#360: Caterina Fake — The Outsider Who Built Giants

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Hello, boys and girls, this is Tim Ferris, and welcome to another episode of the Tim Ferris 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 Katerina Fake at Katerina. That's like catering minus the G plus and A at Katerina on Twitter. Katerina Fake is a longtime 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 will 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, newsfeeds, hashtags, followers, likes, and so on, that have become commonplace online.

Katarina went on to found several more startups, Findery Hunch, and and become an active investor, advisor, and board member helping to build companies like Etsy and Kickstarter from their very beginnings. Other investments include Cloudera, Stack Overflow, and Blue Bottle Coffee, among many others. Katerina is an early creator of online communities and a longtime advocate for the responsibility of entrepreneurs for the outcomes of their technologies. Katerina 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's 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 shouldthis exist dot com. Katerina, 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 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.

So we did. And I remember I was so impressed with uh 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 I was so impressed by the categorical decision to not do any speaking engagements that I made a mental note of that. And Uh There's so many places we could start, but in the process of doing homework for this

uh I found mention and I wanted to do a fact check on this of you having plane tickets automatically cancelled and other issues related to your last name. Is that is that accurate? Did D 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 North West that would throw my ticket out.

My last name being fake. And um I have missed flights and have spent Way too many hours with customer service. trying to fix this problem. And uh But 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. Oh so. And and probably all of my relatives. So do you now do you uh do you use

A work around now to prevent these types of problems? Or is has it has it just been resolved at this point? It has been resolved by my not taking those airlines anymore. I'm serious. I I I I actually will see a flight, you know, on KLM or North West and Um we'll Despite

These travel Challenges. you somehow managed to land in Silicon Valley. And we were chatting before we started recording about your I think the term was stochastic. Uh huh.

Have you got to be a little bit more. uh and eclectic background that you have, but could you describe for people how you ended up in Silicon Valley. Did you do uh Stanford MBA and study computer science before that? And And it was it was the The objective all along? How did it how did it come to be?

That's actually Uh uh not my past the Stanford NBA. However, um what happened was I was living in New York and um had spent the summer in Arkansas uh 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'm from the east coast originally. And I had my 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 Um one of our one of our

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 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 Um who I love dearly and as has always taken care of me throughout my life, her little sister shows up and, you know, six months into my stay there, she says she suggests to me, hey, um

Caterina, you might want to Think about getting a job. So um this being nineteen ninety four, 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? Uh at at that point, 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 the the the following Five to ten years. Did you have uh did you have an idea of where you thought you were going at Prior to the internet entering 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 ten or eleven, I had decided that I was going to be an artist and a writer. And I had studied I'd actually gone, I was an art school dropout. I 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 and

Um The internet, which I've always had an interest in, and had had a a computer and had been hacking around with it since I was young. Um Was another alternate path that I took. So I had actually, you know, I'd I I'd been very interested and had there were a bunch of professors that I went and interviewed with at at Berkeley

Um Renaissance literature was my great love. D do you think that your background which is uh in some respects very, I suppose, atypical for someone who ends up

Uh in tech. D do you feel that, say, literature has provided you with with Some type of advantage or context or perspective or other aspects of your

really assisting you with the uh both operating in the tech world and investing in the tech world. Do you do you feel like those things have been uh in any way an advantage. I 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 were

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 um

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 th 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.

Coming from the Uh interrupted. uh climbing expedition as you did six months or so after landing in San Francisco then being encouraged

Very uh sounds like very gently and uh understand understandingly by your sister to to go consider getting a job. What did the what did the subsequent Twelve 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 a kind of a a funny Terminology. Um it was very early stages and so I had to teach myself HTML, I had to figure out how to design for the internet.

Experimental DIY self education. Um at the time getting getting involved in that at that very early stage. It was just 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. And where did uh Yeah. Where did and when did

flicker sort of enter the scene. Or the Um the embryonic stages. Uh of Flicker. 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. We Um Everybody calls it pivoting these days, but it was it was a pivot. And

came out of a a an unsuccessful game. It was also built during The lull after the dot com boom, there was the dot com bust in two thousand, two thousand one, two thousand two 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 Flicker was a kind of a Hail Mary. that we were able to turn into a a very successful business and then led into

The whole web two point oh 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 if we look at Flicker as a successful Hail Mary, uh and we s s survey the landscape of Hail Marys in the entrepreneurial world. A lot of them don't work out. And a lot of these Hail Marys don't work out. These sort of kinda death knell last gasps for breath as funding is running out.

uh o often those do not work out, but some do. And There are some examples of of these these pivots, whether it's Twitter or Flickr or others that that did work out the Can you

Perhaps the ingredients were that made it uh successful. Pivot. Slash Hale Mary. Is there particular

Uh anything at all that Uh That you that you might attribute the success to? You know, it's funny because there's

A conversation I once had with another um 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 um When I was When I was um you know, kind of in the valley I saw several examples of this. I was um

I was dating Ev Williams, um the the Twitter founder at the time. Um And When It was a ki it was an amazing thing to see, actually, because

Eve. Eve Completely run out of cash. You know, this is the story of startups everywhere. You're it's a race against the bank account, really. Um

And Had nothing. left when he was starting blogger. But he just kept on going. It was it was a miracle. It was 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 Right, 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 liv living on, you know Cup noodles. And um 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. Yeah.

And then a and then a c a miracle happened. What happened was we had submitted an application to the Canadian government Flickr was started in Vancouver, Canada. And Um

We had been rejected actually for this for this funding. Um 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 Um all of that money Had Had um been spent.

I remember this, it was it was December twenty third, it was two days before Christmas, a letter arrived Saying congratulations. um we're giving you this grant, this startup grant. And It 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 and so this came out of nowhere and that was what enabled Flicker to get off the ground.

That's so wild. Yeah. It was it was you know. And we were I mean it was a it was a super scrappy operation. This is days before like AWS and we just didn't have a lot of cash and Literally the

The servers were in a co-location center, and we literally had the phone number of the woman 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 Plugin Uh

new server at the co location center. And Load up the software and keep going. It was just it was a super Sketchy. Uh

foundation on which all of this stuff was built. uh some luck involved uh with the checking of this box. But there were I would imagine also some some good and probably some bad decisions that were made, but uh probably some good decisions that were made That in retrospect. uh contributed to what Flickr then became

Uh I was I was wondering if if maybe we could explore one that I have just here uh under the sort of exploratory Bullets which Talks about You and I think it's George Oates. Spending.

Uh Is that is that is that true? Is that something you guys did sort of manually greeting everyone who came to the site in uh in an effort to build community, or what was the the rationale behind that, if that's true?

Yeah, I mean I think that's Um To some degree true. We had I remember I looked back In the first three months of Flicker. The team

Each had posted something like fifty posts a day in the forums and 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 Um If you read the Bible, there's um you know Abraham begat

you know, so and so begets so and so begets 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 I think the community even now, um, you know, it's been acquired by Smug Mug, 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 that How how many companies that later become very or viewed as very large, like Air B and B in the in the beginning. I mean this also s uh reminds me of this uh

Whether it's you know Brian or or or Joe Debbie, who I 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 s it seems

is sometimes missed by entrepreneurs who start something and beginning on day one want to scale it to a million users or ten million users or however many million users. Um Are there any other decisions or behaviors, best practices that you had In those early days that you think were were critically important.

Or or or mistakes, either one. Yeah, I mean uh 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 um and and one of the things you mentioned earlier, which I think is actually very important. Is that We were extraordinarily lucky.

We had We had invented this at exactly the right time. And what had happened was all of these things were converging at the same time. Um Friendster had come out and had gotten people accustomed to the idea of having a profile of themselves online. And

Um More than half. 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 information. And Bill Gross, who started Idea Lab and has

been the progenitor of I don't know, five hundred companies, many, many companies. He looked at the success of What you know, those businesses. You know, 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 start up 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 ten years before or ten years after, even five years before or five years after it wouldn't have had the same momentum

as it does now and I look at This as an investor now with S V C My my investment firm And we're always looking for companies

that have timed it just right, that have Found it. Found a parade and gotten in front of it that have 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, um, there's something that people believe very strongly in, there's a change that society wants.

It makes it so much easier to people are more inclined to want the product or the service. They're more inclined to talk about it. It's starting It's it's already in a in a in a flow that's moving forward.

How do you um well actually maybe we can look at this in a in a specific example. So let's take And and this may not be an example of this, but it i it could be. Uh if we look at Kickstarter, uh so you 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 it was it was not Um built yet. And Perry and Yancy and um it was it was actually brought to me by um Sonny Bates, who I think remains on the board now. Um

It was so clear. But that Had to happen. And

It was It was something that you sort of felt in the culture. Something that you felt around Um conversations that were happening.

Online. And this was a possibility. That Um needed to bear fruit. It was it was it was very 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 Um Person to person community oriented place.

I've travelled in, for example, in I travelled in Syria. Um and went to those soux. the big marketplaces in Aleppo. Which have now been destroyed. Tragically. Um

And all of the that was kind of the w one of the most ancient marketplaces. in the world people would it was like a caravansery people would bring their camels and you know kind of in medieval times and and form a market There. 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 those 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. And what did you what and what did you see that other people didn't see or what enabled you

To see. what you saw that got you to yes with say Kickstarter uh or Etsy or or other examples that that might come to mind because a lot of these companies that are name brand Now. uh faced a lot of rejection and a lot of no's and people didn't get it.

Even uh including people that uh uh most folks would consider Quite smart. Uh that's true for you know Airbnb Uber was turned down by hundreds of people on Angel List when it went out. Uh and Uh what what did you s what did you see that other people

Missed. Uh or did you uh did you have That could be in the in the in the companies themselves or in the founders or anything else, but what what did you see that that got you to yes? Because I I because I'm sorry to sorry to interrupt myself and you, but the because a lot of founders will come in and they'll all they'll

uh a v a very high percentage will claim that they've found that parade, right? That they're in front of these three converging trends that are inevitably going to sweep the world. Uh So how do you Yeah, how do you how do you end up picking 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 was 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 Um 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? Um and 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

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 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 your deals don't look like anybody else's deals. Your deals look very different. Um the people that your

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 th they've 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 S V C and we wanted to um start a brand new firm. was because we saw that there is a sea change happening in technology and that people that were non typical, people that didn't fit the s the typical pattern of an of an entrepreneur as defined by The valley culture

We're now Liberated. From a lot of prejudices that they've been working against before and If there had been an investor in two thousand and four when I was raising money, um For Flicker.

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 Uh. Of 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 were started, it was actually much harder. To find people who understood those business models.

Those founders. And their orientation. a typical and you as a typical investor for a second, because I uh th this is part of the reason I was so excited to talk.

And Uh I'd love to chat. About a bit more about a few things you mentioned. So 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 gonna 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 Uh Developing a

bit a better perspective or a different lens on culture, society, people and changes. Um that end up getting in some ways represented by these fantastic opportunities like Kickstarter. Or Etsy. Uh I've read in the doing homework for this interview that you've recommended

uh for entrepreneurs books like The Innovator's Dilemma. But I also read on your site, Katerina dot net. Uh a Paragraph you I think you'll recognize this. This is from uh two thousand eighteen. But uh comment on Stuart Brand's work and uh 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 in 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 the ephemeral nature of all the time spent on computers and in online media. So uh I'm I'm curious if say sp 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 C S or prototypical Uh

Silicon Valley background if they wanted to develop some of the perspective that you have. Are there any resources or books or or ways that you would suggest people explore? I love that you brought this up, Tim, because Part of 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. Your books are the four hour

What 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 thirty five thousand foot view.

Time is all we've got. And I have been A Mm time management is possibly the thing that I've done most in my life in terms of

Um Uh generating the kind of life that I have wanted to lead. And that comes from I mean it it went way back. Um back to when I was young and um

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. I actually failed a photography class because it was at eight AM. I there's just no way. I just 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. Whether or not it happens at eight AM or if it happens at ten PM.

And I actually gave a an interview with Business Week once about my peculiar schedule in that I wake up in the middle of the night between two Three hours of work. I don't turn on the computer I um I write everything on on paper. I do my best thinking.

And writing and Um 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 it's a magical it's a magical time. So I've so many questions. This is great. This is great. So I uh so I was gonna ask you about this waking up between two and five AM. I didn't realize that you went back to sleep. So this Yeah, I've been reading up uh I'll explain why maybe another time, but on the history of lucid dreaming. And uh tr it appears that uh biphasic sleeping where people would kinda wake up and have 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 a an example of what you might work on on paper in those three hours. So you wake up at some point between two and five AM Specifically, what do you then do? Is it something that you've already planted Uh the top of a piece of paper as a prompt and you know you're gonna work on a specific problem, is it like longhand

stream of consciousness, what do you do during those handful of hours? I have done It it really depends. Sometimes I wake up and I I um I I've always written books, so I have I've been working on a book now. Um for the past three months.

A new book. Um 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. Um Any kind of big picture thinking, any kind of thinking that involves creativity Intuition

Um All of that. The the kind of the The right brain and not the left brain. And I've studied all of these people. I've I I come across these articles. There was an article that was recently sent to me

That was about this um Actually forget his name, but he was an AI guru. I think he's from Cambridge. And the thing that I d I I I 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 the 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 I D eight It's so precious.

And should be defended. ferociously. At all costs. And I've always felt that way. I've always had this this very um I 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 a hundred and eight different kinds of toothpaste.

Right and 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, which which 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 our society today you need to pick You know. your podcast and hopefully my podcast and eliminate all the others. If you see what I'm saying, you have to 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 to defend our

Our space our happiness And our individual lives. I was I was looking at your site. Uh

earlier today and uh found a an example Of Removing. Noise.

And it was a simple example, but um might be a jumping off point for exploring other examples. This is a D F tube. That is distraction free tube, which is a plug in that you use to clean up YouTube. It removes the recommendations on the sidebar, the crap on the homepage, inane 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 in. I mean the the the waking up sort of in the witching hour and And working for a few hours without a screen is Uh I think a great example. Are there Then you have the very tactical kind of micro tool like something like this extension. Are there 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 that I think are are great.

And During the periods in which I think I'm most most flourish and most productive, what I'm doing is I'm going online. I did this f I did this for As long as I can and I I I fall out of Yeah. occasionally but I always try to get back is

I would schedule a time to do my email in the morning. Ten. ten thirty to twelve or something like this. And then again in the evening. Four thirty to six. 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 and things that we need to do online. But To be super disciplined about the time that you spend online I think is is really important. And I've always done this and I have a a kind of a A a notebook that I keep

Нексто май комп'ютер And it says W N O on the cover, which says When next, which stands for when next online. 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

Um this misinformation on this Wikipedia page. Whatever the thing is that you y 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 Um, unboxing videos on YouTube. Right?

And you're and you're like and you're like, what happened? Where did you know, where did where did it go? And so I think that you need to just get on top of that. I think that's a like one really important thing that you can that you can do. This is 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 an it can be And

Realize also that it's a It's That kind of activity that's That's taking you away. From a life fully lived.

Um I remember reading an article on Quora. Where somebody said I wanna be an entrepreneur, a successful As Steve Jobs and Elon Musk.

How do I do that? Right. Which I thought which I thought was kinda was, you know, kinda you know, many people would like to know the answer to that question. Um and one of the respondents was Justine Musk. Elon Musk's ex ex wife. And one of the things that she re I thought this was this is funny. Wonderful, right? Because like she knows firsthand actually what it takes to become or to be Elon Musk. And um 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 is building Tesla. was off doing that and not Wondering how. If you see what I'm saying.

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.

Um because I think it's true. You can spend a lot of time in preparation, and I think that's good. To an extent and to a degree. But really

Really living it. Really being in it. I think is the most important thing. Yeah. It's uh Yeah, but I always uh

have to reel myself in in a sense because uh I love reading and reading is a very socially acceptable form of procrastinating. So I I uh I I don't do it as much online, although I'm certainly guilty of that at times, but uh the Or Kathy Sierra. uh long time ago said to me, uh or she might have been in a presentation she gave, but I was sitting in the audience, uh, about focusing on just in time information, not just in case information. And that really struck with me, uh stuck with me, excuse me. Uh

'cause I have a tendency to s tr try to stockpile information in case of Um the one percent 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. Uh let me ask you about poetry. So you mentioned that sometimes you write poetry. And um 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 I read

And Something that somebody had written. Let me let me try to figure out who it was. I can't remember. It was it was something that I read just the other day that was 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 Ви ось, вирм, орц. Was vanishing because it was being filled up constantly with Stimulation, entertainment.

And um our compulsion to to be online and and and 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. um 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. You're it's just It's just terrible how much

FOMO Is created by The internet. It's it's it's endless. And you know, 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 possibilists. We're people who believe in You know

Living life to the fullest. And The internet. you know, kind of both cultivates that And

makes those opportunities available to more and more people, hopefully. And Um 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. Um 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.

Um I think my kind of very anti authoritarian nature is also one of the things that led me to becoming an an entrepreneur. And I rebelled against these these structures and one of the very earliest Um

uh instances of this was in first grade when all of the other kids were were learning to read and I already knew how to read. And I was Um becoming a very uh the trouble in the classroom for the teacher because I was like impatient and I I wanted to read and

So I went to the library And I sat and I read poetry with the librarian. I remember this. I was I was uh I was only like five or six years old and um I still remember some of those poems.

And they were just they're like kind of rhymes. Um Here's here's one I remember. Once there was an elephant. Who tried to use the telephant.

Oh no, I mean the Elophone 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 telefunk. The more he tried to get it free, the The louder buzzed the telefi. I fear I better drop the song.

of Elifop and Telephone. It sounds 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 I have this crazy memory and I I have 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 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. Um, from a very young age. And so I started memorizing

Poetry. Um As a bit of an eccentric teenager. Um, and I have I have a lot of that. Love of of poetry, but it it's deep inside.

And I can recover a lot of this poetry. at times when it's when it's needed. When you're going through some kind of crisis or difficult times or Um you know, depression or like some kind of bad state you f you find yourself in, suddenly

Сам урикол. 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. For Those people listening who Uh like me. Have

minimal exposure to poetry. Or at some point were introduced to the wrong poetry, which was just completely confusing and seemingly designed to remain abstract and obscure and confusing. I w is are there any poets? Or uh collections you might recommend people start with if they wanted to dip their toe in the water.

Of poetry. I honestly think that there's no one poet for everybody, and that the best way to start is to just go to Um Po I think it's poetry dot org. It's it's just wonderful.

Wonderful font of poetry and just start digging around and find what you love. I mean you mentioned some of the ones that I love. I love Wallace Stevens, I love Emily Dickinson, I love Shakespeare. Um I wrote my thesis

In college on James Merrill. Um I love WH Auden. It just goes on and on. Um

We could talk for hours about we could talk for hours we could talk for hours about this, but It's It's It's important that we do this. I'm gonna

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 a

You know, his his an amazing He's 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 technic. We live in

A world of um kind of mechanistic being and thought and Science. And All of those

Passions. That Throughout he throughout you know, since time memorial have sustained humanity. are getting lost somehow or they're they're they're slipping away or they're

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. is uh remains just for you. And how much of it do you show to other people?

I would say a hundred percent of it is remains just for me. I haven't it's interesting because many people have asked me this over over the years because I've actually written 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 I in in some ways I have a very strong tendency And desire to be successful in the world and I worry that it will be go out into the world and will be subject to the same Laws.

As have led to my success in business. Which It's a very different thing. And so it's funny because I I I f I find it everyone's like, Oh my gosh, this is great, you should publish this. when it's encountered. And and I'm kind of like, well, maybe.

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 I um you know, I run t into after the after the first after my first book, uh 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. It's Uh I think it's very smart to keep that for yourself.

Uh and and you talked about very deliberately building these things into your life and you also mentioned a name And uh Um Pr I might be pronouncing this correctly, but W H Ouden, am I getting that right? Yeah. Uh and there's a quote. uh of Auden's that I I pulled up because I could only remember the first line. But I'd I'd love to talk a little bit about your routines. And the quote goes as follows Routine in an intelligent man is

is a sign of ambition. Of course this applies to everybody, but routine and 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. Uh I've read that you very often will eat the same entree at certain restaurants. If you decide you like something, are are there Are there routines That are particular

Particularly important to you aside from those that we've already Discussed anything that you make sure you do And 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 uh in structuring. Your life and y and your time. That you can uh that you can think of. I have a

I have a very idiosyncratic schedule. And The The reason for that is that I have You know, like you say.

I I I find I find the thing in the restaurant that I like and I always Order order it. Um 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. And so, you know, famously Albert Einstein had one suit. Of which she had five different versions or something like this. Um he didn't have to think about what he's gonna wear in the morning. he, you know, ate the same food. Like I kinda feel as if these these patterns if you figure out what it is that you're happy No longer making

the decisions about I mean this is kinda one of the one of the principles behind public goods you know, 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've got a default, and so building these defaults into your life. Are super important.

Thing 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, or the arrow of the wolf or whatever you call that. And when I'm I'm 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 Um you know

kind of revelations. That are just not possible if you're kinda crowded into kinda tiny decisions all the time. And uh wha what is your Uh

Well actually let me take take a step back. So you mentioned in passing something when we were discussing poetry and how certain poems or phrases would come to mind at at seemingly the the the perfect moment when you need it the most. Yeah. Uh

Yeah. And H 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 um

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, um, reluctant to expose myself to the world because I felt very vulnerable Um

And needed to basically hide in my cave. And I think that you know, many of us go through these. I mean, it's a I think it's kind of just common to to the human experience that this be A Um

a state and that and I honestly think there's there's a reason for it, right? I d I just I just like the the term depression. Because I think a lot of it is more It's better described as um melancholy or despair, or there's all older words that describe it. It just seems so clinical to to talk about it in in in the terms of depression.

Um Because I think that it's part of a a a fully lived life. To go through these periods of of um deep unhappiness and dissatisfaction and questioning and

uh despair even Um And that Without that, you kind of if you live always on the sunny side of life. I talk about this in in kind of the Jungian sense of

Of the shadow, right? You ca 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 um 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

Um, triumphs. And not their doubts. And basically providing a highlights real of their life and this is very damaging to 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 You know, mistakes.

Um I see it all around and you know, you you see it all around, right? You kind of look at all of your Happy successful friends On Facebook or Instagram or where have you Um

You know, they're always Going fabulous places and doing fabulous things, but what about The shadow. Right? Like what about the shadow? Um there's this really wonderful essay which I encourage everybody to read by the science fiction writer Ursula Le Guin. about the shadow. I 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 ha I 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 Uh a a

dangerously deep or extended state of despair. Like a pit of despair. Yeah. Well I mean I honestly it 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. Mm. Because We have this idea of other people.

As being more you know, rich, successful, beautiful, happy Um they're in a better relationship. They're you know, they have better teeth. Yeah. Their hair.

you know, they've thicker hair. I don't know what the thing is, right? Like some some insecurity that we have, we see in others As As Something that we don't Don't have.

And There's a wonderful um sonnet by Shakespeare. on this subject. I think it's Sonnet what is it? Um It's Sonnet twenty nine by by Shakespeare. When in disgrace with fortune in men's eyes

I all alone beweep my outcast state. And trouble deaf 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 the 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 and I think what it speaks to is the the kind of the envy.

You know, wishing me like one more rich in hope. you know, 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 it it it it You know, happily I think on thee.

Right? And Often this is read as a a love poem. as a a you know kind of a celebration of the relationship that Shakespeare is presumably in when he's writing all of these

On all these sonnets, but when you really think about it. Um 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 kinda 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 Kinda does to me, and I have Um You know, I kind of feel as if if you have all of these poems and uh kind of they're deep inside you.

That They will come to you when you need them. This is uh You're making me

Making me think uh. But I I I haven't thought of it in those terms, but uh only in the last few years I've started reading Some uh very Very easy to read. Very

easily digested poetry by People like Yeah, half as And uh lot of Sufi poetry. Yeah, Rumi as well. Uh and

They do stick. They really do stick. And they seem to have a particular Stickiness. uh greater stickiness than Perhaps more clinical. Nonfiction.

Right. Something that is really artfully woven into beautiful language just has a higher stikiness factor because these poems do come to mind. Uh At the right time.

Just never thought of it. Uh do you Or have you found anything else useful for embracing the shadow but not falling into a a pit of despair or or if you've or 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 uh 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 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

These parts of ourselves that are so Troubled or you know, despairing or unhappy. Or Failing or unsuccessful.

And that we always feel as if we've got it. Present. our best face to the world. And and 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 Um 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. Lake 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 the suffering is universal. That we all

Go through these. Moments of shame, indignity, depression, unhappiness, failure. And That anybody who's pretending That

They don't. It's just not true. Um 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 c 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 I really appreciate you being willing to talk about this uh and explore it a bit because

It is a constant, like you said, and it c and it's uh it's come up so many times in this podcast, whether it's with these brutal stories of rejection that Bret and Stan of Humans of New York is is telling or any number of you know uh hundreds of examples that have come up. It's uh Like you said, it's a it's an illusion and a and a really

Crippling. Um 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. Uh so I I appreciate you.

Being willing to To chat about this. And Uh Maybe we can we can thematically continue on the shadow side for just a a few more minutes and then we'll we'll shift gears. But

Uh I You have an incredible memory. you have an incredible track record. I think a lot of people uh 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

Uh The the profile a bit. Uh 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. I mean if you if you don't like the word failure, you could use something else. Um but Yeah. I mean I It's

It's perpetual. It's hard to single out. A single failure. When looking at the Um you know, y you kinda you kinda 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 uh working towards some kind of failed project or

Some kind of trap that you fell into and You know, it was a it was a struggle to free yourself. Um It's funny because I think that my orientation As a perpetual optimist

leaves me with a a kind of a sense of um 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 Um 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. Um They are very important. You go back to them.

And Um, those moments when you're at your worst at your weakest at your least successful at your Kind of most alone. Um And

Look back at the path that you took out of them. And the ability to emerge from them and to kinda 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 and if you're never tested and you're never

In that kind of situation Yeah, God help you. I mean it's not a it's not a good state. Right. It it's it 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

Um Highs and lows like that and and 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. Two.

uh your talk of optimism. Are there any Any books? Any I know this is kind of a a ru uh the the the type of question that won't die for me, but uh are there any tools, habits, books, anything that you would recommend to people who want to cultivate a more Constant.

Optimism. if if if they might have been just beaten into cynicism by spending too much time on the internet or what what 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. Um Oh. Go long form, not short form. Go deep. Right, and not broad.

I think that this is actually a a really important thing and uh you know, there's a dozen books and maybe we can I I 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 write you like oh my gosh, a list of Yeah, a dozen or more books that have helped me throughout my life. Um Oh, for sure. I a hundred percent yes and yes. Uh if if you can mention any of them now, you don't have to mention all of them, but uh I mean any that really come to mind right now, I'd love to that was that was gonna 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. Um, 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.

Um 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 Cylon, Shakespeare, of course. And

Um you know, contemporary poets. There's like wonderful poets out there that I look forward to their work. Um Natalie Shapiro. Brenda Shaughnessy Uh, the list goes on. I can I can put together a list for you.

Um of poets that I I love and respect. I love also the ones that you're talking about, Hafez Roomy. Khalil Jibran, like there's a lot of a lot of really wonderful Um poets from the east.

Mm-hmm. They're Attention from us. Yeah. A are there any other

Whether it's fiction or non fiction long reads. that uh that you would recommend and and for people listening, I'll definitely put all of these in the in the show notes. Uh so you'll be able to access all of these, but If any others. Yeah.

Jorge Luis Borges is just incredible in terms of the the wordsmithing. And uh Art. of his prose is really staggering. So I definitely second that. I'm going to bring up

I use good reads. And goodreads dot com is actually a really great place. Um, for people looking to discover new books. It's actually now owned by Amazon. And Um I put all of the books that I've read there.

Because Um I read a lot. I I You know, I I read at least a book a week. And um I'm re reading currently The Odyssey by Homer in a new translation by Emily Wilson. Other books that I have

Um, found to be Really great. that I've read in the past year are Really wonderful book, uh Tomb for Boris Davidovich by Danilo Kiss. Um

Hannah versus the Tree by Leland de la Durante. Ethan Frome by Edith Wharton. I mean I I I'm honestly I'm just kind of going through this because I have this massive list. The white goddess. Which is a very meaningful book. By

Robert Graves. Which is about poetry. And its sources I've re read the Upanishads. There is a tremendous Um, there's this writer who I just adore.

W. G Sabald? I don't know if you're familiar with Ken. I'm not But um The emigrants by him is just an amazing

Amazing book. Um Yeah. I could go on and on. What what what books if uh they they could be from that list or otherwise have you gift the most to other people if you gift books?

There's a s there's a couple w 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 Uh Um the artist Louise Bourgeois. Which is fantastic and I've given that to so many people. As well as

But the principles of uncertainty Bye. Myra Coleman. Uh she's famously an illustrator. Um

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 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, um, kind of basically letters that have been collected throughout the ages. Wonderful letters. I've been meaning to grab that uh that compendium. So I'm really glad that you just mentioned that. Mm.

Check and check to add to my ever growing reading list. Uh see so you you were just mentioning sort of rich rich lives and we're and we were discussing or you were mentioning earlier the paradox of choice that many of us face, uh, and certainly you have more opportunities than you could possibly ever Take advantage of in

sort of sum total. Why decide to do A podcast. Uh what what was the The catalyst or the the the reasoning behind that.

Why why why should this exist? Why is why would you you you have s finite time, why apply it to that? Well I think that there's a super important conversation going on in technology right now in in the culture in which we live. That That needs to be had.

Um I was on Um, my friend um Reed Hoffman's Podcast Masters of Skill.

And I loved that experience. I love podcasts just in general, but this one was very Um gratifying for me because I had done what I thought of as a fairly garden variety interview with Reed.

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 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 come going back to the theme of, you know, 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 emerge, 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 Builds.

A future That we're deliberately building And not lead us into unintended consequences. That we've seen happen over and over again. most recently in the story of technology.

Can can you describe uh one of The episodes. That

Is is featured. Of a sample episode. look like and what is what what type of technologies or topics or entrepreneurs are you discussing?

So what we do is we find an entreprene who's building a new interesting technology. And some of the interesting things have to do with AI or CRISPR or, you know, gene editing and um neuroscientific in uh kind of uh supplements to help us learn faster. Um you know technologies which are in development where there's entrepreneurs who 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. Well 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. But Should this exist. Do you think there are uh

Safeguards or externally enforced constraints or regulations of any type that Could or should we steer technology development and company formation or are we dependent on the internal

ethics and moral compasses of of the people who are Developing. It's uh a false dichotomy. You could have both, but uh I'm I'm curious how how you think how how you think about that.

I do think That we have in Silicon Valley enjoyed incredible latitude. And have been Um Basic

Assuming that we have these The ability to self regulate. I don't think that anybody starts off This idea of

being the super villain. Right. I like here like I'm a kind of a bond villain in my mountain hideaway. I'm going to bring about the destruction of the earth. I I nobody starts out that way. I think that we all start out out with um And as Baudelaire has said in one of his many beautiful poems, We

Descend to hell. By short steps. And We end up Um, loving what we hate and hating what we love, we end up doing things that we don't intend.

And um That the constant questioning, the constant vigilance, the practice of asking ourselves the 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 and um

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. Mm-hmm.

Well I'm I'm very much looking forward. Two hearing these episodes and Also seeing how the conversations develop over time, right? Because it's uh I I

I I think it's an important conversation and of an increasingly important set of questions and maybe just a lens through which to look at building. And uh I'm particularly interested in your CRISPR episode. Uh maybe you could could you could you just describe for a moment what for people who don't recognize. the term what what Crisp CRISPR is or what it represents. Um

Well, Crisper is In short, it's gene editing. It's the ability to change people's you know, genes, DNA. And and this has Incredible possibility and Frankenstein like

potential. So 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 any form of life. You name it. Yeah, virus, bacteria, you name it. You name it. Introducing basically the human touch into it. You know, kind of assuming

You know, what what in prior eras, um and in current eras are actually thought of as the hand of God. And putting that in human hands. And this kind of Promethean Uh impulse. That people have to seize

the power, like you know, kind of Prometheus 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

Um Nonfiction. About what happens when We enter the Anthropocene, right? We ent enter the The the era of of humankind

Manipulating the world. In a way that is potentially leading us to Confluor Gration. And the end.

And You know, some say the world will end in fire, some say in ice, right? This is kind of the wonderful Pombay. Robert Frost. I mean you know, we will 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 Brand, who you mentioned earlier. He was one of the progenitors of the whole earth catalogue and in it he said, We are as gods and might as well get good at it.

Yeah. I have I have a copy of the updated Last Whole Earth catalog which is given to me as a Christmas present by my mom, uh about ten feet from my right side right now. It's uh An incredible incredible book and a very very good statement.

Um On Brand's part. I mean it's it's really mind boggling to think about the the promise and the perils of many of these technologies. And like famously, you know, Stuart Brand is now working on bringing extinct life forms back to life, you know, kind of bringing bringing back the saber tooth tiger and the woolly mammoth. Um, is that and that and that kind of awakens possibility and dreams and excitement.

In the sense of you know Wow. wonder like the the wonder of technology and the wonder of science, right? And then also Terror.

And fear. Yeah. Yeah. Well, exciting 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 c you know commentators. Uh

Let me ask one more question. Uh it's it's uh sometimes one that's tough to answer, but I'll ask it and then we'll 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. Uh anything non commercial.

But uh In the 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 the the kind of the the basic truths as being a fairly straightforward Frankly, kind of boring statements. Right? You know, um You know You should brush your teeth regularly.

You should Not let not let the grass grow on the path to your friend's door. You should be kind to one another. They they sound like platitudes. When you When you when you say them

When you see them on billboards. And yet They are profoundly true. So Frankly, nothing excitement exciting.

Um Mainly Uh be kind. Yeah, I think Yeah it's it's a

Two very important words. And I think that uh they may be sort of inversely your your capacity for being kind may be inversely proportionate to the amount of time you spend on the Internet getting Sort of poked in the brain. Bye.

Yeah. Uh sort of really Short form. drivel uh that is just uh Uh

weaponized and commercialized, um which which comes back to the long form recommendations and the poetry and all these other things. I um Really? Enjoy Uh

having a chance to chat with you like this in long form. Uh And uh I thank you for taking the time To have the conversation.

Yeah. So thank you very much. Yeah, no, this has been a great conversation. Thank you so much for inviting me. And uh People can find you on Twitter at Katarina C A T E R I N A. uh find the podcast shouldthis exist dot com or on Apple Podcasts and anywhere else podcasts might be found. Katerina dot net.

uh your writing including the social peacocking in the shadow and the other Posts that have come up in this episode. Uh For people listening, of course I'll add links to everything, including the books. That uh Caterine, I would love for you to to send. to send me and I'll put them in the show notes. I'll put those at Tim.blog forward slash podcast and you can just search

Catarina or fake. Pop right up. Say any Parting comments, things you'd like to suggest to people listening, ask of them, anything at all you'd like to 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

You know, listen, respond, subscribe. That's a that's a a kind of big thing and engage in that conversation. Great. Well we'll Send plenty of people. That direction.

And uh Once again, really appreciate you uh making the time. to have this conversation. I've I've really, really enjoyed it. So hopefully Uh we'll have a chance to to break bread or have coffee in person at some point. And uh 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 gonna put into the show notes that Katerina has recommended. And until next time, thank you. for listening. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet 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 before the weekend? And Five Bullet Friday is a very short email where I share

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