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

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

The Tim Ferriss ShowGo to Podcast Page

Bill Gurley, Tim Ferriss
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14 Clips
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Jul 19, 2023
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3:47
Hello boys and girls ladies and germs. Welcome to another episode of the Tim Ferriss show where it is. Usually my job to deconstruct, world-class performers of all different types to tease out the routines habits, Etc, that you can apply to your own lives. This is a special episode and a turning of the tables this time around. Legendary investor, Bill girly, 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 in favorite, fine.
4:17
Endings 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 girly, you can find them on Twitter at be girly, gu r l, ey has spent more than 20 years as a general partner at Benchmark before entering the Venture Capital business. Bill spent four years on Wall Street as a top-ranked, research analysts, including three years at
4:47
Credit Suisse first Boston, over his incredibly impressive Venture career, he has worked with such companies as GrubHub. 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 dot blog, /, Bill girly. 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,
5:17
In this conversation with Bill was, what started it all in many senses, it's what put my first book. The 4-Hour workweek on the radar of influential bloggers and bigger media Outlets. Ultimately Landing the book on the New York Times bestseller list where it stayed more or less unbroken for the next seven years. It's been a wild ride and this segment. This brief appearance at South by is what kicked it all off. And if you'd like to hear that 2007 presentation, you can find it at Tim Dot.
5:47
/ sxsw which is the abbreviation for South by Southwest. So one more time that's Tim top. Log /, SX s, WN my voice, sounds hilariously different. My presentation skills, hilariously less refined than they are today. Not to say they're perfect but things have changed and we get better day by day little by little and one last thing Q Forest if you are listening, thank you again for giving me a shot way back in the
6:17
Today, 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 Bill girly.
6:33
Well, it's great to be here. It's awesome to have the opportunity to turn the tables on Tim and interview. I was just recently on Tim's podcast. And so I actually suggested this before that, so that it would keep him honest. When we're going earlier, Tim, a lot of you, I assume all know who he is. He's one of the most, celebrated and decorating successful, digital creators of our time. He sold 10 million books. I got a list here. It's got 2 million, email Subs.
7:03
Over 1,000 blog post 7 million followers on social media and it's 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 feels, I thought it'd be great to see if we could dive deep and find out how he got here and what are some of his core, tenants are for being successful. So you graduated from Princeton in the year 2000 with the East Asian,
7:33
Studies Majors that. Correct. That's right. A perfect setup for podcasting. Yeah. And in 2014, you launched your podcast right. Okay. So 14 years, just tell us quickly would happen in those 14 year. Alright. 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 too.
8:03
But up, without making it a doctor Yuval. Life story. Good morning, everybody. Thank you for coming. It's lissy graduate moved to California Northern California to be part of the tech pinball machine for Serendipity. I actually think that was a very important decision, just geographically choosing where to be, and then what to do being really secondary. Worked in data storage selling storage area. Networks had a desk and a fire exit. Definitely not up to code. I remember it was really
8:32
act to the brim learned a lot about selling. I think everyone should have a service job working 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 of these things, translated too 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,
9:03
I know some of the bare-bones aspects of it, from the 4-Hour workweek. That experience was simultaneous with a professor of mine. Ed Chao, who taught high tech entrepreneurship at Princeton and 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
9:26
workweek. How long did the startup
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exist startup existed until
9:32
We'll 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.
9:39
So 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. 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
10:03
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.
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Did you raise money or
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I bootstrap the whole thing? So is 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
10:32
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,
10:49
what did you learn from the start up? What were the key?
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Takeaway a few key. Takeaways from startup work. Number one if you want to reach the decision makers, just call outside of business hours. So if you actually cold calling, I was cold calling smiling and dialing a
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Hot and cold emailing, then just do it before 8:30, and call after 6:30. 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 end up being really, really successful as a salesperson. Not because I studied sales per se, but
11:32
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, wherever you're human, I agree with storytelling is key. It's the kids.
12:02
Crux. So the life as a start-up entrepreneur eventually wasn't working for you.
12:11
It wasn't working because the for me, the learning curve, it kind of flattened out and I wasn't sure how to change that. I knew I wasn't a great manager. I didn't aspire to become a great manager, which continues to this day, I should probably revise, some of that. So then as is the case, now, I have a very lean team. Very, very small team and if we
12:32
A 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 instead of 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 4-Hour workweek is what as a lot of people here. Now 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 question that you
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Just 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 4-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 every 12, right?
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Right. 4-Hour, workweek 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.
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And that I got paid over a year and a half for the four hour work week initially and that type of decision making I think as 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.
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When was the second book and when did the Angel Investing stir
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for our work? We cannot April 2007. The Angel Investing started within I would say 10,
14:32
Months and I oh, Mike Maples, Junior. A debt of gratitude for that. I traded him advice for exercise and diet for
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eating a
14:41
pasta as well meeting at hobie's for breakfast and him telling me about his deals. Just so I could learn about them. And then they, for our body was published in 2010, which means that I was probably working on it for
14:53
two years or you said, you made 75 grand in your hustle and how do you afford to Angel
14:57
guys? Well fortunately the advanced gets earned out I
15:03
The savings from the prior company. So I had some savings and decided to place very, very small bat. So I was co-investing with checks of say, ten thousand dollars 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 going to put in so much effort and try to be so helpful that it will make no sense to you. Because
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Has my Roi is probably not going to pay for the time 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,
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let's run down the angel path for a little bit, and sure I'm back podcasting. So I didn't mention where I mentioned, all the amazing things, you've accomplished your Angel Investing,
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Track record, which is actually pretty good.
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Right? It's turned out.
16:07
Yeah. So tell the audience, some of the companies you invested in.
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I invested in let's see. Investment when I say invest, it's important to note that. I mean time and a lot of these cases because I didn't have the bankroll to pay for investing and I probably couldn't have invested even if I wanted to. So Uber would have been when they're worried about two employees. Yeah, you've heard and
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Shopify first advisor, when they had eight to twelve employees. First investor in Duolingo, that was a bit later. Really secondary on Facebook and
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Twitter. Boomers a rule set back. Then, how are you deciding what to
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do? Early? Ruleset was super simple and it's the same rule set of 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 is work pretty.
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Well, I mean, as you know, there are a lot of whiffs I mean you get a lot of things that are out but it's a power-law game. So you are 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 in all 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.
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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
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it. Our their takeaways you had from specific Investments that became part of your mental model. I
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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
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I really like to work with because a lot of these startups are going to take if they turn out well longer than the average American. 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 it 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
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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 Ubers. 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,
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Let's look at what happened before that without which those great decisions that are on the cover of magazines never would have
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had we were talking about this in the back because it's a question of. Can you increase your optionality for fortune or luck or whatever? Anyone else says by taking meetings? It may seem Superfluous or uncertain or then lead to these big outcome.
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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
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All over the place, and 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 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. 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.
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Everyone's relishing in the fact that they can live wherever they
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want. Yes. 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
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undervalued. Yeah, I agree with it and some of the work I've done in studying, like Danny Meyer. When he wanted to be a great restaurant tour. He moved to Europe and work.
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In any job he possibly
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could. That's all 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
20:42
cool. Now you've mentioned recently publicly that you've backed away from Angel Investing. So for someone that's had such a prolific run and successful. Run why? Step away that doesn't seem to make any sense. Yeah,
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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
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Bad at spending money. So why gather more Skittles until I figured out how to use the skills I have 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
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swap it. Beautiful train to count to eight deck shoe. Exact goodbye.
21:32
This is exactly the game is
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harder and I also feel like as with most things my bolus the majority of my really fast non-stop learning happened in the first few years and that there are a lot of people who can invest and there are few things that I think I'm reasonably good at that I have I don't 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
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Doing something for five plus years, I think. What is something that for whatever reason, I'm attracted to that seems completely unrelated, it's a total left turn and that is something that I'll try to experiment with because it's just worked for me over and over again. If something energetically is pulling me, I want to pay attention to. And right now, that's fiction and animation and Ai and a handful of other
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tools. Let's go back now to your journey as a Creator. So,
22:32
Where does the second book? Become the blog become the email list become the pot,
22:37
I'll put them in order. So the blog was started in 2006 which was of course before the book came out 2007, that's not a coincidence. I had interviewed long before I have 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
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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 ask them about launch and the vehicles and the types of media that seemed to be undervalued but were increasing and impact in their mind and there were patterns blogs where the big thing. They said these things called blogs seem to move a lot of books but most others pay no attention to them. And I was like, all right, I don't have
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A whole lot of wiggle room here for a number of reasons with say, large budget for launch. I know the publisher is going to want to control quite a few variables. I'm going to focus on two things blogs and in-person events to reach bloggers. And to do that, credibly, I thought I really should have blog that has some good articles on it and began that 2006, and that then led to the book or I should say was followed by the book in April 2007,
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March, 2007, really important. Inflection point was presenting here for the first time. Thank you, Forrest, for giving me overflow space think is next to a cafeteria. What it was like a last minute cancellation, I rehearsed at my friend's garage using his Chihuahuas as my test audience. And if they got bored and walked away, I was like, I'm losing them. I'm losing them. And so I do it again and that really planted the toehold in Tech.
24:32
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 that's Gathering email. Beginning in 2007, I knew that email could be important but I didn't send the first email until something like 2014 just collected. I just collected, I didn't do anything with them. And then I continued to work on the blog that became the way I communicate.
25:02
A 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,
25:25
when you're interviewing these other authors, you've transitioned to intentionality, right? At that point, you're trying
25:32
to do the best you possibly can on that
25:35
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
25:45
because the contents more Evergreen I
25:47
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.
26:01
What year?
26:02
Are you aware you're a professional content creator?
26:06
I thought of myself at that time as I would say, a professional writer and books are 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
26:32
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
27:03
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 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
27:32
Seemingly powerful, they said podcasts I went on the whole host of podcast has very lucky to be there at that point. I'm also so, you had Joe Rogan you had Nerdist, you had Marc Maron. And 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 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.
28:03
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 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.
28:32
That sounds fun. Do you
28:34
have a similar story to the book story on podcasting or interviewing where you went out and studied the art or the
28:41
craft? Definitely, I studied anyone I thought I 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
28:55
don't know that one. The audience might tell a Solace about him and why the
28:59
Hardcore History is I would say one of the
29:02
Our 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 cons about Jenga, skon is I think 45 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 again.
29:32
Ernst 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 podcast 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 are no episodes, so he's effectively publishing audiobooks, but it became massively successful and I love studying those outliers because anytime you were told, you have to do a b and c. My first question at least internally is
30:02
Can I find exceptions? And if you can find exceptions, it's not a must.
30:06
And what do you anything? You took away from him or others that you borrow
30:10
don't believe the dot. Any dogmatic rules around? What you have to do or what you should do. Test experiment, doesn't matter to maybe paraphrase, Richard Fineman, it doesn't matter how beautiful how pretty your theory is. It doesn't match with experiment, it's wrong. So test, do lots of tests and I in the early stages also took my transcripts and ended up high.
30:32
Hiring a senior researcher from Inside the Actor's Studio, amazing show to look through my transcripts and identify where I could do a better job. We're 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
31:02
Of talk and you will find so many things that drive you insane. Everyone will have some form of tick that will drive you batty and you'll notice where your sloppy also in your thinking. Because really, I mean, speaking is just thinking out loud and you become a much clearer thinker. You'd become a much more concise deliberate thinker and for that reason, I think everybody should try podcast for at least three episodes. Even if
31:32
You never publish it interview, your family, save that for your kids or grandkids is serious. What makes you
31:38
a great podcaster? Can you reflect on
31:40
that? I'll answer it may be a little bit differently. I think what makes me a successful podcaster, is first and foremost. I chose a format very consciously. That was simple enough that I would, I could persist in doing it. So, I knew I would have the ability to endure. I would have
32:02
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 up or other obligations. So there's this elephant graveyard of three episode podcasts for that reason. Yeah, the second is I chose a
32:32
Category, let's say and I learned the ability to do this. I'm not sure if I could have done this in the beginning for our work week was very narrow for our body then says, hey and I guess it was proved to me that the hypothesis was correct that a lot of my readers would follow me for my thinking, not just for 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.
33:02
Is there 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 where unicorn hat guy on your YouTube channel and God forbid that becomes Mega popular. Like four years later, you still going to want to be the funny voice. You're gonna 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
33:32
A 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 podcast until I don't know if 20 30 episodes in which I still.
34:02
Would recommend to most people, but those are some waiting window that waiting window, because if you focus on this is just my perspective. My two cents, I'm sure there are many counter-examples. I would love for people to point out 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 want to all of my attention to be on that and we all procrastinate in different ways as a writer, my
34:32
Way to procrastinate. Reading socially acceptable. Wow, you're such a such a serious reader. 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 correct. Similarly, as soon as someone dangles, some carrot in front of me that's related to like marketing business models would ever all of thinking about that stuff, I'll just skip the hard work which is focusing on getting better at interviewing
34:58
in kind of learning from your experience and your success.
35:02
One of the things that jumps out you talk about controlling your own destiny and email and podcasting or to content forms, they're both these highly distributed things. Just, by the way, they're technically implemented. Yep. That's been something. That's been your. You've been passionate about all along. Are you feel like it?
35:21
I feel like, it's an existential imperative right to have direct communication with your audience, to the extent possible. And so, I gathered email starting in whatever
35:32
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, and 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 fiber reinforced epoxy cast and it reinforces the
36:02
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. All drop the bullet later, art, and arkana 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
36:32
Let X and just by contrast, I would say, I remember having a conversation from with someone who had a massively successful business built on one or two Facebook pages. This was really five years ago and I asked as to what it was like to run these businesses and he said, it's like having the most profitable McDonald's in the world on top of an active volcano. Because if the algorithms are changed, if your organic reach is throttled, right? Fuck I have a real
37:02
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
37:20
these. Yeah. Maybe
37:21
it's the next recession. That's Parks 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.
37:32
In those places and so risk management standpoint or 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
37:45
Just a quick thanks to one of our sponsors and we'll be right back to the show.
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38:45
To check it out.
38:49
One other thing you talk about a lot is staying lean and you run this thing at a massive scale but you're very little team and infrastructure. Create a very few. You just said something earlier that I keyed on he said endurance is part of the endurance tied to that, like just not having the overhead of it. All
39:09
I think they are tied together and I should say there are many instances.
39:14
For many people, we're 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. I 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 make 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 4-Hour workweek. Honestly which is
39:44
Like Define a there's a Define definition, elimination automation Liberation, we will get deliberation today but defining exactly what your outcome measures, are to use the fancy acronym, kpis rank, what are you measuring week-to-week month-to-month? That matters? Why are you doing this things? What are the priorities 12? Let's just say then eliminating as much as possible. The don't relate to driving those forward. And then automating as much as possible really, really good processes. So we have very, very good processes for the podcast and
40:14
And for that reason, we don't need 20 people, we don't need 30 people and I've pushed back a bit against the trend towards video because it would end up increasing the infrastructure required. It would also fix me to one location and I'm not willing to make that trade-off largely. How do you do prep?
40:36
You're doing this many podcast, you're not reading a thousand books, a
40:39
year. No. Step number one is write a blog post which is called
40:44
And 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 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.
41:14
Is that 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 Passover comments? That weren't fleshed out that I think would make for a good first question, or second question in part because it will prove to the interviewee that I have actually looked at the details and done my homework, which is really important for a lot of interviewees. Because if you don't
41:44
Prove that early they're going to go on autopilot and they're gone. They're checked out there thinking about their next vacation, right? It's she 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, 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.
42:14
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 5 to 10 minutes beforehand, number one just for so everybody can get their hamstrings warmed up. We're not trying to sprint out of the gates after hitting record just talk. But there's a format. I will say you have Final Cut just like every one of my guests. This is no. Got your show. I've had that happen to me. It sucks this
42:44
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 its published, say two months after its 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.
43:14
And that puts people at ease and helps it 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. Yep. Just to provide some transparency because I know that that it sometimes it seems like an awful lot. Sometimes it seems like I'm talking about
43:44
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 200 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,
44:14
Or their lives through friends or acquaintances. Then I will also back channel to a few folks and ask them what topics are questions. Always preface. I was like, 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 send a text to you like that for Danny Meyer when I interviewed him
44:42
recently, right? And you earn,
44:44
People trust through those many of those
44:46
techniques. Absolutely. And then I will also in 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 percent of the guests come from other guests. At this point, you asked me that about my mohsinat. Yeah, just had him on. I did one topic that I adore just as a fan of media is what I call Pure respect.
45:14
Correct. So I remember Shaq went on this 5 minute rant about all the greats that had come before him, which was just super endearing. Tell us about a couple of other podcasters that you respect and a why? There are a lot they mention 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 Roz. So how I built this? Yeah, who is?
45:43
Using, I do want to say This American Life format but he's doing a lot of prep, a lot of recording, and then Immaculate editing with this 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 heinous team were 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.
46:13
And for those wondering, where I get where you might be able to read up on how to do this, there's a chapter called The Law of category in the 22 immutable laws of marketing. A lot of the other chapters are outdated. This one everyone should read. He did an excellent job of number. One. Experimenting. With a brand new format early he has been in the podcasting world for a very long time and he's tested a lot. Yeah. And he found his footing reasonably quickly.
46:43
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.
47:13
Tube not just long form but using Clips on a separate channel. So he has played that game like the consummate professional and so he would be another example. I think Lex Friedman does an excellent job. I'd say our formats are probably closest in some respects Patrick O'Shaughnessy, who we both know who focuses on investing and investors, I think does a fantastic job. I could list another 20. There are some really, really
47:43
The 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
47:58
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. Did a couple of high-dollar, Acquisitions with Joe and get Simmons and
48:13
And at least based on what they've said, publicly with the layoffs and stuff. They backed off a little bit. Yep. What are your thoughts on that in and out? And what it means for your
48:22
world? I think, first and foremost, that it was 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, right? Amazon has
48:44
Put a lot of resources into podcasts and certainly, they are the dominant player. And audiobooks with audiblelistener gold, they could survive without those things. 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
49:13
That once they became a more meaningful percentage of every podcasters downloads, that they would back off of that. Because why by audience, when you get to the point where most podcasters have to pay attention to you, and they're coming to you at the same time, they might go to Apple, to ask for promotional help, you've established a different level of Leverage at that point. So, it doesn't surprise me that they've backed off. I think that would have happened, either way, you're in a position to know this. I'm not how successful have they been.
49:43
And encroaching on Apple's podcast player or others.
49:48
They've got a lot. They've grown really significantly. I can't link that cause lie to write that book. The One lever of that they've pulled in terms of
49:58
where are, you know, on as a percentage at least for you where you know,
50:01
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
50:08
doubt who. And then the second thing I was going to ask you about in this front is just Twitter. Obviously, Twitter's been through
50:14
A lot of changes in the past yet two years but it's also a platform for redistribution. Pretty powerful one and your world.
50:23
I use Twitter in a very particular way. I am not totally convinced of its power as a distribution mechanism. It may be just the same 200 people yelling at one another all the day everyday. 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
50:43
My podcast guest. And it is an excellent means by which you can make contact with someone who would. Otherwise be very difficult to
50:52
get. Hold of a DM
50:53
port, DMB crumbling because if you are reaching out, say to have a conversation with someone through an agent a lawyer a manager, a fill in the blank, there's so many layers and so many hurdles even for me, it's very difficult to make contact with a lot of people Twitter's gets rid of all of that because
51:13
If you both follow each other and in some cases, you have opened EMS but you can communicate with someone and they don't have to share any of their contact information. They're not going to be getting a late night, text from you, thinking of you. How are, you know, they're not gonna have the creep Factor potential is much lower. So I would say probably a third of the people ended up having in my book tribe of mentors came from DMS on
51:38
Twitter. You ever wondered over the years if LinkedIn hadn't polluted there in mail and made,
51:43
Monetized. Yep. And they had done with Twitter did how much of the most powerful conversations in the world
51:50
where? Yeah, 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,
52:13
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, over the algorithm changed. Now, I have to change everything that I'm doing so
52:43
About dogs farting now. Okay great. How long can it be? 27 seconds? OK, 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 and in advance at all.
52:56
Cool. So what I'd like to do now, is this gentleman, Tim Ferriss wrote a book called, treiber 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. Show a little vulnerability, perfect.
53:15
So the first question is, which books are books of you gifted the most? For me, it's complexity about Santa Fe Institute and a wonderful book called mr. China about this guy that lost his shirt, this British gentleman that lost his shirt. Investing in China, those are my two. What are your
53:32
I can't? I would say the moral letters to Luke Ilyas. Better known I'd say through penguin as letters from A stoic. These are letters of Seneca that I
53:43
Are very, very easily applicable to many different situations. So 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
54:01
and you give these out,
54:03
I have bookshelves full of these books at home and I give them to friends and guests and so on
54:09
very cool, the second question, which purchase of a hundred dollars or less
54:13
It is 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, I was ready for it. I have a very peculiar answer like really, really amazing nail clippers like pay 50 bucks for him or something like it, change your life, I
54:34
promise. I mean, you know, like I could use some some some manicuring most of us use
54:40
really shitty nail clip highways for you. Try a really
54:43
so
54:43
Piece of advice from Kevin Kelly just quick when he's like you know that you have that bad pain and that that one bad pair of scissors is like yeah just get rid of all those bad parra's are versions of whatever like actually get high quality version so fingernail clippers $100 or less I would say this is not going to be applicable to a lot of folks I've read nods 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
55:13
In bins without finger dividers and putting Peters cheap disposable heaters
55:19
and don't worry about the fact that they might not look
55:22
cool. They don't look cool and they make everything else harder related to buckling, but I was in some really our temperatures recently. So mittens, there you have
55:30
it. Third is favorite failure or failure? That set you up for success. I was thinking about this last night show, I was very fortunate and got introduced into math competitions in the sixth grade.
55:43
Wade and was super successful. But by 8th 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 getaway was very humbling and gave me a proper perspective on things.
56:12
Yeah, that makes sense. I would say I already mentioned one, which would be the the 4-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's all the 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 4 on new.
56:42
At times which is largely an editor's Choice list if you want to compile lists, something like the Wall Street Journal is is a true reflection of say Nielsen. Bookscan and that was very hard for me to stomach. After also, just doing this suicide run of cramming, it into a year and a half which led to the podcast. If I had not burned out podcast won't happen, 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
57:12
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 switch 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. I don't go. Yeah, I think that cultivated a sensitivity that helped much later. So just add a footnote to that.
57:42
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
57:50
the next one, you asked almost all of your guests about the gigantic billboard. Yep, I just few weeks ago said don't be tribal and I just feel like there's no reason that 50% of the world should just have their opinion on everything decided by one group of people. And then I just think we all need to kind of be responsible for our own thinking.
58:12
What's your answer to your own favorite
58:14
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
58:41
true.
58:42
Fair that correlates with that. Famous saying strong opinions. Loosely
58:47
hell indeed. Yes. I think I might
58:49
know your answer to this one. What is the best investment you've ever made? Mind you were with your
58:58
Yeah, we've got the startup, we got the startup Investments, but I'm going to actually just to try to give a different answer. I'm going to say going to blog Expo. I want to say it was because that is where I met a ton of bloggers in person, including Robert scoble, who ended up being very very helpful and putting something on his blog that I think was a sort of a phase shift moment for the 4-Hour workweek.
59:27
Without any of that, none of the other stuff happens.
59:31
Okay. And then I'll do this one. Last in the last five years, what new belief Behavior habit is 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 use I used to go deep in them and this weekend was a perfect example and as a good transition to Silicon Valley Bank but a lot of people did a lot of crazy manic things this week.
59:57
Ken the didn't matter. Yeah, because it all got solved this morning so that's my that's do nothing and wait my new
1:00:04
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
1:00:25
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 tool kit 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 going to 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.
1:00:54
Out of town. We're out of
1:00:55
time. Bill girly. Thanks everybody.
1:01:03
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. It is basically a half page that I send out every Friday to share the coolest things. I found or discovered, or have started exploring over that week. It's kind of like my diary
1:01:33
A of cool things it often includes articles and reading books, I'm reading albums, perhaps gadgets, gizmos, all sorts of tech, tricks and so on, they get sent to me by my friends, including a lot of podcast guests and these strange, esoteric things end up in my field and then I test them and then I share them with you. So if that sounds fun, again, it's very short. A little tiny bite of goodness before you head off for the weekend. Something think about if you'd like to try it out, just go to Tim do.
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