Turning the Tables on Tim Ferriss: A Conversation with Bill Gurley | SXSW 2023

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 were going earlier. Hugh Forrest of SXSW has asked for my comments on Silicon Valley Bank, which we're going to hold to the end since this is about Tim and not about me. But I promise that we would bring that together at the very end. Tim, a lot of you, I assume, all know who he is. He's one of the most celebrated and decorated and successful digital creators of our time. He sold 10 million books. I got a list here. He's got 2 million email subs, over 1,000 blog posts, 7 million followers on social media, and his podcast is about to pass a billion downloads.

And so since SXSW 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 tenets are for being successful. So you graduated from Princeton in the year 2000 with an East Asian Studies major, is that correct?

That's right, yeah, 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. Let's see, graduated, 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 in 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, 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 4-Hour Workweek. That experience was simultaneous with a professor of mine, Ed Zschau, 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 4-Hour Workweek.

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.

And how long was that experience? Six years?

The experience of building it? Yeah. I would say the building phase was... The first three or four years, first year and a half, I had no idea what I was doing. I'd 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 bootstrapped the whole thing. So it was credit cards, 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 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 830 and call after 630. And very often, even in a company of 100 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 would be a handful of things, and the value of storytelling, ultimately, for everything.

If you're a human. I agree with that. Storytelling is key. It's the crux.

So, so, the, the life as a startup entrepreneur eventually wasn't working for you.

It wasn't working because the for me, the learning curve had kind of flattened out. Yeah. And I wasn't sure how to change that. I 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 publisher is 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 will actually make up for the 75 grand that I got paid over a year and a half for our 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.

So when was the second book and when did the angel investing start?

4-Hour Workweek 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 meeting 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 $75,000 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 get—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.

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, yeah.

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 had wanted to. So Uber would have been when they had about two employees. Yeah, you've heard of it. And Shopify, first advisor when they had 8 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 were 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're really aiming for the handful that return the fund. 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.

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?

Well, 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? 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 StumbleUpon 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, 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, you know, it's, 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 wanted to be in San Francisco. 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, you know?

Yeah. 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.

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.'

Exactly. The game is harder. And I also feel like, as with most things, my—the 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 I could do? 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. Where does the second book become the blog, become the email list, become the podcast?

I'll put them in order. 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, so 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 4-Hour Workweek to try to be better at writing books. I also interviewed, reached out to, best-selling authors—not always the same thing—and asked them about launch and the, the vehicles and the types of media that seemed 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, a large budget for launch. I know the publisher's 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, Hugh Forrest, for giving me an 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 that really planted the toehold 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 2014. 'You just collected them?' 'I just collected. 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 the—most of—Because the content's more evergreen? I think 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?

Well, I thought of myself at that time as, I would say, a 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 4-Hour Chef* burned me out. It was 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 Marc Maron, and this entire cohort, Adam Carolla. 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 wanna 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.

So 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 podcasts. Dan Carlin does a deep dive on some facet of history, some chapter of history. For instance, Wrath of the Khans about Genghis Khan is, I think, four or five parts. Each one is probably four to five hours long. 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, and it was—he has multiple podcasts now, so you 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 were 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. 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 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 tic 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.

Seriously, 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 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. Four-hour workweek was very narrow. Four-hour 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 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 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 the funny voice wear unicorn hat guy on your YouTube channel and God forbid that becomes mega popular.

Like four years later, are you 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—20, 30 episodes in, which I still would recommend to most people.

But those are some of— That waiting window. That waiting window. Because if you focus on... This is just my perspective, my two cents. 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. They're like, 'Wow, you're 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 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 where there's no evil overlord. They're both these highly distributed things just by the way they're technically implemented. Yep. And so that's been something that 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 it 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 Five Bullet 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 bullet reinforced 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 5-BF, I'll draft the bullet later.' Art & Arcana of Dungeons & 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 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, oh, fuck, now you 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. 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.

From a risk management standpoint. And I don't view myself as a risk-taker, first and foremost. I really view myself as a risk mitigator.

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 is part of the endurance tied to that like just not having the overhead of it all i think i think 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 workweek honestly, which is like define There's define

Definition, elimination, automation, deliberation. We won't get into deliberation today, but defining exactly what your outcome measures are, to use the fancy acronym, KPIs. 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 tradeoff, largely.

How do you do prep? Like, you're doing this many podcasts. You're not reading 1,000 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 a Thousand Decisions,' and then in 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?

Right? What's, what's the filter? I'm looking for a handful of things. One would be any odd hobbies or passed-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 going to go on autopilot and they're gone. They're checked out. They're thinking about their next vacation. You might as well be talking to 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.

So 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 ten minutes beforehand, number one, just 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, 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. 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. Let's just say it's—child—could be childhood, could be relationships, could be a business failure.

I will volunteer that information from my side first. Yeah. And to—just to provide some transparency, because I know that 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'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—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 Morrison, and you just had him on.

I did.

One topic that I adore, just as a fan of media, is what I call peer respect. 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, 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 Raz, How I Built This, who is using—I don't want to say This American Life format, but he's doing a ton 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 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 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 Fridman 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 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've 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, an 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... 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. How successful have they been encroaching 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... Do you know as a percentage, or 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. Cool.

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 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—the DM part, DM, because, because if you, 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—you can communicate with someone, and they don't have to share any of their contact information. They're not going to be getting late-night texts from you, 'Thinking of you, how are you?' They're not going to have—the creep factor potential is 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.

I've wondered over the years, if LinkedIn hadn't polluted their InMail and made it monetized, and they had done what Twitter did, how much of the most powerful conversations in the world would have happened?

I will say 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. 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 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 are 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 Tribe of 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 book 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, this British gentleman that lost his shirt investing in China. Those are my two. What are yours?

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 that I think are very, very easily applicable to many different situations. That would be one. Another one is Awareness by Anthony de Mello, 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... like, pay 50 bucks for them or something. It'd change your life, I promise.

I'm in, I'm in. I could use some manicuring.

Most of us use really shitty nail clippers. Wait till you try a really good one.

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 one bad pair of scissors?" He's like, "Yeah, just get rid of all those bad pairs or versions of whatever. Actually get a high-quality version." So fingernail clippers. $100 or less. I would say—and 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. So getting rid of ski gloves—I tried all the fanciest, including heated gloves—just getting mittens 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 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. 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 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 I had not burned out, the 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 asked almost all of your guests about the gigantic billboard. I, just a few weeks ago, said, "You know, 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

one group of people, and then I just think we all need to kind of be responsible for our own thinking. What is—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 de Mello, 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'm going to get a few more, and then we have to save time for the SVB question. I think I might know your answer to this one. What is the best investment you've ever made? Mine's Uber. What's yours?

Yeah, we've got the startup 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, in 2016 or early 2017, because that is where I met ton of bloggers in person including Robert Scoble who ended up being very very helpful and putting something on his blog that that I think was a sort of a phase shift moment for the four-hour workweek 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 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 because it all got solved this morning. So that's my "do nothing and wait"—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.

All right. You're a great interviewer. Ask me a question about Silicon Valley Bank.

Bill Gurley, what are your thoughts on Silicon Valley Bank?

Oh, wow. That quick. You know, it's a Black Swan event. People have read about Black Swan events. It's hard to really prepare for them. I think people that expect that every startup—and there are people with this attitude—that every startup should just have to eat it if they pick the wrong bank, I'm not sure that's particularly reasonable because this stock on March 8th was at $260 a share. So all of Wall Street thought it was okay. So why should every CFO at every startup be as good at analyzing a bank, or better than all of Wall Street? Because that's what it would require. And if we all tomorrow felt like we couldn't trust our bank, then it would just create a lot of chaos. I would also highlight that 14 years ago in 2009, our government,

bailed out Goldman Sachs after Warren Buffett put money in. And in that case, bailed out equity holders. All we're talking about here is depositors. Like in Goldman's case, they protected the equity holders. So, you know, I think at the very least, we should reflect on what's happened in the past before we throw a lot of darts at what's happening here. And we're out of time.

We're out of time. Bill Gurley. Thanks, everybody.