The Tim Ferriss Show: #682: Bill Gurley Interviews Tim Ferriss — Reflecting on 20+ Years of Life and Business Experiments

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Hello, boys and girls, ladies and germs. Welcome to another episode of The Tim Ferriss Show,

where it is usually my job to deconstruct world-class performers of all different types to tease out

the routines, habits, etc. that you can apply to your own lives. This is a special episode

and a turning of the tables. This time around, legendary investor Bill Gurley interviews me,

and the recording is from earlier this year at South by Southwest in Austin, Texas.

The conversation explores some of my lessons learned and favorite findings over the last

two decades or so in areas like entrepreneurship, tech, and podcasting, just to name three.

I also throw in some favorite books and other spicy bits to keep things interesting.

Let me mention a bit more about Bill before we get started. Bill Gurley, you can find him on

Twitter at Be Gurley, G-U-R-L-E-Y, has spent more than 20 years as a general partner at Benchmark

before entering the venture capital business. Bill spent four years on Wall Street as a top-ranked

research analyst, including three years at Credit Suisse, 1st Boston. Over his incredibly

impressive venture career, he has worked with such companies as Grubhub, Nextdoor, OpenTable,

StitchFix, Uber, and Zillow, just to name a few. For more takeaways from his incredible investing

career, you can find my interview with Bill, that's me interviewing Bill, at tim.blog.com

slash Bill Gurley. And as a side note, my 2007 South by Southwest keynote, this was a speech,

my first appearance at South by, that I mentioned in this conversation with Bill was what started

it all in many senses. It's what put my first book, The 4-Hour Workweek, on the radar of influential

bloggers and bigger media outlets, ultimately landing the book on the New York Times bestseller

list where it stayed more or less unbroken for the next seven years. It's been a wild ride,

and this segment, this brief appearance at South by, is what kicked it all off. And if you would

like to hear that 2007 presentation, you can find it at tim.blog slash sxsw, which is the

abbreviation for South by Southwest. So one more time, that's tim.blog slash sxsw. And my voice

sounds hilariously different, my presentation skills hilariously less refined than they are today,

not to say they're perfect, but things have changed. And we get better day by day, little by

little. And one last thing, Hugh Forrest, if you are listening, thank you again for giving me a shot

way back in the day. It made a difference. And that is why I come back to South by

just about every year. And without further ado, please enjoy a wide range of conversation with Bill Gurley.

Well, it's great to be here. It's awesome to have the opportunity to turn the tables on Tim

and interview. I was just recently on Tim's podcast. And so I actually suggested this before

that so that it would keep him honest when we're going earlier. Tim, a lot of you, I assume, all

know who he is. He's one of the most celebrated and decorating successful digital creators of our

time. He sold 10 million books. I got a list here. He's got two million email subs, over a thousand

blog posts, seven million followers on social media. And his podcast is about to pass a billion

downloads. And so since South by, you know, is a lot about interactive and how people can be

successful in these types of fields, I thought it'd be great to see if we could dive deep and find

out how he got here and what some of his core tenants are for being successful. So you graduated

from Princeton in the year 2000 with the East Asian Studies major, is that correct?

That's right. A perfect setup for podcasting. Yeah. And in 2014, you launched your podcast.

Right. Okay. So 14 years, just tell us quickly what happened in those 14 years and how you found

your way there. And I'm very curious about lessons learned and when it became intentional.

Like, when did you know you were doing something versus just experiencing it?

I'll do my best to wrap it up without making it a Dr. Evil life story. Good morning, everybody.

Thanks for coming. So let's see. Graduate, moved to California, Northern California to be part of

the tech pinball machine for serendipity. I actually think that was a very important decision,

just geographically choosing where to be and then what to do being really secondary.

Worked in data storage, selling, storage area networks, had a desk and a fire exit,

definitely not up to code. I remember it was really packed to the brim. Learned a lot about

selling. I think everyone should have a service job, work in a restaurant or something like that,

and have to sell for a period of time. You learn so much about human interaction and I learned how

to reach out to CTOs and CEOs and so on, how to reach them playing the long game, not trying to

sell a seven-figure system in one phone call. All these things translated to many things later.

I couldn't have seen that coming, but they did. Then I started this sports nutrition company,

Long Story. A lot of people here probably know some of the bare bones aspects of it from the

four-hour work week. That experience was simultaneous with a professor of mine, Ed Schau,

who taught high-tech entrepreneurship at Princeton, which had a huge impact on me,

inviting me back to guest lecture twice a year. That went from 2003 to 2013 or so. Those notes

later became the outline for the four-hour work week. How long did the startup exist?

Startup existed until, let's see, I want to say 2009 or so when I sold the company. Not for any

huge sum of money, but I sold the company around 2009. How long was that experience? Six years?

The experience of building it? I would say the building phase was the first three or four years.

First year and a half had no idea what I was doing. I'd say the subsequent year and a half to two

years was building out distribution. Then I became very bored with the entire thing and was looking

for a graceful exit, which turns out selling a company, even if it's for a very small sum of

money, is one way to do something new. Did you raise money? I bootstrapped the whole thing.

As credit cards, savings, trying to play, buying remnant advertising against incoming revenue,

getting prepayment from distributors, you'll be the exclusive distributor featured in this print ad.

If you pre-purchase X amount, which would then give me the money to pay for the ad in the first

place that I'd negotiated 80% off of because it was last minute, things of this type. All of those

games were what drove a lot of the growth, figured out that playbook, and then the focus really

became trying to figure out what the hell I wanted to do when I grew up. I mean, I'm still doing that,

I guess. What did you learn from the startup? What were the key takeaways? A few key takeaways

from the startup were, number one, if you want to reach the decision makers, just call outside of

business hours. If you're actually cold calling, I was cold calling, smiling and dialing a lot

and cold emailing, then just do it before 8.30 and call after 6.30. Very often, even in a company

of 100 people, you'll get one on the top brass answering the phone at the end, which was astonishing

to me. Next, I would say, if you're going to talk to technical people, and I was not technical,

but if you're going to talk to, say, VPs of engineering and CTOs, do your homework. I end

up being really, really successful as a salesperson, not because I studied sales per se,

but because I actually took the time to try to understand what RAID was, what all the bits and

pieces were that made up the hardware, what use cases would lead to them using Solaris versus

something else, and being able to guess correctly what their setup was without them telling me

anything, which opened the door to more involved conversations. Those would be a handful of things

and the value of storytelling, ultimately, for everything. For everything. If you're a human,

storytelling is key. It's the crux. So, the life as a startup entrepreneur eventually

wasn't working for you? It wasn't working because for me, the learning curve had kind of flattened

out, and I wasn't sure how to change that. I knew I wasn't a great manager. I didn't aspire to become

a great manager, which continues to this day. I should probably revise some of that. So then,

as is the case now, I have a very lean team, very, very small team. And if we flash forward,

then the notes of that class become the basis for the four-hour work week. I did not want to

write a book, but a friend of mine who was an author suggested it and started making intros

to editors and agents and so on. And I had to reply to those people and that gathered its own steam.

And the four-hour work week is what, as a lot of people here know, opened the floodgates for

everything that got the visibility that led to the angel investing that bought me permission to

write a second book. And I'd say to a question that you posed before we got on, and you may have

also just asked it, when did I start doing something intentionally or thinking about a

trajectory? And I would say that's probably when I made the pitch for the four-hour body,

because I don't have a grand five-year plan. I don't have a grand 10-year plan. That's today,

was true then as well. But I wanted to choose the door that opened more doors. And I realized that

despite, or maybe because of the pressures that I felt externally from just about everyone to

write the four-hour work week, 2.0 or the three-hour work week, I could very quickly paint myself

into a corner where that was my only niche and the only place I felt comfortable and the thing I

felt I needed to defend. And so I thought, well, I can always come back and do that later. That

will be available. So let me do something in a completely different section of the bookstore.

The publishers are going to say yes, because they are willing to at least take this bet.

They'll give me a decent, not even a decent, a very good advance, which we'll actually make up

for the 75 grand that I got paid over a year and a half for the four-hour work week initially.

And that type of decision-making, I think, has typified and defined a lot of my key decisions,

which is entirely seemingly out of left field, but of interest to me that will potentially

open new doors. When was the second book and when did the angel investing start?

Four-hour work week came out April 2007. The angel investing started within, I would say,

10 months. And I owe Mike Maples Jr. a debt of gratitude for that. I traded him advice for exercise

and diet for... And Austin and like yourself? Austin as well. I'm beating at Hobie's for breakfast

and him telling me about his deals just so I could learn about them. And then the For Our Body was

published in 2010, which means that I was probably working on it for two years. So you said you made

75 grand and you're hustling. How do you afford to angel invest? Well, fortunately, the advance gets

earned out. I had the savings from the prior company. So I had some savings and decided to

place very, very small bets. So I was co-investing with checks of, say, $10,000. And the intention

really early on, which comes back to playing the long game that I mentioned earlier, I wanted to be

the cheapest, most valuable labor on the cap table, meaning like here's $10,000 check. Now I'm

going to put in so much effort and try to be so helpful that it will make no sense to you because

my ROI is probably not going to pay for the time I'm putting in. But that was to create raving fans

and get referrals. And so that's what I did for the first six months, very small checks, putting in

way too much time. But for me, it was actually the perfect amount of time getting referrals. And then

that steam rolled in such a way that I was able to get advising. So I was able to get sweat equity.

Let's run down the angel path for a little bit and come back to podcasting. So I didn't mention

when I mentioned all the amazing things you've accomplished, your angel investing track record,

which is actually pretty good, right? It's turned out. So tell the audience some of the companies

you invested in. I invested in, let's see, invested. When I say invested, it's important to note that

I mean time in a lot of these cases, because I didn't have the bankroll to pay for investing. And

I probably couldn't have invested even if I wanted to. So Uber would have been when

there were two employees. Yeah, you've heard of it. And Shopify, first advisor when they had

eight to 12 employees, first investor in Duolingo, that was a bit later, early secondary on Facebook

and Twitter. What was your rule set back then? How are you deciding what to do?

Early rule set was super simple. And it's the same rule set. It hasn't changed for me. And that is

something that addresses a personal problem that I have that I understand that I could be a power

user of that I think I could feel very good about recommending to my audience. That's it. And that

has worked pretty well. I mean, as you know, there are a lot of whiffs. I mean, you get a lot of

things that zero out. But it's a power law game. So you you're really aiming for the handful that

return the fund. And I was always betting this is actually another maybe key framework that I would

say I've used over and over and over again. And that is I viewed the angel investing and all of

that as a real world MBA, assuming that I would lose all of the money I put in, right? You don't

get your tuition paid back to you by the same institution, but that the skills I would develop

and the knowledge I would acquire and the relationships that I would end up cultivating

would in the long term pay for all of it. Are there takeaways you had from specific investments

that became part of your mental model? I think the most consistent lesson for me, and I'm not

recommending anyone try to replicate this, but the timing was also really good in that period of time.

But choosing people that you really like to work with, because a lot of these startups are going

to take if they turn out well, longer than the average marriage. So you really want to make sure

these people pass the beer test, like, are you going to want to go out and have a beer with this

person? Right. And that doesn't always apply. And I think really good founders are often pretty

cantankerous. But I stuck to that. And for instance, you know, I was thinking about

some of the decisions in this area, and it's true for so many others, I could say, well,

becoming an advisor to Uber was a really good decision. But that's not really the right story.

The right story is working with Garrett on stumble upon was the right decision, which didn't pay off,

but we got to know each other. And that led directly to Uber. So rather than looking at the

decisions that are most well known for, say, successful people, I even to this day, when I'm

interviewing people, I look for the antecedents like, okay, well, let's look at what happened

before that without which those great decisions that are on the cover of magazines never would

have happened. We were talking about this in the back, because it's a question of can you increase

your optionality for fortune or luck or whatever anyone else says by taking meetings that may seem

superfluous or uncertain or that then lead to these big outcomes. Yeah, totally. And for me,

moving to the Bay Area, and then later moving to San Francisco, so it wasn't enough to just be in the

Bay Area, I moved all over the place, eventually got to San Francisco, because I realized if I want

maximum serendipity, if I want it to be easy for someone to say, hey, I'm over at this place,

come and have a drink, rather than driving an hour to an hour and a half to get there,

I needed to be in San Francisco, or I want it to be in San Francisco. And the question of where I

think, in an increasingly virtual world, actually becomes more and more important. If you can operate

in person, you have a huge competitive advantage. And it's a contrarian mindset today, where everyone's

relishing in the fact that they can live wherever they want. Yeah, so choosing at least seasonally,

if you're not willing to kind of bet the farm in terms of moving to one place, to be in certain

locations, if you're still in that growth phase of your career or life professionally speaking,

then I think that's undervalued. Yeah, I agree with that. And some of the work I've done in

studying, like Danny Meyer, when he wanted to be a great restaurateur, he moved to Europe and worked

in any job he possibly could. It's all the same. People ask about patterns across the 700 or so

interviews I've done. I'd say that's easily one of the most obvious. That's cool. Now,

you've mentioned recently publicly that you've backed away from angel investing. So for someone

that's had such a prolific run and successful run, why step away? That doesn't seem to make any sense.

Yeah, I'd say number one, I didn't grow up with much money or spending much money. And I still

think I'm actually quite bad at spending money. So why gather more skittles until I figured out

how to use the skittles I have, I think is one thing that comes to mind. Number two is things

have gotten more difficult, I think, in angel investing. There's just more noise, more competition.

It's like in the early days, I learned how to count cards with single deck blackjack with a

handful of friends. And now they're like, Yeah, we think we're going to change the odds. We're

going to swap in. You need a different brain to count to a deck shoe. Exactly. The game is harder.

And I also feel like, as with most things, my bolus, the majority of my really fast nonstop

learning happened in the first few years. And that there are a lot of people who can invest.

And there are a few things that I think I'm reasonably good at that I've, I don't want to

say neglected, but paid less attention to and I prefer to return to some of the creative stuff.

And also, I've been doing it for a long time. So generally, when I've been doing something for

five plus years, I think, what is something that for whatever reason I'm attracted to,

that seems completely unrelated. It's a total left turn. And that is something that I'll try to

experiment with because it's just worked for me over and over again. If something energetically

is pulling me, I want to pay attention to it. And right now that's fiction and animation and

AI and a handful of other tools. Let's go back now to your journey as a creator. So

where does the second book become the blog, become the email list, become the podcast?

I'll put them in order. So the blog was started in 2006, which was, of course, before the book

came out in 2007. That's not a coincidence. I had interviewed long before I had the podcast. I

interviewed people. That's part of the reason it was easy for me to segue to the podcast. But

I interviewed best writing authors, so people who had books that were acclaimed and that had won

National Book Awards and so on. While I was writing the four hour workweek to try to be better at

writing books, I also interviewed, reached out to bestselling authors, not always the same thing,

and asked them about launch and the vehicles and the types of media that seem to be undervalued,

but were increasing in impact in their mind. And there were patterns. Blogs were the big thing.

They said these things called blogs seem to move a lot of books. But most authors pay no

attention to them. And I was like, All right, I don't have a whole lot of wiggle room here for

a number of reasons with, say, large budget for launch. I know the publisher is going to want

to control quite a few variables. I'm going to focus on two things, blogs and in person events

to reach bloggers. And to do that credibly, I thought I really should have a blog that has

some good articles on it and began that in 2006. And that then led to the book, or I should say,

was followed by the book in April 2007, March 2007, really important inflection point,

was presenting here for the first time. Thank you, you forest for giving me overflow space.

I think it was next to a cafeteria, but it was like a last minute cancellation. I rehearsed at

my friend's garage using his chihuahuas as my test audience. And if they got bored and walked away,

I was like, I'm losing them, I'm losing them. And so I do it again. And that really planted

the toehold in tech that I think directly contributed to the success of the book in the

certainly in the first year. And then you have, let's see, email gathered with the very first

website. So I was gathering email beginning in 2007. I knew that email could be important,

but I didn't send the first email until something like 2014.

You just collected them.

I just collected it. I didn't do anything with them. And then I continued to work on the blog.

That became the way I communicated directly with my audience, which maybe we'll come back to

based on WordPress, which meant I did not feel captive to any platform. I knew that I could

take this open source platform. And if I wanted to migrate my blog and my content, I could do that.

And that flexibility of migration has been a core tenet of my professional life, I would say ever

since. When you're interviewing these other authors, you've transitioned to intentionality,

right? At that point, you're trying to do the best you possibly can on that product.

Yeah, on the books, on the books for sure. And I wanted books that would last and thankfully

they have. I mean, these books still continue to do very well. I think most of

because the content's more evergreen, I think it's, it's almost all evergreen.

And that's true for the podcast as well. I really don't want to produce content that has

an expiration date that is really obvious. That just requires more work for me.

What year are you aware you're a professional content creator?

I thought of myself at that time as I would say professional writer. And books are a very

particular thing. They have a permanence and they have a static nature. You can update them,

but it's harder. It's easier now with Kindle that requires a lot of forethought. And I think

that that's something I also try to use now. I still try to measure twice cut once with producing

any content, which in a world of kind of be fast to be first, I do think that pause gives you an

advantage. And then as far as say, I've never thought of myself to be honest, as a content

creator, it's always been as a writer or an interviewer, something that makes it more finely

categorized, because it helps me then to work on a craft. If you say I'm a creator,

that doesn't give you a great search function for trying to improve your craft. So I've always been

very finely sliced. And it was author, it was then investor, early stage consumer facing tech

investor to be clear. Then in 2012, the four hour chef burned me out. It was a probably a

three to four year project that I put together in a year and a half, very proud of the output,

but it just physically demolished me. And in the process of doing the launch, I'd asked

another cohort of bestselling authors, which platforms were neglected, but

seemingly powerful, they said podcasts, I went on a whole host of podcasts, I was very lucky to be

there at that point in time also. So you had Joe Rogan, you had Nerdist, you had Mark Marin, and

this entire cohort, Adam Corolla, those really moved the needle. They were also such a sharp

contrast to the morning TV shows and so on that I'd done previously where I could actually get

into nuance, I could curse, I could be myself. I had a blast and decided I am too burned out

to do another book. I want to try something else. Let me try podcasting. I'll do six episodes to

give myself a graceful exit. I'll set that expectation up front. It was either six or 10

episodes. And even if it fails, this is coming back to something I mentioned earlier,

even if it fails, meaning the audience doesn't like it or I don't continue doing it,

I will get better at interviewing. And I will deepen relationships or make new relationships,

all of which will persist after the hypothetical failure. And then I just kept doing it because

I was having fun. Do you have a similar story to the book story on podcasting or interviewing

where you went out and studied the art or the craft?

Definitely. I studied anyone I thought had something to offer, even if the format was

very different. That would include people like Dan Carlin, Hardcore History, which I think

is one of the most spectacular podcasts of all time.

I don't know that one. The audience might tell us about him and why.

Yeah, Hardcore History is, I would say, one of the super, super first gen,

long-form podcast. Dan Carlin does a deep dive on some facet of history, some chapter of history.

For instance, Wrath of the Khans about Jengus Khan is, I think, four or five parts. Each one is

probably four to five hours. And there's no one who, if he had gone to a market research firm

and said, what do you think of this idea? Uniformly, he would have been told it was a

terrible idea, doomed to failure. If they could bet the farm against him, they would.

And it worked. And even to this day, I think he just had a new episode come out a month ago.

He has multiple podcasts now, so he can scratch the itch of doing something more

frequently on current events. But the Hardcore History podcast, I think there was an eight-month

interval where there are no episodes. So he's effectively publishing audiobooks,

but it became massively successful. And I love studying those outliers, because anytime you're

told you have to do A, B, and C, my first question, at least internally, is, can I find exceptions?

And if you can find exceptions, it's not a must. And anything you took away from him or others

that you borrowed? Don't believe any dogmatic rules around what you have to do or what you should do,

test, experiment. It doesn't matter to maybe paraphrase Richard Feynman. It doesn't matter how

beautiful, how pretty your theory is. It doesn't match with experiment. It's wrong. So test,

do lots of tests. And I, in the early stages, also took my transcripts and ended up hiring a

senior researcher from inside the Actors Studio, amazing show, to look through my transcripts and

identify where I could do a better job. Where did I not follow up on a question that was a gem?

How could I have reordered the questions for a better flow? All of these types of things.

And that was fruitful, that exercise. Very fruitful. Yes. And at the very least, I think

everybody here should record a podcast just so you have to listen to yourself talk. And you will

find so many things that drive you insane. Everyone will have some form of tick that will drive you

batty. And you'll notice where you're sloppy also in your thinking, because really, I mean,

speaking is just thinking out loud. And you become a much clearer thinker, you become a much

more concise, deliberate thinker. And for that reason, I think everybody should try a podcast for

at least three episodes, even if you never publish it. Interview your family. Save that for your kids

or grandkids. Serious. What makes you a great podcaster? Can you reflect on that? I'll answer

it maybe a little bit differently. I think what makes me a successful podcaster is

first and foremost, I chose a format very consciously that was simple enough

that I would I could persist in doing it. So I knew I would have the ability to endure,

I would have the endurance to do a long form interview, and then follow that with minimal

editing and share it. I knew I could do that. And many podcasters, I think commit to failure

before they even start by choosing a format that is going to be too difficult or too exhausting,

given other obligations. So there's this elephant graveyard of three episode podcasts for that

reason. The second is I chose a category, let's say, and I earned the ability to do this. I'm

not sure if I could have done this in the beginning. For our workweek was very narrow.

For our body then says, hey, and I guess it was proved to me that the hypothesis was correct,

that a lot of my readers would follow me from my thinking, not just for a single topic.

And then it kept broadening. And by the time I got to the podcast, landed on the very

unoriginal title of the Tim Ferriss show, because I didn't want to apply a label that would constrain

what I could do. And you see what can go sideways. There are a lot of things that can go right with

a very narrow niche. But if, for instance, and this is very common, you decide you're going to be the

funny voice, wear a unicorn hat guy on your YouTube channel. And God forbid that becomes

mega popular. Like four years later, you're still going to want to be the funny voice unicorn hat

wearing guy on YouTube, maybe not. And many people end up feeling like they can't escape

a monster of their own making if things go right. So I was able to make it very broad,

which means I can explore my interests wherever they might fall, which also gives me endurance

which is a competitive advantage. If you are not able to endure, especially with the amount of

noise and the number of entrants now, I think it's very, very challenging to establish any

type of firm footing upon which you can build a business, which was never my intention. I didn't

monetize the podcast until, I don't know, 2030 episodes in, which I still would recommend to

most people. But those are some waiting window, that waiting window. Because if you focus on,

this is just my perspective, my two cents, I'm sure there are many counter examples. I would

love for people to point at examples that prove this to not be correct for everyone. Because

of course, that's true. For me, I wanted to focus on becoming as good as possible at the craft. I

wanted all of my attention to be on that. And we all procrastinate in different ways. As a writer,

my favorite way to procrastinate reading socially acceptable. Wow, you're such a such a serious

reader. It's amazing. I wish I could be so dedicated. I'm like, damn, right, I'm dedicated. But

really, what I'm doing is procrastinating doing the thing I should be doing, which is the writing.

Similarly, as soon as someone dangles some carrot in front of me that's related to like marketing,

business models, whatever. Oh, I love thinking about that stuff. I'll just skip the hard work,

which is focusing on getting better at interviewing. In kind of learning from your

experience and your success, one of the things that jumps out, you talk about controlling your own

destiny and email and podcasting are two content forms. They're both these highly distributed

things just by the way they're technically implemented. Yeah, that's been something that's

been you've been passionate about all along. Or you feel like an I feel like it's an existential

imperative to have direct communication with your audience to the extent possible. And so I

gathered email starting in whatever was 2007. Didn't email I want to say I'm getting the dates

slightly off until maybe 2013 or 2014 somewhere around there. And then started Fible at Friday

in 2015. So this very short format, easily digestible. Here are the five coolest things I found

through my enormous network this week. Check them out. You can read it in 60 seconds. So that

that five will reinforce the podcast. It reinforces the podcast in some instances. It is

legitimately whatever I have found most interesting that week, took a photograph of a book I'm

reading right now and sent it to my team saying add to 5bf all draft the bullet later.

Art and Arcana of Dungeons and Dragons, if anyone's interested, beautiful book. And that

ended up being, I think, one of the fundamental key decisions for increasing direct access to

my audience because podcasting is largely a black box for analytics. And just by contrast,

I would say I remember having a conversation with someone who had a massively successful

business built on one or two Facebook pages. This was probably five years ago. And I asked

I asked him what it was like to run these businesses. And he said, it's like having the

most profitable McDonald's in the world on top of an active volcano. Because if the algorithms are

changed, if your organic reach is throttled, right, fuck, they have a real problem on your hands.

And I never wanted I have enough trouble sleeping as it is, I did not want to be kept up at night

worrying about those types of things. So yes, I use Facebook. Yes, I use Instagram. Yes, I use

all these platforms. But I fully anticipated that at some point, organic reach would be

throttled across all of these. Yeah. Maybe it's the next recession that sparks it and

people need to improve their bottom line. But at some point, that's going to happen.

And I don't want to have all of my chips. I don't want to even have the majority of my chips

in those places. And so risk management standpoint, risk management standpoint. And I am

not I don't view myself as a risk taker. First and foremost, I really view myself as a risk

mitigator. Just a quick thanks to one of our sponsors and we'll be right back to the show.

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One other thing you talk about a lot is staying lean. And you run this thing at a massive scale,

but you have very little team and infrastructure. Yeah, very few. And you just said something earlier

that I keyed on, you said endurance. Is part of the endurance tied to that? Like just not having

the overhead of it all? I think they are tied together. And I should say there are many instances

for many people where building out teams makes perfect sense. Because I recognize some of my

weaknesses, as I mentioned earlier, I don't think I'm the most effective. Actually, I think I am an

effective leader. I'm not the easiest person to have as a manager. And I recognize that. So I have a

very lean team. I mean, currently just have three employees. And we do everything effectively with

that team. We have very well defined processes. And it maps back to the four hour work week,

honestly, which is like define, right? There's define, definition, elimination, automation,

and liberation, we will get deliberation today. But defining exactly what your outcome measures

are to use the fancy acronym KPIs, right? What are you measuring week to week, month to month that

matters? Why are you doing these things? What are the priorities one, two, let's just say,

then eliminating as much as possible that don't relate to driving those forward and then

automating as much as possible with really, really good processes. So we have very, very good

processes for the podcast. And for that reason, we don't need 20 people, we don't need 30 people.

And I've pushed back a bit against the trend towards video, because it would end up increasing

the infrastructure required, it would also fix me to one location, and I'm not willing to make that

trade off largely. How do you do prep? You're doing this many podcasts, you're not reading a

thousand books a year? No, step number one is write a blog post, which is called, I think it's

called the decision that removes a thousand decisions and then a parentheses why I'm not

reading any new books this year. So make it a policy. If you want to say no to a category of

thing, make it a public policy. So number one is making it a public policy. I'm not reading any

books published this year. That way I can tell every guest not reading books without having to

ruffle feathers. The next step is looking at before I even invite someone looking at long form

video and audio to the extent possible. And maybe I have to find something that was recorded

behind doors, that's something I'm usually pretty good at doing. Interviews, Wikipedia, what am I

looking for though? What's the filter? I'm looking for a handful of things. One would be any odd

hobbies or Passover comments that weren't fleshed out that I think would make for a good first

question or second question, in part because it will prove to the interviewee that I have actually

looked at the details and done my homework, which is really important for a lot of interviewees.

Because if you don't prove that early, they're going to go on autopilot and they're gone. They're

checked out. They're thinking about their next vacation. She might as well be talking to a Max

Headroom or something. It's just not going to be very interesting. And then I would say beyond that,

I will try to identify what has been neglected, what has not been mentioned. And that can lead

some interesting places, not always comfortable places, but that can lead, for instance, if they

haven't talked about their childhood at all. I might ask them if they're okay with me asking

about their childhood. A few other key, I would say housekeeping. And this is also in the category

of prep. It's just right before we record. I will talk to anyone, we did this even though we know

each other, for five to 10 minutes beforehand. Number one, just for so everybody can get their

hamstrings warmed up. We're not trying to sprint out of the gates after hitting record. Just talk.

But there's a format. I will say you have final cut, just like every one of my guests. This is no

got your show. I've had that happen to me. It sucks. This is a friendly. My job is to make you

sound as good as possible. You have final cut, we can send you the transcript. So don't worry about

it. It's not live. So bathroom breaks, water breaks, you want to restate something, we can do that.

And then I ask them and people comment on this because almost no one asks this,

what would make this a home run for you? Looking back after it's published,

say two months after it's published, what would make this one of your favorite interviews or

something that you would point people to? Great. And then I can help steer it. And that puts people

at ease and helps them to be vulnerable. Another thing that I will think of, if I want to try to

unbox something that hasn't been explored before, there's probably a good reason it hasn't been

explored. So I will find something in that same category. It could be childhood, could be

relationships, could be a business failure. I will volunteer that information from my side first

just to provide some transparency because I know that sometimes it seems like I'm

confident. Sometimes it seems like I'm talking a lot and I am, but there are reasons for,

in this case, doing that. I'll ask the question so they can think about it. Then I buy them time

so that they don't feel too under pressure. Then I volunteer an answer from my own life that

basically makes me vulnerable simultaneously and it makes people much more likely to reciprocate.

So those are a few of the things that I do. If I have any access to that person or their lives

through friends or acquaintances, then I will also back-channel to a few folks

and ask them what topics or questions. I always preface, I'll say I'm obviously doing a ton of

my own homework because people don't want to help you, including my friends, if you're being lazy.

So I'll say I'm doing a ton of my own homework, but are there any questions or topics that you think

could be fun or uncommon to explore with someone? So I did this with, I sent a text to you like

that for Danny Meyer when I interviewed him recently. Right. And you earn reciprocal trust

through those, many of those techniques. Absolutely. And then I will also, and this leads to

a lot and it smooths out the entire process. I will very frequently ask guests, not always,

but ask them if there's anyone they think would really have fun having a conversation on the

podcast. So I'd say 70% of the guests come from other guests at this point. You asked me that

about Mike Moveson and you just had them on. I did. One topic that I adore just as a fan of

media is what I call peer respect. So I remember Shaq went on this five minute rant about all the

greats that had come before him, which was just super endearing. Tell us a couple of other podcasters

that you respect and why. There are a lot. You mentioned one. Yeah. Yeah. I mentioned one. There

are many and I respect them for a whole lot of different reasons. I would say it runs the gamut

from say like a guy, Roz. So how I built this, who is using, I don't want to say of this American

life format, but he's doing a lot of prep, a lot of recording and then immaculate editing with his

team and telling a story arc. So they might move things around. And that is a particular game. That's

a very particular game and he's very, he and his team are very, very good at it. I would say

this is going to seem like an easy one, but Joe Rogan has done an excellent job of becoming a

category of one. He wasn't emulating someone else. And for those wondering where I get,

where you might be able to read up on how to do this, there's a chapter called the law of category

in the 22 immutable laws of marketing. A lot of the other chapters are outdated. This one everyone

should read. He did an excellent job of number one, experimenting with a brand new format early.

He has been in the podcasting world for a very long time and he's tested a lot.

And he found his footing reasonably quickly and the combination of entertainment and in-depth

interview and tripling down on long format. I think he deserves a lot of credit for popularizing.

He also made incredibly, incredibly good strategic decisions before most. I'll give you an example.

YouTube, one of the world's largest search engines who did one of the very first spectacular

jobs of capturing podcasts on YouTube, not just long form, but using clips on a separate channel.

So he has played that game like the consummate professional. And so he would be another example.

I think Lex Friedman does an excellent job. I'd say our formats are probably closest in some

respects. Patrick O'Shaughnessy, who we both know, who focuses on investing and investors,

I think does a fantastic job. I could list another 20. There are some really, really good

interviewers out there, but it's not enough to be a good interviewer. I really think you need to

seek to be a category of one. It's a lot easier to be the only than it is to be the best when you

have millions of podcasts to compete against. So it's spend a lot of time thinking about positioning.

I have a couple of questions about big events in your world that have happened in the past two

or three years. So Spotify leaned heavy into podcasts, did a couple of high dollar acquisitions

with Joe and Bill Simmons, and at least based on what they've said publicly with the layoffs and

stuff, they backed off a little bit. What are your thoughts on that in and out and what it means

for your world? I think, first and foremost, that it was a very smart strategic decision to acquire

talent, and that podcasts and audiobooks or some form of audiobooks are probably

existentially important to Spotify versus, say, in Amazon. Amazon has put a lot of resources

into podcasts, and certainly they are the dominant player in audiobooks with Audible,

but they could survive without those things. And for that reason, for Spotify to acquire talent

at whatever price necessary to fold in existing audiences to get a lot of PR, which gets the

attention of other high-profile creators who then might reach out through their lawyers or agents

to have conversations, I think it was very smart. And I expected, no matter what, that once they

became a more meaningful percentage of every podcaster's downloads, that they would back off

of that. Because why buy audience when you get to the point where most podcasters have to pay

attention to you, and they're coming to you at the same time they might go to Apple to ask for

promotional help, you've established a different level of leverage at that point. So it doesn't

surprise me that they've backed off. I think that would have happened either way. You're in a position

to know this. I'm not, how successful have they been in croaching on Apple's podcast player or others?

They've grown a lot. They've grown really significantly. I can't link that causally to

the one lever that they've pulled in terms of... Where are, do you know as a percentage,

at least for you? I don't, and I would share it if I had it, but it's easily tripled or quadrupled

in the last handful of years without a doubt. And then the second thing I was going to ask you

about on this front is just Twitter. Obviously, Twitter's been through a lot of changes in the

past two years, but it's also a platform for redistribution, pretty powerful one in your world.

I use Twitter in a very particular way. I am not totally convinced of its power as a distribution

mechanism. It may be just the same 200 people yelling at one another all the day, every day.

It's hard for me to tell sometimes, but Twitter principally for me is a way of connecting with,

I would say, a third of my podcast guests. And it is an excellent means by which you can

make contact with someone who would otherwise be very difficult to get hold of.

Oh, the DM part.

DM, because if you are reaching out, say, to have a conversation with someone through an agent,

a lawyer, a manager, a fill in the blank, there's so many layers and so many hurdles.

Even for me, it's very difficult to make contact with a lot of people. Twitter just gets rid of

all of that because if you both follow each other, and in some cases you have open DMs, but

you can communicate with someone and they don't have to share any of their contact information.

They're not going to be getting a late night text from you thinking of you. How are you?

They're not going to have the creep factor or potential as much lower.

So I would say probably a third of the people I ended up having in my book,

Tribe of Mentors, came from DMs on Twitter.

You have wondered over the years if LinkedIn hadn't polluted their in-mail and made it monetized,

and they had done what Twitter did, how much of the most powerful conversations in the world would

I do think LinkedIn is going through a powerful resurrection of sorts where I

actually think LinkedIn is going to become a more powerful platform than people expect

for broadcast. I've seen inklings of that. However, I should add a warning, which is

if you don't have a focal point like an email newsletter or you don't have a focal point like

the craft of improving your podcast because quality always has a market. If you aim to be

the best in a category of one, right now I know I'm combining a few things I said,

might be separate. They're not mutually exclusive. If you don't have that type of focus,

you haven't made those definitions ahead of time, you are going to be like a rabbit in a maze trying

to find a piece of carrot. You're going to be jumping from one platform to the next to this,

to this, and even on one platform. Oh, the algorithm changed. Now I have to change everything that I'm

doing. It's all about dogs farting now. Okay, great. How long can it be? 27 seconds? Okay,

that's what I'm going to do now. And you're going to lose. You're not going to actually,

I think, achieve any of the goals if you have defined those goals in advance at all.

Cool. So what I'd like to do now is this gentleman, Tim Ferriss, wrote a book called

Triva Mentors, where he came up with a list of questions for a whole bunch of different people.

So I'd like to turn them on you because I want to earn your trust. I'll answer them first and

show a little vulnerability. Perfect. So the first question is, which books or books have you

gifted the most? For me, it's complexity about Santa Fe Institute and a wonderful book called

Mr. China about this guy that lost his shirt, this British gentleman that lost his shirt,

investing in China. Those are my two. What are yours? Okay, I would say the moral letters to

Luke Killius, better known, I'd say through Penguin as letters from Astoic. These are letters of

Seneca that I think are very, very easily applicable to many different situations. That would be one.

Another one is Awareness by Anthony DeMello, a long since dead now, but Jesuit Priest who is also a

psychotherapist, Awareness, and then I would say Assorted Poems, mostly of Hafez.

And you give these out? I have bookshelves full of these books at home and I give them to friends

and guests and so on. Very cool. The second question, which purchase of $100 or less has most

positively impacted your life in the last six months? Now, I was hoping you were going to ask

me this question, but you didn't. So I was ready for it. I have a very peculiar answer, like really,

really amazing nail clippers. Like, pay 50 bucks for them or something. Like, it changed your life,

I promise. I mean, you know, I could use some manicuring. Most of us use really shitty nail

clippers. So a piece of advice from Kevin Kelly, just quick one. He's like, you know that you have

that bad pen and that one bad pair of scissors? He's like, yeah, just get rid of all those bad

pairs or inversions of whatever, like actually get a high quality version. So finger nail clippers,

$100 or less, I would say this is not going to be applicable to a lot of folks. I have Raynaud's

disease, so my fingers and toes get brutally cold in the winter and really hot in the summer.

Getting rid of ski gloves, I tried all the fanciest, including heated gloves, just getting bins

without finger dividers and putting heaters, cheap, disposable heaters. And don't worry about the fact

that they might not look cool. They don't look cool. And they make everything else harder related

to buckling. But I was in some really cool temperatures recently. So mittens, there you have

it. Third is favorite failure or failure that set you up for success. I was thinking about this

last night. So I was very fortunate and got introduced into math competitions in the sixth grade

and was super successful. But by eighth grade, I was getting my head handed to me. And there was

just a whole influx of new students and new people, a lot of immigrants, and it just got harder. And

in retrospect, I think feeling the victory, but then having it kind of get away was very

humbling and gave me a proper perspective on things. Yeah, that makes sense. I would say

I already mentioned one, which would be the four hour chef burning me out and also getting boycotted

by a lot of retailers because it was the first major title out of Amazon publishing at the time.

And for that reason, even though it sold 120,000 copies in the first week, which is a lot.

And I think number two on the New York Times list sold something like

10,000 copies. It ended up number four on New York Times, which is largely an editor's choice list.

If you want a compiled list, something like the Wall Street Journal is a true reflection of, say,

Nielsen Bookskin. And that was very hard for me to stomach after also just doing this suicide run

of cramming it into a year and a half, which led to the podcast. If I had not burned out,

podcast wouldn't have happened. I would add to that flashing back much earlier.

When I was initially an undergrad, I wanted to be a neuroscience. I was a neuroscience major,

and I couldn't do the animal testing required in the lab within which I wanted to work. And I

think it's important. I do think actually this type of testing is important. I couldn't personally

do it at the time. And I switched to East Asian studies with the focus on language acquisition.

And without that obsessive focus on language and language acquisition, I don't think the fidelity

of my hearing and awareness would be such that I could do my podcasting the way I do it.

That's cool.

Yeah, I think that cultivated a sensitivity that helped much later. So just to add a footnote to

that, do whatever gives you the most energy because energy is that currency that drives

everything else. So I don't regret majoring in East Asian studies at all.

The next one you asked almost all of your guests about the gigantic billboard,

I just a few weeks ago said, don't be tribal. And I just feel like there's no reason that

50% of the world should have their opinion on everything decided by one group of people. And

then I just think we all need to kind of be responsible for our own thinking.

What's your answer to your own favorite question?

I'll piggyback on the thinking theme. And I'm going to borrow mine from

BJ Miller, hospice care physician, who he does a lot more, but he's helped thousands of people

to die. And I had him on the podcast. And his answer was don't believe everything that you think,

which ties into the awareness book, Anthony DeMello, I mentioned earlier, but don't believe

everything that you think. I think many of our ills come from not cross examining the things we

take to be true.

Fair. That correlates with that famous saying, strong opinions loosely held.

Indeed, yes.

I think I might know your answer to this one. What is the best investment you've ever made?

Mine, Tuber, which year?

Yeah, we've got the startup, we've got the startup investments, but I'm going to actually just to

try to give a different answer. I'm going to say going to blog expo, I want to say it was,

because that is where I met a ton of bloggers in person, including Robert Scoble, who ended up

being very, very helpful and putting something on his blog that I think was a sort of a phase shift

moment for the four hour work week. Because without any of that, none of the other stuff

happens.

Okay. And then I'll do this one last. In the last five years, what new belief, behavior,

or habit has most improved your life? For me, I've learned that if you just wait a little bit

of time, a lot of problems go away. And I used to go deep in them. And this weekend was a perfect

example. And there's a good transition to Silicon Valley Bank, but a lot of people did a lot of

crazy manic things this weekend that didn't matter. Because it all got solved this morning.

So that's my, let's do nothing and wait for my new habit.

I would say mine is probably studying things like nonviolent communication. I encourage

everybody to check it out. Get the audiobook by Marshall. I'm blanking on his last name.

Learning how to navigate conflict well. And I don't think I was terrible at it before,

but nonviolent communication and also pro tip, if you are so dysregulated, if you're just so

amped up that no matter what, it doesn't matter which tools you have in your toolkit,

because you're going to blow it, you're allowed to say to someone, which comes back to kind of

doing nothing. I really just don't think I'm in a place right now to have this conversation go well.

So let's just take a little breather and maybe we can do this later this afternoon or some other

time. Just giving yourself permission to wait. We're out of time. We're out of time. Bill Gurley.

Thanks everybody.

Hey guys, this is Tim again. Just one more thing before you take off and that is Five

Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little

fun before the weekend? Between one and a half and two million people subscribed to my free newsletter,

my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is

basically a half page that I send out every Friday to share the coolest things I've found or

discovered or have started exploring over that week. It's kind of like my diary of cool things.

It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos,

all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast

guests and these strange esoteric things end up in my field and then I test them and then I share

them with you. So if that sounds fun, again, it's very short, a little tiny bite of goodness before

you head off for the weekend, something to think about. If you'd like to try it out, just go to

tim.blog slash friday. Type that into your browser tim.blog slash friday. Drop in your email and

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