Co-Founder of Blogger, Twitter, Medium, and Mozi — The Art of Pivoting, Strategic Quitting, and More

Why greatness cannot be planned. I recommend this to a hundred people. Love this book. It's by a guy named Ken Stanley and another guy who were AI researchers. 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. And 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 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.

Hey, everybody. I don't get asked about VHS enough these days. In fact, I don't even know what it stands for. Video. I think what Tim is referring to is my very first internet product. That's right. Which was a video cassette that was about how to use the internet. You watched it on your TV. The year was 1994, folks. It wasn't that odd for the time, but how are you going to learn about computers on the computer when you don't have the internet? So, I made a tape in my basement with my college buddies and that was my very first internet product. It was 2 hours basically of me explaining how to FTP by terminal. I think I talked about the web for about three minutes. Yeah, there's this new thing called the web. So, we're talking Usenet, Gopher, that type of stuff.

It I think we broke even on a very low budget production.

Yeah, we were talking earlier today actually about social media and how the word social has changed. Remember when social used to mean like getting together in real life, getting to know people? And now social is just this catch-all word that kind of just means the internet. And that was I think an evolution that started in maybe Facebook days. Facebook was actually in the news feed was I think a social media new format really because it was media from people you knew. We borrowed from some of that for Twitter. We also borrowed from blogs for Twitter. So, but Twitter we never saw as necessarily social. I wasn't very focused on social personally. I think that's the somewhat ironic thing is that I come from a very small town in Nebraska on the farm. I didn't know a lot of people and maybe subconsciously I liked the internet because I actually wanted to make friends but I didn't know that at the time. So in all these technologies I was really focused on information and ideas until fairly recently in my current stage of life. I don't want to say later stage of life but the golden years, I started thinking a lot more about relationships and I personally had underinvested in relationships and overinvested I think in just maybe business. So yeah, been thinking about that a lot lately.

I started a company called Mosy within the last year and Mosy is an app for finding out where your friends are and getting together and it's we like to say it's actually a social app because it's really about getting together with friends by knowing where they are. So I'm in Austin. Who do I know in Austin? I know a bunch of people in Austin. I may have forgotten who I know in Austin, but Mosy tells me who's in Austin. Tells me what they're doing. That type of thing. The way I look back on some of the early ideas about social and the internet is of course we connected with people. We've all made friends through the internet. We've built meaningful relationships or maintain relationships, but I think humans fundamentally, we're wired to be deeply social, but that wiring was way before screens and that wiring to be social didn't happen in public. And so Mosy is a very simple idea where we said, well, what would an actual social network look like? And so that's what we're building.

Yeah. So, Odeo was a podcasting company that I co-founded in 2005, which if you recall was pre-iPhone, so and not to correct Kevin, but Twitter was 2007 when it was here. So, this was before Twitter. And podcasting seemed cool. I don't know if you've heard about it, Tim, but we're like, let's build a platform for podcasts. And we worked on it for maybe 6 months. We raised some money because I had previously sold the company to Google. I was fortunate enough to get some VC funding before we even had a product, which turns out isn't always fortunate. So, we had high expectations from kind of get-go. This is in 2005. Apple released podcast in iTunes that summer in 2005 which completely blew us away. It was totally unexpected. This is very, very early for podcast even though the name comes from the iPod. They basically obsoleted what we had been doing for 6 to 9 months overnight. And then we were like, oh maybe we create a podcast creation tool. You know, we were trying to pivot and whatnot. And I think I just came to the conclusion at some point, the way Biz Stone tells the story is that I went and wrote this big strategic doc about how to succeed in the podcasting business and it was very convincing and about the pivot we could do and should do and I was like, I don't want to do this. And so I went to the investors and said, I don't think this company is on a great trajectory. May wish you to stop. But that was unusual because this was kind of pivoting now of course is taken for granted that your idea isn't right the first time out. That was less assumed back then. And so I was embarrassed. I was like, I said I was going to start a podcasting company and I raised this money. I have these employees. I have these investors. But I don't believe in it. I don't believe in this vision anymore even though it's sort of you know it wasn't dead as you said.

I wasn't that into it personally. I wasn't a podcaster. And I think that was another principle that I've learned over and over is I think some people can build products for other people and thank goodness they do. But I just build products for myself and I was like I don't know what the product is here we need to build that I want. But I think to your question about strategic quitting, I think a ton of companies and a ton of people just get into these life situations where they just keep going. And that's certainly what I was taught. In fact, Blogger which is the company I sold to Google. I completely ran out of money after the dot-com bust, had to lay off all my employees, was barely able to pay my rent and kept working on it, kept working on it, kept working on it, eventually sold it to Google and very happily and to me that was like yes that is the triumph of perseverance and that's why you should stick to things and then Odeo thankfully we did create another company out of that but I think this idea of it's okay to quit is underappreciated and the main reason everyone knows about sunk cost fallacy. There's a great book by the way by Andy Duke called Quit which I highly recommend. And it's actually was part of the reason a couple years ago I stepped down from Medium which is my last company I was running for a long time. I quit my job. The company is still going. But I realized that I was just working at like it was ego. It was pride. It was expectations of other people. And the book is really great if you don't know it because it just points out all the reasons beyond sunk cost fallacy that people do things way longer than it makes sense to do them. And the biggest thing is they underestimate opportunity costs. If you're working on one thing and there's identity and ego and all those other things, but it's like you don't know what else there is until you clear your attention away from the thing that you've been struggling with. And so I think if you're in a situation where it feels like a slog, quitting is probably a good idea.

I think one big difference is I believed in the vision of Blogger the whole time and that was where Odeo was like I don't know it's like I would keep coming to work and make it succeed. It was also I was lucky because Blogger being my first real company and I was a little bit younger. I believed in the vision but I also just was petrified of failing. I just couldn't accept that possibility for myself. I also didn't have a lot of other prospects. I'd never really had a job. I didn't have a degree. The dot-com boom was over, it was like well I don't know what the hell else I'm going to do if I don't make this succeed. So I'm going to stick with it. But it didn't really make sense. To your prior comment about the opportunity cost. Yeah, exactly. Good point. Yeah. Like your opportunity cost was not as high maybe at that point. Fair. Yeah. By pursuing something else. Yeah.

A company called Twitter. I still call it that. I don't know about you guys.

Well, the investors thankfully, my board I went to board and said this is my honest assessment of Odeo and they as good investors do said well we didn't invest in podcasting we invested in you have a great team you got any other ideas and I thought hmm I must have other ideas so I always prided myself on having ideas but I went back to team and said I don't have any ideas you guys got any ideas and we ended up doing a hackathon where we basically for a couple internal hackathon we just said hey let's all how many employees did you have at the time I think it was around 12, 12, 14 something like that okay and then so people worked on a bunch of stuff a lot of it was related cuz we were doing audio and recording in the browser with flash and stuff like that again pre-smartphones. So, but we were dabbling with text messaging. There's a couple of the engineers had were familiar with how to send text messages en masse, which was little known at that time. There was no real APIs for that. And so, people were trying a lot of things along those lines. Maybe we send a send an audio voice memo, maybe we record something browser, little kind of social things. Then there one of the ideas was to the way I remember first it was record a message actually via your phone and then it got broadcast text to people and then they could listen to it and then that quickly evolved to what if we got rid of the audio maybe it was just text broadcast and then you know having come from the blogging world that we were familiar with RSS and subscribing which turned into following and yeah kind of evolved from there. That was of course Biz Stone and Jack Dorsey's project and it also was informed by Jack's previous work on couriers and status systems and whatnot.

We were pretty intrigued right away. Okay. I mean, we certainly didn't know the extent of it by any means, but it felt new and interesting and we kept evolving it. It definitely wasn't right. I mean, I think you know, no ideas come out fully baked and so there was a lot we had to get right like what is the graph? The very first version actually was highly informed by status messages which were a thing in Facebook but this is pre-Facebook being available to outside of colleges and we were too old to be on Facebook so we didn't even know about statuses on Facebook but it was kind of like that and it was kind of like AIM messages and the very first version there wasn't a whole feed it was just the latest person who had updated their status was on top and it went out via text message and so but we're like hmm interesting. And we felt it was interesting when we had maybe 10 people on it. 10 people worked at the company and then we started getting our partners on it and we were intrigued. But so this is 2006 and it really wasn't growing for months and months and really we hit an inflection point here in Austin in 2007.

Yeah, that was the idea we had. So it was starting to take off amongst the people we knew in SXSW was always the conference where like the indie cool tech people came and these were our people and they were the ones our early adopters of Twitter because they came from the blogging world and their friends and so we sensed that we could get critical mass here and so we talked to Hugh and whoever from his team and of course they were like well you could have a trade show floor and like no no no no one goes to trade show can we buy a screen and put it in the hall where everybody's hanging out and that was the move and people saw that and were like oh that's amazing I didn't realize that backstory and this cost $11,000 it's a great investment $11,000 a little more expensive these days I think since you're competing against AT&T and god knows who else.

It's early for Mosy. The way we think about it in our wildest dreams, it is a ubiquitous social network in the way Facebook was at one time, but actually designed for enhancing people's social lives and relationships, which means it's not a media platform. It's not an advertising platform. It's not a performative platform. It's not a status building platform. It's really about sharing information that's important to you with people you care about and enabling. It won't all be about IRL, but that's where we're focused on right now, but it's early. We haven't figured it out yet. And I think that's part of the fun is figuring out where it goes.

Where'd you get that list? That is New York Times. Ev Williams favorite books.html. Yeah, I probably wouldn't pick those. Now it's been a while. I'm not an executive anymore, so that's not as useful. Zen and the Art of Motorcycle Maintenance 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 a hundred people. Love this book. It's the subtitle is the myth of the objective. And the premise it's by a guy named Ken Stanley and another guy who were AI researchers. And the way it starts out is they this is early AI researchers like 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 were 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. And the premise of the book is that works if it's something that's been done a lot and that's formulaic and you can set a goal to run a marathon and you can download a training regime and you can go run the marathon and probably you can't do that to invent the computer or Twitter or create amazing art. You just 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 Medium, my last company. And 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. I saw like companies and particularly products as a creative process. You know, it's like writing a book or painting a painting is like 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 has happened to me is you have this intuition. You kind of know what it is. You start develop it. You're like, 'Oh, it's this, not that. Let's try 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 meets with some success in the world, then in at least in the tech world, employees and investors and business people come in, it's like, okay, where are we going next? What's the plan? What's the road map? How are we going to make the numbers go up? And it just doesn't work very far. It works like a little bit to get to 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. Anyway, this book is good and it makes this point. It's 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 stuff. Trial and error.

My kids are here in fact. Whatever they want. I mean it depends on what the goal is. I mean I think I can frame it a little more or constrain 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? For 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. 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 a report or some analysis where the product is very important like 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. And one of the reason 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. Who knows? I think we're in a lot of trouble if that gets removed from you in life.

I don't spend a lot of my time investing, but what comes to mind I have a venture firm called Obvious Ventures. We try to invest in things that are going to address big problems. So climate is something we've been doing for a long time and I if you think generally like now actually kind of a weird time in climate investing, but it's going to be a bigger and bigger problem. So if companies figure out how to address that issue like that space, I think is good investment. The other thing I would say much more specifically is psychedelics.

I don't know. More quickly. Is that what someone said? Publicly. Publicly. Oh, publicly. Got it. Well, where do you think that ball is going? Any thoughts? I don't think I have a smart answer to that. You probably have better. Well, I mean, this is why I don't invest. My partner would have a great answer to this. We've done some psychedelics companies but yeah I will people aren't going to like this but I mean I think there are some grand experiments afoot right there there's no historic or indigenous example of tens of thousands and hundreds of thousands of people consuming compounds that are effectively sort of neuropsychological nuclear power. Right? It was typically reserved for a very very very small percentage of a given population. So I do think there's tremendous therapeutic applications, but it remains to be seen if it can be fit into the healthcare system that exists where it's also possible. When I say I'm long psychedelics, I'm long psychedelics for their ability to help people. Maybe they're not a great investment because they're not hopefully they're not going to get patented, although I know there's a couple of companies that have had some public fights with. Yeah. So hopefully it doesn't fall into that business model and they can impact lots of people and remain generic.

I love this question. I might overthink it. And 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 in thinking about this. What comes to mind first of all is the category is something that will help people heal, you know, 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 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 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. Then I think there's a little bit of tension between like the most fundamental truths and how actionable they are or how much they will actually. 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 this the spectrum of usefulness of what's a fundamental truth that's more useful you might have like some Buddhist saying like all of our suffering comes from 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. It's a little bit easier to imagine that. I think so much of our suffering. I say this as someone who told their first therapist, I don't understand the point of feelings. I was like they are just a nuisance and get in the way. And 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 6 months and see how you feel. Not tonight though. It's fine. We're in Not tonight. Nice. Starting tomorrow. Starting tomorrow.

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 6 months. I've gone through a lot. I've done a lot of work particularly in the last couple years and that's been super super important.