How I Built This with Guy Raz - Twitter, Medium and Blogger: Ev Williams

Episode Date: May 6, 2024

As co-founder of Twitter and founder of Blogger and Medium, Evan Williams literally helped change the conversation: he understood that real-time connectivity—being able to write a post and have people read it seconds later—was the future of engagement online. A Nebraska farm boy who dropped out of college, Ev ran into several business failures before starting Blogger, and—after it sold to Google—launching Twitter with Jack Dorsey and others. Ev also came to learn that he understood product better than people, a trait that would contribute to his eventual ouster as Twitter CEO. After that crushing blow, he returned to his first love by starting Medium, a blogging site for posts that are neither too short or too long.This episode was produced by Kerry Thompson with music by Ramtin Arablouei. It was edited by Neva Grant. Our audio engineers were Josh Newell and Gilly Moon.You can follow HIBT on Twitter & Instagram, and email us at [e-mail] Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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to be interesting, informative, inspiring, and most importantly, fun. It's 100% free. And to sign up, just visit guyraz.com. That's g-u-y-r-a-z.com. How did you feel when you found out that you were being let go as CEO? I was devastated. I was also shocked. I didn't even think it was possible.

And I went from owning 100% of this company to being kicked out. At the height of my success, I was just knee-key. And it felt like nothing I did before mattered because I failed at the biggest thing I ever did. Welcome to How I Built This, a show about innovators, entrepreneurs, idealists, and the stories behind the movements they built. I'm Guy Raz, and on the show today, how a college dropout from Nebraska moved to California, started two major blogging platforms, and somewhere along the way, co-founded a little company called Twitter. One day, far in the future, there's a possibility you'll find yourself in a bookstore and come across a history book about this time, about our era.

When that happens, thumb to the index section, and I'm pretty sure you'll find lots of entries under the word Twitter. Now, just to get the elephant out of the room here, I don't think Twitter is entirely guilty of the things that it gets accused of. misinformation, polarization, cancel culture, etc. But I do think that over the past 10 years or so, Twitter did help to shape the politics and culture, at least in the United

States, in good and bad ways. None of this was anticipated by Ev Williams. Twitter was never supposed to do any of this, and it's possible that Ev and Jack and Biz and Noah, the original founders, were just naive.

And the product they came up with, like many successful products, wasn't even supposed to happen. At the time, Ed was pursuing, believe it or not, podcasting. In 2004, Ev co-founded a podcasting platform called Audio. Now, going into podcasting at that time was a little like getting into electric cars in the 1990s, just a little too far ahead of its time. So not surprisingly, audio didn't work out. But a side project of audio, one that was being worked on by Jack

Dorsey did. And that side project would become Twitter. Twitter, of course, became Ev's best-known brand, but he also founded Blogger and later Medium, three hugely influential products in the era of social media. Along the way, Ev learned what it meant to be a really bad people person, something he spent much of the past 10 years working to get better at. Now, like a few well-known tech founders, Ev Williams is a college dropout. He barely made it through two years before striking out on his own. Ev grew up on his family's corn and soybean farm in a rural part of Nebraska. It was a tiny place, only about 400 people.

I feel very fortunate that that's where I grew up. I think there's tons of great stuff that I drew from that, from a values and character perspective that was just fundamentally ingrained in me and very fitting with being an entrepreneur. To a lot of people, the juxtaposition of going from Farm Boy to Tech Founder sounds weird, but the things that are very aligned are these ideas of independence and self-reliance.

And all farmers are basically entrepreneurs. And that ethos of figuring things out yourself, actually having to be fairly innovative, that was what I saw my dad doing from birth. And there was just, so the idea of starting a company was very natural to me because it was just like, well, why would you go like align with some institution? That seemed like a much stranger idea. So in many ways, I adopted those values and didn't question them at all.

Yeah. I think the part that I didn't resonate with as much was really the culture. and it was very sports-centric. Literally, every boy in my high school played football except for me. And that was, I was somewhat athletic, but I was fairly small, and I just didn't, I wasn't into it. I didn't like it. And I was like, that's not what I want to do.

So, all right, so you're, and would you describe yourself, obviously you're smart, but would you describe yourself as a good student? Were you a standout student in high school? No, no. I was never a good student. and I wasn't rebellious and like I was getting in trouble with the law or doing anything super dangerous, but I really didn't want to do what I was told or in kind of in any regard. Like I never lined up to institutions or anything. And I was like, I'm not going to try

hard and get good grades. I'm not, I'm in, I'm just not going to do that. And so I never did any homework. I also, for some reason, I think I didn't sleep at night and I fell asleep. in every single class in high school. So, yeah, it was a bad student. But I read that you were, like, growing up, you were really into computers, right? And then eventually when you went to college, I don't think you majored in computer science or had any specific kind of plan, right? In fact, I think you dropped out.

And I guess you lasted about a year and a half or so at the University of Nebraska. Why? I mean, why do you drop out? I was just in such a rush. The whole time, I was like, I got to do something in the world. I thought, I am not going to get a degree and go get a job. That's just not me. I'm going to make something.

I'm going to build something. And for some reason, I was in a tremendous rush to do it. I always had some scheme or something that I thought I was going to go do. I was in a really embarrassing, like, get rich mail order ideas. I was like, you know, like drop shipping. Okay. Or like, I'm going to, I would read like entrepreneur magazine and order stuff out of the back. Like, or success magazine.

There were all these like multi-level marketing things. There was, there was, I probably got into some multi-level thing. But yeah, there's multi-level stuff and mail order. Mail order was really like the get-rich path that I was like, oh, I could do that because you can do it from home. It doesn't matter who you are. It's sort of like pre-internet. So when you dropped out, what was the first thing you started to do to support yourself? I actually moved to Key West Florida because there was this marketing guru there who I wanted to,

study under. So I wasn't necessarily, I would just, I knew I didn't know anything. I knew, I had a very strong sense in my abilities. And again, that like kind of fearless independence, like, I'll figure it out. But I was aware I didn't know anything and I didn't have any money. And so there was this guy at that I was like, I'm going to go work for that guy. I'm just going to show up and then I'll be able to do stuff. What was his name? His name was Gary Halbert. Okay. So I showed up at Gary Halberts office. He was like, who are you?

And I told him I was there. I was going to, I wanted to write. I was like, I could write for you. And he was like, okay. He thought it was joking. He was a, I just looked him up. He was a copywriter. He was a famous copywriter.

Famous copy. Yep. He wrote copy for other people. That's how he made his name. And then he started like selling his own newsletter and seminars. stuff. Okay. But in retrospect, I was like, oh, that was really, it's sketchy and cheesy thing to be a part of. But I didn't know. I was a farm boy from Nebraska. So, yeah, I was just like, I'm going to, I want to write for you or with you or whatever. And it gives me an assignment to bring back in the morning. Turns out as Memorial Day weekend, so the office is closed for three days.

And so I'm literally sleeping in my van in Key West. Terrified, no money. And the first night, I stayed up all night to write to do this assignment. Finally bring it back on Tuesday. And again, he thought it was, he thought someone else did it. He thought it was like a, he didn't believe I wrote it. And then he was like, okay, I'll pay you to write. I'm looking into Gary Halbert and I mean, he's kind of a legend.

So I didn't know he was, but like apparently the most legendary copywriter of all time died in 2007. But this was your first kind of mentor. Yeah. Yeah. It's true. How long did you end up staying in Key West? Seven months. Huh.

Okay. So pretty relatively short time. And I guess after that, you go back to Nebraska to kind of try your hand at a couple of businesses and, you know, they don't really pan out. And then you land on this idea eventually to start a website business. This is around, I guess, the early 90s, to sort of make websites for local businesses. Is that right? Yeah.

With my friend Paul and Craig, and we figured out how to make websites. So that's when we really got started on the internet. 93, 94, ended up doing some website development for companies. in Lincoln. Yeah. And did that pan out? I mean, there's lots of, we've had people on the show

who started that way in the 90s and really built successful businesses that way. Totally could have. I think it was poor execution. Also, location-wise, we could have been selling website development to anyone, but because of where we were,

trying to sell it to local businesses in Lincoln. And, you know, they weren't really that into it. And to their credit, they shouldn't have been. Their customers weren't necessarily on the Internet. So we, you know, we barely, you know, we were not paying the bills with that. Was really broke the whole time. It was very broke. But you're a young guy.

You were a young guy. I mean, you eventually moved to the Bay Area in 97, I think. And this was, you were, what, 25 at this point, maybe a little older, actually. No, it's 25. 25, yeah. But no degree. No degree. But you had a couple of failed ventures behind you.

So when you came out to California, did you come out with a job? Or did you just come out and say, I'm going to look for something? I actually did get a job. So after the, we really shut down that company in Lincoln. Does the internet? The internet company, we called Plexus, and then finally shut the doors on that. I felt terrible. I just felt like this big loser.

And I went back and I was then living on the farm again with my dad. And my girlfriend, because of that company, she was helping for a while and then ended up getting a job at another internet company in Lincoln. And then they offered her a position, or maybe she requested it, in San Francisco. And so she moved to San Francisco. And I had never even been to California. But of course, by the time I was consuming every bit of information there was in every magazine and on the web about Silicon Valley. And I so wanted to be a part of it. But I think I was just scared.

And it was like, oh. And even though I was bold enough to start an internet company in Nebraska, but I was terrified of moving to California and trying to be a part of the real thing until she moved. And I actually drove her out from along that I-80 goes straight. from basically the farm into the heart of San Francisco. Yep. And then I drove over of that Bay Bridge and like, holy shit, this is where it all happens. Yep. And then I went home and I was like, maybe I could, maybe I could go.

And yeah, and so you do. You do, eventually you do move to the Bay Area and get a job here. I think you got a job of a software company called O'Rour. Riley Media, which is just north of about an hour north of San Francisco in the town of Sebastopol, which I love. I know it very well. And I think that you were hired to do marketing, right, like to write ad copy and that kind of thing.

So was that good? Was that interesting? Yeah. So I found myself in this company. I remember distinctly being in a meeting. This is conference room with maybe like a dozen people in it and thinking, oh, so this is what a meeting is like having spent a couple of years trying to have meetings and after shutting that my own company and thinking maybe you should work out a company before you start

a company. Yeah. Which is a tip that I would recommend to most people. But so that's a very important advice. And here you are 25. For the first time you're working for a company rather than your own startups. And how did you do in that environment? I mean, you described yourself in high school as just kind of like an outsider a little bit. and somebody who is not really good working within the confines and structures of other people's rules and, and so here you are now in a company. Right. How did that, how did you do in that environment? Not great, not great.

Unlike high school, I tried very hard. I worked my butt off the first few months. Well, I was only there a few months. I worked really hard. I did good work. but I was not a good employee. I was rebellious, and I would have lots of opinions

about what the company's strategy should be because I'd read a bunch of business books, and I would write Tim emails or memos about how we shouldn't be doing this or that. There was some product that I didn't think was very good that I was assigned to write copy for, and I sent an email to the whole team saying why it wasn't good,

and we shouldn't release the product. I was like, doesn't everybody love a 25-year-old who does that, the new employee? Oh, my gosh. Cringe. And by the way, if you're listening to your 25 and you do that, do that. It's okay. There's nothing wrong with it. I'm just saying that you will piss everybody off, but that still doesn't.

Still, you should do it. All right, so you're like, you're trying. And while you were there, I guess, something else you started to do it on the side for fun was, wasn't it called blogging? but you were started to like put your, I guess you started your own website and you started to just write your own thoughts on it. Well, tell me what this website was. It didn't quite overlap.

I did have my own website from even before I moved to California. And yeah, I had written some essays. I had some stuff on Evhead.com. We called them personal homepages at the time. There was a couple essays I wrote that were, the only one I remember is why Amazon shouldn't expand beyond books, obviously very, very wise. Prussian. What else?

I don't remember. I think a lot of it, for a short while I wrote just like kind of newsy technology updates. At this website, ebbhead.com. And you would just post things. This is before people use the word blogging, I think. Yeah. Yeah, there wasn't a ton of writing and there certainly were probably even fewer readers. but it wasn't quite a blog yet.

The big blogging innovations came later where there's actually like a chronological scroll of posts. And so this was all hand-rolled and it was a little bit later and it was actually after I started my next company that I really turned it into a blog. Right, I got it. Okay. And so by that time I knew how to code

I wrote software to do it. A lot of people were doing weblogs by hand, like editing HTML and then uploading. And I just wrote software. And I made it so I could go to my own website. I could hit in and a little form would pop up. And I could type something and hit a button. And boom, it was at the top of my web page. And that was a just, I can still picture that moment because that was new and different.

the idea like having a thought and then putting that on the worldwide web available for the entire world of course no one's looking at it but just that going from thought to something published publicly in a matter of moments felt like an entirely new thing so meantime okay so that's happening that's one one thing kind of happening but but meantime you would left o're you had some programming experience, right? You weren't, I think, by your own, even your own account. You weren't a great programmer, but you were probably getting better at it. And you met this woman named Meg Hurahan.

This is in the late 90s. And I guess she was a developer and designer living in San Francisco. You meet her. And I guess by chance, and the two of you decide to start a business together. Tell me about that. that what happened? So when I left O'Reilly, actually, I'd gotten paid enough. By the way, when I got to O'Reilly, I was in debt to the IRS because I didn't pay payroll taxes at my first company.

But I made enough money to pay off the $10,000 or whatever it is, which seemed insurmountable before that. And then, and I had learned enough more programming that they actually hired me as a contractor at O'Reilly after I quit as an employee in marketing. And so I rolled that into some other contract programming jobs. I ended up working through agencies. That's when I met Meg. I had already decided to start a new company. I knew what it was. And we started what we called Pira Labs. We called a project management or productivity app that was web-based collaboration. Collaboration project management, that space. How did you finance that? I mean, this is the, end of 98, I think, and this is the height of the dot-com, boom.

Was there, I mean, as a 20, I don't know, now 28, 26-year-old, was it easy for you to raise money? No, it was. And it was frustrating because everything you read is like, oh, it's so easy to raise money just rolling down to sandhill road. And I didn't know anyone. Like, especially the time is very, very much a connection game. So I was like, I don't know. Like people say money is easy. where do I go?

Whose daughter I knock on? But that's why I was doing the contract programming. So that's how we paid for it. Entirely bootstrapped. And so was able to then Meg and then Paul, who joined later, were able to do some of the programs. Paul, he's your high school friend. My high school friend.

Yeah, he moved out. Yeah. So, and did you ever find any customers to sell this software to? No. And we never charge for, we never charge for. it. Yeah, there was just a handful of users. It was very beta. And so from what I understand, fairly early on in the company, you made a pivot. You moved away from project collaboration, project management software to this other thing, which was this side thing that you'd been working on, which was basically web logging. Yeah, so Paul and Meg and I were all into, we all had our own web logs. I had that moment I told you about where I turned my own. I just wrote,

code to easily post my site. And that gave me the idea. It's like, this could be a product. But it's too simple. That's what actually told myself. And we talked about it as a team. It's like, it's too simple. It's not interesting.

Anybody could do that. Our collaboration thing was not simple at all. It's very, very complex. And I didn't appreciate at the time the power of simplicity. But eventually, we didn't pivot at first. We just created another product. as a three-person company that was bootstrapped and also doing outside stuff.

And the product was, what was the product called? That was called Blogger. Blogger. Yeah. Yeah. So you go to blogger.com, create an account, put in where your website was, and then easily post.

I imagine that the word blog or blogger was not yet popularized at that point. No, not at all. Especially blog. even weblogs were quite niche and I remember for a few years the hardest thing about blogger was explaining what it was. Okay, I guess on the strength of this,

you did manage to raise some money for it about half a million dollars. We did. We raised half a million dollars in, I think, April of 2000, which was technically right after the stock market crash from the dot com. It was the beginning of the crash. But we were still able to get the money. I think the crash took a while to reverberate.

So you raise half a million dollars. The crash happens. And that's probably not going to be enough money to keep this company going for that long. So did you go out and try and raise more money? I mean, in that environment? Yeah. Although half a million dollars was more money than I'd ever seen in my life. So it wasn't clear.

I was like, we can do anything on a half million dollars. That was going to last us forever. Of course, we stopped doing the contract programming. We hired a few people. I think we got up to six or seven people. And then, you're right, in like six months, we're running out of money. Because you had no revenue. You weren't selling this.

You were just giving it away for free. What was the business plan? How were you going to make money? This is why it took us a while to drop the collaboration tool because we thought we could charge money for that. We didn't think we could charge money for blog. necessarily. I'm not sure what the plan was. I think the plan was to raise more money. And then it was like, oh yeah. Figure it out. This maybe. And then it was in the fall of 2000 when things started

getting really bleak. And then we started getting nervous. And a thing a ton of companies did, a ton of consumer internet companies did at that time was pivot to enterprise. We'll take our product built for consumers and we'll go sell it to businesses. And then there was a moment where Meg and I really had to come to Jesus, because it was bothering me. I didn't like that path. And I think this, in retrospect, was a very important moment because I was just like, I don't want to build that. That's not why I'm, by that time, I had gotten very excited about this idea that anyone

in the world can share their ideas and knowledge to the internet was a very powerful idea. And it's what really got me most excited about the internet in the first place. And so I loved what we were doing. And I loved the idea of bringing that to millions of more people. And so, like, company blogging, I was like, fine, maybe we can make money. But I'd kind of rather go out of business. It's, that's not interesting. Let's, let's not do that. I guess you did basically get close to going out of business, right? Because as a certain point, point, Pira, you stopped being able to pay employees. That was a very stressful time. Basically, we didn't pivot to enterprise. We didn't get any customers.

We still didn't have any revenue. And then eventually just got to point, it was like, look, guys, we're not going to be able to, I think there was even a payroll we missed. And then I sat everybody down and said, we don't have any money to pay you past this next pay period. So you're welcome to come back. I think this is on Friday, you're welcome to come back. I'm going to keep working. If you come back and work, we'll pay you when we make money, but we're out of money. And then the next Monday, I came back and I was the only one there.

When we come back in just a moment, how Ev brings blogger back to life. And then heads into a whole new venture, which does not go anywhere until it's, turns into Twitter. Stay with us. I'm Guy Raz, and you're listening to How I Built This. Hey, welcome back to How I Built This. I'm Guy Raz. So it's around 2001, and Ev Williams is determined to get blogger up and running, even if he has to do it alone. Yeah, I couldn't imagine stopping. Once everybody left, my costs went from $50,000 a month to $5,000.

in a month. Still have to pay for the servers. And I just wanted to keep building it. So I kept building it. And just by yourself working on this site, updating it, trying to improve it. Yeah. It was both really sad and very freeing. And it was sad because, I mean, you reached that point in a company, there has been a lot of stress and a lot of angst. And I think that's just natural. And my company was also my social life. And so there was this overlap with my roommate didn't work at the company, but dated someone who did, and brother worked at the company. And so and everyone was mad at me at the end. And I felt really bad because I felt like I failed. They were mad at you when it failed. They were mad at me when it failed. Yeah. And we had been

fighting and all my friends went away. It wasn't just my employees went away. It wasn't just my employees went away. My friends went away. I felt really guilty. I didn't, wasn't talking to anybody, but I was able to show up at work every day and not explain anything to anybody, not have to argue. I was just like, I am going to build whatever the heck I want. And that felt great. And that feeling of creation was really what always drove me. And so that was very liberating and very fun. Did you this is you know, this is a little bit

complicated, but I think that at the time some of the people who had left Paira felt like burned. Your view was, well, I stayed. I kept running this thing. So like what do you expect? But some of the people said, Ev doesn't know how to

manage teams. And by the way, I say this is somebody who still struggles to manage people. It's really hard. But you were criticized. Was that a fair criticism that you just were not good at, I don't know, at managing teams? I would say worse than that, I don't think I was good at relationships, which even more fundamentally. I mean, management is a particular skill, but I wasn't good at relationships, i.e. how to deal with conflict, the most important thing. And I avoided conflict, especially in those days.

and I at the time really considered the people part of company building a necessary evil. And so I didn't invest in relationships. I didn't know how. I never had any model for that. I never, because I never worked at companies, I never saw. So yeah,

I was terrible, terrible in those days at dealing with people, for sure. I mean, blogger eventually started to gain traction. What started to happen? I mean, you know, within a year, I mean, this is 2001. And of course, we know what happens in 2001, September 11th.

I wonder if that had something to do with more people using it. It did. More people going to blogs. What happened? Yeah. So blogging was kind of growing the whole time despite the dot-com boom and, or bust. And that was part of the reason that I didn't want to give up. Like, it was, the numbers were good.

And then, yeah, 9-11 was actually a big moment for blogs. And it's when the way I would describe it, it's when journalists started taking them seriously. Actually, 9-11, the day 9-11 happened, I actually spent the day aggregating. Because there wasn't really real-time search, and of course there's no Twitter or anything, but people are writing about their experiences,

including a lot of people in New York. And it was hard to find, find out, you know, hard to find this on the ground information. So I actually spent the day coaling these posts as they're coming in from database and put up special pages about that. And some really big blogs emerged after that time that were really covering the news. And then, of course, newspapers and magazines started creating their own blogs around probably after that time. And then, yeah, we continued to see growth for sure. So by 2002, you were able to actually start charging for blogger.

And it started to bring in some revenue. Like, you guys were getting people paying money to use it. Yeah. Somewhere along the line, we offered to host blogs, but we had ads on them. And the ads never made any money to speak of. There's like a very tiny trickle of money. But then the first thing I started charging for was you could remove the ads from your blog. That was the first thing.

And that made a surprising amount of money for me at the time. Maybe I could pay my rent. And then I launched what I call Blogger Pro. And yeah, people paid for it. Of course, many people who know the story know where this is going because it attracted Google's attention. And they made an acquisition offer to you. And in February of 2003, they bought Blogger from you. And here you are, you're 31 and you come into some money.

Yeah, that was pretty amazing. All right, so you go to work for Google. You become a Google employee because they acquired blogger, which was a really big deal at the time. Was it clear to you soon after you arrived to Google that you were not fit to work in a big organization? Yeah, I felt like a stranger in a strange land. And I was employee number 800 at Google,

so it's laughable how small it was. size as the high school I went to. And it felt similar. It felt, well, felt like a college. But yeah, I didn't know how to operate. And they didn't know what to do with me either because they had not done any acquisitions. We were literally the first acquisition that involved people. They had bought some IP. But we're the first group of employees to come in who were Googlers but not. And so we were just kind of plopped in there. And I, trying to figure out how to survive. And to their credit,

a lot of tons and tons of big companies bought these tiny internet things at the time and then they would just die. It killed them. It killed it. Blogger, I'm happy to say 20 years later, is still running. And anything written on blogger 20 years ago,

unless the author took it down or it was like a violation, is still up on the internet for free. And Google has, you know, paid for that and you probably lost money that entire time. Yeah. So that's amazing and super lucky to have felt that. But I didn't know how to operate within Google.

And so, yeah, after Google went public, I left. All right. So 2004, you leave Google. And you start to noodle on a new idea because you made some money from Blogger. and the new idea would become... Yep. You started a podcast platform in 2004 called Audio, which must have been...

I mean, this is before Apple Podcasts. This has got to be one of the first podcast. What even was a... Did you call it podcasting? Did you say, hey, let's make an audio platform? Tell me about this idea. Yeah, it's funny how this came about. I had this neighbor named Noah Glass.

who was a fun, boisterous, entrepreneurial guy who invented a way to call a telephone number and leave a voicemail that would end up on the web. And then Biz Stone, later co-founder of Twitter, he worked with me a blogger. And we were driving home from Google one day and just kind of brainstorming about it. it was one of those moments of independent invention

kind of to help Noah because we're like, no one's, you know, it's cool you can record these, but no one's going to listen to these things on their desktop computer. What if you get them on their iPad? And we were thinking about what the technical solution is to that. And then we started looking into it. It was like around the same time, people like Adam Curry and Dave Weiner

had started talking about podcasting. Adam Curry, the performer MTV VJ, a lot of people don't know, is truly the pioneer of podcast. Totally. Yeah. Adam Curry was doing like a daily show, I think, around there. When nobody was listening to, I mean, who knew even knew how to connect your iPod to the computer to download this stuff? Exactly. And so we find out these guys are talking about it, but there's no software to do it. And so then the idea was obvious, like make it easy to do this. Make it easy to listen. Make it easy.

Commercialize this idea. And it's another democratizing media. Anyone can have a radio show. That seemed obvious. And so I was really encouraging Noah to do that, to take audio blogger and create a podcasting company. I didn't want to create a podcasting company, but I thought Noah should. Yeah. And I didn't have a job then. And I was determined to take some time off, but Noah kept arriving at my door. So I fell into it.

So that was it. Yeah. And so we built a audio.com was a directory of podcasts. We were basically collecting all the feeds. We were making them easy to find. You could listen to individual episodes on the web. But then there's a piece of software that you could install on your desktop that would sync whatever podcast you subscribe to onto your iPod. So you built this entire platform to make it easy.

There was nothing like it. Exactly. So you've spent the time and money on building this. And then Apple comes out with their own podcast service on iTunes. And what did that mean for your business? It basically obsoleted every. everything we had done for the last six months, and that we raised money to do.

We made the mistake of actually raising too much money. Pre-product, really pre-product, we raised $5 million, which was a terrible mistake because it allowed us to grow the team to the point where we just weren't nimble enough to easily pivot. And so we told ourselves, as every small company does,

when a big company moves in their space. Oh, we can compete. We'll do it better or whatever. But they had an insurmountable advantage. Like people, they had the software. Yeah. So when that happened, what did you do? I mean, you raised $5 million to start a podcast company,

and all of a sudden the big 800-pound gorilla is like, actually, we'll take it from here. Yeah. And so what did you do? We tinkered for a few months. Like I said, we were like, okay, maybe we'll create, tools for podcasters. And that was another big lesson for me because I listened to podcasts, but I'd never

created podcasts. And one of my fundamental rules I can't believe is unless you are really good at user research, build products for yourself. I had no sense of, because I didn't create podcasts, I had no sense of what the tools needed were or how the software should work. that's where I think great products come from is feeling that and so we took some stabs at that

but our product wasn't good all right in this this company audio that you started with Noah Glass there was a guy you hired and I guess he kind of approached you he had he had written to you

and sent you his resume and he was a young programmer named Jack Dorsey And I guess you hired him on the strength of his resume. Tell me about him and what he was doing at Odeo. Yeah, we hired Jack just as a programmer and we liked him. I think around the same time, we also had Kevin Sistram, founder of Instagram. Instagram, yep.

Was working for us as an intern. So Kevin and Jack paired to write our, I think our, installable pod catcher, as we called them. And I guess Jack, on the side, had some kind of idea that he was talking about, that was intriguing to him, that was more about, like, not audio blogging, but micro blogging? Sort of. That evolved. I'm not sure how long Jack had been thinking about this, but basically we came to a point

where I didn't have faith in the original plan of audio. I actually went to the board. I think we had three of the $5 million left and said, I can't sell you on the future of this company. Maybe we should just give the money back and go away. And the board was like, well, we didn't invest in podcast and we invested in you.

So you come up with something. You have other ideas? And I always prided myself on having lots of ideas. But we were still, I think, fairly attached to audio and so there's a lot of basically we had a two-week what we'd call a hackathon where we divided into teams

and just let people come up with ideas to find the new course of the company and that's when Jack presented what he had been thinking about I guess this idea for a while of like a status update service and the first version that I heard

it was actually attached to audio I do remember a conversation where at first there was a version of what became Twitter presented that had audio. And I remember asking, what if it didn't have the audio piece? And I don't remember the first form and I don't want to take credit from anybody. Jack had an idea, which I didn't probably even see the very first version of. And he started working with Biz. And so they were a team. This is Biz Stone, who also had worked with you on blogger, I should mention.

Because Biz came over to Odeo fairly early from Google. And so Jack and Biz were working on a thing. There was maybe three or four teams. And then Noah, the original founder of Odeo. So the thing that we saw in one stage of the hackathon that was intriguing was the ability to send a message with your phone and it would arrive on other people's phones. So instead of just, but why would you just send them a direct text message? because I guess it costs money. Well, you could send it to multiple people at once.

That was harder to do at the time. That was harder to do. There were a couple of services that let you do that, create groups. I know there was a lot of conversation around the time. We all used AOL Instant Messenger on our desktops, and there's this status line, which was just like, you know, not a message, but it's like what you're doing and you could update it.

Facebook had the same feature. Like, update your status. Like, say like, okay, go, to the park might be your status. And you could see your list of friends. You could see them in the order updated of their status. And that was the whole thing. And we knew everyone kind of had a sense that mobile computing was the future, but building things for phones was a pain in the butt. And so we thought, well, SMS is ubiquitous. You don't have to install any software on the phone. That would be pretty amazing if we could leverage that.

So at a certain point, this seems like, I mean, you guys had to make a decision, like, let's pursue this thing. So even when it debuted, because I think it was like March of 06 when it was like it went live, but it was still tiny. It was just a part of the podcasting business still. It wasn't, okay. And you guys had already called it Twitter by this point. Twitter, my opinion, one of the best names, may it rest in peace, for this, for a tech product. I think Noah came up with that on a list of names. Noah Glass, he came up with a name.

I remember seeing an email where he had been brainstorming names and it was on a list. I'm like, ooh, Twitter, he always explained it. It was like, what's that feeling when you feel your pocket buzz? And it was like a Twitch. And he looked up Twitch in the dictionary. And next to that was Twitter, which is a dictionary word. Another good name. Twitch. Twitch. It could have been Twitch.

Yeah. So, yeah, we called it Twitter, but audio still existed. So when at the end of the hackathon, the two weeks officially, we declared, it probably wasn't named Twitter yet, but we had an internal joke name called Friends Stalker. And it's sort of like, yeah, you're stalking your friends. You're seeing what they're up to all the time. Right. Okay. But we still had audio.

And Biz said this very wise thing, I think, at the time, which was, even though we were only a dozen people, it's like Twitter was such a nascent idea. He's like if we put everyone on this idea, it's like a, this idea is like a small ember that if it gets too much oxygen is just going to go out. And so we need to keep the team on Twitter small while we develop it. So most of the team went back to Odeo, and Twitter was another side project. Yeah. and people still think Twitter is a dumb idea. Imagine the very first, very first day is like, what? That makes no sense.

And, okay, so what are the numbers, even after we launched publicly, it's like, oh, there's like 500 people using it, and we know 200 of them. And so it didn't look like a thing. It felt like a thing, which has, I've come to realize, is the most important thing. and it's feeling is much more important than metrics early on. Why did it feel like a thing to you?

It felt like a thing because once we had a handful of people on it, most of whom we knew and we're using it through our phones, to get and send these real-time updates. We used the term real-time a lot then because the internet wasn't real-time. Email was asynchronous. Web got updated. kind of slowly.

And so it was the first thing we felt where you could send a message and buzz a bunch of people's pockets. It would update. And that was new. And it was such a unique and immediate sensation. When we come back in just a moment, how Ev makes the right moves to grow Twitter,

but then fails to realize that he's no longer the right guy to run it. Stay with us. I'm Guy Raz, and you're listening. to how I built this. Hey, welcome back to how I built this. I'm Guy Raz. So it's around 2006, and Ev Williams and his partners are juggling a few things.

Audio, a struggling podcasting service, and Twitter, a site that only a few hundred people are using. And Ev realizes that for Twitter to get off the ground, he has to change how the company is run. There was a board meeting where it was assumed we were just going to decide to give the remaining money back to investors. Twitter wasn't growing. We didn't believe in Odeo.

I made an offer and I said, well, I'll actually buy it. And that was, obvious was the name of the company that I bought Odeo with. Right. And just to clarify, you buy it. And obvious is the company you form that includes both Odeo and Twitter. And yeah, I mean, very smart decision on your part. I mean, I think probably some investors wish that they could have been a part of it, you know, maybe some somewhere eventually. But did you know, in your mind, did you have an inkling that Twitter, I mean, you say there was an energy, there was a feeling you had.

Did you already in 2006 feel like, okay, this thing, I think, could be the next blogger, could be bigger? I think there's part of me that felt that. I think today I would value that part of me much more strongly than I did at the time. I think one of the things that I've learned

through my own efforts and watching others is that, that's why I mentioned that feel being more important than the numbers. I didn't trust that enough at the time. It's so easy to get overwhelmed by

data, especially in tech. And as soon as you have anybody using your product, the attention turns to numbers and testing and people try to be very scientific about it. If you're in those conversations like, no, but it really feels like something. And as someone who really has gone by feel and has that intuition, you just kind of, you downplay that. It's like, ah, well, there's no evidence to back up what I'm feeling. Yeah. And so I can't defend it, but yeah, there's enough, I feel enough that I'm going to keep investing in it. So you basically now are the owner of this new company.

And Twitter is this thing that you really start to pursue. I think by the end of 2006, you had about 60,000 users. And it was initially, right, it was like a status update. Like the question was, what are you doing, right? that was the first thing, and then you would just populate it with, I'm at the grocery store, whatever it is. But this is, and it's still before the iPhone comes out. So people are doing this on, most people are like, I'm sitting at my desk, working on my computer. Yeah, or here's the link.

And this whole time we're tweaking, we're changing out the system works. And even though the original idea that it was going to be through our phones and via SMS, which is why messages were or what became known as tweets were limited to 140 characters. I think it was in late, it was a few months in that we made it easier to use on the web. And that's when we saw our first real bump of growth because people were, our audience especially, was sitting at their desktop all day.

Yeah. I guess the turning, really the turning point happens in March of 2007, which is South by Southwest. Right. You take Twitter to South by South. It becomes a turning point from many companies, Airbnb and others later on. But in 2007, you go to South by Southwest. And what did you do to attract attention there?

We did something kind of unusual because we had a sense that that was our audience. And I knew from experience that going in the trade show floor is not where you wanted to be. and that everyone hung out in the hallway. I spent many hours hanging out in the hallway at South by Southwest, so we contacted the organizers there and said, can we actually set up a screen in the hallway? A screen, a TV screen. There was a screen that had these little tweets floating by of people...

Just scrolling, tweets scrolling up. Yeah, they were like, I think moving across the screen from people who were there. And so that was pouring gasoline on the fire because it had the density. It was like classic network building. You need density. And there was also,

the real-time nature was very valuable because people were walking around and didn't want to pull out their computers to know what was going on. And so what happened? I mean, people started to see other people. Basically, everybody there got on Twitter. and, you know, there's a few thousand people.

And, again, lots of journalists, lots of bloggers. And so then they talked about it and wrote about it. It was a moment. Just capturing lightning in a bottle amongst that community, it was the perfect thing at the perfect time with enough density to reach a tipping point. Wow. And so when you left South by Southwest, how big did it grow? I don't know the numbers. I know the shape of the charts

was very hockey stick. The service definitely started falling down. I mean, getting overwhelmed and we were running into scaling issues immediately. But it's certainly still tiny. I mean, South by Southwest, it's not even, at the time, I don't know, maybe a few thousand people were using it,

but they were using it a lot. And I have to imagine that that what happened at South by Southwest starts to attract a lot of attention. And so did you start to get investors kind of banging on your door, wanting to get involved? We did. We did. We got a lot of investors knocking on our door. I still owned 100% of it at that time through obvious, but it was clear that we needed to grow. We needed to raise money. So we started taking those conversations. Can I ask you about the broader idea of Twitter?

As you started to see this thing really grow, and I've seen you talk about it, like, at the time, already at the time saying things like, this is going to be a way for people to really build community and connect, and if there's like an earthquake in San Francisco, like, this is a way. And some of that happened, a lot of that happened. And like there was an idealized vision of what this was going to bring to the world, that it was going to bring the world closer together and make us all happier and friendlier and kinder. But it really has been a force for division two.

Did you in any way anticipate that that would happen, that Twitter would actually exacerbate division and tension? I did not. Certainly not in those very early days. The team over the years gotten a lot of flack on the trust and safety side. Those people are some of the most earnest, hardworking,

integrity-driven folks I've ever seen in the world of business. And we didn't realize, it's sort of like, in some ways, like when we figured out processed food manufacturing and we're like,

oh, this is an easy, cheap way. to get calories, not realizing all the implications of that, you know, let's keep working on it. Tell me a little bit about, because basically you were running audio, but it was clear that Twitter was the product now in this bigger company.

Yeah. And Jack was, I think he had been named the CEO of Twitter, and you were the chairman of Twitter, And this is a little tricky, I understand, because we're talking about personalities and big personalities and people who were friends and had falling outs. But how did your relationship with Jack Dorsey begin to change? Because I know, I mean, this is no secret. It's been written about. There was a falling out.

Yeah. So the course of events was Twitter and audio were just products inside of obvious, which I ran. And so, and I had around this time also sold odios. So Twitter was the only thing we had, but I had lots of other ideas. And I was just kind of want to tinker and invent new things. So that was the time when we spun it out into Twitter, Inc. That offered Jack the job of CEO. And I, again, like, Jack is not here and others aren't here to take this.

This is not a documentary show. It's a one person's perspective. The story that I've read is that he became frustrated because you, were, you know, I don't know, maybe you were frustrated with his leadership when he was CEO. He was frustrated with your meddling. That's a, that's an old story. That's happened in every company. Yeah, I think, yeah, I think we were frustrated with each other and goes back to what I said earlier about being not good at relationships. I didn't know how to deal with that. And I didn't do a good job of dealing with that. I was senior to Jack in age and experience. So I should have been the one to really

work on lead working on the relationship and stress gets high when you have something stress was very very high because we had something we knew was working and it felt incredibly precarious twitter always felt precarious our stuff kept breaking like we couldn't handle the growth facebook was always looming over us and feeling felt like they could eat our lunch at any time and they were trying to and it was so the stress was incredibly high. And Jack went from individual contributor. He had never been a manager, I believe,

before he became CEO of this very fast growing company. I wasn't a great manager, but I had a few years on him. You had some experiences with failure to say the least. For sure. For sure. And so, yeah, we didn't see I-to-I. We're very different, actually. We both desperately, desperately wanted it to succeed and both thought we were correct, and we didn't talk about it in a healthy way.

Yeah. All right. So eventually, the frustration got to a point where you asked the board to relieve him of his duties. And he was, this is well known. He was basically kind of pushed out. And that, I'm assuming, was that the end of your relationship? Was that more or less? Kind of the break.

That was the break. Yeah, that was the break for sure. And again, I would handle that very differently because I hadn't been giving him clear feedback. And it looked, he was pushed out and then I became CEO, which is hard to believe, but it wasn't actually my plan. I still didn't necessarily want to be CEO. And we talked to a few other candidates, but then I was like, okay, maybe I'm the best person to be CEO. So it really looked like it was just, oh, this thing is successful. I'm going to push him out.

and take over. So understandably, he was hurt and upset about that. Have you guys ever talked since then or repaired your relationship or not really? Yeah. I mean, we've talked. I was, you know, long story in the Twitter saga. As you know, he eventually came back as CEO. And you were on the board.

And I was on the board. I had gotten pushed out as CEO. And I was on the board for multiple years. And he was also on the board the whole time. Even after he left his CEO, he was still on the board. And so we were on the board together for a decade. And so, yeah, and we were, yeah, we were fine. We're friendly.

We have dinner, but, yeah, we're not best friends. Yeah. So he left. You became the CEO. And this would be kind of a two-year stint for you. You didn't know that at the time. You also, I guess, were approached in 2008 by Mark Zuckerberg to buy you out. What, I mean, what happened?

What was the story? Because from what I understand, you guys said, well, you know, we think we're worth half a billion dollars. And Mark Zuckerberg was like, okay, yeah, that sounds right. But the sale never happened. Yeah. What happened? there's a story that Biz tells about Biz and I going down to Palo Alto and meeting with Mark. And it was just Mark and Biz and I in a room with soft seating.

And it was very awkward and strange, but wanted to hear him out. And I felt I had no interest in selling, but you got to listen to these things. And Facebook, of course, was private at the time. But based on their valuation, they could do a stock deal that may value us around a half billion dollars and that was a lot of money and we were maybe no we were we were 30 people at the time wow so yeah that was serious we had to take that seriously we of course didn't know what facebook would become either you know eventually that half billion would be who knows like i don't know if you did the math on that but i went to the board and i thought about very deeply

And I came up with this like, okay, why would you sell a company? I think there are three reasons, and none of these meet that criteria. Three reasons being you don't want to do it anymore. And so you need someone to do it for you, or you're in trouble. So there's famous cases like YouTube sold to Google. Obviously, amazing acquisition for Google. But YouTube was really in a lot of trouble, both with copyright infringement and the scaling and infrastructure costs of YouTube

really needed this shelter that Google could provide and lost money for years and years and years. And so I thought that was another reason that didn't seem to apply to us. And third was that if, just from a fiduciary perspective, if the offer clearly was a no-brainer from a financial perspective, then you might be inclined to do as well.

And so my letter to the board was, I think these are the reason to sell. I think none of them apply. And so we shouldn't sell. And so that was the end of conversation. All right. I want to go back to your leadership. And just to point out, being CEO, Twitter is like being an Italian prime minister, right?

Like, you don't last that long, okay? And that just was the theme, right? Like, it's a hard horse to ride. You're just not going to last that long. But there was a wrap on you. And I say this not to make you feel bad or criticize you. But I'm curious just from a self-reflective perspective on what you think about it and whether you learned from it if it was, if it's in retrospect, helpful. But the wrap on you was, you're too slow to make decisions.

And also, you were prone to hiring people you knew, which is a big no-no for some people. Again, not saying that's right or wrong. That was the criticism that's, you know, in the massive, you know, millions. millions of column inches have been written about Twitter, that's come out. Do you think that's fair? I think both are fair. I was not a great CEO by any stretch. And I think I was getting better.

What I was very good at was product and knowing, in my opinion, product and strategy, and knowing where to take the company, what we should build. but the company got to a size where lots and lots of other things were important for the CEO to do. Certainly management, finances, leadership, giving confidence to the entire team. But I think in a lot of cases, I was slow to make decisions because I was avoiding conflict. I didn't want to make decisions that other people disagree with. I didn't have my, if I felt something intuitively, but, But the evidence or the data or the logic, everyone was arguing something else, then I would just, I got frozen.

Or if the decision was about a person and I was lacking the confidence to really upset people. And that was a huge weakness for sure. And so how did you overcome that or did you ever over? I mean, we'll go on to your next company. I got better. Having conflict aversion is, for some people, it's a character trait. And what I respect, because I identify with it. Yeah, it's not like embracing conflict is a great character trait either.

But I think conflict aversion comes from fear. Fear of what? Fear of rejection. I think, especially if you have imposter syndrome. And look, I'm a farm boy from, Nebraska who was running this company. I was like, I'd never had a job where I rose through the ranks. Even with the success that you had and the psychological kind of, let's say, foundation of wealth that you had built, you still had that?

For sure, for sure. That didn't really change anything. And I hadn't really done any work on myself at the time. And I think this is, like for entrepreneurs, so, so important. to realize what is driving you and where your blind spots? I had no idea. So when I would hear, I got a little bit of feedback. And by the way, somewhat ironically, the board of Twitter had a lot of conflict

diversion because they never gave me that feedback to my face. I didn't know I was going to be fired at all because no one ever told me I was doing bad job. So there was a whole culture of conflict diversion. and my execs who were complaining about me to the board also weren't telling me everyone was avoiding conflict. Yeah.

But yeah, I had a lot of, I had a ton of fear and a lot of, I had both, a lot of confidence about what I was good at and a ton of fear and that I didn't think I actually even could be ousted, so it wasn't that, was just really about being called out for not knowing what I was doing.

How did you feel, when you feel, when you found out that you were being let go as CEO. Were you devastated? Was it a dark time? I was devastated. Devastated. I can't like describe how

I was also shocked. I didn't even think it was possible. And I went from owning 100% of this company to being kicked out. That was my own fault. I had like why I didn't get the, legal protections. There's no way I had to lose control of the company. I just trusted my investors and the board. And I was like, oh, we're all on the same side. And so I knew, you know, I was barely

keeping things together, but it's also the nature of fast-growing companies. The company grew 10x and users and employees and valuation in the two years I was CEO. So I'm like, guys, on paper, this isn't going that badly. And so I had a meeting. It was a meeting. It was. my coach at the time hired by a VC, which is a bad idea, Bill Campbell, who told me, and I was just like, what? What? What? What? Couldn't believe it. And then I was very upset and very mad, went through all the stages of grief. Yeah. It's interesting because from one perspective, people might say, well, who cares? You're going to walk out of this rich guy and who cares? But but personally it felt like a failure

like you had you had not succeeded as running this thing yeah it felt like the huge failure and so much of me I honestly thought that it was going to destroy the company and and so it was really sad about that but it was also terribly embarrassed and like I spent years trying to prove myself and like and this at the height of my success, I was just knee-capped.

And it felt like nothing I did before mattered because I failed at the biggest thing I ever did. Okay. So this chapter of your life is over. But you clearly, you have an energy and a drive, and you clearly were going to do something else, which you did. It's no secret to people listening. It was going to be medium, which is kind of amazing. because it's like the first, your first really, the thing that you first really had success in,

which was blogging, you kind of go back to that. It's like a 360 return. Tell me about what did you want it to do? Medium, the seeds of medium were really planted while I was still at Twitter. And the initial genesis, Biz and I, Biz who came over from Twitter, he and I were talking.

One of the things we learned at Twitter, which we really believed him, was this idea of constraints. So we're like, what if we created a writing platform that wasn't so short as Twitter, but still was, you know,

not too short, not too long. And I walked up to the whiteboard and I wrote medium. I was like, I don't know what it is, but we should call it that. And then the idea was essentially

what we had learned from social networks was that the value was in the connectivity. Like, If Twitter just did what blogger did and posted your tweet to a web page and didn't fan it out if there wasn't this follow mechanism, it wouldn't be very interesting. It would essentially just be bloggers. So it's the distribution system that created all the value. And that's why I call my company's obvious.

It was obvious to me that that should exist. So the idea of Medium was basically to, I mean, how was it going to be different from what blogger was? It was the network. It was giving people a place to write these longer things, but connecting them so they could be discovered. And that's what blogger wasn't. There was no network to blogger. You create a web page. You couldn't follow the web page.

And there's no real reason to write on blogger versus anywhere else because there's no audience on blogger. Tell me about how the rest of your life and career unfolds. And you don't know. You have no idea. But you're not old. I mean, you're in your, you know, early 50s. And, you know, you've achieved incredible success and built amazing, well-known brands, blogger, Twitter, medium. I mean, very few people can say that.

You obviously, as a result of that, became incredibly wealthy. You can't possibly spend a fraction of the money that you earned in your lifetime. how do you imagine the rest of your life unfolding? I mean, starting more businesses, investing. How do you think it's going to go? So after I stepped down from Medium, which was almost coming up on two years, a guy named Tony Stubblebine,

also someone who I've known for a very long time. I hired him to run that company. He's doing a great job, doing a better job than I was doing running Medium. medium is going great. I co-founded another company recently. It's a company called Mozy, which is a social app. It's another social app, but it's not a social media app.

It's really about relationship building and getting people together in real life. And so I'm starting that, but I wasn't, I didn't want to run another company. I am not running it. I'm really getting more and more just into the creative side and just like, and back, creative side, I mean of life, being like, I also recently got divorced. I have two kids trying to create a great environment for them. I'm working on some art projects. I do a little philanthropy. And other than that, I don't know, could be music, could be events. But that's what I'm focused on right now. When you look back on your career so far, because this is so far, you still have

a long life ahead of you. How much of, of what? Where you got to, do you attribute to the work you put in, the grind, and how much do you think happened because you were lucky? You were here at the right place, the right time. A whole lot of both, a whole lot of both for sure. And I think anyone who has success, who doesn't mention luck, is fooling themselves. And it's, like everyone says, you can increase your chances of luck. I worked incredibly hard from those first days of those first companies to the extent where I didn't sleep.

I worked too much to the point of decreasing returns for sure. But I learned everything I possibly could about what I was doing and I kept trying stuff. And again, I attribute maybe my upbringing, maybe the way I was wired, but that sense of I have to completely rely on myself. and I'm not going to give up, certainly paid off. That's Ev Williams, founder of blogger and Medium, and co-founder of Twitter. Hey, thanks so much for listening to The Show this week. Please make sure to click the follow button on your podcast app, so you never miss a new episode of the show, and as always, it's free.

This episode was produced by Carrie Thompson with music composed by Rumtine Arablewe. It was edited by Neva Grant with research help from Carla Estevez. Our audio engineers were Gilly Moon and Josh Newell. Our production staff also includes Alex Chung, Chris Messini, Casey Herman, J.C. Howard, Sam Paulson, John Isabella, Catherine Seifer, and Malia Agadello. I'm Guy Raz, and you've been listening to How I Built This.