REID HOFFMAN: Silicon Valley tends to lionize entrepreneurs who take hairpin turns in their careers. The sharper the turn, the greater your prestige. Steve Jobs made his name not just at Apple but through his diversion to Pixar and back again. Elon Musk is approaching demigod status with Tesla. SpaceX. Hyperloop. And the Boring Company. His career is downright swashbuckling. 

Those daring, shape-shifting figures can inspire us to shoot for the stars and burrow through the earth — at the same time. But watch them too closely, and you may derail your own destiny. You may start telling yourself something like this.

EV WILLIAMS:I should do something completely new and different. Maybe I’m just stuck in a rut…

In some ways, that didn’t excite me, it felt a little bit derivative of the things I had already done…

I actually hesitated because I’d been doing the same thing for so long.

HOFFMAN: That Hamlet of the entrepreneurial world is my friend, Ev Williams. The Ev Williams. He’s the co-founder and former CEO of Twitter. Before Twitter, he was Co-Founder of the service Blogger. Those two services transformed the way we communicate online. They popularized verbs like “blogging,” “tweeting” and “following” — of course, “following” predates Twitter, but it was redefined by it. 

With Blogger and Twitter under his belt, you’d think this maestro of online communication would double down on his next disruptive venture in the world of self-publishing. But this is where Silicon Valley’s obsession with all things “new” and “different” can go a bit too far. It can lead established entrepreneurs into an eddy of self-doubt, until they’re circling around questions like this.

WILLIAMS: Do I want to actually do this? Is that my thing? That’s a big decision. 

HOFFMAN: Fortunately, Ev made that big decision.

WILLIAMS: It’s very valuable to do the thing you’re obsessed with that you just think about all the time. If I have all of this time and intuition that has been built, that’s an investment, that’s actually an asset. But like, not doing this I thought I would regret much more.

What excited me originally was just that feeling you get sometimes from technology of the seeming magic to it; you did something, it was just delightful to have this idea in your mind, and it’s on a webpage, when you create something yourself and you’re like, “Oh, wow, I did that.” 

HOFFMAN: And like that, Ev launched his third venture: Medium, a one-stop shop for every thoughtful, medium-length article online. Medium is Ev’s third attempt to reinvent the world of self-publishing in his long, but not so winding career.

Make no mistake — while a career that twists and turns and nearly flies over a cliff is certainly fun to watch — it’s not necessarily the path you should follow. In fact, if you’re a thoughtful, reflective, mission driven entrepreneur, like Ev, you may find yourself chasing the same big idea. Again and again, you return to it, sometimes wittingly, sometimes unwittingly. 

And just when you think you’re out, it pulls you back in — to quote Michael Corleone from the Godfather part III. 

But here’s the thing, you shouldn’t feel fatigued by the repetition. Instead, you should celebrate your single-mindedness, your focus. I believe you can never know the full reach of your first idea. It could span your entire career.

[Theme Music]

I’m Reid Hoffman, founder of LinkedIn, investor at Greylock and your host. I believe you can never know the full reach of your first idea. It could span your entire career.

There’s a set of entrepreneurs who see a transformative change taking place in the world — a change that is so profound they can spend a lifetime playing out the possibilities in their heads. They say to themselves, “I know the world’s moving in one particular direction and I’ll just keep betting on the world going in that direction.” 

And suppose you’re right — the world does, in fact, start moving in that direction. You’ll be surprised how many times you’ll want to ride that wave.  It doesn’t matter if you end up having the ride of your life or an epic wipeout — you’ll just keep paddling after it.

Ev Williams and I are similar in this regard. Ev, to me, is the embodiment of the serial entrepreneur who’s been riding the same massive wave of change throughout his career.

And to understand how Ev first caught this wave, you have to go all the way back to his childhood — to a farm outside of Clarks, Nebraska. 

WILLIAMS: It was a very small town. It was around 400, 450 population. Where I grew up, we were actually outside of town, so we drove four miles to school, and there were 12 to 14 kids in my class from K through 11.

HOFFMAN: And in this tiny community, Ev didn’t exactly fit the mold. 

WILLIAMS: It was a very isolated experience. It was literally in the middle of cornfields. You knew everybody. Football was the main interest of people that brought the community together, lots of sports, lots of hunting, not much else. And that was my life. 

HOFFMAN: That was his life in the real world at least. But Ev, like many lonely kids in the 80’s, was leading a double life. He had one foot planted in Clarks, the other planted in the virtual world. It turned out his family farm was just the right place for Ev to get an early introduction to the dawn of computing.

WILLIAMS: My dad had—did have a computer in the ‘80s. He was an early adopter for farm purposes. So he had an IBM PC with some spreadsheet software and different farm software. I tried to figure that out. Didn’t really succeed much. But then in high school, we had some Apple IIs in our computer lab. We had mandatory basic programming when I was a sophomore, and I loved it. 

That was when I was just stricken by, oh my gosh, I can—this works for my brain. I stayed up late. On more than one occasion, the school shut down, the lights were shut off, and the doors were locked while I was still sitting in that computer lab.

So, that feeling of flow that you’re really just doing something that is creative, and exciting, and technical, and hard, and that’s when I felt that.

HOFFMAN: Programming was just the spark for Ev. What really set his imagination on fire was an article in Wired magazine. Ev still remembers the piece to this day.

WILLIAMS: I picked up the second ever issue of Wired on a newsstand. I remember talking about connecting all the brains on the planet, and about the instantaneous publishing of text and ideas, and all these utopian ideals. 

HOFFMAN: Utopian as it may have been, Ev took it deadly seriously.

WILLIAMS: That got me very excited. And I got it because of playing with bulletin boards. And I had a PC at the time that I would dial into things with, and that just immediately, I found very exciting.

HOFFMAN: Now this is the wave that Ev will start riding. From the outside, it might seem like his passion is to empower self-expression. But there’s a deeper force that will carry him from Blogger to Twitter to Medium.

WILLIAMS: I have been focused on essentially the same problem throughout most of my career. The Internet was very exciting because of this idea that all these minds were connected.

And that there is great stuff in these minds out there in the world somewhere. And the Internet is this big machine that takes certain bits from these minds and puts them in other minds.

And so to me that’s like this fascinating possibility, and then these tools that we build are like different approaches to make that machine work.

HOFFMAN: Now this idea of connecting minds into one great, big thinking machine may sound a bit abstract. But over-arching visions often are. It’s exactly what makes THIS kind of vision one that can stretch over an entire career. 

But the challenge of these big, broad areas of fascination is you don’t always know how to start. And your biggest opportunities will change from year to year. 

Technology changes, business changes, competitors change the landscape. 

But if it’s a vision that’s meant to guide you, you’ll start to feel the pull. And Ev felt an early pull.

WILLIAMS: I was trying to think of, what’s the business? What’s the product that I can do on this? So, I was thinking very creatively with what can I create that I actually know how to create? And though I had programmed, I didn’t really know much about how to do that. So, I just said, well, the biggest problem with the Internet is most people don’t know how to use it. So, we need to teach people how to use it. 

HOFFMAN: Now bear in mind, we’re talking about the late 80’s internet — which was a decidedly unwelcoming place for people who didn’t know how to code. The web had just been invented. Only a handful of people had email addresses. The first step toward Ev’s vision was simply to get people online. So he created a guide for the confused internet user. 

WILLIAMS: So, I thought, the way to teach people how to use this is to show them, so I made a video on how to use the Internet — we actually made a VHS tape. And it was just before the web, actually, was taking off.

And so, the World Wide Web, of course, makes a brief mention. But a lot of it was command line, how to FTP a file, and how to email with Pine. And it was an incredibly tedious and incredibly amateur how to use the Internet video. That was my first Internet product.

HOFFMAN: This may sound like a quirky high school project. But this idea — that the internet should be easier to use — is actually the wellspring of Ev’s creativity. Throughout his career, he’ll keep returning to the same question: what’s preventing people from sharing their thoughts online? The question never grows boring, because the answer is constantly changing. It evolves along with technology and culture. 

I actually think Ev and I are similar in this way.

As you may have noticed, I’m really interested in how people connect online. My interest pre-dates LinkedIn and PayPal. It predates my investments in Facebook and Flickr. 

It began back in the 90’s, when I began studying the original online communities. Where could you meet other users online? You could go play in a virtual world, you could join a chat room, you could post on a message board, and so forth. All of these unregulated spaces were sort of like costume balls — you arrived in any sort of disguise you liked. 

There was a New Yorker cartoon at the time that summed up the pervasive failing of mistrust. Sheryl Sandberg, Chief Operating Officer of Facebook, reminded me of it in our interview.

SHERYL SANDBERG: It’s hard to remember but you know this is where they had that cartoon you know with the dog at the computer saying, “On the Internet, no one knows you’re a dog.” The whole idea behind all the stuff we did online was anonymous.

HOFFMAN: You could be an angel one minute and a troll the next minute — and no one would know you were the same person — just unleashing your superego and your id. And that’s what it meant to go online — to alternatively present and disguise yourself — to be part you, part fantasy. And a lot of people figured that this was just the very nature of our online identities. They wouldn’t match the real world and they never would.

But then there were the optimists — like me — who couldn’t stop thinking about the power of these communities, once users could shed the role-playing habits — and really be themselves.

People like me would say to the skeptics: no, no, these patterns, this participation in these networks, these communities, these communication tools, these are all part of our real world and what really matters to us is our real-world identities and our real-world lives. The change was coming — and the bets you could make on that change were mind boggling. And that’s the long game I’ve been playing ever since. I suspected at the time that this change was huge — I could never have known where it would take me — and how much I would learn along the way. But this intersection between the online world and the real one, that remains the guiding force of my career.

And Ev, as we’ll see, also has a guiding force. After creating that VHS guide to the Internet — he followed the natural pull to move to Silicon Valley, where he worked for O’Reilly Media, writing technical manuals for the first generation of web engineers. While he was there, he started a website called “EvHead.com” where he captured his own thoughts. 

WILLIAMS: It was one of those scratch your own itch things. So, I had had a personal website and started reading what people called weblogs at the time. I was like, well, I’m gonna make my EvHead.com into a weblog. And because I knew how to write code and web applications, I wrote a very simple script that let me go and type in a box, and I hit a button, and that was at the top of my homepage. And I remember doing that, and it’s that feeling that we’re all very familiar with now, where you have a thought and you consider putting it on the Internet, and closing the gap to doing that to literally seconds. That’s where the inspiration came from.

HOFFMAN: Ev called that tool “Blogger” — and it’s the reason the term blogging stuck. More importantly, it was outside of the quirky little community of programmers. Blogger heralded a much bigger shift in online behavior.

The more people come online, the more accustomed they became to sharing and consuming ideas in this way — and then Ev builds a solution that taps a geyser of self-expression.

When a blogger posted to the internet, they essentially live streamed their lives in as much detail as they pleased. Stranger still, they invited friends to follow and reply in the comments section. And that behavioral shift paved the way for Facebook, Twitter, LinkedIn, Airbnb and any other social site or marketplace that simply couldn’t exist in a world of anonymity.

As blogging took off, Ev devoted more time and more people to his growing platform. But he wasn’t quite sure how to turn Blogger into a viable business. He had raised a seed round of $500,000, but it was dwindling.

WILLIAMS: That money ran out in late 2000, that was, for us, the beginning of the dark times.

I sat the team down and said, “Look, in two weeks, we’re not gonna be able to pay you.” So, essentially, this is the last paycheck we can pay. We had already like skipped one. I told them, “You’re welcome to come back tomorrow. I’m gonna come back.” But none of them came back. That was hard.

HOFFMAN: There’s a myth in Silicon Valley, that successful entrepreneurs, like oil prospectors, ultimately just get lucky. They sink a well in the right field at the right time, and they’ve been cashing in on that geyser ever since.

And I won’t deny that luck plays a huge role in any highly risky career. But I don’t know of many entrepreneurs who strike oil on their first try, or their second, or even their twentieth attempt. You need some reason to keep going. And this is what we normally call grit or persistence. 

That persistence, that endurance, that grit, can actually lead you to scale.

To understand a little more about where grit comes from — and what inspires it — we reached out to Angela Duckworth, a psychology professor whose research cemented the connection between perseverance and success. Google the word “grit” and the second result is her TED talk. She says that grit actually begins with goals.

ANGELA DUCKWORTH: Human beings have goals. You want to have lunch today. You want to call this person back. 

The reason why I’m trying to do these things is trying to reach these other goals that are actually of more enduring importance to me. “Oh, well, the reason I have to call that person back is actually that relationship matters to me.” Why does that relationship matter to you? You keep asking this question of why until you get to the top level goal, that gives meaning and purpose to everything else that you do.

HOFFMAN: Whatever’s at the top of that hierarchy makes everything else fall into perspective. And that’s what keeps someone like Ev — or me — in pursuit of that one idea. You keep going because every single thing you do is in service of your vision.

DUCKWORTH: When you’re a truly gritty person, you have tremendous clarity about what that top level goal is, that life philosophy that drives everything else, and you actually are very good at aligning your day-to-day actions, your to-do list task list to that top level goal. You don’t waste time doing things that are unrelated to the top level goal, and you’re really stubborn. When you’re trying to reach that top level goal, and one of your low level tactics isn’t working out, you get up again, and you think of some other way that you can get the job done.

HOFFMAN: Ev found ways to get the job done. For two years — after his funding ran out and the rest of his team left — he kept developing this new service, Blogger. Most other entrepreneurs would have packed it in. And I’d argue that this is why many entrepreneurs fail. 

Ev stuck with it. He stuck with it because he had a vision that focused on a bigger problem. And this is the hallmark of an entrepreneur — or an artist, or a scientist, or an activist, or anyone really — whose first idea can span their entire career. 

You just tell yourself, “I know this problem needs to be solved, this solution needs to be built, it needs to happen.” 

And after two years of working out of his apartment, without a paycheck, someone came knocking. Google. You might have heard of them.

Ev sold Blogger to Google in 2003, and went to work inside the mothership. This validated his single-minded dedication. And he also got a few shares in Google, which would turn out to be quite valuable.

Then, Blogger was eclipsed by the competition.

WILLIAMS: So, I was at Google a little over a year-and-a-half working on Blogger the whole time—we started to build things that were attempts to make it an aggregation. But our frustration was really, we’re building this software. It’s the easiest way to start blogging. And then people would move off Blogger, because there was no network effect. There was no reason for them to stay there.

That’s when we started on it more, and we built profiles, and we built links between the profiles. 

HOFFMAN: He was in a race to build features that were precursors to a social network. But there was just one problem — Ev never really aspired to build a social network.

Remember, his vision is to connect brains — not to connect friends or foster a sense of community. The lifeblood of social media is not just self-expression — it’s communal interaction: The friend invites, likes, pokes, comments and other notifications that deliver a dopamine hit and keep you engaged. 

The fact is, those features never really engaged Ev. 

WILLIAMS: We didn’t build comments into Blogger for a long time.

And that actually hurt us as because for some people like it was all about the comments, all about hearing from people. I was like, “Eh, I don’t really want to hear from people. I just want to puts some thought out there and read other thoughts.” 

HOFFMAN: So what features did he want to build? Any feature that enabled a deeper exchange of ideas.

WILLIAMS: There was a feature that I was really enamored with called NextBlog, 

was meant to do was drive traffic to blogs, obviously. And there was in theory going to be some intelligence to it, so you could see something related or something that you followed before we even had the word follow. And but the very first version of it was literally some script I wrote where that would go query a database and randomly select a blog out of the thousand most recently updated blogs, and redirect you to it.

HOFFMAN: But the NextBlog feature wasn’t sufficient to fend off the competition. Blogger eventually slipped under a tidal wave of social media trends. Why maintain a blog, when you’re already spilling out your life on MySpace, Friendster, and ultimately Facebook?

You may think this was a huge missed opportunity for Ev. He had a nascent community of users. He had users identifying themselves, sharing confessional posts. It sounded like all of the ingredients for a primordial social network. 

I’d argue Ev’s advantage is that he’s never distracted by the business model in vogue that season. He stays focused on that first vision, which will rapidly define the arc of his career.

He’s interested in elevating the conversation — in sharing the most insightful posts. 

He never could have related to the users who aspire for more followers or watching the number of “likes” climb on a witty Facebook post. Most of our brains deliver a dopamine hit from this sort of digital applause. Ev’s brain? I won’t claim to understand how it works — but here’s a clue of just how little satisfaction he derives from casual socializing online:

WILLIAMS: And so that’s not motivated me, not to say I’m completely antisocial, but this is not how I look to where the most value of online interaction was.

HOFFMAN: So it might seem rather ironic that Ev, the champion of deep, meaningful monologues — should end up scaling the shortest, most reactive form of self-expression in internet history: Twitter.

How did Ev, of all people, wind up as Twitter’s co-founder and CEO? Unexpectedly. It actually grew out of a dead end on Ev’s road to scale. Here’s how it happened… After Blogger, Ev was drawn to a new medium: Podcasting. This was 2005, and the first generations of podcasts had just emerged. They were taking certain segments of the tech community by storm. 

If everyone was so eager to express themselves in writing, Ev figured it would only be a matter of time before they’d start sharing ideas in audio. He figured: Speaking was even easier than writing. So the quickest path to share a thought from one brain to another might just be audio. 

So, in 2005, he launched a new company, Odeo. He envisioned it as the premiere platform for podcasting. 

And not just podcasting. Switching from writing to speaking, it would be even bigger than Blogger. It had to be.

WILLIAMS: I thought audio given my experience with blogging I thought, “Oh, well, this is even easier because talking is easier than writing.”

And it turned out talking maybe easier than writing, but creating listenable podcasts or listenable audio content is actually much harder than creating readable text. 

HOFFMAN: As a new podcaster, I can tell you, Ev is absolutely right about that.

WILLIAMS: I realized audio was actually a less casual form, if you will, and could be very powerful, but it’s just much harder to do and not within the bounds of what most people can sit down and do even if they had great stuff in their head.

HOFFMAN: Ev secured $5 million in funding, he built a platform for podcasters to publish their work and listeners to discover content. It was expensive. It was ambitious. You might even call it a marketplace. Or not.

WILLIAMS: I don’t know if we called it a marketplace, but we were gonna do discovery and creation, and you know, this big comprehensive thing. And before we launched anything, Apple came out with podcasts integrated into iTunes, which kind of blew our minds, because it was so early.

HOFFMAN: When Apple beats you to market, it’s never a good sign. Especially when your company’s potential audience is Apple’s installed base of iPod owners. Ev wasn’t sure what his next move would be.

WILLIAMS: So, I went to the team and we did this very deliberate process where I said, I don’t know if podcasting or Odeo’s our thing. Who’s got ideas? And we did essentially a hackathon.

HOFFMAN: The hackathon has become a tried-and-true method of generating ideas. The process is simple: You bring together all your employees — traditionally, it would focus on the technical employees, but smart companies engage everyone. And you challenge them to come up with an idea they can build in one marathon hacking session. Usually, everyone is trying to solve for a specific problem. In Ev’s case, they were solving for the company’s future: What should they do next?

This Odeo hackathon proved unusually fruitful. Historically so. Odeo’s Co-Founder Biz Stone and web designer Jack Dorsey came up with the winning idea. 

WILLIAMS: A lot of the ideas were in a similar space because we had been toying around with messaging, and SMS, as well as audio. One of the ideas was a group texting type product. But then what became Twitter didn’t have the name Twitter. It was one of the others that Jack and Biz came up with. 

It just seemed like something. It was simple. It was elegant. It seemed fun. 

HOFFMAN: This simple, elegant, fun messaging service actually felt oddly familiar to Ev. It turns out, he had sent tweet-like messages in the past, back in his Blogger days.

WILLIAMS: I built a blog for status updates, and it was completely private. I shared it with my team. And I went on this short trip for family purposes. And on the trip, I was sending what essentially were status updates, which is how we thought of tweets at the time before we called them tweets.

And before we had even built something, or maybe while the team was building something, I just built this prototype using existing technology where I sent status updates to a private blog, and that resonated with me. That felt like something interesting and unique. It was sharing this thing that you didn’t normally share

HOFFMAN: Of course, the buzz around Twitter forced Ev to answer a tough question. 

WILLIAMS: Do we need to actually pivot? Every board meeting, I would present them Twitter and what was going on with Odeo. Odeo was—even though it was going sideways, it had users. I remember realizing at the time that sometimes it’s better to fail than it is to not fail if you’re not gonna, you know, succeed. And Odeo —it had, you know, usage. We couldn’t ignore it. It wasn’t a total failure. And so, we kept iterating on that and thinking, well, maybe there’s something here.

HOFFMAN: In April of 2007, Twitter spun off from Odeo. Odeo was gradually wound down, and once more Ev was on the cusp of changing the way we communicate online. 

Twitter may sound like a departure from Ev’s goal of connecting the world’s brains. On the contrary, Ev argues, that vision shaped Twitter from its inception. He saw Twitter as one way of getting people to share their thoughts at unprecedented speeds. 

To him, it sparked the world’s first collective brainstorm.

WILLIAMS: I have a thought and now not only is it online but it could be in other people’s brains in seconds instead of somewhere within the next week if someone happens to find my blog or reads the RSS feed. It’s very visceral. And the one example we always referred to is early on and there’d be an earthquake in San Francisco and you’d turn to Twitter. And at times we even experienced a phone buzzing with tweets about the earthquake while still feeling the earthquake.

And so that idea of feeling, being connected in real-time, is really the real-time that made all the difference as well as the idea that you are really broadcasting, not publishing. So I think it was just more a pure expression of brains being connected.

HOFFMAN: For the first few years after Twitter’s founding, Ev was adamant that Twitter would never become a venue for kibitzing, like Facebook. Twitter was a forum for broadcasting, for speaking out loud to the wider world — not just your social network.

WILLIAMS: This came up a lot, of course, when we were doing Twitter, which many people classify as a social network. And I kind of railed against that especially early on when we’re still trying to figure out what all these things were, and Facebook was fairly well-established. Twitter is not a social network. I argued, I argued Twitter is an information network or real-time information network. Social information was a subset of what Twitter provided, and actually it wasn’t the point, some of the people you want to hear from are social connections, but there’s a whole world of other people.

HOFFMAN: This vision of Twitter as a public forum deeply influenced every facet of its design. The word “follow,” for instance, reminded users that Twitter wasn’t just a place to tell your friends were thinking. Strangers could follow your thoughts as well. 

WILLIAMS: There was a talk I gave a year or two into Twitter, where I talked about how at first, we thought the big thing about Twitter as compared to blogging was that it was short, which enabled real time-ness. It enabled mobile-friendly. It was built through SMS. But we invented this follow button, and I think we invented the follow term. In fact, I remember that we had debates about follow. Is it creepy to say you follow someone? And—

HOFFMAN: You didn’t prefer I stalk someone, or?

WILLIAMS: Well, yeah. We thought about that. We had lots of jokes about that.

That’s why although the very first version of Twitter had a concept of “friend”, eventually it was like, no, it’s not “friend”, it’s not two-way, they don’t have to approve you. It’s a follow, subscribe model. And even things like retweets, the design of those got influenced by this idea that it’s about the dissemination of information more than it is connecting with your friends or having social interactions.

And what is interesting is that framing at the time was also, well, Facebook was very much focused on the social. And, of course, all these things expand to do the adjacent thing as well.

HOFFMAN: Notice how Ev’s thinking has evolved since the Blogger days. Remember his original reaction to the idea of user comments on blog posts? 

WILLIAMS: Eh, I don’t really want to hear from people. I just want to put some thoughts out there and read other thoughts.

HOFFMAN: He has a newfound appreciation of the value of user comments. And you can actually spend a whole career discovering how odd little behaviors that emerge online can redefine the network you thought you knew. 

A network isn’t simply a web of users. It’s a launching pad for more robust communication, deeper trust, and greater understanding. New behaviors emerge as they grow accustomed to one another in this unfamiliar new venue. And that’s when the true value of the network first comes into view.

For example, in the early days, when I said, “LinkedIn can help you search for a job.” Most people would then say, “Oh, so you can browse the classified ads.” And I’d say, “No, no, no: “You can look for a company. You can actually look for a hiring manager. You can look at the profiles of other people who work at that company. And a company can search for job candidates like you. And then ask you, ‘Who else do you know?’”

And why stop at job searches? LinkedIn could also answer questions like: “How do I stay up to date on information on my industry? How do I learn the right skills? How do I find the right people to do business with? How do I connect to them?” All of that becomes applications on top of this network, which then, in turn, feed back into the network. 

It’s exceedingly hard to imagine all of those emergent properties as a first-time founder.

In fact, if there’s one thing Ev wishes he could tell his younger self, it’s about this emergent power of the network.

WILLIAMS: It’s about the network. The value is in the network, the value is not in the software that the Internet enables, the value is in the network, because there are so many implications of that.

I’m obviously preaching to the choir and talking to the king of networks, but I didn’t realize that, certainly in the Blogger days.

HOFFMAN: As flattering as it is to be called the king of networks — I’m going to have to refuse that crown. To be clear, I understand the dynamics of networks. I understand how quickly they can change and how rapidly new opportunities can come into view. But I would argue that networks are such strange, fast evolving organisms — no one could claim any and all networks as their personal, royal dominion. 

In fact, I would argue that Ev has developed an expertise over a specific kind of network — a network that enables the discovery, and distribution, and transmission of information. 

And he’s become a master of building the platforms for those kinds of conversations. And this is a skill uniquely suited to Ev, after a lifetime of trying again and again to build this network.

Of course, that’s not the only lesson Ev had to learn as CEO. As the company grew exponentially, Ev found himself — as so many founders do — in uncharted territory. 

WILLIAMS: It was an incredible two years that I was CEO. The company in general grew 10x across every measure that we were counting, including ones that maybe we shouldn’t have been. But I was definitely in over my head. It was by far the biggest thing I’d done. The company grew from 30 people to 300 people during that time. I grew an exec team from nothing. And I never considered myself a great manager, and I think I didn’t spend enough time thinking about the people and the pressures that they were under.

HOFFMAN: Ev had started the company to build a product — the great connected brain. But he soon realized that he also needed to grow a team. And the skills that make someone a brilliant and visionary product developer — someone intensely focused on vision — aren’t always married with the skills to manage the team to get there.

WILLIAMS: I underinvested in relationships, I underinvested in the time to really understand what was going on with people around me. And that’s what caused the turmoil. And it the classic lesson of communicate, talk, listen to people. I was obsessed with the product and the strategy and where we were going next, and capturing the opportunity we had. And less on the team. And we had raised a lot of money, and the company was growing, so I assumed the board was happy, and they weren’t telling me otherwise, so I didn’t invest in that either. And that got me into trouble.

HOFFMAN: With some turmoil unfolding between his executive team and his board, Ev took a step back. Dick Costolo became CEO of Twitter, allowing Ev to focus on product. And the leadership lesson Ev took from this period of time will serve any founder well. The top line: Ask for feedback.

WILLIAMS: If you’re not getting feedback, there’s probably some negative feedback that you could be getting. That probably would have helped me a lot. I wasn’t getting any, so I assumed everything was great.

HOFFMAN: By 2010, Twitter was a huge success — but Ev saw it only as a half-step toward his vision of a robust virtual meeting of the minds. If the internet is one big machine of connected minds, Twitter helped get all of the synapses firing willy nilly — which was an extraordinary accomplishment— but that’s not a thinking machine. It’s more of a twitchy, gut-reaction machine.

There was another part of this thinking machine that hadn’t been built yet — you might call it the “cerebral cortex:” a place for deep thinking, a place where users could spend a little bit more time polishing and expanding their thoughts before wheeling them out for the public.

Nice idea, but Ev was the founder of Twitter. That ain’t the platform for polish. Never will be. And this meant that Twitter became Ev’s gilded cage. A huge, irresistible opportunity for scale, and a stunning success — but it didn’t feel like he’d reached his ultimate vision. 

This can happen to anyone in the business of creating something new: You put your blinders down and speed down one path, and suddenly you realize you’re miles away from where you were trying to go. And at that point, it’s hard to double back and find where you went off-course. Especially when the company is highly successful, and has its own natural path — and doesn’t reach the destination of the founder’s vision.

Ev was torn. He took a year to retrace his steps – and not only retrace them, but figure out where he was trying to get in the first place.

WILLIAMS: There is about a year after I left Twitter and before we started Medium. And my next thought was whether or not I wanted to pursue that opportunity.

And I thought, if I believe in this, this principle that you should actually focus on what you naturally focus on, and really it coming down to impact.

HOFFMAN: So many people would have been delighted to found a company like Twitter and scale it for the rest of their working lives. But Ev couldn’t stop thinking about his larger vision. 

This idea of the thinking machine is like his creative center of gravity. And no amount of success can pull him away from that vision for long. He keeps returning to it.

It’s as if he had said in the middle of Twitter’s fabulous growth, “Who cares about that tower of Babel? Metrics like monthly active users are not my measure of success. I care about what they’re saying, and who’s listening.” 

Ev wanted to elevate the conversation. Not just make it louder.

Turns out, this part of the thinking machine had been utterly neglected by every founder of social media. And by publications that historically generated that thought-provoking, insightful content that Ev was after. Ev thought that those publications were making a serious mistake by trying to manage their websites themselves. Their efforts resulted in a critical failure of innovation: their content didn’t have the potential to go viral, or be retweeted, or get applauded.

WILLIAMS: We’re just talking non-social media, that was still published on individual, isolated websites, often with outdated and cumbersome CMS software.

That certainly didn’t find its audience efficiently. It didn’t have built-in feedback loops and mechanisms. So, if you’re publishing on the Internet in a few years, it’s gonna make less and less sense to do that on a standalone isolated website that you build from scratch and then try to get people to come to. And even if you get them to come there, they’re not logged in, and any sort of engagement is hard to garner. If you could instead publish into a platform and build an audience, that’s gonna be more efficient and more likely to succeed.

HOFFMAN: Think about the arsenal of learnings Ev has acquired by now. He’s launched Blogger — one of the first venues for freeform publishing. He took his lumps at Odeo — and learned how hard it was to populate a platform with meaningful content. He helped Twitter grow from a company side project to a global powerhouse of a network.

It’s like with each company, he’s seen a different part of the promised land — but hasn’t put them all together until now, with Medium.

WILLIAMS: That was the opportunity. And because it hadn’t happened yet, there was no place that really owned that for a particular type of content. Creating a place where substantive, thoughtful, high quality ideas and stories would reside and find a good audience.

HOFFMAN: That place? Medium. And Ev might have finally found his place, too.

WILLIAMS: We’re five years into Medium now, which is actually longer than I had worked on anything.

HOFFMAN: I can relate to Ev’s trajectory, at least a little bit. I’ve been trying to move closer and closer to one vision for most of my entrepreneurial history.

In fact, my very first startup was an online dating site called Social Net. But no one ever introduces me as the founder of Social Net, because no one remembers it as vividly as I do. It means something really different to me than it does to anyone else. It was my first ride on the larger wave of social networking. I may have wiped out – but it was an invaluable wipeout.

Because after that – when I was investing in Facebook, and founding LinkedIn – I knew a lot more about how people connect online. I was better equipped to get a little bit closer to my vision.

Someone like Ev isn’t necessarily asking, “What’s the next big thing?” They’re really asking, “How do I realize my vision? How do I take one more step toward THAT future?”

In Ev’s case, Medium is working toward being an answer to that question. 

WILLIAMS: When we started Medium five years ago, I told friends who were in the tech business that I was gonna create a place to publish on the web. And they were like—kind of scratched their heads and like, “Mm, isn’t that already a solved problem?” “Well, actually, you know, we think we can create a better solution for that.”

In the marketplace for stories and written content and ideas, you can slave away, and maybe you can garner an audience after a few years, but then if you’re lucky, you’ll get a job.

Or if you’re lucky, you’ll get a book deal. And so—and there’s really nothing in between. And so, I think what we really haven’t democratized yet when it comes to the Internet is the ability to compete at a professional level in this form. And we don’t yet know what comes of that because it hasn’t existed yet. But that’s what I’m most excited about.

HOFFMAN: Even Ev doesn’t know what’ll come out of Medium. Just like he didn’t know where Blogger would take him, or what the future of podcasts would be, or the new kinds of interactions that Twitter would create. You never know just how far your first idea can take you. It might take Ev away from Medium, onto another part of that giant thinking machine he wants to build. It may lead him to company number four, or five, or six. We don’t know what it is yet, and maybe Ev doesn’t yet either. He just knows what he’s working towards.

I’m Reid Hoffman. Thank you for listening.