scheduled that they just don't have the time to find what they love, and

to really fall in love with something that they can turn into a career.

And so I wrote this book with just one objective in mind, which is to help unlock human

potential.

I want people to believe they can go do something that maybe their parents or some of my

folks are told to not do, and have the motivation and the methods to go do it.

You know, you're an entrepreneur.

I've been an entrepreneur in my career, and so I've gotten some things right, Bill.

I've gotten some things very wrong.

I've had career setbacks.

I infamously went to the politics for a little while, got my ass fired after 11 days,

so I've had my bumps and scrapes along the way, but there's something that you write

about in this book that I want you to address, because I do believe this, and this is something

that you cite Daniel Pink's research in this about the regress of inaction.

So that's me.

I feel like whatever has happened has happened.

I'm willing to accept it primarily because I've been on the playing field, throwing

interceptions, and a few touchdowns.

So talk about the regress of inaction as you beautifully write about it.

And you mentioned earlier, you know, career regret.

We did a survey, first on survey monkey, and then we did it again with Wharton People

Analytics, because we wanted to make sure we got it right, where we asked people that

had been to college, you know, if you start your career over again, would you do it differently?

And in our original survey monkey, seven out of ten said yes with Wharton, it was six

out of ten, it's still a vast majority of people.

Daniel Pink in his book, The Power of Regrets, notes that humans dwell on regress of inaction.

He calls them boldness regress.

These are things you didn't try.

And the older you get, the more they weigh on you.

Humans are fabulous for giving themselves for mistakes, kind of what you just walked

through.

Those are action mistakes.

We're like, oh, that's all right.

Water into the bread.

I learned something and you move on.

But the thing you never tried is the thing that each is you get old.

So young people listen to this podcast and thank God for that.

So I want you to grab the young men and women that listen, grab them by their shirt, grab

them by the collar, and shake them a little right now, and give me the message bill.

Yes.

So first of all, we have a phrase in the book, life is a user that lose a proposition.

And I think young people don't see the end of times, it seems very far away, but older

people really weigh by the time you're 40 or 50, I think it weighs on you.

And so my argument is you're going to end up working 80,000 hours in your life.

And why not do what you love?

And I fear that our society has been steering people towards, quote, safe jobs, which in

a day of AI may not even be that safe anymore.

And I would argue the safest thing you could possibly do is find a career in something

that you're totally fascinated with.

And the reason is all the techniques in the book that tell you how to be the most successful

thing you can possibly be, they're all 10 times easier if you're fascinated and in love

with the subject matter.

Like everything gets easier and you get energy rather than it costing you energy.

So I would also tell them, I would also tell them one last thing, and I would just tell

them, if you don't know what that is, that's completely fine.

Don't stress out about it, just keep trying things, take shots on goal, see what really

interest you until you can find it.

And the whole chapter in our book called Chase Your Curiosity is about that journey.

So it doesn't presume you know this going in.

I mean, it just is a fast thing, and the reason why I was going to step in is related

to something that you write about, which is the ethos of the reality of most people can

afford to be wrong.

And again, it's something to do with their self image, but it could also be an economic

reason.

Somebody like me at the early part of my career, I didn't have the guts to start my own

business.

In fact, I wrote down the day I graduated from law school bill.

I said, I'm going to have my own business, but not until I pay off all this school that

it took me seven years, and I worked at Goldman Sachs for seven years.

When the debt was paid off, I left start my own business.

And by the way, by the way, it was scary even then without that financial rock or that

boulder on my shoulder.

So how do you get through that?

Tell me about it.

I think it's difficult.

I would tell you that so the free listeners, the books divided into profiles and printables

and they interleave and alternate and the profiles are stories.

A couple of the stories people have zero dollars when they start certainly the Bob Dylan

do other stories when he went to New York, he had ten dollars.

It's a great, the Dylan story, which even though I saw the movie, I didn't really see

in your context.

Yeah, they missed this part.

Most of our cover just pre the movie.

I love the Dylan.

I want to get to the Dylan story, but we did it in with this.

Yes.

But Jim Ackins, I was going to say Jim Ackins went to New York or LA with $200.

Now your situation is worse because that is negative money, which is more of a handcuff.

I would tell people, one thing they can do and AI can be super helpful on this is you

can plan and imagine without actually doing something.

I think the more you do of that as an exercise, the more confidence you will build that you

could possibly go in that direction.

Dave Evans, who wrote, designing your life, talks about this as a way to find which where

you want to go.

He says like battle card three or four scenarios, but it sounded like you knew what you wanted

to do.

So literally is a hobby at home, like, have AI help you build a game plan.

Like what are the first five steps going to be?

How can I do this with this constraint?

And I'm not saying jump tomorrow, but I think the more that you visualize what's possible

and think through the difficulties, the steps you would take, the more confidence you

are going to have in taking that leap.

Yeah, I know this.

I think it's really true and I always tell young people that it's not as scary as it

looks.

That's the weird thing about it.

I remember when I left Goldman, one of the old partners at Goldman, still a very close

friend of mine, is in his 80s now, he says, you know, you'll figure it out.

And you know, and you know this expression entrepreneurs, they jump off a cliff, they're

trying to build an airplane on the way down, but you figure it out.

And I think that's something that we need to tell young people that believe in yourself,

recognize that you have levels of resourcefulness and energy for the things you're passionate

about way more than the fears, you know, the energy and passion can overcome the fears.

That was about Bob Dylan, though, sir.

I thought that that was, to me, you know, when I think of your book, I'm going to think

of the so many great ideas and concepts, but it's really the Bob Dylan story that resonates

with me the most.

Tell us about Bob Dylan.

So this isn't covered in the movie and it is, there is some detail in the score says

you documentary, but Dylan is a, and always was going way back to when he got started.

He's a historian.

He liked, and he's insanely studious about music.

And so when he got to, got to Minneapolis, he started studying folk music and I have a

high confidence level based on what I've read that he knew more about folk music than

anyone else in Minnesota when he left for New York.

And the friends they talked to, he would sit in record stores that had these listening

booths back then and he just went over it and over and over.

And now, you know, obviously, so successful, you can see this.

He did a podcast for a while where he went through different genres of music and you can

just see how much details in his brain.

And then he released this book, coffee cable book recently, about the 50 most impactful

songs of all time.

And you just see that I think people have a perception that he's just sitting there

writing his own songs.

But the guy has just studied everyone under the sun.

And the second tenant in the book is Hone your craft, you talk about continuous learning.

And it's a vector that I see run through all the most successful people.

You know, do you go home at night and study the thing you love and does it feel like an

alternative to watching Netflix?

Yeah.

So I mean, that's, that's the follow question.

Do you think the curiosity driven path that he was on that you wonderfully describe in

this book is harder in the attention economy that rewards, you know, it rewards breath

over depth as an example.

Potentially, but I would tell you that, you know, a lot of people have brought up the

threat of AI recently and I realized I didn't, I wrote this, I started writing this book

way before the AI wave, but, but most of the, most of the people that are just hyper curious

about their field, they act like artisans or craftsmen.

And part of what's really cool about an artisan or a craftsman is they're really studying

the nuance at the edge of the field.

And that's the stuff that's not in the AI model, you know, if you just go to school and

learn all the wrote stuff and you think you have a defense, defensible, you know, differentiation

because of that, that's the stuff that AI can do really great.

And the thing that the experts do or these artisans do is really study what's on the edge

in the nuance that's out there and they they're able to use that confidence in the nuance

to really differentiate themselves.

So I am, I'm certain that there was Mark Cuban had a great quote the other day, he said,

there are two types of people in the world, those that use LLMs to learn faster and even

more in those that use LLMs to avoid learning.

And I thought it was pretty profound, like if you want to be studious about something,

there's never been a better time on the planet, like these tools will allow you to learn as

fast as you possibly want to go.

But you have to have the interest, as you said, if you don't, if you don't, you don't

get there.

But this is, this goes back to the test being, are you fascinated with this?

Like, you know, it's a good, it's a good segue into what you talk about in terms of people

wanting success or people just excited about building things, right?

It's sort of the same sort of concept.

So tell us about your observation as a venture capitalist of founders that you've met.

You can tell early on, can't you, when someone's generally, I mean founders, founders, right?

Founders have two, two things that are, first of all, they just have a super high motor,

they're very determined, at least the best one, they're like hyper determined, they're

going to do this, come hell or high water.

But the second thing is they are hyper curious about what they're doing.

And so almost the way that a founder entrepreneur takes advantage of some new technology wave

is they go understand what it's capable of more than anyone else.

So just as I'm talking about, maybe Bob Dylan did it, folk music, they're doing that with

the new AI wave and they did it with the mobile wave and the internet wave.

These are the people that are on that edge studying that nuance and exploiting.

Yeah.

I mean, see, to me, that's, that's the real love, right?

You know, I like building things and I have intellectual curiosity and, you know, they'll

give you wrong.

I'm in a first success.

I'm not saying I'm not, but I'm not, it doesn't overly inspire me, it inspires me.

And one of the reasons why I do this podcast is that I love talking to authors.

I mean, the fact that you took the time to synthesize and put all of these thoughts

down for all of us, you know, I used to tease people, but you and I are roughly the same

age.

I used to say for $10, you can get, you can read in 10 hours, 10 years of an author's

experience.

Now, with inflation, it's probably $30, but you get my point.

And it's also about the peer group.

You know, I always tell my kids, you're the weighted average of the five people you hang

out with.

You write a great, your theme about the power of peer groups and the people you surround

yourself with, you know, how much of long term success is talent and how much of

it is just getting yourself into the right space and into the right peer group to help

propel yourself.

Look, I mean, I think one, having written this book, I would hope one thing people would

walk away from is the belief that the techniques that I have in here don't require some excessive

amount of intellectual power, some natural talent to go do them.

Most of the people in the book are hyper fascinated by their field.

They study their butts off and they collaborate and connect in multiple ways with both mentors

and peers.

And my favorite principle in the book is this one on peers because I think a lot of people

say what you just said, like being a good friend group, but I don't think they are taught

to proactively create a peer group to help them along their career path.

And we have some wonderful examples in the book.

I think too many people come out of the college experience, sharp elbowed mainly because it's

so competitive, like, you know, you're trying to get good grades, you're trying to get the job,

someone else couldn't get.

But what I would tell people is the world's not zero sum in any field that we're in, there's

many, many winners, many, many great winners.

And if you can find a group of people that are on the same journey you are, they're on

the same wrong of the ladder climbing up.

And you guys can share and trust one another.

It is just so wonderful.

You get so much extra horsepower, you get shared learning across the group, you get to

share each other's networks, you get a support group on bad days, which is there's a lot

of them.

And it's just fantastic.

And I think this is not once again, this is a technique that's not taught a lot.

I think I think this is the, maybe the first book that's really pounding the table on,

but it can be really powerful.

Two other themes.

If you don't mind me going to these, Sam Hinky, you give a great example of him, okay,

Crosstinary Tale, but it's really about trusting the process.

And let's go to McConaughey, who I think is a philosopher king, you know, in addition

to being a great looking a list actor, his depth and his insights, and I love his writing

by the way.

And so it sounds like you guys are close and he says something which we have to say to

our kids every day and even to ourselves, don't have ass anything, right, because his

dad fed that to him.

So take those two guys, talk a little bit about those two guys and the impact that they've

had on you.

Yeah.

So I've gotten to meet Matthew here in Austin where I relocated a few years ago.

His book Greenlight is oddly, I think, has a similar objective as my book, which comes

from a very different place.

He uses the metaphor of a green light to be knowing you should put the gas pedal and

run at things.

And you know, at that, it's funny, I got to meet Rick Rubin through this process.

And his book The Creative Act is very different in my book, but I think it has the same goal,

which is to encourage people to get out there and do their thing, you know.

And there's this great anecdote in Matthew's history where he told his dad he was going

to be a lawyer and he was at the University of Texas pre-law track and met some people

at the film school and had a change of heart.

He wanted to go do this thing.

And he was afraid to tell his father, but when he did his father said famously now, don't

have acid.

And he said it was the last thing he expected his father to say and the best thing his

father could have said, because it wasn't only encouragement, but it was responsibility.

Now, he called it rocket fuel.

And that, I mean, it's kind of where I hope the book can do.

The concluding chapter of the book's title, it ain't easy.

And I don't want anyone to think that, you know, you can read this book and everything

just comes actually.

It's hard out there.

But one of the reasons you want to be fascinated by what it is you're doing is so that you have

the ability to go do all these pieces that bring it all together.

And so he, you know, I think he's a great example of someone who's risen up but also gives

back that's another principle we have in the book.

His writing, I think, is intended to help and motivate people.

And yeah, he's a great, he's a great role model for a lot of the younger adults out there.

That was, and I mean, it's just such great messaging.

It's a, it's a short, you know, Bill, it's a lot of dense information in a short book.

I mean, this book took me a few hours to read and I was like, wow, this is great.

And even you've got your book lists in the back as well, which I tell people they should

look through.

And I've read some of these books and now because of you, I'm going to read more of them.

But if I said to you, I'm going to get a kid in front of you and I said, okay, there's

one thing that I would like you to do differently tomorrow.

Okay, you just finished my book.

The comments sit down right there in your office and you say, okay, there's one thing I'd

like you to do differently tomorrow.

What is that?

What would that hope be for you for that person?

For me, it's specifically the young adult is just to start, start thinking about contemplating

what it is that they're truly fascinated with.

Like that's the lane that if they can get in, I think they're going to have just a wonderfully

fulfilling life.

And I'm one of the things that motivated me right to book it and I'm fortunate enough

that people that saw this video online many years ago, some of them shifted careers

and have reached out to me and they're people paint.

And like knowing that you had this chance to get people into that lane where they're

just so happy and so fulfilled.

A lot of the podcasters I've met are in that lane.

They're thrilled to talk to people and be excited and learn all the time.

And so it's doable.

Like, and there's a ton of examples in the book.

I'm glad that it went fast for you that the way the stories were written were intended

to make it like super consumable.

It was it was very consumable.

I think of my 26 year old son who is a creative guy, I want to be in the film industry.

So okay, he's in the film industry, he's produced two films and he got the chance yesterday

to tour George Lucas's new museum, I guess, of narrative art is what it's called in

it's in LA.

And he said to me, it was the greatest day of his life, Bill, greatest day of his life.

How good is that?

And I want to share that with people because he is not following me in my career, nor did

I ask him to, this is something he really wants to do.

And I always tell people that Mel Brooks is my spiritual advisor, you know, I don't

have never met Mel, but Mel Brooks at 99 has said, relax, none of us are getting out

of here alive.

And I think that message in this book is so vivid, you know, and look, if a kid goes

in a museum and it's the best day of their life, that is the right direction.

Well, I think most young people go in museums and don't have any positive experience whatsoever.

But I mean, he's he's walking around in the museum with one of the greatest filmmakers

of all time.

And of course, Anthony, my son, Anthony wants to be a filmmaker and George Lucas puts

this on.

You know, making films very hard.

Yes.

Okay.

But you know what?

So is Wall Street, so is venture capital.

But if you like it, you can take the body blows that that happened.

Oh, it's so great.

When you're running down a dream, you're going to get your ass kicked a few times.

And that's the big message of this book.

And I got to tell you, I was inspired by the book.

And I'm grateful to you for writing it and thank you for coming on the show.

We're down to the five words.

Okay.

So if you ever listen to my podcast, my producer, and I come up to five words, really quick,

especially if you're going to have some listeners who audio only, when you were telling me that

story about your son in the museum, and I had a huge smile on my face because that,

that type of fascination is exactly like I now that I've talked to so many young people,

that's exactly what you're looking for.

And you can see that.

And then blow more wind behind his sales, like that's just so great.

So thank you for sharing.

Yeah.

Well, 100%, but that's why I brought it up because it's elements of that is right here

in your book.

So, all right.

So we have five words, Bill.

Okay.

I'm going to say the word a little bit of a raw shodtash.

You give me a sentence or two.

Okay.

And then more or less pull these words from your book.

So if I say the word regret, you say, does it have to be a single word?

No, no.

It doesn't.

Oh, yeah.

Yeah.

I just avoid it.

It's avoidable.

It's avoidable.

It's avoidable.

Like, start to read my book, first of all, but start to think about how you can do that

thing that's weighing on you.

I think you can't.

I think the, and the tools have never been better.

Like the methodology in my book, the AI tools that are out there for learning and connecting

have never been, this is the best time in the history of the world to go chase your

dreams.

You know, so fascinating.

When you say the word regret or I say the word regret, I think inaction leads to regret.

Yeah.

I feel like, you know, I've done some things well and some things not so well, but at

least I'm acting.

Yeah.

So get there, get in there and start acting.

Okay.

I say the word dream, Bill, you say what?

Like possibilities.

I go back to this word fascination, which I actually borrowed from Jerry Seinfeld.

Like, if you are just hyper fascinated by something, I want, I want anyone out there

to contemplate and likely and hopefully believe that they actually can do it in a career,

you know.

All right.

I love that.

And that's the whole reason, the whole synthesis of the book.

What about passion?

I say the word passion.

The word has been become a bit of a cliche because people say it so much with a career.

And that's why I tried to use the word curiosity or the Seinfeld word fascination.

Like the real, the real question is, are you curious about it to a level where you study

the history, you know, like, want to understand the nuance, study all the great.

Now, do you, do you naturally want to study the grades like your son does with George Lucas?

If you do, I think you're pointed in the right direction.

That may not be passionate, like, it requires more than that.

So again, Valley, um, special place, man, special place.

There's a, there's a chapter in the book we didn't talk about this title, go to the

epicenter.

And there are a few industries where there is a geographic nexus.

And if you get to that place, you will discover that, that lots of the parts that are highlighted

in my book, accelerate and you should be unfearful of that step.

It's, if you, if you know, you're pointing in the right direction, you should want to get

to that place as fast as possible.

So I, you know, it's interesting because I, you know, look, I've been out in Silicon Valley

a lot, but I'm, it's not my place, you know, Wall Street in the financial center of New

York has been more of my place.

But what I would say about Silicon Valley for me, I'd like Silicon Valley to stay Silicon

Valley.

Yeah.

You know, we've got to get the right policies and we've got to get the right, you know,

the ideas around government.

So when I have everybody leading Silicon Valley and turning it into Austin, that would be

my recommendation.

Okay.

Uh, last two words and I'll give you the last word.

Okay.

Bill Gurley.

I, I mean, that's a hard thing to talk about yourself.

My, my story is embedded at the back of the book in the apologue and my version of my

story.

And I feel very fortunate to have found my way to my dream job.

It took two stops along the way that I think we're building blocks.

They weren't wasteful.

I was an engineer for just over two years and then I worked on Wall Street for four years.

But I found the way to, to my place.

And so I feel very fortunate to have had that experience, um, you know, at this point

in my life, I'd like to, I'd like to give back, I'd like to be impactful.

This book is the first step in, in that journey.

And uh, yeah, that's where I, that's where I'd leave it.

Well, listen, I really appreciate you and thank you so much for coming on.

The title of the book is running down a dream.

It's a great cover, by the way.

I had a live in a career you actually love by Bill Gurley.

Thank you so much for joining us today on Open Book.

Thanks for having me.