Lessons on co-founding Twitter, Medium and Blogger with Ev Williams

Welcome back to the Eric Ries Show. Today's guest is a legend whose products have probably shaped your daily life more than you realize. Ev Williams has an extraordinary track record of turning groundbreaking ideas into internet mainstays. He created Blogger, the original blogging platform acquired by Google and kept running for over 25 years, revolutionizing online publishing for millions of people, including my blog, Startup Lessons Learned, which still runs on Blogger to this day. But he's most famous for being the co-founder of Twitter, which has fundamentally reshaped global communication, politics, and culture. And on top of all that, he's also the founder of Medium, now a hub for millions of thinkers and writers worldwide. In this rare conversation, Ev shares powerful lessons on why strong personal relationships are crucial for long-term success. Drawing from his own experiences with Google and Twitter, he reveals how resisting short-term pressures, especially from investors, can lead to stronger, more resilient companies, and why placing intuition and craftsmanship alongside data is essential for true innovation. Ev also dives deep into the pitfalls of blindly following metrics using real-world examples from Groupon and Medium, and highlights the importance of empowering creative voices within every organization. Most importantly, Ev reflects on his multi-decade journey from obscurity to being a person who has shaped the lives of billions of people. Whether you're building a company, creating content, or just fascinated by the hidden behind-the-scenes mechanics of what drives Silicon Valley, I hope you find this conversation interesting, full of practical insights from a true master of the digital age. Please enjoy my conversation with Evan.

Ev, thank you for coming on. I really appreciate taking the time.

Now, I have a confession to make. It is true that even after all these years, my main blog, Startup Lessons Learned, is still on Blogger.

I'm a diehard old school Blogger user. And somehow miraculously through all these years, Google has not taken it out. It still runs and it's still run on Blogger.

No way. Started 25th.

Well, including me. So thank you. I can't tell you how many times people have tried to talk me into doing some new fangled thing instead.

And I just, yeah. How does it feel 25 years later to have created something like that?

Well, I wanted to start with that because I think it's actually kind of unusual in the tech world to have had that experience of such longevity of like multiple different projects that have lived and also have outlived your personal involvement. And, you know, I feel like we've been suffering from an epidemic of short-term thinking of late as everyone who heard me talk the last 10 years already knows and certainly you have as well. But I'm just curious what you think is behind that. Like obviously there's luck, there's fortune, but like do you feel like there's something about the way you built those things that allowed them to have that kind of longevity?

And I'm going to bring it back to relationships because the reason the Google deal happened was purely about relationships. Because Tim O'Reilly was an investor of mine in Blogger. He was an investor because I worked at O'Reilly and what was then called O'Reilly and Associates when they were primarily a book publisher. Kind of very well respected. That was my first job in California. And I went and worked at Tim's, a highly respected but small little company up in Sebastopol in Sonoma County. I wasn't a good employee, but I got to know Tim a little bit enough that when it came time to raise money for Blogger, I came back and he put money in via his newly formed fund. And because of that and he knew Larry and Sergey and was talking to them and in a conversation I think Blogger just came up and he was like, 'Hey, think about Blogger.' No way it would have happened without those relationships. So that relationship I made with him, the relationship he had with them. It was just like and that's, you know, how so many things work and I've just learned time and time again. And even Dick Costolo who became the CEO of Twitter was someone I knew 10 years beforehand and had pinged him when I knew I was going on paternity leave for Twitter and he ended up taking it public. And Medium which we haven't mentioned yet. Medium is now 12 years old. And doing very well as a business. And that was I handed the CEO reins over to a guy named Tony Stubblebine who worked for me at Odeo, which was 2005. And however many 15 years later, he becomes CEO of Medium. And then Obvious just to round it out, James who I formed Obvious with I knew for 10, 15 years. Vishal is one of our next partners, I didn't know before but then Andrew, Vishal and James and I knew each for 10 years before he joined the firm as heading our climate practice. And so that really to me is the through line through all this. And I haven't always managed them well. In fact, most of my mistakes in business have become not knowing how to manage relationships. But the longevity and so many of the success really I attribute to these very long-term relationships.

So it's funny. I had forgotten that you were an employee at O'Reilly and Associates back in the day until I was prepping for this interview and I was like, 'All right, that's the connection.' Now, we had Tim, he did an episode of the show and talked a lot about, you know, his ethos of creating more value than you capture and a bunch of the other ideas that have been foundational to so many people's careers in Silicon Valley. But I just wanted to get a sense of, you know, you grew up on a farm, right? Like you were not from the tech world at all. I can imagine, you know, the sense of isolation you might have had growing up. You, I don't want to project onto you, but like a lot of us, I think maybe felt a little bit different growing up. Like just how on earth did you wind up at O'Reilly and Associates from where you started? Like that seems like a crazy story to me.

So many people have that story. Yeah.

Really?

But then would have been what like the beige IBM XT era like kind of box. What kind of manual was it?

For those who know, Sebastopol is a small town bigger than the one I grew up in, but it's rural and I never thought about that. Kind of a good transitional portal if you're used to being in a rural environment.

Yeah, it's quite remote. So but it was a great stepping stone and, you know, thankfully I met Tim and who I both learned a ton from and was this, you know, critical supporter down the road.

So I can really vividly remember the idealism of those days and the feeling that the internet was going to be transformational. And I think, you know, I don't know if you feel this way but I feel like kind of a naive sense that as the internet would roll through disrupting and changing one thing after another it would basically always make them better. Like it would take the values they already had and then it would add transparency and openness and connectedness and especially for those of us I think who felt isolated and for whom the internet was like an awakening or an opportunity to connect with other people especially the early internet, you know, before it became what it is now like you got to see kind of the whole arc of this enterprise, like this global enterprise, this movement, you know, from its most earliest idealistic beginnings to what's happened now. So just like from the vantage point now being able to look back on it like what do you remember about how it felt in those days like to be part of that early enthusiasm?

Yeah. I mean, it's such a short blip in time and, you know, there's not even a generation that was born with it that's, you know, fully grown and come into power. So, it's, we just don't know is now the way I look at it. It's like, and I stopped for a long time when things started to be clearly more complicated than we thought. I was like, was, you know, has what I've helped create good or bad, you know, and now I don't wrestle with that question because I just think yes, it is. It is all these things.

I don't think I've seen that.

God, that's so true. Not entirely altruistic. It's like, yes, yes, it's for, you know, even change the world for the better, but before someone else, before somebody else.

Yeah. And I think I felt like we were very vulnerable to that kind of deception because we all just wanted so badly to believe in it. And it's a, I think, a strong aspect of Silicon Valley culture is I've noticed, and maybe this is why Stewart Butterfield's in my mind because he had this great manifesto I think it was Flickr or Slack or one of his companies that said something like, we want to win. It was like, we want to play, we want to create great things and we want to win. It was like acknowledging the fulfillment one gets from doing great things and winning which struck me at the time as, it's like, that's so great because it's so honest. And where there's like, in what I noticed again is this black and white thing with a lot of Silicon Valley rhetoric is either people talk about the mission and changing the world like we're all altruistic or the people who are like, 'Oh, that. I'm just like I'm here to make money or here to do the business.' And I think Stewart's thing, and I'm mangling it, but it wasn't just we want to win like be the competition, it was we want to create great stuff. It's like that creative impulse. We want to put amazing things out into the world, which over time I've realized like that's what I want to do. That's always been my number one motivation even and I may have couched it in we want to, you know, the mission or we want to, and it was more of the artistic motivation for lack of a better word of I see something that I want to put into the world and yes I believe I'm like out of all the things I can put into the world I want to do the thing that will help people that will make people's lives better that I'll be proud of over something that is none of those things. And so everybody and then to recruit employees, everybody wants to be part of something good. So you reinforce that narrative every chance you get and you justify, you can kind of justify anything. Humans are amazing at doing that.

Oh, it was a very powerful part of the ethos in those days. Very powerful.

Oh yeah. In the index. That reminds me of the study that they've done that shows that companies that strongly believe they are a meritocracy have the most bias in them. Like if you just measure it objectively and it's not that being a meritocracy is bad, it's that having the ideological commitment that you are a meritocracy like takes away the desire or the motivation to improve because you're already perfect. And I just feel like that's such a great example of that at Google because if they had been more honest about what they were doing, I bet the search would have been better today. Like they basically, that argument by saying that it's always making it better has allowed them to degrade the search to the point now where it's like basically unusable and the ads dwarf the whole screen. Like I just feel like the early Google ethos would have looked at today's search and vomited. I think like what a disaster that's been because you brought up the 'don't be evil' thing. I really want to get your take on this because to me that's like the incredibly shrinking motto. And I feel bad. I've picked on Google a lot in these conversations and I feel bad because Google's actually a great company. I have a lot of respect for them. It's just they are an easy target because we all had such incredibly high hopes for what they could have become and, you know, over time I like 'don't be evil' was like such a strong part of the ethos and then it's just been kind of shrinking like so like it was very prominently on the website for a while and then it kind of got rid of it and then they kind of had like a thing that's like, well we used to say 'don't be evil' but now we say anyway. I saw this story and I just got to get your take on it. There was a story where they had basically the last place in Google the 'don't be evil' motto was in the employee handbook. You know, the end of the handbook. It basically said like despite all these policies and whatever, like if you see something that you think is evil, don't forget the motto is 'don't be evil', da da da. And then some employees sued them a couple years ago because they were, I think, wrongfully terminated or something. I think they sued them saying that they were violating their employee handbook that they had tried to call attention to something that was evil and they got terminated for it and so they basically sued for violating the motto of 'don't be evil', which is never a good look for any company. And they actually, I couldn't believe this, they had to settle the lawsuit which I kind of read as a tacit admission that like yeah they kind of did succeed, the lawsuit they made it go away. And among people that I talked to at that time there were two really different reactions and I want to see what camp you're in but also just like what does this mean to you that to see this as kind of like a proxy for the whole tech industry. Half the people said to me, 'See, that's why you don't put stuff like that in your employee handbook because you're just going to get sued.' And the other half are like, 'See, that's why you should have stuff that in there and then actually do it.' Like the problem wasn't the motto. The problem is they didn't institutionalize that intention. It was just something they told themselves to make themselves feel better, but they didn't really take the steps that would have been necessary to safeguard it over time. Like how does that line up with what you have observed? You've had the inside look at this.

Oh yeah, yeah, don't worry about the case but just more just like the broader trend of the industry going through this transformation.

Okay. Something I really wanted to ask you about because I've been counseling a lot of AI entrepreneurs lately as you can imagine going back to, you know, when...

Oh, yeah. Really? Well, there's two kinds. There's people that have added AI to their pre-existing pitch deck. And then there's the handful that actually know something about AI. But, you know, but I remember like when the team that became Anthropic when they left OpenAI, for example, and were talking to me about like how should this company be governed? How should it be structured? I've had that conversation with basically all of the big AI players and tons and tons of little guys. And what's interesting about this generation of entrepreneurs, a very common sentiment is they're like, we do not want to see a replay of what happened with social media for AI, which I think is really fascinating. Like if you talk to investors about social media, they're like, 'Social media was the best.' Investors made a ton of money and very warm and positive feelings about social media.

The rest of the world, you know, not as much, you know, it's not the feeling. And certainly among entrepreneurs, there's this fear that like there's this feeling that something went wrong. And that we kind of, it was okay for it to go wrong for social media, but the stakes for AI are a lot higher, which I don't know if I even agree with that. Stakes for social media turned out to be pretty high also. But like you were there, you've been on the inside of this from its very inception and so, you know, you've had the benefit of, you know, having all these lessons, see all kinds of things go right, all kinds of things go wrong, like what advice would you give people who are like how can I do what you've done but avoid the pitfalls, avoid the downsides of it? Is that possible?

You think it's inevitable? The exploitation inevitable?

Well, but let me push back a little bit because you're telling me you don't think that if Twitter had been a public benefit corp and you guys had had dual class shares and the ability really to resist these Wall Street pressures, you don't think that would have made a difference in how it played out?

So, no. And I don't want you to give me any inside information. I just, you know, but this is your, it was your baby. Like, how does it feel? I want to get your perspective on it. Yeah. People are looking to you and saying like, 'How do I be like Ev?' And there's a lot of people like, 'How do I not be like Ev?' Like, they want to know. Tell them what to do.

Every founder I know finds that story horrifying. I mean, just so you know, because you just like, and take it away from Elon because obviously that's polarizing right now. But I, you know, the thought exercise I often ask people to do is like, you tell me who you think the most evil company in the world is. My father's a pulmonologist. So growing up, Philip Morris is always the most evil company in the world. You know, the way I was raised. So like if Philip Morris wants to buy your company and they're willing to pay more per share than it's worth, you know what do you think you should have to sell to them? And every founder's like, 'Oh, of course not.' Because and you even said it earlier, you said, 'Well, the reason you felt good about selling Blogger to Google is you like that was ultimately going to be good for the product, for the super organism for this baby that you created.' And it listen, 25 years in, it worked out. Yeah. It worked out pretty well. So like having the freedom to make that choice and not have it forced on you to me seems like one of the fundamental rights every founder should demand.

Yeah. To shut it down. Um, and such things have probably happened.

Yeah. I mean, I'm a huge believer that we should have governance structures that do not force that sort of thing. That seems bad.

Yeah. Yeah. I mean I think to me the question is like is that unconscious pressure that companies feel for like relentless growth at all costs. Like I think I actually don't think, I think you're the cartoon villain version of it where it's like oh look over here the right thing. Let's make sure to go whatever that is. Let's do the opposite. I don't think that's going on. I think the question is like psychologically knowing that you could be so easily fired, knowing the company could be so easily acquired or destroyed, does that start to um nudge you into the direction of taking exploitative actions that maybe at some level really weren't in the company's long-term best interest?

Yeah, absolutely.

Exactly. Make the numbers go up that made the value in the first place.

What I think is really about Apple is it's leaked out over many years the various projects they didn't pursue because then they would work on something for years and Steve would say no we're not doing it throw it out. Yeah. Very few of those projects when you look back you're like man if only they had pursued that it would have been awesome. Conversely conventional companies that are managed the quote unquote optimal way are loaded with these disruptive innovation stories like Kodak and the digital camera. Or you know you pick take your pick where it's like actually by kind of only focusing on the metrics and only doing the OKR system and only make number go up they're like missing out on trillions of dollars of value creation they could have had part of. And to me the idea that that's being done in the name of efficiency is hysterical.

Totally. Oh, I know that story.

Exactly. No, I can tell you story after story after story of companies that, um, I call it the culture bank. This like depository of trust that you build up with all the people that you touch and you make these right decisions. You make decisions that are a sacrifice on behalf of your customers, on behalf of your employees, on behalf of whoever we're talking about. You build up this trust account and the like the deep deep flaw in the way we teach MBAs and the whole OKR system is that at any given time anybody in the company can make their personal OKRs go up by just borrowing against that account. It's like, well, you can always if you... What's so funny about that story is if two emails are good, why not four emails, right? Why not eight emails? Why not 16 emails? And I was with a CEO, I kid you not, the other day, who had gotten kicked out of his company and was coming back to clean up the mess. And he came back and they were sending I think he told me 20 emails a day on average to customers per customer. 20 people were getting absolutely bombarded, but the unsubscribe rate still wasn't that bad cuz customers weren't like unsubscribing. They were just like whatever. They just learned to tune those emails out. So, the emails were ineffective and people were pissed at them. Like their brand equity with customers were going down. But like no, he was like, 'Well, first thing we have to do, my first act as CEO is we have to get rid of these 20 emails.' And people howled. Yeah. You're not going to take my email away. My OKRs are that our numbers are going to go down. It's like, but you we're not trusted. And it's like there's this like deep illogic to it.

Yeah. And you know, listen, I take a lot of flack of it because, you know, I'll tell you this story, maybe you'll relate to this. Some of you that I was talking about early stage company I'm really bullish on and their product sucks. You know, it's an MVP. It's like got a lot of cool things going, but like the experience is not there yet and they know it and they're trying to make it better. And they're like, 'Well, we want to make it better in these five ways, but we have to wait till we have the data to do the AB test to make it better because we're not sure.' And I was like, listen, I may be one of the foremost advocates for the use of metrics in business in the whole world and even I can tell you that that's stupid. What are you talking about? You know the product is bad and you know those things are going to make it better. You don't have the, the reason you're paralyzed, you don't have enough data to make that call. This is a call that's going to have ramifications for many years. Like do what you know to be right and trust that the data will be there. Look, if eventually after you make the product better for months and months and months, the metrics don't move, then I call BS on your idea that it's better. I'm not saying the metrics don't matter, but the idea that you have to wait for the metrics to tell you what to do to give you permission, that was like, did people not read the book? Like that was the whole idea behind the pivot was optimization and honestly people think they read the book and they miss the idea.

Yeah, tell me.

Yeah, for sure.

Exactly. There was no...

Yes. The thing I last thing I wanted to ask you about on this thread is I call them the torchbearers. Like within any organization there's certain people who just they get it, they're the true believers, they really believe that and they're not necessarily the fanciest people. They're often not the executives. They're not, you know, you find them all over the organization at every different level. Often times like they do the unheralded work every day of like they come into work. It's like, okay, I got to do battle with the MBAs again today. It's like, no, I really don't think, you know, I really think we should invest in the creator experience. I really think we ought to invest in that. We got to do the right thing. Someone says, 'Hey, let's send more messages. I got my spreadsheet here.' It's like, I don't want to see your spreadsheet because I know that that's not the right thing. And those people in most organizations are beleaguered. It's like every day I got, oh my god because they can't really win any arguments in conventional thinking. It's like well you have, I've calculated the ROI down to 12 decimal places. What do you have? And it's like I just know what the right thing to do is. What do you want from me? And so like to me the reason going back to the reason to do better governance and the reason to install a strong culture and to do the culture bank and all these practices that people sometimes are like that seems like a lot of extra work. It's like, yeah, but the extra work, it's extra work for us. It's a lot less work for the torchbearers. We are equipping them with the tools they need to defend the company and its mission. And, you know, it's its intention to create long-term value from this wider world and all this pressure. And I just think we dramatically undervalue that role and the role of us as leaders in empowering those people.

That resonate with you?

Totally. Oh my god the guardian angels of the customers is such an important place to be. You're right they're just delighted to get a meeting and be heard by the people who are actually like changing the product and they're just like guys I know like this is the problem right and like stop adding stuff like make it better. Stop adding. And uh yeah, they're so important and you're right completely. They don't have the right tools to defend their arguments. And um yeah, I even, you know, think now she bring it up. It's like I didn't even listen to him enough. And I was often like on their side, but it was in that room with the product managers and the spreadsheets.

Yeah. No, that's true. Just tell us quickly about the new startup.

Wait, what?

I've been in the beta for a while. So, I mean, it's just one of those products where like every notification is one you're so delighted to receive because it's like it's actually about a friend and it's relevant to you. It's not some like influencer blah blah blah thing to make you feel bad about your life. It's like someone I actually care about is doing something that's ironically really hard to keep track of with social media.

Well, yeah, but people like their friends aren't the most entertaining people in the world in most cases and therefore that's not who they're going to get enough page views. So, uh, what if you really design something for that?

You got a few minutes. Can we do a lighting round? Okay. I just ask you a couple questions because you know we feel like we could do this for hours and so many provocative interesting things over the years. But anyway, I just I want to ask you about one like piece of business advice that I feel like I heard you say this to me and I was delighted. I saw it on the record somewhere. You just said the formula to build a billion dollar internet company. I was like, 'Yeah.' I'm like, 'Yeah, tell me the formula. It's really good.' And then here's what it is. Simply this. Identify a human desire. Preferably one that's been around for a really long time.

No, that's, yeah. Go ahead. Go ahead.

Yeah. Yeah. Is it really that simple?

A little while ago, you shared a poem on Medium that you wrote when you were 17. Now, my general view is that people should not be asked about the poetry they wrote when they were 17, but you publish it on Medium and it's so prescient. I don't even know if you feel how prescient it is. I have to ask you, can I read this poem and get your reaction? Are you willing?

Okay. Well, that's, I want, I figured Ev Williams circa, well, whenever you were 17, you don't have to say. Okay. Here's what you wrote. I'm going to bring it over a second and read it to you. 'Persons yelling, noisy people all around, flaring up and calming down. Down through the gutters in the streets. They flutter and float and romp in the bogs of life like dogs, teasing flesh and chewing bones, ignoring the rising tones of moans and death.'

Wow. You said you're doing better now, but I was like, is that basically where we're at with social media? Is that how it feels to be on? I was like, I have days now where I'm like, yeah, that's how it feels.

How's it feel to hear that now all these years together with social media on that?

Thank you. Thank you for letting me read the poem. I just thought it was very cool to get a glimpse into your mind at that time and yeah, how strange to feel from that moments of idealism about how the internet would become to this feeling of like it's become this very like violent thing.

Last question, are you still optimistic about the internet?

All right. Thank you. That's a great way to end. Thanks for taking the time. It's better than ending on the death poem.

And I feel like I want to say that I appreciate your optimism in spite of everything and like especially the work you do through Obvious Ventures like trying to invest in world positive things. Like I think there's still a role for optimism to say like you know yes we learned some lessons but there's work to be done. So thank you for doing it.

You've been listening to the Eric Ries Show. The Eric Ries Show is produced by Jordan Bournestein and Kiki Gwe. Research by Tom White and Melanie Rehack. Visual design by Reform Collective. Title theme by DB Music. I'm your host Eric Ries. Thanks for listening and watching. See you next time.