Caterina Fake — The Outsider Who Built Giants | The Tim Ferriss Show (Podcast) | Transcription

Transcription for the video titled "Caterina Fake — The Outsider Who Built Giants | The Tim Ferriss Show (Podcast)".


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Intro (00:00)

"Optimal minimal." "I think this altitude I can run flat out for a half mile before my hands start shaking." "Can I also do a personal question?" "Now we're the same in appropriate time." "I'm a cybernetic organism living tissue over a metal endoscope." "Slee-tune pharas show." This episode of The Tim Ferriss Show's brought to you by Athletic Greens. I get asked all the time. If I could only take one supplement, what would it be? The answer is inevitably athletic greens. I view it as, and a lot of you now view it as all-in-one nutritional insurance. I recommended it way back in 2010 in the four-hour body, and I did not get paid to do so. I've been using it since before that, and I use that in a lot of different ways. I travel with it to avoid getting sick, or to help mitigate the likelihood of getting sick. I take it in the morning to ensure optimal performance, and overall, it covers my bases if I can't get what I need from whole food meals throughout the rest of the day.

Interview With Katarina Fake And Early Start-Ups

Welcome Katarina Fake! (00:57)

If you want to give Athletic Greens a try, they're offering a free 20-count travel pack for first-time users. I nearly always travel with at least three or four of these one-dose bags. In other words, if you buy Athletic Greens as a first-time buyer, you now get, for a limited time, an extra $79 in free product. Check out the details at Again, that's for your free travel pack with any purchase. This episode of the Tim Ferris Show is brought to you by Uber, which I use pretty much every day. Uber makes getting around town and the world, for that matter, easier than ever before. Now Uber is introducing Uber Rewards, a new rewards program that helps keep modern life going. Some of you know this already, but I've used Uber thousands upon thousands of times since 2008 or 2009 when I first became an advisor and it was even just in prototype stage. I've since used it to save my skin in many countries where I don't even speak the language to help transport my dog around, to save on delivery fees from big box retailers. The list is really countless for the number and types of ways that I've made in my life easier with Uber. As a company, Uber has been doing a ton of really interesting great things in the past year. Uber Rewards is going to make you love Uber even more. It's a brilliant idea and you can earn points on rides and Uber Eats. So you earn points whether you're staying in or going out and the more you use it, the more you get and you unlock rewards such as Uber Cash, which you can apply to rides or food orders. There's a lot more though. You unlock all sorts of new benefits at each membership level, such as flexible cancellations with gold. This means you get your cancellation fees refunded when you rebook within 15 minutes for a limited number of uses. You get price protection with platinum. This means you get price protection on UberX between your two favorite places. So you choose the two places, you ride between the most and during busy hours when prices might be higher, you'll be protected above a certain amount in either direction. You might get complimentary surprise upgrades with diamond, for instance. This means that at no extra cost you request UberX and you can get upgraded to premium rides like black. And there's a lot more priority support, priority pickup at EricPorts, getting access to highly rated drivers, all the different levels and it goes on and on and on. So you should check it out, go to for all sorts of examples. The more you ride, the more you eat, the more you get. So for the terms and to learn more about all the ways you can earn Uber Rewards, go to Let's Check out the program terms, the details, examples at Chances are you're already using Uber so you might as well opt into this and get more out of it and if you're not, these are all the more reason to install, download and try it today. Hello boys and girls, this is Tim Ferriss and welcome to another episode of The Tim Ferriss Show where it is my job to interview and attempt to deconstruct world class performers from all different fields ranging from business to military, chess to sports, everything in between. And today my guest is Katarina fake at Katarina. That's like catering minus the G plus an A at a Katarina on Twitter. Katarina fake is a long time Silicon Valley pioneer. She's the co-founder of YesVC, a pre-seed and seed stage fund investing in ideas that elevate our collective humanity and we'll talk about what that means. Previously, she worked at Founder Collective as a founder partner, served as chair of Etsy and was the co-founder of Flickr. At Flickr, Katarina and her team introduced many of the innovations, news feeds, hashtags, followers, likes and so on that have become commonplace online.

Should This Exist? (04:54)

Katarina went on to found several more startups, finderie, hunch and become an active investor, advisor and board member helping to build companies like Etsy and Kickstarter from their very beginnings. Other investments include cloud era, stack overflow and blue bottle coffee among many others. Katarina is an early creator of online communities and a long time advocate for the responsibility of entrepreneurs for the outcomes of their technologies. Katarina sits on the board of public goods, the Sundance Institute and McSweeney's. She was given the Silicon Valley Visionaries Award in 2018 and has received two honorary doctorates, one from the new school and the other from RISD. She is also the host of the brand new podcast, Should This Exist? Which asks the question, what is technology doing to our humanity? Should This Exist can be found on Apple Podcasts, wherever podcasts are found or at Katarina, welcome to the show. I'm super excited to be here, Tim. And you've been long requested as a guest on the show and I am really so thrilled to finally have a chance to spend some time together because I feel like it's been many, many years in the making. It has. I remember actually when you first moved out to San Francisco and you and I had some kind of conversation or email exchange very early on. We did. Indeed. And I remember I was so impressed with at one point one of your responses because I asked if you would I think be a panelist or a speaker at some conference might have been South by Southwest could have been another. And you said I'm taking a year break from conferences and I was so impressed by the categorical decision to not do any speaking engagements that I made a mental note of that. And there's so many places we could start, but in the process of doing homework for this, I found mentioned and I wanted to do a fact check on this of you having plane tickets automatically canceled and other issues related to your last name. Is that accurate? Did those things actually happen? This has happened to me many times in fact and I discovered that it was actually the systems at KLM and Northwest that would throw my ticket out, my last name being fake. And I have missed flights and have spent way too many hours with customer service trying to fix this problem. And so the other thing too, here's another thing too, is that I was unable for the first two years of Facebook to make an account there also and probably all of my relatives.

Almost unable to get on Facebook... (07:27)

So do you do you use a workaround now to prevent these types of problems or has it has it just been resolved at this point? It has been resolved by my not taking those airlines anymore. I'm serious. Like I actually will see a flight on KLM or Northwest and will not take it. I'm not even sure if those airlines are around anymore. I think I'm not up to speed on the airlines. It's like magazines and airlines which go out of business faster. But despite these travel challenges, you somehow manage to land in Silicon Valley and we were chatting before we started recording about your, I think the term was stochastic path and eclectic background that you have. But could you describe for people how you ended up in Silicon Valley? Did you do Stanford MBA and study computer science before that? And it was the objective all along. How did it come to be?

Grad School in Technology/Literature (08:43)

It's actually not my path, the Stanford MBA. However, what happened was I was living in New York and had spent the summer in Arkansas rock climbing and was big into rock climbing and had hooked up with a group of people there. And we were on our way to Nepal to do a big climb. And so I showed up at my sister's apartment in San Francisco. She had moved there first. I am from the East Coast originally. I had my ice pick and my crampons and my backpack full of gear and was planning on doing a big climb in the Himalayas. So she being my older sister put me up for a couple weeks in her house and I was visiting her on the way out to Asia. But what happened was my trip was delayed because one of our kind of head climbers had become injured. And then the trip was delayed and delayed. And then finally it was avalanche season and it was no longer possible for us to do the trek through the Himalayas. And so I ended up staying in my sister's spare bedroom. At the time San Francisco was cheap enough that people had spare bedrooms. And so I just stayed. And my delightful sister who I love dearly and has always taken care of me throughout my life. Her little sister shows up and six months into my stay there. She suggests to me, hey, Katarina, you might want to think about getting a job. So this being 1994, the most interesting thing that was going on at the time in San Francisco was the internet. And so I got started then as a web designer. And did you have a design background? At that let's flash back six months. So you're landing in San Francisco en route to this climbing expedition. At that point in time, what did you think you were going to do when you grew up, so to speak, or over the following five to 10 years? Did you have, did you have an idea of where you thought you were going prior to the internet entering the picture? Oh, yeah. I mean, my background is in art and literature, mostly. And from the age of, I would say probably about 10 or 11, I had decided that I was going to be an artist and a writer. And I had studied, I had actually gone, I was an art school dropout. I graduated from Vassar with a degree in English literature. And I had applied to grad school at Berkeley before this whole internet thing happened and was planning on getting a PhD in Renaissance literature. That was really my true love. I've always loved poetry.

Is a background in humanities an advantage for investing in technical companies? (11:36)

And the internet, which I've always had an interest in, had had a computer and had been hacking around with it since I was young, was another alternate path that I took. So I had actually, I had been very interested and had, there were a bunch of professors that I went and interviewed with at Berkeley. Because literature was my great love. Do you think that your background, which is, in some respects, very, I suppose, atypical for someone who ends up in tech, do you feel that say literature has provided you with some type of advantage or context or perspective or other aspects of your background that ended up really assisting you with both operating in the tech world and investing in the tech world? Do you feel like those things have been in any way an advantage? I really think that people come from outside of the industry have a superpower that people who have lived within the industry their whole lives or have spent all of their time in that mindset. It does give you a superpower, it does give you an ability outside of to be able to see things in a different way. And if you look at all of the companies that I've been involved with and the investments that I've made, they are companies that emphasize creativity, communication, connection, collaboration and community. And, and a lot of that comes from this background in humanities that I, that I have. I really am a big believer in people's creativity flourishing when they come at things from a different direction and see things in a different way. And in many ways, I've always encouraged entrepreneurs and investors and people who are interested in entering technology to come at it from a different field and really emphasize those parts of themselves that are different from the mainstream expectation of who you're supposed to be and what you're supposed to know, where you're supposed to go to school. Coming from a different direction is almost always an advantage. And in coming from the interrupted climbing expedition as you did six months or so after landing in San Francisco, then being encouraged very sounds like very gently and understand, distinctly by your sister to go consider getting a job. What did the, what did the subsequent 12 months or so look like for you when you, when you stepped into that world? This was a very early stage in the internet and there were no manuals or guides or blog posts or anything like that to help you shape your approach to the industry. And so you had to make it up yourself. It was a very small community of people that were interested in the web at that time. They were all centered down in South Park, which we at that time called multimedia Gulch, which is a kind of a funny terminology. It was very early stages. And so I had to teach myself HTML. I had to figure out how to design for the internet and it was a very experimental DIY self education at the time getting involved in that at that very early stage. It was a so it was such a small community that I just happened to be really lucky that my friend, my friend's roommate actually worked at one of the very first web companies and was able to teach me HTML.

Enter Flickr (15:21)

And where did and when did Flickr sort of enter the scene or the embryonic stages of Flickr? When did that come onto the radar? Well that happened. It's interesting because we were actually in the process of building something different when Flickr came about. They call it pivoting these days, but it was a pivot and came out of an unsuccessful game. It was also built during the lull after the dot com boom there was the dot com bust in 2000, 2001, 2002 is when it was when things were actually looking very bad for technology and technology businesses and startups and the ability to get funding. We were unable to get funding for the game that we were working on. And so Flickr was a kind of a Hail Mary that we were able to turn into a very successful business and then led into the whole web 2.0 era social media as we know it now, although when we conceived of it, it was not social media, it was an online community. And if we look at Flickr as a successful Hail Mary and we survey the landscape of Hail Marys and the entrepreneurial world, a lot of them don't work out.

Successful Hail Marys (16:57)

And a lot of these Hail Marys don't work out. These sort of kind of death knell, last gasp for breath as funding is running out. Often those do not work out, but some do. And there are some examples of these pivots, whether it's Twitter or Flickr or others that did work out. Can you discern what perhaps the ingredients were that made it a successful pivot slash Hail Mary? Is there a particular way you guys thought about it? Anything at all that you might attribute the success to? You know it's funny because there's a conversation I once had with another investor who said that there's some entrepreneurs that are just so bullheaded and stubborn and they won't quit, that companies really go out of business when the founder just quits, when they stop, when they're like, I can't take it anymore. And when I was kind of in the valley, I saw several examples of this. I was dating Ev Williams, the Twitter founder at the time. And when it was an amazing thing to see actually because Ev had completely run out of cash. This is the story of startups everywhere. It's a race against the bank account really and had nothing left when he was starting blogger, but he just kept on going. It was a miracle. It was amazing to watch. He was eventually, his company was eventually acquired. Blogger was eventually acquired by Google. Google went public. He then had more cash, was able to start the obvious corp, which then incubated Twitter. And having seen that first hand close up, that kind of willful determination, I see that again and again. And when you see things like the pivot that we went through, I mean, we were living on cup noodles and not getting paid. And the only guy that was getting paid was the guy who had three kids on our team. And we were, I mean, you talk about fumes, we were really driving on fumes. And then a miracle happened. What happened was we had submitted an application to the Canadian government. Flickr was started in Vancouver, Canada. And we had been rejected actually for this funding, for our startup Game Never Ending. And we had apparently checked a little box that said, "Resubmit next year," because what happened was we were truly going out of business. I think we had taken money from our friends and family. And all of that money had been spent. And I remember this. It was December 23rd. It was two days before Christmas. A letter arrived saying, "Congratulations. We're giving you this grant, this startup grant." And it came out of nowhere. Really, I mean, we didn't have enough money. We had like maybe a month or two left to pay our front end engineer. And that was it. And so this came out of nowhere. And that was what enabled Flickr to get off the ground. That's so wild. Yeah. It was, you know. And we were, I mean, it was a super scrappy operation. This was days before like AWS, and we just didn't have a lot of cash. And literally the servers were in a co-location center. And we literally had the phone number of the women who worked down on customs who would call us up and say, "Hey, your new server has arrived from Austin, Texas. Dell has sent you the new server. We would rush down there, plug in our new server at the co-location center." And load up the software and keep going. It was just, it was a super sketchy foundation on which all of this stuff was built.

If george did this... (21:34)

That's each, there's certainly some luck involved with the checking of this box. But there were, I would imagine also some good and probably some bad decisions that were made, but probably some good decisions that were made that in retrospect contributed to what Flickr then became. I was wondering if maybe we could explore one that I have just here under the sort of exploratory bullets, which talks about you and I think it's George Oates spending, you know, 24 hours a day, seven days a week, greeting every single person who came to the site. Is that true? Is that something you guys did sort of manually greeting everyone who came to the site in an effort to build community? What was the rationale behind that if that's true? Yeah, I mean, I think that's, to some degree, true. We had, I remember I looked back in the first three months of Flickr, the team each had posted something like 50 posts a day in the forums on people's photographs and had really been very strong participants in the community as it was being built. And I really am a big believer in this. I actually wrote an article for Wired at One Time talking about how, if you read the Bible, there's, you know, Abraham begat, you know, so-and-so begat, so-and-so begat, so-and-so. And it goes on for pages and pages. And I really do believe that the entrepreneur is the, is the Abraham of the company. And so therefore is dictating what the practices are of the community, how everybody behaves, how people respond to other people's photos. All of those things, I think, are, are basically how communities are built and staying involved and being involved and having that conversation and being live in that conversation all the time is a really important part of building an online community. And all of this went off the rails a bit when online community was renamed and repackaged as social media, because then it became a media platform in which people's attention could be sold. And as we later discovered, people's data could be harvested and also sold. And that's a very different way of building something than building a community from the ground up, which is, I think, what we were trying to do. And so I think the community, even now, you know, it's been acquired by Smugmug, it's, it's got a new life ahead of it. That's really the foundation of why it was such a strong community and how, even after the Yahoo acquisition and many years later, continued to be a very strong community and a model of community online. It also strikes me how, how many companies that later become very, or viewed as very large, like Airbnb, in the, in the beginning.

What Susan was looking for in early start-ups she funded (24:37)

I mean, this also reminds me of this, whether it's, you know, Brian or, or Joe, Gabriel, who I know better, talk about the early days of Airbnb. It was highly, highly manual and they would do things that didn't scale very deliberately until they had to create a system for it. But in the beginning, it was really, really high touch to build that community in the very early days. And it seems to be something that is sometimes missed by entrepreneurs who start something and beginning on day one, want to scale it to a million users or 10 million users or however many million users. Are there any other decisions or behaviors, best practices that you had in those early days that you think were critically important? Or, yeah, or, or mistakes, either one. Yeah. I mean, it's hard to say. I mean, it's funny because when you look back at something that has been successful, I think there's a tendency among entrepreneurs to attribute it to some action that they took. And one of the things you mentioned earlier, which I think is actually very important, is that we were extraordinarily lucky. We had invented this at exactly the right time. And what had happened was all of these things were converging at the same time. Friendster had come out and had gotten people accustomed to the idea of having a profile of themselves online and were then half of the households in America had broadband for the first time, more than half of the phones were being shipped with a camera on them. It was just an unstoppable juggernaut because of the time in which it was invented, right? And part of that was being smart and addressing that market. But a lot of it was also, I think, we are extremely lucky and well positioned to be taken advantage of all of these flows of information. And Bill Gross, who started IdeaLab and has been the progenitor of, I don't know, 500 companies, many, many companies, he looked at the success of what those businesses, many of them succeeded, many of them failed, and tried to figure out what it was about the companies that succeeded that helped them to succeed. And he looked at the team, execution, the financing, the market they were addressing, the timing, all of the things that potentially contribute to a startup success. And what he discovered was that more than anything, timing, timing was the thing that made this company successful. And I think that if this had happened 10 years before or 10 years after, even five years before or five years after, it wouldn't have had the same momentum as it does now.

The stories of Kickstarter and Etsy what inspired Susan to invest early (27:36)

And I look at this as an investor now with SVC, my investment firm. And we're always looking for companies that have timed it just right, that have found a parade and gotten in front of it, that are part of a movement. Because when you have that kind of movement behind you, there's some kind of cultural change that's happening. There's something that people believe very strongly in. There's a change that society wants. It makes it so much easier to get ahead. People are more inclined to want the product or the service. They're more inclined to talk about it. It's already in a flow that's moving forward. How do you, actually maybe we can look at this in a specific example. Let's take, and this may not be an example of this, but it could be. If we look at Kickstarter, so you were the first investor in Kickstarter? Or one of the first? One of the first. And I actually invested in it when it was still a PowerPoint deck. It was not built yet. And Perry and Yancey, it was actually brought to me by Sunny Bates, who I think remains on the board now. It was so clear that that had to happen. And it was something that you sort of felt in the culture. Something that you felt around conversations that were happening online. And this was a possibility that needed to bear fruit. It was very clear. And I think a lot of the things, if you look at, for example, Etsy. Etsy was at the forefront of the DIY handmade movement. It was a kind of a rebellion against Big Box retail and a return to the marketplace, which has always been a very person-to-person community-oriented place. I've traveled in, for example, in Syria. And went to those souks, the big marketplaces in Aleppo, which have now been destroyed, tragically. And that was one of the most ancient marketplaces in the world. It was like a care of ancestry. People would bring their camels in medieval times and form a market there. And you could see that that was the genesis of. You talk about the genesis of Airbnb or Flickr or all those other companies. The genesis of markets was really sitting down, having a cup of tea and negotiating for your rug. And Etsy had that, right? Etsy had that. And Kickstarter had that. And there were these very kind of person-to-person experiences that were manifested in places like Etsy and Kickstarter and Flickr. And a lot of these products at the very outset. And I think that that's another thing that happened at the very beginning of Airbnb. It was very much about people coming together in a very essential and human way. And that was what set those companies on such a strong foundation.

Going to see the movie no one else wants to see (metaphor) (31:05)

And what did you see that other people didn't see or what enabled you to see what you saw that got UDS with, say, Kickstarter or Etsy or other examples that might come to mind? Because a lot of these companies that are name-brand now faced a lot of rejection and a lot of no's and people didn't get it. Even including people that most folks would consider quite smart. It's true for Airbnb. Uber was turned down by hundreds of people on AngelList when it went out. And what did you see that other people missed? Or did you have... That could be in the companies themselves or in the founders or anything else. But what did you see that got UDS? Because I'm sorry to interrupt myself and you. But because a lot of founders will come in and a very high percentage will claim that they've found that parade, that they're in front of these three converging trends that are inevitably going to sweep the world. So how do you end up betting on the right horses? Like we were saying earlier, my difference helped me. I'm also a woman in a male-dominated industry. I'm a mom. I have... There's many things about me that are non-typical. And when I first saw Etsy, it was this beautiful thing and I actually took it to Reed Hoffman who had invested in my first company, Flickr. And a bunch of other people in the valley and they kind of lifted their eyebrows and said, "Okay, so let me get this straight. This is a bunch of women, mostly knitting sweaters and selling it to each other." And I said, "Exactly." Don't you see the opportunity here? And I think coming from this humanities background where I had spent a lot of time studying culture and society and people and what was happening around me and human interactions and how the culture was changing gave me a special view into that world that was missing, that somehow other people weren't seeing that was non-typical, was outside of the pattern recognition of Silicon Valley. And a lot of the investments that I have made have fallen outside of the typical pattern recognition that everybody takes advantage of in order to spot success. And I think I've always had that. My partners at Founder Collective used to tell me this all the time. I would bring in deals. They say that your deals don't look like anybody else's deals. Your deals look very different. The people that you're backing, the people that you consider as potential entrepreneurs fall far outside of what is typically understood in the valley as a typical investment. And they said this to me kind of over and over again, like, "Wow, where did you find these folks?" And most of the time they found me. And I think part of the reason that we started SVC and we wanted to start a brand new firm was because we saw that there was a sea change happening in technology and that people that were non-typical, people that didn't fit the typical pattern of an entrepreneur as defined by the valley culture were now liberated from a lot of prejudices that they've been working against before. And if there had been an investor in 2004 when I was raising money for Flickr that looked like me, I would have gone straight to her, but there just weren't that many. And so I think things have changed a lot. And non-typical investors, people from outside of the valley, people that are in different regions, people of color, women, I think there's so much more opportunity right now for those kinds of businesses to flourish and are being given a voice. And when all of those companies were started, it was actually much harder to find people who understood those business models, those founders and their orientation. Let's talk about atypical and you as atypical investor for a second because this is part of the reason I was so excited to talk.

The importance of cultivating an atypical perspective / voice (36:03)

And I'd love to chat a bit more about a few things you mentioned. You mentioned your familiarity with culture, society, people, and then whatever it was, five or ten minutes ago, we talked a little bit about timing. And so the question that jumped to my mind, and this is going to be a bit of a long question, so bear with me, was how could someone who wants to cultivate that type of awareness go about developing a better perspective or a different lens on culture, society, people and changes that end up getting in some ways represented by these fantastic opportunities like Kickstarter or Etsy. I've read in doing homework for this interview that you've recommended for entrepreneurs books like The Innovators Dilemma. But I also read on your site,, a paragraph, I think you'll recognize this, this is from 2018, but a comment on Stuart Brand's work, and I'll just read this because it's pretty short. So through Stuart Brand's work, beginning with How Buildings Learn, one of my favorite books and parentheses, and his work with the Long Now Foundation, I learned to look at time differently and technology differently and to think about how time is cooked into everything we do today, especially as regards to the ephemeral nature of all the time spent on computers and in online media. So I'm curious if, say, how buildings learn or Stuart Brand's work would be something that you would recommend to people who are coming out of more of the sort of CS or prototypical Silicon Valley background if they wanted to develop some of the perspective that you have. Are there any resources or books or ways that you would suggest people explore? I love that you brought this up, Tim, because part of the reason I was super excited to talk to you about this is because I think you and I share an obsession with time. Yes. And your books are the four-hour work week, the four-hour body, all of these things having to do with time, managing your time, thinking about time. And when you really look at it, you know, kind of from the 35,000-foot view, time is all we've got. And I have been a time, time management is possibly the thing that I've done most in my life in terms of generating the kind of life that I have wanted to lead. And that comes from, it went way back, back to when I was young and I was actually forbidden by the dean at my school from taking any classes before noon because I'm just one of those people I work really well at night. I'm a night owl and I could not make it to my classes in the morning.

Maximizing Life Quality And Self-Improvement Techniques

Manage your own time to maximize your life quality. (39:00)

I actually failed a photography class because it was at 8 a.m. There's just no way. I couldn't do it. And I honestly believe that one of the reasons I'm an entrepreneur and that I have always worked for myself is so that I can manage my own time. And I have always thought that the highest quality of living, the highest standard of living really comes from being the master of your own time, deciding where you want to go in the morning, what you want to do, and that that is so important. And knowing that when you have the energy to put into your work, you can do that. After or not, it happens at 8 a.m. or if it happens at 10 p.m. And I actually gave an interview with Business Week once about my peculiar schedule in that I wake up in the middle of the night between two and five in the morning and I do three hours of work. I don't turn on the computer. I write everything on paper. I do my best thinking and writing and ideation during those hours in the middle of the night. And then I go back to sleep and get up and carry on with my day. But without that, that kind of pocket of time where I'm uninterrupted, I'm offline, I'm free and liberated in a way that you just don't get during the work day, it's a magical time. I have so many questions. This is great. This is great. So I was going to ask you about this waking up between two and five a.m. I didn't realize that you went back to sleep. So this I've been reading up, I'll explain why maybe another time, but on the history of lucid dreaming. And it appears that biphasic sleeping where people would kind of wake up and have a first sleep, wake up and then go back to bed at various points in history has been quite common. It's not something that I've done a whole lot of. But could you give us an example of what you might work on on paper in those three hours? You wake up at some point between two and five a.m. Specifically what do you then do? Is it something that you've already planted at the top of a piece of paper as a prompt and you know you're going to work on a specific problem? Is it like a long hand stream of consciousness? What do you do? What do you do with this handful of hours? I have done it really depends. Sometimes I wake up and I I've always written books. So I have I've been working on a book now for the past three months, a new book. I write sometimes poetry. I sometimes just open up my journal and start writing. I can be working on a big problem. The five year plan for my startup or something like that. Any kind of big picture thinking any kind of thinking that involves creativity, intuition, all of that the kind of the the right brain and not the left brain. And I've studied all of these people. I come across these articles. There was an article that was recently sent to me that was about this actually forget his name, but he was an AI guru. I think he's from Cambridge. And the thing that I did not manage to read the whole article because I got stuck on the very first half where it described how this Cambridge AI genius woke up and he didn't communicate with anybody until noon and that he managed to have a relationship with his family and they had developed a language of grunts and smiles. So that he didn't have to his thoughts didn't get interrupted. And then when he finally went to work around noon, he had one meeting and I was like, oh my God, this is a master of time management and preserving that flow state in your head and preserving the ability of yourself to think and wonder and ideate is so precious and should be defended ferociously at all costs. And I've always felt that way. I've always had this this very I call it like cognitive defense, really powerful cognitive defense. And this it's interesting because this also shows up in some of the investments that we made. For example, one of my theories about cultural movements right now is that there's this very strong desire to simplify your life for being constantly bombarded with information, with marketing, with new products and you walk into a grocery store and you're confronted with 108 different kinds of toothpaste, right? And like like a thousand articles that you could be reading at any given moment of the day. And one of the investments that we've made is this company called Public Goods, which basically gives you one shampoo, one conditioner, one dish soap and sends it to your house and so you're not confronted with all of this paradox of choice, right?

Allie curates her podcast to keep the noise low and info most helpful. (44:17)

Which actually people want to reduce and people want to constantly reduce the amount of stimulation so that they can focus and so that they can live a more deep and fulfilled life. And I really think that in our society today, you need to pick your podcast and hopefully my podcast and eliminate all the others. But if you see what I'm saying, you have to focus in and narrow down and eliminate a lot of the noise in your life as much as possible. It's a very difficult thing to do. And so I see the time management part of our lives as being just the crucial thing to defend our space, our happiness and our individual lives. I was looking at your site earlier today and found an example of removing noise. And it was a simple example but might be a jumping off point for exploring other examples. This is a DF tube that is distraction free tube, which is a plugin that you use to clean up YouTube, removes the recommendations on the sidebar, the crap on the homepage, in name commentary poof. So I made a note to use that myself. Are there other tools, any other tools or books that you found helpful or approaches that you believe very strongly? And I mean, the waking up sort of in the witching hour and working for a few hours without a screen is I think a great example. You have the very tactical kind of micro tool like something like this extension. Are there other things that come to mind that you've found or find particularly helpful? When I am at my most flourishing and productive self, I'm actually online a lot less. And there's now all of these tools, screen time on Apple on the Apple phone and all of these things that I think are great. And during the periods in which I think I'm most flourishing, most productive, what I'm doing is I'm going online. I did this for as long as I can and I fall out of the practice occasionally, but I always try to get back is I would schedule a time to do my email in the morning 1030 to 12 or something like this. And then again in the evening, 430 to 6. And I would be offline as much as I could during the times in between. Now a lot of us have work that we need to do and things that we need to do online. But to be super disciplined about the time that you spend online, I think is really important. And I've always done this and I have a kind of a notebook that I keep next to my computer and it says WNO on the cover, which says when next, which stands for when next online.

Steps to eliminate unintended trips online. (47:32)

And you just write a list and it says, you know, I need to email my accountant. I need to look up what the name of Bob Dylan's second album was. I need to go fix this misinformation on this Wikipedia page. Whatever the thing is that you have these urges during the course of the day to go online. And then the next thing you know, three hours have passed and you're watching unboxing videos on YouTube, right? And you're like, what happened? Where did it go? And so I think that you need to just get on top of that. I think that's like one really important thing that you can do. This is a kind of a major thing. I fall out of this all the time. I am, you know, you see me watching unboxing videos on YouTube all the time. And so you just have to constantly bring yourself back to that and realize how much of a time suck that is and it can be. And realize also that it's that kind of activity that's taking you away from a life fully lived. I remember reading an article on Quora where somebody said, I want to be an entrepreneur as successful as Steve Jobs and Elon Musk. How do I do that? Right? Which I thought was kind of, you know, kind of, you know, many people would like to know the answer to that question. And one of the respondents was Justine Musk, Elon Musk's ex wife. And one of the things that she, I thought this was wonderful, right? Because like she knows firsthand actually what it takes to become or to be Elon Musk. And she responded, she said, well, first of all, Elon Musk would never be asking this question in a Quora forum. And that response stuck with me because it's true, right? He was, he was off building PayPal, he's building, Tesla was off doing that and not wondering how, if you see what I'm saying? Yeah. He wasn't kind of reading forums endlessly about, about that, but was, was out instantiating those ideas. And that, that really stuck with me. Because I think it's true. You can spend a lot of time in preparation. And I think that's good to, to an extent, to a degree, but really, really living it, really being in it, I think is the most important thing. Yeah. It's, yeah, I always have to reel myself in, in a sense, because, I love reading and reading is a very socially acceptable form of procrastinating. So I, I, I don't do it as much online. All of them certainly guilty of that at times. But the, I'm a, Kathy Sierra, a long time ago said to me, or it might have been in a presentation she gave, but I was sitting in the audience about focusing on just in time information, not just in case information. And that really struck with me, stuck with me, excuse me. Because I have a tendency to try to, try to stockpile information in case of the 1% chance that I need A, B, and C in the next six months, but it's not a very, it's not a great use of time. Let me just give up poetry. So you mentioned that sometimes you write poetry and can correct me if I'm wrong here, but I have some of your favorite poets, including Wallace Stevens, Shakespeare, Emily Dickinson. Why do you write poetry? What do you, what do you get out of writing poetry? What does that do for you? It seems to be a, a kind of an external expression of an internal state. It seems to be the recognition of and valuing of the inner life. I read, and something that somebody had written, let me try to figure out who it was. I can't remember. It was something that I read just the other day that was, was worrying and was very concerned that our modern world made it impossible for people to have an inner life. That the inner life was vanishing from the world, that our life was so much of the time that we would normally spend with ourselves, with our dreams, with our thoughts, was vanishing, because it was being filled up constantly with stimulation, entertainment, and our compulsion to be online.

The importance of an inner life keeping yourself mentally stoked. (52:15)

And basically what I see is sort of security exploits of the brain that the internet has managed to insinuate into our lives. And that poetry, writing, dreaming, paying attention to those kinds of things, and the cultivation of an inner life is something that you have to deliberately do, that you have to protect in your, in your life and make time for and recognize as important. And frankly, not do many things, many of the opportunities that present themselves. It's just terrible how much FOMO is created by the internet. It's endless. And there's a thousand places that you and I could be right now, and a thousand experiences that we could be having and things that we could be doing. And those of us who are like you, like me, like a lot of the listeners are optimists. We're possibilities. We're people who believe in living life to the fullest. And the internet kind of both cultivates that and makes those opportunities available to more and more people, hopefully. And yet, too much possibility as we've discovered, shuts us down and deprives us of fully lived experiences. And so, I mean, it's interesting because poetry has always been part of my life. I was a bit of a rebel as a kid and as a student, and I've always had a very difficult relationship with institutions.

Why he has memorized poetry (54:18)

I think my kind of very anti-authoritarian nature is also one of the things that led me to becoming an entrepreneur. And I rebelled against these structures. And one of the very earliest instances of this was in first grade when all of the other kids were learning to read, and I already knew how to read. And I was basically becoming a very trouble in the classroom for the teacher because I was impatient and I wanted to read. So I went to the library and I sat in a red poetry with the librarian. I remember this. I was only like five or six years old and I still remember some of those poems from when I was a kid. And they were just kind of rhymes. Here's one I remember. Once there was an elephant who tried to use the telephant, oh no, I mean the elephant who tried to use the telephone. Dear me, I am not certain quite that even now I've got it right. It seems somehow he got his trunk entangled in the telephunk. The more he tried to get it free, the louder buzz the telephy. I fear I better drop the song of Elephop and telephone. It sounds like a great metaphor for what happens to brains when they encounter the internet for hours a day. Exactly. So how on earth do you remember that? That's incredible. I have this crazy memory and I have for a long time, I think since I was in my early teens, I decided that I would memorize poetry as a way of bringing the beauty of thought and language and I always felt that poetry was one of the highest achievements of human thought and beauty and a kind of an embrace of the world and so I wanted it to be part of me. And so I started memorizing poetry as a way of bringing it into my unconscious as a way of having it always with me from a very young age. So I started memorizing poetry as a bit of an eccentric teenager. And I have a lot of that love of poetry but it's deep inside and I can recover a lot of this poetry at times when it's needed, when you're going through some kind of crisis or difficult times or depression or like some kind of bad state you find yourself in. Suddenly, some oracle from deep in the unconscious will come out and Shakespeare will have said exactly the right thing and you'll then know what to do. It's a kind of this amazing strategy that I've kind of carried with me my whole life.

First English Poem (57:16)

For those people listening who, like me, have minimal exposure to poetry or at some point we're introduced to the wrong poetry which was just completely confusing and seemingly designed to remain abstract and obscure and confusing. Are there any poets or collections you might recommend people start with if they wanted to dip their toe in the water of poetry?

Creativity, Poetry, And Dealing With Personal Struggles

Recommendations for the not so poetically inclined (57:43)

I honestly think that there's no one poet for everybody and that the best way to start is to just go to Just start digging around and find what you love. You mentioned some of the ones that I love. I love Wallace Stevens, Emily Dickinson, Shakespeare, I wrote my thesis in college on James Merrill. It just goes on and on. We could talk for hours about this, but it's important that we do this. I'm going to, Tim, if you don't mind, dig up this quote from Charles Darwin. I do not mind. There's this beautiful thing that he says. I think that this is a beautiful thing because he is an amazing scientist and he lived the life of the mind and Darwin's regret was that he had become, he said, a machine for grinding out facts and figures. He had become a machine like in his thinking and he said later on in his life, if I had to live my life over again, I would make it a rule to read some poetry, listen to some music and see some painting or drawing at least once a week for perhaps the part of my brain now atrophied would then have been kept alive through life. The loss of these tastes is a loss of happiness. And I think that's very powerful coming from as great a scientist as Charles Darwin because we live in what I call the technique. We live in a world of kind of mechanistic being and thought and science and all of those passions that throughout, you know, since time memorial have sustained humanity are getting lost somehow or they're slipping away or they're not part of our daily life. And I think we have to deliberately put it back in and continually put it back in and make sure that we don't lose it. Do you, how much of the poetry that you write for yourself remains just for you and how much of it do you show to other people? I would say a hundred percent of it remains just for me. I have it. It's interesting because many people have asked me this over the years because I've actually written a half a dozen novels. I have written probably at this point two or three books of poetry if it were to be in published form. But I have somehow never let any of that out into the world. And part of it is that it's such a precious part of me that in some ways I have a very strong tendency and desire to be successful in the world. And I agree that it will be go out into the world and will be subject to the same laws that have led to my success in business, which it's a very different thing. And so it's funny because I find it, everyone's like, "Oh my gosh, this is great. You should publish this when it's encountered." And I'm kind of like, "Well, maybe."

Why Rich has refused to publish his books of poetry (01:01:32)

But in the end, it's so valuable to me that in some ways if it were to escape out into the world, it would lose some of its power. Yeah, I think that's very wise to protect that. And after my first book, I have run into a lot of entrepreneurs who talk about, say, taking as a lifestyle business, something they love doing in their spare time on, say, Saturday, afternoons, going surfing, something like that and turning it into a business. And I'm always very hesitant to recommend that because if it's something that is this creative outlet that is pure in a sense and gives them some reprieve from the expectations and pressures of the outside world, I think it's very smart to keep that for yourself. And you talked about very deliberately building these things into your life. And you also mentioned a name and I might be pronouncing this correctly, but WH-O-D-M-I getting that right. And there's a quote of Oden's that I pulled up because I could only remember the first line, but I'd love to talk a little bit about your routines.

On a verdant index card, G.K. Chesterton describes eggs. (01:02:45)

And the quote goes as follows, "Routine in an intelligent man is a sign of ambition." Of course, it's blessed everybody. "But routine in an intelligent man is a sign of ambition. A modern stoic knows that the surest way to discipline passion is to discipline time. Decide what you want or ought to do during the day, then always do it at exactly the same moment every day and passion will give you no trouble." Okay. I've read that you very often will eat the same entree at certain restaurants. If you decide you like something, are there routines that are particularly important to you aside from those that we've already discussed? Anything that you make sure you do in the mornings or that you make sure you do in winding down or that you do once a month, once a week, once a quarter, are there any particular routines that help you in structuring your life and your time that you can think of? I have a very idiosyncratic schedule. And the reason for that is that I have, like you say, I find the thing in the restaurant that I like and I always order it because it's been proven again and again that the burden of decision making wears you down and that the fewer decisions that you make over the course of the day, the better decisions that you can and the more energy that you have left over for the important decisions in your life.

Applying simplicity to optimize creativity (01:04:05)

And so famously Albert Einstein had one suit of which he had five different versions or something like this. So he didn't have to think about what he's going to wear in the morning. He ate the same food. I kind of feel as if these patterns, if you figure out what it is that you're happy, no longer making the decisions about, I mean this is kind of one of the principles behind public goods into this company that I mentioned earlier is that you don't have to think about what shampoo to buy. You just don't have to think about it anymore. You kind of check that box. It's done. You've got a default. And so building these defaults into your life are super important. Then things that you don't want to think about anymore and whether that be what you eat, what you wear, things that you're less invested in so that when you're in, you know, like my my my witching hour, you know, the hour of the wolf or whatever you call that, I mean in that state, I can go wide, right? I can I can make a thousand decisions. I can I have I have freedom to go into, you know, dark corners that I haven't yet explored that I can can think really broadly and be more creative and have dreams and, you know, kind of revelations that are just not possible if you're kind of crowded into kind of tiny decisions all the time. And what is your well, actually, let me take a step back.

Depression after college (01:05:50)

So you mentioned in passing something when we were discussing poetry and how certain poems or phrases would come to mind at seemingly the perfect moment when you needed the most. And you mentioned depression very briefly is that that's certainly something I have some some personal experience with. Is that something that you also have personal experience with? Yeah, I mean, when I was a teenager, I was actually quite a depressed teenager. I went through a super bad period of my life when, you know, I was I was in that kind of state that's familiar to a lot of depressed people where I just couldn't get out of bed in the morning and just wanted to stay there all day and was, you know, reluctant to expose myself to the world because I felt very vulnerable and needed to basically hide in my cave. And I think that, you know, many of us go through these. I mean, I think it's kind of just common to the human experience at this be a state. And I honestly think there's there's a reason for it, right? I just I just like the term depression because I think a lot of it is more is better described as melancholy or despair or there's older words that describe it. It just seems so clinical to talk about it in in the terms of depression because I think that it's part of a fully lived life to go through these periods of deep unhappiness and dissatisfaction and questioning and despair even. And that without that, you kind of if you live always on the sunny side of life, I talk about this in kind of the Jungian sense of of the shadow, right? If you if you're constantly rejecting the shadow, if you're constantly living life on the sunny side, I mean, this is what happens on social media and this is why social media can be so diminishing of people's humanity is that people are always I call it social peacocking, right? They're showing how great their life is. They're showing all of their happy moments. They're showing all of their successes and not their failures, all of their triumphs and not their doubts and basically providing a highlights reel of their life. And this is very damaging to the psyche, to people's humanity of not acknowledging, living and frankly, giving time and space to those parts of yourself that are less savory that are in a mistakes. I see it all around and you know, you see it all around, right? You kind of look at all of your happy, successful friends on Facebook or Instagram or what have you, you know, they're always going fabulous places and doing fabulous things. But what about the shadow, right? What about the shadow? There's this really wonderful essay which I encourage everybody to read by the science fiction writer Ursula Le Guin about the shadow. I talk about it, there's a blog post on my website that's called Social Peacocking in the Shadow and in it I link to a short story by Ursula Le Guin about the shadow, which I think is a very important part of people's humanity, which somehow is not being given space online. How I've not yet read the piece, but how would you suggest whether, well, how would you suggest, you can either suggest or talk about your personal experience, people accept the shadow or work with it without falling into a dangerously deeper extended state of despair.

Managing your shadow side (01:09:35)

Like a pit of despair. Yeah, exactly. Well, I mean, I honestly, you know, it's interesting because I actually think that the way to start out with that is to accept the shadow in other people. Because we have this idea of other people as being more rich, successful, beautiful, happy, they're in a better relationship, they have better teeth. Their hair, they have thicker hair. I don't know what the thing is, right? Like some insecurity that we have, we see in others as something that we don't have. And there's a wonderful sonnet by Shakespeare on this subject. I think it's sonnet. What is it? It's sonnet 29 by Shakespeare. When in disgrace with fortune and men's eyes, I all alone be weep my outcast state and trouble death heaven with my bootless cries and look upon myself and curse my fate, wishing me like one more rich in hope, featured like him, like him with friends possessed, desiring this man's art and that man's scope, with what I most enjoy contented least. Yet in these thoughts myself almost despising, happily I think on thee and then my state, like to the lark at break of day arising, from sullen earth sings hymns at heaven's gate. For thy sweet love remembered such wealth brings, that then I scorn to change my state with kings. Beautiful. It's a beautiful poem and I think what it speaks to is the kind of the envy, wishing me like one more rich in hope, featured like him, like him with friends possessed, and you see it all around you, especially when you're in the state of despair. And it seems as if the world all around you is full of delight and success and happiness that is somehow unavailable to you. But what this poem does is it, you know, happily I think on thee, right? And often this is read as a love poem, as a, you know, kind of a celebration of the relationship that Shakespeare is presumably in when he's writing all of these, when all of these sonnets. But when you really think about it, you know, Mr. Rogers famously says, like think about all of the people that loved you into being, right? Those people are not necessarily your lover, but they're your mother, they're your sister. There's that teacher that saw something in you that other people didn't see. It's your friend. And it's all around you. All you just have to do is kind of stop looking at those people that have the thing that you wished that you had and look to those people that saw that in you and realize that they're all around you. So that's what that poem, that's what that poem kind of does to me. And I have, you know, I kind of feel as if if you have all of these poems and kind of they're deep inside you, that they will come to you when you need them. This is making me think a bit, I haven't thought of it in those terms, but only in the last few years I've started reading some very, very easy to read, very easily digested poetry by people like, you know, Hafez and a lot of Sufi poetry.

Learning From Failures And Self-Reflection

The importance of admitting weaknesses even to yourself. (01:13:11)

Yeah, Ruby as well. And they do stick, they really do stick and they seem to have a particular stickiness, a greater stickiness than perhaps more clinical nonfiction, right? Something that is really artfully woven into beautiful language just has a higher stickiness factor because these poems do come to mind at the right time, just never thought of it quite in the way that you're presenting it. Do you, do you, or have you found anything else useful for embracing the shadow but not falling into a pit of despair or if you, or if you've run into entrepreneurs who are going through a pit of despair, which is certainly not uncommon. Are there any particular recommendations that you've made or would be prone to make? Well I think that when people are depressed, they're also in some ways ashamed of it. And I think that's one of the things that makes it feel so isolating is that we feel that other people will judge us that bad things could happen as a result of our revealing these parts of ourselves that are so troubled or despairing or unhappy or failing or unsuccessful. And that we always feel as if we've got to present our best face to the world. And this can be one of the things that makes it impossible to get out of it. And so one of the things that's most important in, especially in our world of diminished relationships with others is to constantly be in communication with others, to know who our friends are, to revive those lost friendships that we've had in the past that are very meaningful to us, to resume our closeness to others and frankly, to, as Rumi would say in one of his beautiful poems, cry out in your weakness. Of course there's a poem for everything. But this one is, you know, cry out in your weakness because there are helpers in the world who will rush to save anyone who cries out. Like mercy itself, they run towards the screaming and cannot be bought off. And if you, if you address your suffering to others, you find that this suffering is universal, that we all go through these moments of shame and dignity, depression, unhappiness, failure. And that anybody who's pretending that they don't is just not true. And, you know, crying out loud and weeping, Rumi says, are great resources, right? Give your weakness to one who helps. It's a beautiful poem. It's, I think if you, if you search for it, it's like, cry out in your weakness. And that is a very meaningful poem, I think, for people who are suffering because it's basically giving you permission, which I think a lot of people need to cry out in your weakness. Yeah. It's, I really appreciate you being willing to talk about this and explore it a bit because it is a constant, like you said, and it, and it's, it's come up so many times in this podcast, whether it's with these brutal stories of rejection that bread and stand of humans, of New York is telling or any number of, you know, hundreds of examples that have come up. It's, like you said, it's an illusion and it, and a really crippling illusion when you're not only depressed, but are ashamed of it, feeling like you're somehow uniquely flawed because that's just not the case. So I appreciate you being willing to, to chat about this. And maybe we can, we can thematically continue on the shadow side for just a few more minutes and then we'll, we'll shift gears, but you have an incredible memory. You have an incredible track record.

Perpetually learning from failures. (01:18:17)

I think a lot of people listening or some people would certainly find that very intimidating, which is part of the reason also why I wanted to bring up the depression just to sort of humanize the, the, the profile a bit. Are there any failures? We've talked a lot about successes and known names, but are there any failures or apparent failures of yours that have set you up in some way for later success? Any, any noteworthy failures that come to mind. And if you, if you don't like the word failure, you could do something else. But. Yeah. I mean, I, it's, it's perpetual. It's hard to single out a single failure. You know, looking at the, you know, you kind of, you kind of look back at your, your miseries, your failures, the companies that didn't succeed, the relationships that didn't succeed, the, you know, great hope that you had, you know, for this or for that and kind of realize that you spent years and years working towards some kind of failed project or a relationship that didn't work out or, you know, some, some kind of trap that you fell into. And, you know, it was a, it was a struggle to free yourself. It's funny because I think that my orientation as a perpetual optimist leaves me with a kind of a sense of kind of forward motion from all of those things. I mean, I do think, you know, one of the things that we talked about was how when I was a teenager, I went through a very deep depression and a state of despair and melancholy and, you know, to use different terminology around it. And I think that always those, those periods are very formative. They are very important. You go back to them and those moments when you're at your worst at your weakest at your least successful at your kind of most alone and look back at the path that you took out of them and the ability to emerge from them and to kind of keep going in spite of them are some of the most meaningful parts of your life is that you have, you have really just reached a depths of despair and then have kind of recovered from them. And the importance that that gives you going forward and your strength comes from that, right? And if you're never tested and you're never in that kind of situation, you know, God help you. I mean, it's not a, it's not a good state, right? It's kind of the fullness of your humanity is kind of emerging from those depths. I've always, I've always kind of felt that. And without that, you know, without that experience, when I was a teenager, without some of those experiences from my childhood, without those experiences kind of like perpetually throughout life, life cycles through highs and lows like that. And to appreciate those periods and not just struggle to ignore them or eliminate them from your life is I think one of the healthiest things that you can do. And for people listening who are willing to have that broad spectrum of experience, including the dark moments, but are listening with envy to your talk of optimism. Are there any, any books? Any, I know this is kind of a, the type of question that won't die for me, but are there any tools, habits, books, anything that you would recommend to people who want to cultivate a more constant optimism?

Foster optimism with unfamiliar voices. (01:22:08)

If they might have been just beaten into cynicism by spending too much time on the internet or whatever it might be. Yeah. What would you, what would you recommend to those people? I mean, honestly, I think that a great deal of, of emphasis on long form reading, I think you and I both embrace this and love books and love reading. And you know, I know you read, you know, philosophy and Seneca and I read Jung and poetry. Go long form, not short form, go deep, right? And not broad. I think that this is actually a really important thing. And you know, there's a dozen books and maybe we can, I can even write a list of these and you can post it in the, in the podcast, in the show notes. Exactly. I can, I can, I can, I can write you like, oh my gosh, a list of, you know, a dozen or more books that have helped me throughout my life. Oh, for sure. I 100% yes and yes. If you can mention any of them now, you don't have to mention all of them, but I mean, any that really come to mind right now, I'd love to, that was, that was going to be the next place I went. So yes, good. Okay. Well, I mean, let's just start. I'm, I've got, I'm a huge fan and part of the reason that I'm actually probably on the internet and love the internet so much is because of Jorge Luis Borges. Oh, yes. Who I'm a huge fan of and actually was the motivation for me going online because I had discovered a community of Borges fanatics in Denmark that I communicated with very early on in my internet career. So that was, that's a big one. I think the best book of his to start with is labyrinths. And it's so much about the internet. It's kind of the internet before the internet. It's a beautiful thing. As I mentioned, poetry has been a huge part of my life. I love, I love all of the ones mentioned previously, W H Auden, Wallace Stevens, Emily Dickinson, Paul Ceylon, Shakespeare, of course, and, you know, contemporary poets. This is a wonderful poets out there that I look forward to their work. Natalie Shapiro, Brenda Shaughnessy. The list goes on. I can put together a list for you of poets that I love and respect. I love also the ones that you're talking about, Hafez, Rumi, Khalil Ghishibran. There's a lot of really wonderful poets from the East that I think bear attention from us.

A tool for finding good reads. (01:24:53)

And there are any other, whether it's fiction or nonfiction long reads that you would recommend. And for people listening, I'll definitely put all of these in the show notes. So you'll be able to access all of these. But if any others come to mind, Jorge Luis Borjas is just incredible in terms of the wordsmithing and art of his prose is really staggering.

Reflective books for oneself or others. (01:25:16)

So I definitely second that. I'm going to bring up, I use Goodreads. And is actually a really great place for people looking to discover new books. It's actually now owned by Amazon. And I put all of the books that I've read there because I read a lot. I read at least a book a week. And I'm rereading currently The Odyssey by Homer in a new translation by Emily Wilson. Other books that I have found to be really great that I've read in the past year are really wonderful book Tomb for Boris Davidovich by Danilo Kiss. Hannah versus the Tree by Leland de la Drante. Ethan Frome by Edith Wharton. I mean, I'm honestly, I'm just kind of going through this because I have this massive list, The Wake Goddess, which is a very meaningful book by Robert Graves, which is about poetry and its sources. I've reread the Uponoshads. There is a tremendous, there's this writer who I just adore. W.G. Seybald. I don't know if you're familiar with him. I'm not. But the emigrants by him is just an amazing, amazing book. I could go on and on. What books, if they could be from that list or otherwise have you gifted the most to other people if you gift books? There's a couple wonderful books that are actually illustrated books that I have given out to many people. And I think it's unfortunately out of print. There's one called Drawings and Observations by the artist Louise Bourgeois, which is fantastic. And I've given that to so many people, as well as the Principles of Uncertainty by Myra Coleman. She's famously an illustrator. Really beautiful books and full of just kind of life-giving thoughts. And you can tell that these women have lived very rich, profound lives, very thoughtful lives, very meaningful lives. And it's there in the books. There's another really wonderful book that's also I've given out to a lot of people called Letters of Note. And that is letters, kind of basically letters that have been collected throughout the ages. Wonderful letters. I've been meaning to grab that compendium.

Why Kevin has chosen to do a podcast. (01:28:11)

So I'm really glad that you just mentioned that Letters of Note. Check and check to add to my ever-growing reading list. See, you were just mentioning, rich lives and we're discussing, or you were mentioning, earlier, the paradox of choice that many of us face. And certainly you have more opportunities than you could possibly ever take advantage of in some total. Why decide to do a podcast? What was the catalyst or the reasoning behind that? Why should this exist? Why would you have finite time? Why apply to that? Well, I think that there's a super important conversation going on in technology right now in the culture in which we live that needs to be had. I was on my friend, Reid Hoffman's podcast, Masters of Scale. And I loved that experience. I love podcasts just in general, but this one was very gratifying for me because I had done what I thought of as a fairly garden variety interview with Reid. And they had turned it into a story with conflict and suspense and drama and made it super interesting. I loved it. I loved the podcast. I thought these producers are geniuses. And June Cohen of Wait What, who produced Masters of Scale, started a conversation about this new podcast. And realized that the next conversation to be had in technology was about the human consequences of the technology that we've been building. And I think that there has been kind of going back to the theme of the sun and the shadow has been all about the sun. And we're suddenly realizing that the shadow, which is always there, has now emerged. And we've seen what damage technology can potentially do to our humanity. And it was time for this podcast to come into being. So it just seemed as if it in some ways this podcast is kind of inevitable. It seems as if this is a conversation that's happening now that needs to be emphasized and can potentially build a future that we're deliberately building and not lead us into unintended consequences that we've seen happen over and over again. Which recently in the story of technology.

Implications Of Tech Development And Final Thoughts

How events on "Should this exist?" are shaped too. (01:30:54)

Can you describe one of the episodes that comes to mind? Whoever is featured, what is the structure of a sample episode look like? And what type of technologies or topics or entrepreneurs are you discussing? So what we do is we find an entrepreneur who's building a new interesting technology. And some of the interesting things have to do with AI or CRISPR or gene editing and neuroscientific kind of supplements to help us learn faster. Technologies which are in development where there's entrepreneurs who are actually building it currently now. And we have those conversations and then we bring in people from the industry, from outside the industry, people who have different ideas, psychologists, sociologists, historians perhaps. And people who have a different perspective on technology and how it might impact our humanity. And then we have a conversation and kind of workshop with the entrepreneur about the potential outcomes utopian or dystopian of this technology and how to steer it towards its best possible future. That is really kind of the format of the show. And I think that this conversation hopefully will become part of the dialogue about how companies are built, how they're thought about and how at the very beginning of building these technologies from frankly carried out throughout the process of building these technologies that we not only ask the question, can this exist? Because so much of technology has made it possible for so many things to exist.

On the need for regulations and guidelines for tech development (01:32:47)

But should this exist? Do you think there are safeguards or externally enforced constraints or regulations of any type that could or should steer technology development and company formation? Or are we dependent on the internal ethics and moral compasses of the people who are developing these companies? Certainly it's not. It's a false dichotomy. You could have both. But I'm curious how you think about that. I do think that we have in Silicon Valley enjoyed incredible latitude and have been basically assuming that we have the ability to self-regulate. I don't think that anybody starts off this idea of being the super villain. I don't think anybody kind of starts off and like, "I'm a bond villain in my mountain hideaway. I'm going to bring about the destruction of the earth." Nobody starts out that way. I think that we all start out with best intentions. As Baudelaire has said, and one of his many beautiful poems, we descend to hell by short steps. We end up loving what we hate and hating what we love. We end up doing things that we don't intend. The constant questioning, the constant vigilance, the practice of asking ourselves as a question, should this exist? Who is this harming? How do I remove bias from my AI? How do I make sure that this doesn't fall into the hands of the wrong people? How is it that I continually think about the outcomes of my technology and its effect on people and what it might do to them and their behavior? Constantly having that as part of the process of building something new is a very important part of putting it on its right track and building the kind of future that everybody had hoped to build from the outset. I'm very much looking forward to hearing these episodes and also seeing how the conversations develop over time.

On the wonders and horrors of biological engineering (01:35:30)

I think it's an important conversation and an increasingly important set of questions and maybe just a lens through which to look at building. I'm particularly interested in your CRISPR episode. Maybe you could describe for a moment what for people who don't recognize the term what CRISPR is or what it represents. Well CRISPR is in short its gene editing. It's the ability to change people's genes DNA. This has incredible possibility and Frankenstein like potential. I think that people have become very alert to and alarmed by the possibilities, the unintended consequences of introducing edited people, edited animals, edited any form of life. You name it. Yeah, virus bacteria. You name it. Virus is bacteria. Introducing basically the human touch into it. Assuming what in prior eras and in current eras are actually thought of as the hand of God and putting that in human hands and this kind of permethian impulse that people have to seize the power, like kind of permethias famously seizing the power of fire from the gods and just wrecking untold destruction. Upon the Earth there's just constant warnings throughout historical literature and Greek mythology and biblical literature and kind of modern day nonfiction about what happens when we enter the Anthropocene, right? We enter the era of humankind manipulating the world in a way that is potentially leading us to conflagration and the end. Some say the world will end in fire, some say in ice, right? This is kind of the wonderful poem by Robert Frost. You know, we will somehow bring about our own destruction and because of our incredible power and ability and I think that we should take responsibility for having that power. And you know, Stuart Brandt, who you mentioned earlier, he was one of the progenitors of the whole Earth catalog and in it he said, "We are as gods and might as well get good at it." I have a copy of the updated last whole Earth catalog which is given to me as a Christmas present by my mom about 10 feet from my right side right now. It's an incredible book and a very good statement on Brandt's part. I mean, it's really mind boggling to think about the promise and the perils of many of these technologies. Right, and like famously, Stuart Brandt is now working on bringing extinct life forms back to life, you know, kind of bringing back the saber tooth tiger and the woolly mammoth kind of amazingly is that and that kind of awakens possibility and dreams and excitement in the sense of, you know, wow, wonder, like the wonder of technology and the wonder of science, right? And also, terror and fear. Yeah, well, exciting and scary time to be alive. So I look forward to listening to you explore it with these various entrepreneurs and also sort of commentators. Let me ask one more question.

If Caterina could have a billboard anywhere, what would it say? (01:39:41)

It's sometimes one that's tough to answer but I'll ask it and then we'll wrap up in just the next few minutes but the question is one I like to ask and that is if you could have a gigantic billboard metaphorically speaking anywhere with anything on it could be a quote, could be a word, could be a question, anything non-commercial. But in the interest of getting a message of some type out to say billions of people, what might you put on that billboard? It's funny, I think of the kind of the basic truths as being a fairly straightforward, frankly kind of boring statements, right? You know, you should brush your teeth regularly. You should not let the grass grow on the path to your friend's door. You should be kind to one another. They sound like platitudes when you say them, when you see them on billboards and yet they are profoundly true. So frankly nothing exciting, mainly be kind. Yeah, I think it's two very important words and I think that they may be sort of inversely your capacity for being kind, maybe inversely proportionate to the amount of time you spend on the internet getting sort of poked in the brain by sort of really short form, dribble that is just sort of weaponized and commercialized, which comes back to the long form recommendations and the poetry and all of the other things. I really enjoy having a chance to chat with you like this in long form and I thank you for taking the time to have the conversation.

Parting thoughts. (01:41:53)

Yeah. So thank you very much. Yeah, no, this has been a great conversation. Thank you so much for inviting me. And people can find you on Twitter @caterina, C-A-T-E-R-I-N-A. Find the podcast, or on Apple podcasts and anywhere else podcasts might be found. is where they can find your writing including the social peacocking in the shadow and the other posts that have come up in this episode for people listening. Of course, I'll add links to everything including the books that Caterina would love for you to send me and I'll put them in the show notes. I'll put those at and you can just search Caterina or fake and it'll pop right up. So anything else you'd like to say, any parting comments, things you'd like to suggest to people listening, ask of them, anything at all you'd like to mention before we wrap up? Well, I think that the biggest thing that I've been working on recently has been the should this exist podcast. So listen, respond, subscribe. That's a kind of big thing and engage in that conversation. Great. Well, we'll send plenty of people that direction and once again, really appreciate you making the time to have this conversation. I've really, really enjoyed it. So hopefully we'll have a chance to break bread or have coffee in person at some point. And I really look forward to listening to the show. So thank you again for that. And to everybody listening, be kind, be kind, experiment, go deep, not necessarily wider and check out some of the books that I'm going to put into the show notes that Caterina has recommended. And until next time, thank you for listening.

This episode is brought to you by Uber, which I use pretty much every day. (01:43:55)

Hey guys, this is Tim again, just a few more things before you take off. Number one, this is "Fibollet Friday." Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun for the weekend? And "Fibollet Friday" is a very short email where I share the coolest things I've found or that I've been pondering over the week that could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out, just go to That's All is spelled out and just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode of the Tim Fair Show is brought to you by Uber, which I use pretty much every day. Uber makes getting around town and the world, for that matter, easier than ever before. And now Uber is introducing Uber Rewards, a new rewards program that helps keep modern life going. Some of you know this already, but I've used Uber thousands upon thousands of times since 2008 or 2009 when I first became an advisor and it was even just a prototype stage. I've since used it to save my skin in many countries where I don't even speak the language to help transport my dog around, to save on delivery fees from big box retailers. The list is really countless for the number and types of ways that I've made in my life easier with Uber. As a company, Uber has been doing a ton of really interesting great things in the past year. Uber Rewards is going to make you love Uber even more. It's a brilliant idea and you can earn points on rides and Uber Eats. So you earn points whether you're staying in or going out and the more you use it, the more you get and you unlock rewards such as Uber Cash, which you can apply to rides or food orders. There's a lot more though. You unlock all sorts of new benefits at each membership level, such as flexible cancellations with gold. This means you get your cancellation fees refunded when you rebook within 15 minutes for a limited number of uses. You get price protection with platinum. This means you get price protection on UberX between your two favorite places. So you choose the two places, you ride between the most and during busy hours when prices might be higher, you'll be protected above a certain amount in either direction. You might get complimentary surprise upgrades with diamond, for instance. This means that at no extra cost you request UberX and you can get upgraded to premium rides like black. And there's a lot more priority support, priority pickup at airports, getting access to highly rated drivers, all the different levels and it goes on and on and on. So you should check it out. Go to for all sorts of examples. The more you ride, the more you eat, the more you get. So for the terms, to learn more about all the ways you can earn Uber Rewards, go to Check out the program terms, the details, examples at Chances are you're already using Uber so you might as well opt into this and get more out of it and if you're not, these are all the more reason to install, download and try it today. This episode of the Tim Ferriss Show brought to you by Athletic Greens.

Sponsors For The Episode

This episode is brought to you by Athletic Greens. (01:47:28)

I get us all the time. If I could only take one supplement, what would it be? The answer is inevitably Athletic Greens. I view it as, and a lot of you now view it as all in one nutritional insurance. I recommended it way back in 2010 in the four-hour body and I did not get paid to do so. I've been using it since before that and I use it in a lot of different ways. I travel with it to avoid getting sick or to help mitigate the likelihood of getting sick. I take it in the morning to ensure optimal performance and overall it covers my bases if I can't get what I need from whole food meals throughout the rest of the day. And if you want to give Athletic Greens a try, they're offering a free 20-count travel pack for first-time users. I nearly always travel with at least three or four of these one-dose bags. In other words, if you buy Athletic Greens as a first-time buyer, you now get for a limited time and extra $79 in free product. So check out the details at Again, that's for your free travel pack with any purchase.

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