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

Transcript from https://podmenti.com/t/acef562c29ffcb0f

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Hello, boys and girls, ladies and germs, welcome to another episode of the Tim Ferris 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 Gurly, you can find him on Twitter at B Gurly, G U R L E Y, has spent more than twenty 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 and
Including three years at Credit Suisse First Boston.
Over his incredibly impressive venture career, he has worked with such companies as Grubub and
Next door, open table, stitch fix, 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 slash BillGirly. And as a side note, my 2007 South by Southwest.
Keynote This was a speech, my first appearance at South By.
that I mention in this conversation with Bill was what started it all.
in many senses. It's what but my first book, The Four Hour Work Week
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.
In this segment.
This brief appearance.
At South by the
is what kicked it all off. And if you would like to hear that two thousand seven presentation, you can find it at Tim.blog slash
S X
SW, which is the abbreviation for South by South West. So one more time that's Tim.blog slash S X.
SW and my voice sounds hilariously different. My presentation skills are
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, Q 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 ranging conversation with
Yeah.
Girly.
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.
A lot of you, I assume, all know who he is.
He's one of the most celebrated and decorated successful digital creators.
Of our time.
He sold
Ten 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 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 two thousand with the East Asian studies
Major, is that correct?
That's right. Yeah. Perfect setup for podcasting. Yeah.
And
In two thousand fourteen you launched your podcast.
Right.
Okay, so fourteen years
Just tell us.
Quickly.
What happened in those fourteen 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
Doctor Evil Life Story. Good morning, everybody. Thanks for coming.
Graduate
Move 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 Shao.
who taught high-tech entrepreneurship at Princeton, which had a huge impact on me.
Inviting me back to guest lecture twice a year.
And that went from 2003 to 2013 or so. Those notes later became the outline for the four hour work week.
How long did the start up
Exist.
Startup existed until let's see, I want to say two thousand nine or so.
when I sold the company, not for any huge sum of money, but I sold the company around two thousand nine, so and how long was that
Experience. Six years.
The experience of building it.
The building phase was
the first three or four years, first year and a half, I had no idea what I was doing.
Say the subsequent year and a half to two years was building out distribution and then I
became very bored with the entire thing and was looking for a graceful exit, which turns out, you know, 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 or I bootstrap the whole thing. So it was credit card, savings
Trying to play
buying remnant advertising against incoming revenue, getting prepayment from distributors, you will 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 negotiated 80% off of because it was last minute.
Things of this type. So all of those games
were what drove a lot of the growth, figured out that playbook and then uh 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. So if you're actually cold calling, I was cold calling, smiling and dialing a lot and cold emailing, then
Just do it before eight thirty and
call after six thirty. And very often, even in a company of a hundred people, you'll get one of 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.
And I ended 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 those would be a handful of things.
And the value of storytelling, ultimately.
For everything.
If you're a human. I agree. Storytelling is key. It's the it's the crux.
So
The
Life as a start up entrepreneur eventually
Wasn't working for you.

It wasn't working because the for me the learning curve had kinda flattened out. Yeah. 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

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 ten 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 work week.
two point oh 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 publisher's gotta say yes'cause they they are willing to at least take this bet.
They'll give me a decent, not even a decent, a very good advance, which will actually make up for the seventy five grand that I got paid over a year and a half for the for our work week initially.
And
That type of decision making I think has
Tipified and defined a lot of my key decisions.
Which is entirely seemingly out of left field.
But of interest to me that will be a little bit more.
Potentially open new doors.
When was the second book and when did the Angel Investing start?
For our work week came out April two thousand seven.
The angel investing started within I would say ten months and I owe Mike Maple's
Junior.
A dead of gratitude for that. I traded him advice for exercise and diet for meeting. Austin as well, meeting at Hobie's for breakfast and him telling me about his deals just so I could learn about them.
And uh then the for our body was published in two thousand ten.
Which means that I was probably working on it for two years. So you said you made seventy five grand and you're hustling how how do you afford to angel?
Yeah.
Uh.
Well, fortunately the advance gets earned out.
I had the savings from the prior company. So I had some savings and uh 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 ten thousand dollar check. Now I'm gonna 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 gonna 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
Steamrolled in such a way that I was able to get advising. So I was able to get sweat equity. 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 it's turned out. Yeah so tell the audience some of the companies you invested in.
I invest 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'd wanted to. So Uber.
Would have been
When
Two employees, yeah, you've heard of it.
And uh Shopify.
First advisor when they had eight to twelve employees, first investor in Duolingo, that was a bit later. Early secondary on Facebook and Twitter. 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 minimal 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

if they turn out well longer than the average marriage. So you really wanna make sure these people pass the beer test. Like are you gonna wanna go out and have a beer with this person? Right.
And that doesn't always apply.
Yeah, and I think
Really good founders.

But
I stuck to that and s 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're 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 it 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 wanted 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 kinda 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, than 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 forget. It's all it's all the same. People ask about patterns across the seven hundred or so interviews I've done, I'd say that's easily one of the most obvious.
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 gonna change the odds. We're gonna swap in. Exactly. The game is harder.
And I also feel like as with most things, my
Bullus, the 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 like
Completely unrelated. It's a total
Left turn.
And uh that is something that I'll try to experiment with because it's just worked for me over and over again. If 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'em in order. So the blog was started in two thousand six.
Which was, of course, before the book came out in two thousand seven. That's not a coincidence.
I had interviewed
long before I
at the podcast I interview 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 it won national book awards and so on.
while I was writing the four hour work week to try to be better at writing books. I also interviewed, reached out to
Best selling author is not always the same thing and ask 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's gonna want to control quite a few variables.
I am 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 blog.
That as some good
articles on it and began that in two thousand six.
And
That
then led to the book, or I should say
was followed by the book in April two thousand seven.
March two thousand seven, really important inflection point.
was presenting here for the first time.
Thank you, Hugh Forrest, 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'd do it again.
And uh
That really planted
The toe hold in tech.
that I think directly contributed to
the success of the book in the first 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
Two thousand fourteen. You just collected. I just collected. I didn't do anything with them. And uh
then 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 a core tenet of my
Professional life, I would say, ever since. Trevor Burrus, Jr. 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 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 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 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 two thousand twelve, the four hour shaft
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 best selling authors, which platforms were neglected. But
seemingly powerful. They said podcasts. I went on.
A whole host of podcasts.
Very lucky to be there at that point in time also. So you had
Joe Rogan.
You had Nerdist, you had Mark Marin and uh this entire cohort, Adam Carolla.
Those really move 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 ten 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'cause 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 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 in the audience might tell us tell us about him and why the hardcore history is I would say one of the super
Super.
First gen.
long form podcasts. Dan Carlin does a deep dive on some
facet of history, some chapter of history, for instance, Wrath of the Khons about Genghis 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 months?
Interval where there are no episodes?
So he's effectively publishing audio books.
But it became massively successful. And I love studying those outliers because if any time 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 what anything you took away from him or or others that you borrowed.
Test. Experiment.
It doesn't matter to maybe paraphrase Rich Richard Feynman, it doesn't matter how beautiful how pretty your theory is, if 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 actor studio.
amazing show to look through my transcripts and identify where I could do a better job.
Where did I not follow up?
On
uh 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 fruit. 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 baddie. 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 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'll 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 you know three episode podcasts for that reason. Yeah. 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. Four-hour work week was very narrow.
for our body then says hey and I guess it was prove to me
that the hypothesis was correct that a lot of my readers would follow me for 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 we're a unicorn hat guy on your YouTube channel and God forbid that becomes mega popular.
Like four years later, are you still gonna want to be the funny voice in your current 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, twenty, thirty episodes in.
Which I still would recommend to most people, but
Those are some That waiting window. That waiting window.
Because if you focus on this is just my perspective, my two sets. I'm sure there are many counterexamples. 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.
Like wow.
You're such a such a serious.
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, w 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're you've been passionate about all along.
Or you feel like an in existential imperative to
Have direct
communication with your audience to the extent possible. And so I gathered email.
Starting in whatever it was, two thousand seven.
didn't email I want to say I'm getting the dates slightly off until
maybe two thousand thirteen or two thousand fourteen, somewhere around there.
And then started Five Bullet Friday.
in two thousand fifteen. 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 sixty seconds. So that that five. 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 five BF, I'll draft the bullet later.
Arton 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 from s 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 reaches throttled.
Right.
Oh fuck.
May 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 worry about those types of things. So yes, I use Facebook. Yes, I use Instagram. Yes, I use all these platforms, but I fulcipated that at some point
Organic reach would be throttled across all of these.
Maybe it's the next recession that sparks it and people need to improve their bottom line, but at some point that's gonna 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. So risk management standpoint. From a 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.
I
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I
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, correct? Yeah, very few.
And you just said something earlier that I keyed on you said 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

And I recognize that. So I have a very lean team. We currently just have three employees.
And
We do everything.
Uh 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. There's define
Definition elimination automation liberation. We won't get into liberation 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.
than 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 twenty people. We don't need thirty people.
And I've pushed back a bit.
Against the trend.
Towards.
Video?
Because it would be
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 you're not reading a thousand books a year, I don't know. No. Step number one is write a blog post, which is
Called
I think it's called the decision that removes the thousand decisions and then a parentheses why I'm not reading any new books this year. So make it a policy. If you 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 that 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
Pass over 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 gonna go on autopilot.
And they're gone. They're checked out.
They're thinking about their next vacation.
Right. S she might as well be talking to Mac's headroom or something. It's just not gonna 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, that they haven't talked about their childhood at all.
I might ask them if they're
okay with me asking about their childhood.
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 ten 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 gotcha 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, if you want to restate something, we can do that.
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.
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. Could be childhood, could be relationships, could be a business failure.
I will volunteer that information from my side first.
Yeah.
Just to provide some transparency because I know there's that it sometimes it seems like I'm sometimes it seems like I'm talking a lot. And I am, but there 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're
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.
Two
That person.
or their lives through friends or acquaintances.
Then I'll also back channel to a few folks.
and ask them what topics or questions. I'll 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 so and so. I did this with sent a text to you like that for Danny Meyer when I interviewed him recently.
Right. And you earn
reciprocal trust through those uh many of those techniques. Absolutely. And then I 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 seventy percent of the guests come from other guests at this point. You asked me that about Mike Mobison and you just had him on. I did.
One topic that I adore just as a fan of 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 a couple of other podcasters that you respect and why.
There are a lot. Yeah, yeah, I mentioned one. There are many and I respect them for
whole lot of different reasons. I would say it it runs the gamut from say like a guy Raz.
So how I built this. Yeah. Who is
using I don't want to say 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 gonna seem to be.
uh 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 and the Twenty Two 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 test it a lot.
Yeah.
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
Yeah.
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.

Patrick O'Shaughnessy, who we both know, who focuses on investing in investors, I think does a fantastic job.
I could list another twenty. 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. Yeah when you have millions of podcasts to compete against. So it's spend a lot of time thinking about positioning.
I have a couple questions about big events in your world that have happened in the past two or three years. So Spotify leaned heavy into podcast that
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've backed off a little bit. Yep. What are your thoughts on
That in and out and what it means for your world.
I think
First and foremost that it was very smart.
strategic decision to acquire.
Talent and that podcasts and
Audio books or some form of audio books are probably existentially important to Spotify.
versus, say, an Amazon, right? 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. Mm-hmm.
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. Uh I'm not how successful have they been encroaching on
Apple's podcast player or others.
They've grown really significantly. I can't
link that causally to
Right.
uh that they've pulled in terms of where are do you know on a as a percentage at least for you where you know 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.
Who and then the second thing I was gonna ask you about on this front is just Twitter. Obviously Twitter's been through
A lot of changes in the past. Yeah.
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 two hundred people yelling at one another all the day, every day. I 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 the DM part. DM because unbelievable because if you are reaching out, say
To
have a conversation with someone through an 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 they're not gonna be getting late night text from you.
Thinking of you, how are you?
The creep factor potential is much lower. So I would say a
Probably a third of the people I ended up having in my book Tribe of Mentors.
came from DMs on Twitter. Yeah, I've wondered over the years if LinkedIn hadn't polluted their in mail and made it monetized. Yep. And they had done
What Twitter did how much
of the most powerful conversations in the world would you I will say I do think LinkedIn is going through a
Powerful resurrection of sorts where I
actually think LinkedIn is gonna become a more powerful platform than people expect.
for broadcast.
And 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 gonna 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? Twenty seven seconds. Okay, that's what I'm gonna do now. And uh you are going to lose it. You're not going to actually
I think achieve any of the goals if you have defined those goals in in advance at all.
Cool. So what I'd like to do now is
This gentleman, Tim Ferriss, wrote a book called Triver Mentors, where he came up with a list of questions.
For a whole bunch of different people. So I'd like to turn'em on you. Um because I want to earn your trust, I'll answer'em first and show a little vulnerability. Perfect. Um
So the first question is which books or books have you gifted the most?
For me, it's complexity about the Santa Fe Institute and a wonderful book called Mr. China about this guy that lost his shirt.
It's British.
Gentleman that lost his shirt investing in China. Those are my two. Okay. I would say the moral letters to Lucilius, better known, I'd say, through Penguin as letters from a stoic.
These are letters of Seneca.
uh that I think are very, very easily applicable to many different situations. So that would be one. Another one is awareness by Anthony DeMello.
Yeah.
long since dead now, but Jesuit priest who was also a psychotherapist.
Awareness and uh 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 a hundred dollars or less has most positively impacted your life?
in the last six months. Now
I was hoping you were gonna ask me this question, but you didn't, so I was I was ready for it. I I have a very peculiar.
Like really, really amazing nail clippers.
Like pay fifty bucks for'em or something like
It change your life, I promise.
I mean you know, I could I could use some some some manicuring. Most of us use really shitty nail flips. I wait till you try a really good thing. So a piece of advice from Kevin Kelly.
Just a quick one, he's like, You know that you have that bad pen and that that one bad pair of scissors he's like Yeah, just get get rid of all those bad
Paras are versions of whatever, like actually get a high quality version. So fingernail clippers. Uh a hundred dollars or less, I would say this is not gonna be applicable to a lot of folks. I have Ray Nod'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
Peters.
It's cheap.
disposable heaters. They don't look cool and they make everything else harder related to buckling, but
I was in some really cold 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 too.
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 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 the four hour chef burning me out and also getting uh 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
Yeah.
You know, 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
Ten thousand 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 is a truer reflection of, say, Nielsen book scan. 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 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 a 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 ask almost all of your guests about the gigantic billboard. Yep.
I just a few weeks ago said
Don't be tribal.
And I just feel like
There's no reason that fifty percent of the world should dis have their opinion on everything decided by one group of people. And then I I just think we all need to kinda be responsible for our own thinking.
What's your
Answer to your own favorite question.
B J 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.
Yeah.
That correlates with that uh
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 too, but your
Yeah.
Uh yeah, we've got the startup we've got the startup uh investments, but I'm gonna actually just to try to give a different answer, I'm gonna say going to blog.
expo, I wanna say it was, because that is where I met
a ton of bloggers in person, including Robert Scobel, 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?
Formi
I've learnt that if you just wait.
A little bit of time, a lot of problems go away. And I used I I I used to go deep in'em and this weekend was a perfect example and it'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.
Yeah.
'Cause it all got solved this morning. So that's my that's do nothing and wait.
My new habit.
I would say
Mine is probably studying things like
nonviolent communication. I encourage everybody check it out. Get the audio book 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 gonna 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 subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel.
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