Stone is the latest interviewee in The Washington Post's ongoing "On Leadership" video series, which explores the personal experiences that have shaped prominent figures' character and views of leadership. In the video above, Stone talks about how an episode of "Star Trek: The Next Generation" influenced his early thoughts about leadership. The longer conversation with him — about dropping out of college, confronting failure, and keeping in mind some of Twitter's management blunders now that he's CEO of Jelly Industries — follows below.
Q. What's your definition of leadership in 140 characters?
A. Leadership can be defined as good communication plus confidence without ego.
Q. And the longer version?
A. I’m being nerdy now. One of my favorite episodes of "Star Trek: The Next Generation" is when the captain and the doctor are stranded alone on this planet, and their brains are linked by some kind of alien device so they can read each other’s thoughts. They’re trying to get somewhere and the captain says, “We’re going this way.” And the doctor says, “You don’t know which way to go, do you?” Because she can read his thoughts.
He explains to her that sometimes part of being a leader is just picking a way and being confident about it and going, because people want to be led. I remember that episode, because it rang really true to me. Sometimes you just have to lead, even if you don’t have all the answers. In fact, you shouldn’t have all the answers. If you think you have all the answers, then you’re probably doing something wrong. Good leadership means being willing to have the confidence to move forward, even if you don’t have all the answers.
Q. What leadership lesson did you learn most from watching Twitter grow?
A. One of the keys to being a CEO is communication. In the early days of Twitter, we just assumed that since we were all sitting in the same room we were all on the same page, so we didn’t really need to communicate that much. It turns out we were totally wrong. That was one of the reasons why Twitter’s service was constantly breaking in the early days.
With this new company I’ve founded, Jelly, it’s the first time I’m CEO. I now realize that half the job of being a good leader is making sure everyone knows everything at all times that they need to know, because it’s human nature to fear the unknown. And in the business world, fear translates to the assumption that something’s going wrong. If you don’t hear anything, you assume the worst.
So in my new role, I try to over-communicate as much as possible. Every Sunday I spend three hours writing the ups and downs of the week, and I send it to the board and all the employees and anyone who’s an adviser or stakeholder. I have Monday morning meetings, Friday afternoon meetings, as much communication as I can possibly have. Probably too much. But I’ve found that it’s a critical component to being a leader — that and some humor.
Q. What experiences in your youth had a big impact on your character today?
A. When I was 19 years old, I had this full scholarship for excellence in the arts to UMass, but on the side I got a job moving boxes at a publishing company. When the art department went out to lunch one day, I snuck onto the art director’s machine and I designed a book jacket. I printed it out, matted it up for approval, and when the art director got back he wanted to know who had designed this cover.
I said, “me.” And he said, “the box kid?” He offered me a job, so I decided to drop out of college.
He was my early mentor. I grew up without a father, so this guy taught me a lot. He didn’t just teach me how to design book jackets, and he didn’t just teach me about graphic design. He taught me that creativity is a renewable resource. He taught me to take my ego out of the job of creating the right cover for the book, because there are infinite covers. There’s not one right cover. If it doesn’t work for sales, if it doesn’t work for editorial, try again.
I also learned early on that opportunity can be manufactured. When I got to high school, I wanted to be on a sports team but I hadn’t played any sports as a kid, so when I tried out I held back because I didn’t know any of the rules. I did a little research and found out that the school didn’t offer lacrosse. So I went to the administration and said, if I can find enough other boys and a coach, can I start a lacrosse team? They said yes, and I did. My reason was that if everyone was as clueless as me, then I didn’t have to worry. In retrospect, I could have just learned the rules of one of the other sports, but that’s not how I was wired.
So I founded this lacrosse team and we were good, and I became captain. The lesson I learned from it was to take a step back and realize that you can architect the circumstances, which then uniquely positions you to take the opportunity. It’s a lesson I have taken with me throughout my career — if something doesn’t exist, you just create it.
Q. What do you think about founder CEOs, when that works and when it doesn’t?
A. Being a founder and CEO is the ideal situation, if the founder of the company is ready to take on that responsibility and suited to it. That’s not always the case. Some founders are people who are very creative and want to pop from one project to the next.
Also, a lot of the founders these days are kids. And the best way for them to grow into that CEO role is either with time or by surrounding themselves with people who can really educate them. I’ve always subscribed to that theory — that to be a great leader you should surround yourself with people who are smarter than you and challenge you.
I’ve spent most of my career being a founder but not a CEO. Now is my first time as both. I finally know what it feels like to want to build something that lasts and to want to stick with your project all the way.
Q. What made the difference, that this time you wanted to be CEO?
A. I feel like I’ve matured. I’ve been on the front lines for so many years that I’ve been able to soak up the best qualities I’ve seen in CEOs. I tend to have a habit of picking up traits that I like.
I’m a father now, and I think that makes a big difference. There’s a sense of responsibility that has come with that. Also, the thing that brings me the most joy in life is helping other people, and this company is a platform for people helping other people — so it’s a productization of my own personality. It makes sense for me to be the chief executive officer, because I’m the living, breathing embodiment of the company and the product itself.
Q. Which talent issues have you wrestled with most in your work on start-ups?
A. When I think about retaining talent and finding talent, I actually seek out failure. People who have tried and failed, then tried again, are really valuable people because they’ve learned incredible lessons.
I definitely also hire for funny. My current co-founder, Ben Finkel, and I laugh so hard together sometimes that we can’t breathe. You’ve got to have that kind of connection.
But more than that, when it comes to keeping people motivated and engaged, I think the key is offering a kind of meaningfulness to the work that’s above and beyond the product itself. In other words, the company and its product have to be on a trajectory to make a positive impact on the world. If you have that woven into the very fabric of the business from the beginning, you attract the kind of people who can work anywhere they want for any amount they want, but they come to you because of the philosophy behind the work.
Q. You mentioned how important recovering from failure is, which is something many entrepreneurs say, but there have to be times when you seriously considered giving up. How did you get yourself past that psychologically?
A. There was a point in the early days of Twitter when yet again the service had gone down and it was really frustrating. We were trying to figure out what was wrong, and I had a particularly stressful morning and I just kind of lost it. I stood up and blurted something out about, “Why can’t we get our act together?” And Jack Dorsey, the CEO at the time, just very quietly asked me to take a walk with him.
He said, “Biz, you’re the guy who’s always optimistic and looking on the bright side and putting on a happy face. We need you to do that, because we are having such a tough time and we need that element to keep us afloat.”
That was a really meaningful piece of advice for me. Up until that point, I didn’t realize how optimism could play such a powerful role in keeping a company running. It wasn’t a point where I threw in the towel — I never really wanted to give up on Twitter, we were always so much in love with it — but it was definitely an inflection of sorts.
When I started my first company in 1999 and then quit in 2000, I quit because I didn’t like the way the company culture was going. I’m sort of sorry that I did. I realize now that I was too green to understand that I should have just worked harder to change it, not give up. I gave up. That’s not what I would do now.
Q. You’ve had the rare vantage point of seeing Twitter go from infancy through IPO and beyond. What management challenges have you seen throughout that scaling up?
A. So many. The company is almost like this organism that needs who it needs when it needs them, just as a child needs different types of parenting as it grows older.
You start out really small. Then as the company grows, someone else starts doing your job. Some people get afraid and think, am I becoming obsolete? The answer is: No, you’re being asked to step up a level and take on a bigger piece of the pie. That rapid growth doesn’t work for some people though, because they feel like they’re being pushed out when actually they’re just being asked to take on more responsibility. It’s a challenge to communicate that effectively.
Fast growth is very dynamic. If you don’t move with it and evolve with it, then the company freezes up in certain sections and you can really stumble. At Twitter we stumbled a lot, but we managed to find that dynamic flow and go public. It’s the end of the beginning for Twitter, but it’s certainly the beginning of something new.
Q. Can you share your best Twitter tip?
Just be authentic. That’s the only way to go. Over and over and over it comes back to that. People try all kinds of different things, and when they just present themselves as human, that’s when people connect with them.
Q. What’s one challenge in your life that tested you the most?
A. There were several difficult decisions I had to make in my life. When I decided to drop out of my full scholarship at college to take a job working side by side with this art director, that was a difficult decision.
I grew up intermittently on welfare, with no money and always working since I was nine years old. In my adult life, I was always in debt. I miraculously got a job at Google before it IPOed. Then I had this decision to make when Evan Williams left Google — I asked myself, did I move out to California to work with Evan Williams? Or did I move out here to work at Google?
I realized I moved to work with Evan Williams, which meant that since he left I had to leave. And that meant leaving millions of dollars behind. That was very difficult, because my whole life was a struggle with regard to money.
But now when I look back on it, each one of these big and difficult decisions came down to following a person rather than an organization or institution. I realize now that’s a smart way to go, because that’s what it’s all about. It’s all about people.
More from this series: