I grew up in a very affluent town, but my parents divorced when I was young. My father wasn’t much involved in my life, and we were poor. Many kids I knew played Little League baseball and Pop Warner football, but I didn’t—by the time I was eight, I was mowing lawns and trying to earn money.
When I got to high school, it was immediately obvious that if you were on a sports team, you’d automatically be more plugged-in socially. I’m naturally athletic, but I’d never played organized sports; I tried out for basketball, baseball, and football, but I wasn’t good at any of them. Our school didn’t have a boys’ lacrosse team, and I figured that since no one else knew how to play lacrosse either, everyone would be as clueless as I was. So I persuaded the administration to start a team if I could find a coach and enough boys to sign up. And I did. Eventually I got very good at lacrosse and became team captain.
There’s a valuable lesson in that experience—one that applies to business, too. Some people think of opportunity the way it’s defined in the dictionary—as a set of circumstances that make something possible—and they talk about it as if it just arrives organically. You “spot opportunity” or wait around for “opportunity to knock.”
I look at it differently. I believe that you have to be the architect of the circumstances—that opportunity is something you manufacture, not something you wait for. As I reflect on the first 40 years of my life, one of the patterns I recognize is that I’ve continually manufactured opportunities instead of standing by waiting for them to occur. This was true early in my career; it was true when some friends and I created Twitter; and it’s apparent in my latest ventures. Entrepreneurship is really all about creating your own opportunities. That’s especially true with a start-up. You simply declare yourself the CEO and start filling out the plan.
An extreme example of creating an opportunity led to my first full-time job. I was attending the University of Massachusetts Boston on a scholarship, and I wasn’t really enjoying it. I had a part-time job at the publishing company Little, Brown, moving boxes as part of an office relocation. I got to know some people there who designed book jackets. At the time, they had just shifted from X-ACTO knives and paper to Mac computers. Growing up, I had a friend with a Mac, so I’d been using Photoshop and Quark for years.
One day, when I was alone in the office, I found a transmittal sheet—basically, an assignment to design a jacket for a particular book—and quickly created one on the computer. I stuck it in the pile of submissions and didn’t tell anyone that I’d done it. A few days later the art director began asking who’d designed that cover, which the editors and the sales team had chosen as the best. He was surprised to find out that the box guy had done it. Once he learned that I knew how to use design software, he offered me a full-time job. I figured that since people go to college to get jobs like this one, I’d give up college, take the job, and treat it as an apprenticeship. The director became an important mentor and a close friend of mine, and I learned a lot about design and creativity.
Building Culture, Smoothing Transitions
Eventually I left Little, Brown to start my own design shop, and I quickly discovered that there weren’t enough freelance book jacket assignments available to keep me busy. This was in the late 1990s, when the web was just becoming popular, so when someone asked me to design a website, I learned how to do it. Over the next few years I learned more about the web. I moved to New York to cofound an early social-networking start-up, but I didn’t like the way the culture was evolving, so I returned to Boston.
In 2003 Google announced that it was buying Blogger, an early blogging site. I’d been reading the blog published by the site’s founder, Evan Williams, and I e-mailed him to say I thought we should work together. Evan arranged for Google to hire me. I went out to California thinking I already had the job, but what I really had was a full day of interviews at Google. None of the people I talked to there knew why they were thinking about hiring a guy without a college degree when Google tended to hire people with graduate degrees in computer science. But Evan talked them into it. I loved working at Google with Evan, and after it went public, my stock options started to become very valuable. If I’d stayed, I would have been a millionaire, which is a big deal for a kid who grew up on welfare. But Evan left to start a new company, and I had to decide: Had I moved to California to work at Google or to work with Evan? I chose Evan.
Evan’s company was called Odeo. We were trying to create an early form of podcasting. I wouldn’t say it failed completely, but it wasn’t successful, partly because Apple moved into podcasting aggressively as the iPod became popular. By early 2006 it was clear that our business model wouldn’t work. So Evan told everyone to pick a partner and spend two weeks hacking together an idea for a new product.
My closest friend at the company was Jack Dorsey, and it was kind of like gym class when you have to pick a partner—I knew I would pick him. Jack used AOL Instant Messenger at the time, which allowed users to post a status update if they were going to be offline—“I’m at lunch,” for example. “Maybe we can turn short status updates into a thing,” Jack said.
Originally we focused on mobile phones, with the statuses arriving by text message. We came up with a prototype, and at the end of the two weeks we showed it to the rest of the team. They were underwhelmed, but Evan suggested we continue working on it anyway, and as we did, it improved. To choose a name, we had a bunch of colleagues write suggestions on scraps of paper. One of them suggested Twitter, and I advocated loudly for that choice. Later I drew the bird that became the site’s logo. I also developed some of the key terminology, such as the idea that you “follow” another person. (The original plan had been to have a “Listen” button.) Jack and I share the patent for Twitter’s technology. As a child I’d always wanted to be an inventor, so I’m very proud of that patent.
Everyone else at Twitter was a coder or a computer science graduate. I wasn’t, so I had to create my own opportunities to contribute. I was a designer. My job was to bring humanity to the technology. I focused on the product and made suggestions to improve it. I also helped shape our story for the outside world. At first people tended to focus on how many users we had—the engineers were particularly concerned with the numbers. I convinced everyone that when people asked about our numbers, we should say “Numbers don’t matter,” and we should try to make the brand sound bigger than it was. Early on a friend from Google had asked me, “What do you want Twitter to look like five years from now?” I tried to keep us focused on that question.
I also made it my job to build the company’s culture. A culture is going to form whether you like it or not, and if you pay attention to it, you can craft something that makes the company stronger. One way I tried to build culture was by blogging on the company’s website every day. I wanted to show our humanity and vulnerability, which are things more companies and leaders should embrace. Our website went down very often in the early days, and I tried to be transparent about it: “We broke. Here’s what happened. All I can say is we won’t break in exactly that way again.”
The other role I took on involved Twitter’s public-policy stance. I had strong views about freedom of speech and the idea that we shouldn’t delete content just because we’re unhappy about it. We created a very narrow set of reasons—primarily legal ones—for deleting content. I was also adamant that Twitter remain neutral about politics. That was very important when it became a tool for participants in the Arab Spring and other political events. Later on, when reports about the National Security Agency’s domestic surveillance activities came out, they noted that Twitter was the only technology company that declined to make it easy for the government to track its users. I was very proud of that.
I never wanted to be the CEO of Twitter, and I never served in that role. I always thought of myself as a supporting actor. I don’t crave power—I admired my friends who did serve in that role, and I just wanted to support them and have their backs. This became particularly important when the company made management changes—I felt it was my job to try to smooth out those transitions. Jack Dorsey was our first CEO, but later the board wanted to put someone more experienced in that role, so Evan succeeded him. Some people wanted to escort Jack from the building immediately, but I advocated to keep him in the company, to create a more graceful transition.
Later Evan and I hired Dick Costolo as chief operating officer. He’s a great product guy, a smart thinker, and hilarious—we loved hanging out with him. When the board decided to move Evan out and make Dick the CEO, I urged the directors to keep Evan at Twitter in a new role, which they ultimately did. Each time we had a CEO transition, I worked to help employees switch their gaze from the old leader to the new one and to encourage everyone to think about what was best for the company, not just the people in it.
It’s unfortunate that boards have a tendency to fire CEOs so frequently. The reality is that it’s their only tool. They’re not going to make company products better. They’re not going to grow any key metrics. So if things don’t look good, they change the leadership. Now that I’m on boards, I try to resist that impulse. I usually say, “No, let’s not fire the CEO, let’s help the CEO. Let’s figure out where he’s weak and make him stronger.” Even when it’s necessary to change CEOs, it can usually be handled much more gracefully than it is.
Tapping the World’s Knowledge
I came across the idea for my latest venture, Jelly Industries, almost by accident. I like to go on walk-and-talks—I regularly schedule meetings with smart, funny people during which we go for long walks. In 2012 I was walking with Ben Finkel, whom I’d worked with at Twitter. We began talking about how search engines work and what we would do if we needed to build a new one. I remembered something the vice president of search at Google had said: Even though there’s now a huge amount of information on the internet, most of the world’s knowledge still remains locked inside people’s minds. So how would you create a search engine to tap into that?
We wound up building an app that rolls all people’s various social networks into one and allows them to ask it questions. We named it Jelly, after the decentralized neural network of a jellyfish. It feeds off the idea that people want to help one another out, so they like answering questions. The app did fine, but not fine enough. Even if we worked on it for four years, it would be only a mild success. I wanted to create something with a bigger impact.
In 2014 we produced a new app called Super, short for Superlatives. It resulted from our team’s trying to find the bright spot within Jelly. It gives users an emphatic prompt—“The best…” or “The worst…” or “I love…”—and allows them to finish the phrase. It enables people to get out thoughts they wouldn’t ordinarily share on other platforms. It celebrates mashup and remix culture and allows people to post things that are emotional and expressive.
At Jelly I’m a CEO for the first time. After seeing what has and hasn’t worked for other chief executives in the past, I’ve learned that lack of communication is what usually causes a start-up to fail. Our company is only seven people right now, and we’re all in the same room, so it’s easy to assume that we’re all on the same page. But we’re not—I have to work to make sure we get there, even if I spend 50% of my time communicating.
The same is true for the board. If directors aren’t hearing from you, they assume you’re doing badly. If you tell the board, “We’re doing badly,” at least they’ll think, Great, he’s got it—he knows they’re doing badly. I write an e-mail to my board every week. I respond to every user e-mail. I’m constantly communicating, because I’ve learned that it’s the most important job a CEO has.
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