#800: Ev Williams — The Art of Pivoting (e.g., Odeo to Twitter), Strategic Quitting, The Dangers of Premature Scaling, Must-Read Books, and More

26:18Where'd you get that list? That is New York Times. EvWilliamsFavoriteBooks.html Yeah, I probably wouldn't pick those now. It's been a while. I'm not an executive anymore, so I mean, that's not as useful. Zen The Art of Martyrs of Cyclemanes is great, but I will mention one book very related to the conversation, which is, have you read Why Greatness Cannot Be Planned. No. Great title, though. Why Greatness Cannot Be Planned. I recommend this to 100 people. Love this book. The subtitle is The Myth of the Objective. And the premise is by a guy named Ken Stanley, another guy who were AI researchers.

27:03And the way it starts out is they, this is early AI researchers. Ken, when worked at OpenAI later, they were building bots. And the example they talk about is trying to build a robot to go through a maze. And how they've tried to program all kinds of smart algorithms into it. And then they found that the most effective strategy was just try something new. And they go on from that and extrapolate this idea that if you are trying to do something that hasn't been done before, You know, we're taught from birth and from school and everywhere is like, set your goal, make a plan to get to the plan, persevere, go through that.

27:44And the premise of the book is that works if it's something that's been done a lot and that's formulaic. You can set a goal to run a marathon and you can, you know, download a training regime and you can go run the marathon. You can't do that to invent the computer or Twitter or create amazing art. You can't plot it. And to the extent you try to plot it, you shoot yourself in the foot because you cut off the possibilities that lay before you. And I read this book when I was running media in my last company. It had a great effect on me because I felt this deep sense of relief because my entire business and startup career, I've been deeply driven to create things.

28:29I saw companies and particular products as a creative process. It's like writing a book or painting a painting. You have to figure it out as you go. You don't have it fully baked in your head from day one. But what I've seen happen a million times and it happened to me is you have this intuition. You kind of know what it is. You start to develop it. You're like, oh, it's this, not that. let's trade this, not that, and you feel your way into what's the best first version of it, if you're lucky and good enough that that first version, you know, meets with some success in the world, then at least in the tech world, employees and investors and business people come in and it's like, okay, where are we going next?

29:13What's the plan? What's the roadmap? You know, how are we going to make the numbers go up? And it doesn't work to very far. It works like a little bit to get that next stage but it doesn't work to really innovate it doesn't work and so you have to be comfortable with the ambiguity of not knowing where you're going to go and this book is is good and it makes its points very short it also talks about evolution a lot and how like the most creative force in the world is clearly nature and like it has no plan it just tries shit Trial and error. Yeah. All right. Taking notes. That's going to be one of my next reads.

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31:23You mentioned AI, and it is the topic du jour, but I can't believe everything you read on the internet, but I believe that 25 % of the latest Y Combinator class wrote 95 % plus of their code using AI. And I'm curious, you have kids, what would you suggest your kids study in school? My kids are here, in fact. Whatever they want. I mean, it depends on what the goal is. I can frame it a little more. I can strain it. I would say if people are wondering here how to... I don't want to say AI-proof themselves because good luck predicting where that's going to go, but are there any fundamental skills or specific skills that you think will increase in value over time?

32:16For instance, I don't know if I had kids if I would suggest they take a legal path necessarily since I already use AI in 30 seconds to draft most of my legal documents before I send it to human eyes. Do you have any thoughts? I haven't thought about this deeply, but what comes to mind is social, human things. Two things. One is I do encourage them to read and write still because I think that's how you figure things out. That's like the best way to think and have ideas and get clarity is to write. And you can't write if you don't read. So even if the AI can write for you, That's fine if it's a paper or, you know, a report or some analysis where the product is very important.

33:06Like, this is the information and text that I need. But it robs you of the process of thinking. So I think problem-solving, creative ideation is useful no matter what you do ever. So I think those core skills and then social skills. One of the reasons I love the school they go to is actually they have a thing called SEL, which maybe you all had, but I sure as hell didn't have in rural Nebraska in the 70s, is social emotional learning. And that's just like, how do you connect with people? I mean, we know that's critical to any job, no matter what you're doing. And I think that's probably, well, hopefully not going to go away.

33:42Who knows? I think we're in a lot of trouble if that gets removed from you in life. So let's shift gears a bit. And I'll just ask a question I like to ask. If it goes nowhere, it goes nowhere. But, all right, so metaphorically speaking, the billboard question. So if you were going to put a message on a billboard, could say anything, could be an image, anything at all that you would want a lot of people to see and understand, what might you put on that? I love this question. I might overthink it.

34:21And understand. so we can assume though the and understand I threw on there with a little creative flourish it may complicate your thinking I'm going to build on that and thinking about this what comes to mind first of all is the category is something that will help people heal just be their whole and true selves because I think that's where all our problems come from is the lack of that and as much as I care about climate I think that the key to solving climate is to heal ourselves, to heal culture, to heal the planet. And so I start with the self. And then my mind goes to, well, what's a big fundamental truth that we want everyone, let's pretend if they read it, they'll actually get it and know it.

35:07Then I think there's a little bit of tension between like the most fundamental truths and how actionable they are. So if we said, we are all one, which I believe, it's like, okay, we're all one. The universe is one big thing. We're all connected. What do I do with that? I mean, maybe if you really ponder that and meditate on that a long time, it'll actually, it will do you some good. But then if you move toward the spectrum of usefulness, of what's a fundamental truth that's more useful, you might some you know have like some buddhist or saying like all of our suffering comes from you know our thoughts or inability to accept reality which is a little bit more useful but maybe for the masses not still not very actionable and then you could move to like feel your feelings which i think would do a tremendous amount of good if people adopt oh feel your feelings a little bit easier to imagine that like so much of our suffering i say this as someone who told their first therapist, I don't understand the point of feelings.

36:07I was like, they are just a nuisance and get in the way. So it took me a long time to appreciate that and the avoidance that so many of us go through. And then one step further might be stop drinking alcohol for six months and see how you feel.

36:28Not tonight, though. It's fine. We're in a bar. Not tonight. Nice. Starting tomorrow. Sorry, tomorrow. So following up just on the feeling your feelings, you said for a long time, and you said this to your first therapist, right? They're just a nuisance. I'd like to know how to rid myself of these irritations. What changed? How did you end up going on to team feelings? So, I mean, it was a long, long process. I mean, the therapy helped. The psychedelics helped. Meditation, growth, learning, reading books, having friends, stopping drinking, actually just for six months and I've gone through a lot I've done a lot of work particularly in the last couple years that's been super super important just a note on alcohol look I'm going to have some drinks tonight I do enjoy drinking but just a PSA for people because ketamine is in the air ketamine is probably in a few people's pockets here they're both dissociative anesthetics so if you want to feel your feelings, it's a good idea not to engage with those things excessively.

37:35And if you have a history of alcohol overuse, I would also stay away from any at-home ketamine. But in terms of books or types of therapy, did you find if there are people in the audience who are like, yeah, you know what, actually that makes sense to me, but I've never been able to find a handhold to get started. Is there any advice you might give? Probably the best thing I've ever done in that realm is Hoffman. Have you done Hoffman? Hoffman, I haven't done Hoffman, but quite a few of my friends have. So there's this thing called the Hoffman process. It's 20 years of therapy in a week in terms of the effect.

38:11I mean, I've got much more out of it than I ever got in therapy. It's a week-long retreat. There's a few different places. The main one's in Petaluma, California. You hand over your phone. You go and do some exercises with 36 strangers and yourself. for a week, and you'd come out a new person. So I've spoken, well, not directly, I've more listened, but had a conversation on this podcast where the Hoffman process came up, and a lot of listeners have gone to the Hoffman process, and I get letters literally every week from people who are thanking me for not really the proper credit because there's someone else who brought it up for the Hoffman process.

38:55I'm very curious, you mentioned the strangers, part of the reason I haven't gone is I'm like, I don't want to air all of my dirty laundry in front of 20 strangers. I don't know these people. And I know you're also, I think it's fair to say, pretty introverted. I would say I am, even though I'm on stage, like, safely speaking into the darkness. Was that an issue at all for you, or how did you get past that? It wasn't easy, but it's just in the context of it, it just feels very safe. One of the fascinating things is, as strangers, you are not allowed to say your last name or what you do in the real world when you get there.

39:35So you connect with people. And I realized, after a few days, I relied so much on people knowing who I was or what I did, that it was this veil between me and other humans. So you get to know people at such a deep level without really knowing any of the normal things. That we would say, you meet someone here. What do you do? where do you live? And that, it just feels incredibly safe. But the process is, they've been doing it for 50 some years. It's very evolved. It's very well done. You take any of it out of context, it sounds weird. Like I knew nothing going in. And about five people brought it up to me in random conversations over a week.

40:16And I'm like, okay, this is a message. I'm gonna go sign up for this thing. Show up. I had no idea. And then you just dive in. And it's incredible. Yeah, from what I can tell, it's somewhat like Fight Club. It's like first rule of Fight Club is don't talk about Fight Club. You're not going to find much detail on the Hoffman process. This also ties into a question I was planning on asking anyway, which is, are there any habits or beliefs that have really positively impacted your life in the last handful of years? It could also be 10 years ago, but you've talked about doing a lot of work in the last handful of years.

40:52any new habits, beliefs, tools, anything come to mind that have been really helpful? Yes, but I feel like they're the ones that everybody knows. Well, I mean, sometimes the fundamentals are worth a review. I mean, it is exercise and meditation. I dabbled in for a long time, and then I got much more serious a couple years ago about both and really, really dramatic life improvement. Why did you get more serious about them? You just wake up one day and you're like, today's a new day? Or was there a breaking point? It was early COVID. I was like, what the fuck am I doing? I'm going to turn 50 and I need to work a hell of a lot harder to be in shape than I was.

41:39So I just started doing it. I was at home. I had the time. So I did that. Although that's increased because you get the positive reward cycle and it feels great. and meditation I've always found super valuable and I just last year on January 2nd 2024 I had meditated the day before I was like I could meditate every single day this year and it was just that sort of psychological hook that you find motivating even though it's arbitrary and I was like yes I'm going to meditate every single day in 2024 that's a goal and I don't normally set goals like that But I was like, okay, let's see what happens.

42:21And my teacher says, you can't boil water if you keep turning off the flame. And so the consistency of meditation, I underestimated what dramatic difference that makes and how fast you can drop in if you do it every single day. What type of meditation did you decide on? Just mindfulness, meditation, breath, and awareness. Not TM, just... Just like an open monitoring, feel what you feel, see what you see. are you noting things or are you just observing? Sometimes noting. You like to know about products. You know about this product. But I was using The Way. You've probably talked about that before.

43:00The Way is a meditation app. I hadn't used a meditation app for years. I started using The Way. Kevin sent it to me actually when it was still in beta. And I started doing that around that time. Yeah, The Way is fantastic. Yeah, Henry Shookman. Just an incredible guy. Hope to meet him in person someday. Do you have a favorite failure or any favorite failures that come to mind? I mean, you've got a greatest hits list that's pretty outstanding. I'm just wondering. I have a lot of failures. Yeah, and anything that has either taught you a lot or in some way set you up for successes later. That's two possible ways of approaching it.

43:45We're already talking about Odeo, which is kind of a failure. that led to Twitter, so that's obvious. But a thing that took me very long time to appreciate that felt like the biggest failure possible was getting fired from Twitter, which I did. I co-founded the company. I was CEO for two years, and then I got fired to my great shock and dismay. And I was just devastated, absolutely. Now I looked and I was like, wow, I'm probably way happier today than I would have been had I not. But it took me a while. It took me a long while to appreciate that. What was the silver lining on that in retrospect?

44:29It kind of goes back to all our unhappiness comes from thinking things shouldn't be how they are because I was very upset because of the injustice of it. and what I thought was just dumb. Now, in retrospect, and even at the time, I knew I was in over my head to a certain extent, and Dick, who became the CEO, was much better at certain aspects of the job. I wasn't even that attached to being the CEO long term. I was just like, maybe we should talk about it before you fire me. That seemed rude. But, I mean, it's my company. But the silver lining, I didn't have to do the job anymore. That's one. I mean, I still owned a bunch of the company.

45:20I didn't have to do the job. I mean, objectively, it wasn't that bad. But as an identity and ego hit, it was tremendous. I also thought the best thing for the company was for me to stay, and even not in CEO role. And I tried to negotiate that, and that wasn't accepted. But it was more like, this is so wrong. It was like, okay, what can I learn from this? What is, once I was out of that, you know, some deep reflection happened and I think a long-term path of personal growth. Are there any people who come to mind who you're tracking right now or anyone you think people should pay more attention to?

46:06Innovators, technologists, thinkers, alive or dead I'll mention another book what I've been geeking out on recently is how the universe works small side project you know which I used to I used to read a lot of physics books and quantum physics just for fun and it had been a while so I started delving into that just set a bubble bath light a candle read some quantum physics there's a book i'm reading right now called the one by henry posse i don't know anything about him yes the one is about it's about how it's monism the idea that the universe is just one thing and nature and us and this glass is all one thing and that the separation is an illusion how that fits with quantum physics and and the whole history of quantum physics and how this idea had come up but rejected it was very interesting to learn how the implications of that which we've heard about with multiverse and all these crazy ideas were rejected by scientists who were materialists and it was interesting to learn that materialism in the science is basically a religion and that's fascinating so how did you find this book my partner james Joaquin at Obvious.

47:33We like to talk about how the universe works and then invest in startups. Sounds like a great job. All right. Do you tend to find books, again, just riffing on how you choose your intake, right? And there's finding the signal and then there's tuning out the noise. I mean, I haven't had any social apps on my phone for years at this point because I just don't have the control to be like the heroin addict wandering into the heroin den. But then there's choosing the signal. And I think books are still, if you can do it with a slightly longer attention span or to cultivate that, a great way of finding these, like I said earlier, scent trails to follow.

48:17But you still have a problem because there are 100 ,000 plus books published in hardcover alone in the US every year. How do you choose your books? And do any other books come to mind? I wish I had a better way. I should ask you, how many books do you read a month? Probably four or five. Okay. You read a lot more than I do. But I may read two a month. But I think it's kind of haphazard, which is scary because you're going to select a very tiny portion. Yeah, Tim Urban style, right? It's like you get time for however many books left in your life. Right, right. Great book, by the way, Tim Urban's book.

48:56It's pretty random. It's just like wandering. Like I'll buy tons of books. I read mostly on my phone, but I'll buy physical books to remember that the book exists. And then, so I'll have it laying around the house and be like, oh, oh, this is interesting. And then I'll go, because I'll just read it on my phone. But I feel like I should have a better way. I also watch a lot of YouTube, I have to admit. What do you watch on YouTube? It's got to be better than what I watch. I end up in some weird corners. I watch music content, like how to make music. It's like make music as a hobby as well. And then like quantum physics stuff.

49:39Do you have a background in physics? No, I don't even understand it. I don't want to give the impression that I'm an expert on any of this. I just follow my curiosity. Yeah. I used to just exclusively consume business and technology and startup stuff. Most of my adult life, I was CEO of a company and just waking up every day, desperately trying to make that succeed. And so a lot of my new stuff, like music, it was just fun. Do you read any fiction? I'm trying to read more fiction. I tried reading that book that you recommended a little while back. Oh, it's so hard. It's so hard. Little Big. Little Big.

50:21Little Big by John Crowley. This is the one book that I hesitate to recommend because nine out of ten people are just like, what the fuck? You even said that in the recommendation. I'm like, I can handle it. I got this. I'm going to do it. I gave up. Yeah. The more drugs one is done, the easier it is to eventually get into the talking fish section of the book. Okay. When then you kind of cross the Rubicon and it's all in. But yeah, John Crowley. Any other fiction books? Sid, you're trying. I just read this Miranda July book, All Fours. Okay. It's good. She's hilarious. It's random. Yeah. Got it.

51:02All right. So if we look back at the products that you've built, if you were to build any of them again today, are there any features you would either remove or add that come to mind? I think a lot of cases, I was much too eager to add things, especially medium. Medium, I definitely prematurely scaled. And I just wanted to create a nice... Why do you say that, that it prematurely scaled? I'm good at seeing systems. And a product, most of the things I build are systems. They're not just a product. and with Medium, I had lots of experience understanding the internet and publishing and some platform and I was like, wanted to build everything new and that may or may not have been possible, but I tried to do it all at once, which was, I think, the mistake.

52:05And so that's why I say we're prematurely scaled is just that it takes time to get everything right and the company and the product, et cetera. and because when you're trying to do a whole bunch of things at once, it's classic failing mode to try to bite off more than you can chew. And almost every, I'd say 80 % of the time, if I meet with a startup or founder, which I don't really do anymore, if they ask me their advice, they say, do less. And so Medium, it was like that. It was like build a great writing platform and then got impatient for growth. and... Was that due to outside pressure or was that an internally generated pressure?

52:50It was internal, but it was self-imposed by me, but it was also... This is part of prematurely scaling is if you get beyond a handful of employees, it's as much pressure from employees as it is from investors. Right. And if you have everyone around the table and everyone's seeing all that, then you can kind of take your time more. But if people are having doubts and you have to sell internally all the time before you figure it all out, that's a dangerous place to be. So that's where we were for a while. So when you say do less, right, I'm sure a lot of folks in this audience, I've been in a position where I'm trying to do more things than I should, taking a maybe shotgun approach to trying to impatiently get seven things done when I should probably put them in some type of logical sequence.

53:42So if you're trying to take a more rifle-like approach, and you could give the example with Medium or it could be with Mosey or otherwise, how do you choose the first few things to focus on? When you have this ocean of possibilities, looking back, we can use this as a starting point at, say, Medium, what would you have focused on in terms of feature set or otherwise? I'll use Mosey as an example of that, because it's fresher in my mind, but where we've done a much better job. So Mosey I originally conceived of as a better contacts app. And the idea was, it's a very old idea, like the Plaxo idea, if you remember that.

54:24I do remember. I remember hearing about Plaxo 2001 or something like that. And the idea of Plaxo, pre-smartphone, desktop, like a Rolodex on your computer, but if I have your business card in my Rolodex, you can update it on my Rolodex. I heard that idea. I'm like, duh. That's like one of the many things that the internet is going to change is like the difference of being in a connected world versus a disconnected world and what utility and great stuff comes from that. And then fast forward 2023, we still don't have that, which is kind of crazy. Like I have this contacts app and it's lacking information, it's incomplete, it's outdated.

55:06So it's like, I'm going to build a better contacts app. And then it led to the idea of, okay, if you managed to do that and got lots of people connected, then you would actually have this private social network. Then you could do all kinds of things. And one of the ideas we had was location sharing or city-level location sharing. But we also have these ideas around customizing. If it's a digital business card, it was like, what if you could customize it, make it look really cool, and choose your fonts and colors, and wouldn't that be just fun and kind of a throwback? So we actually built that.

55:40We built this whole system for making these cool-looking cards that would show up for your friends in your Mosey, and then we killed it all, thankfully. And that was painful because, you know, you've gone down a path with the team, they work really hard, and like, actually, you know what? this is complicating our vision because what we're hearing from people and what we're sensing is that's kind of noise compared to the utility. What I just want to know is when my friend's in town or I just want to know when I'm going to a city, like where are my friends? And all the rest of this is noise, so we rip that out.

56:17How are you going to approach the invite process to show your contacts? Because this seems to have been a challenge with some previous attempts of this work. If I look at my contacts, I've had, I mean, my contacts is this bloated monster full of people. A lot of them are sort of acquaintances I don't really want to keep in touch with. They're probably a handful of frenemies where I'm like, definitely don't want to see those people. Some crazies, don't want to see them either. But they're still somewhere hidden in my contacts. So how do I just have my real friends notified? Good question. we are assuming, for starters, and maybe this is a false assumption, if you are in the phone book of someone else and they're in yours, that you're willing to share more than your phone number.

57:07You're willing to share your private profile. And we're not sharing anything that's never public, but that's, if you've given your phone number to them, then you can see what we build in ModeZ profile, which is just, it's not addressed. It's like social handles. It's more or less what would show up on a social network profile. But some people are nervous about that. So, I mean, you can not sync your contacts and build it from scratch would be the answer. And then plans have a separate mode. So what people are most nervous about, and we want to make very clear, is it's not going to tell everybody in your address book where you are.

57:42We don't even automatically update your location. You put in plans. And then at the plan level, there's another level of privacy where you just say, you have to actually opt in to say, this person can see my plans. Does that make sense? Yeah, it makes sense. We're trying to take a conservative approach to privacy but balance that, obviously, with ease of use and growth and having enough nodes in the network. But we're not compromising on privacy. We never want to surprise someone that they're sharing information with that random ex or crazy person who happens to be in their phone book. So we're coming up on time pretty quickly.

58:21You guys excited for a fun night? There's a lot coming. you mentioned I think it was January 2024 I could meditate every day this year do you have anything on the docket for 2025 that's like that do you make resolutions no that's the only one I'd made in in years actually other than the just general themes like dance more here we are tonight you guys are in luck you guys ready alright well we're gonna we're gonna land the plane anything else you'd like to say have any closing comments? Thoughts for the audience? I would just say, Tim, thank you for having me. Tim and I have known each other for like 20 years.

59:06I've never been on a podcast. That was fun. And it's just a whole night of nostalgia because we're back in Austin and it's Dignation and it's good time. So I hope you guys enjoy it. Yeah, I will say, guys, it feels like the mojo's back to South by after COVID. It took a few years. And you have an amazing night in store. So we'll get more people out here in just a minute. I will be back out in maybe a half hour. I have a surprise and maybe even some gifts for everybody here. So stick around. And Ev, thank you. So much fun. Have a great night, everybody.

59:55fun before the weekend. Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums perhaps, gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field, and then I test them, and then I share them with you.

1:00:36So if that sounds fun, again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about. If you'd like to try it out, just go to tim.blog slash Friday, type that into your browser, tim.blog slash Friday. Drop in your email and you'll get the very next one. Thanks for listening. I want to give my pooch Molly the best of everything. She is my companion. She is my guardian. She's been with me for almost 10 years now, 24 seven. I want to give her the absolute best. And that includes food, especially food. It is the bedrock of her health. That's why I give for Sundays for Dogs, this episode's sponsored.

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1:03:41All of that contributes to fat loss and reducing the risk of various diseases. And now you guys, listeners of the Tim Ferriss show who buy four boxes, get a fifth box for free. You can check it out. You could also buy one box at a time. Try them for yourself at davidprotein.com slash Tim. Learn all about it. That's davidprotein.com slash Tim to get a free box with a four-box purchase or simply learn more. Check it out. davidprotein.com slash Tim.