Dick Costolo, Former Twitter CEO

In the early 1990s, Dick Costolo spent several years in Chicago trying to make it in comedy. When that didn’t pan out, he put his computer science degree to use.

Dick went on to start a number of companies, most notably FeedBurner, which he sold to Google in 2007. He became the COO of Twitter in 2010, and quickly transitioned into the role of CEO—a position he held through much of the company’s 2010-2015 expansion, including the 2013 IPO.

We’re not here to cover his success in business, but to learn more about what gave a straight-talking guy from the Detroit suburbs the confidence to build these companies while staying true to his roots. 

Dick and I sat down in November 2017 at the small fourth-floor office of his soon-to-be-launched fitness startup, Chorus, in San Francisco’s South Park neighborhood. He’s in very good shape, and has the energy and enthusiasm of someone just coming out of college. I’m sure he would run circles around me if I met him at his local CrossFit gym.

While we spoke, Dick shed light on his routines, his favorite books, his choice to leave Twitter, and what it’s like to walk on stage to deliver a commencement speech to 45,000 people.

Our conversation has been edited for clarity and brevity. 

March 2017 Update: Dick’s startup, Chorus, has been shut down according to his conversation with Business Insider.

A Return to the Startup World

David Swain:
Tell me about your new company, Chorus.

Dick Costolo: At its core, it’s a social fitness platform. The hypothesis is that in the real world, social motivation and social accountability are the ways people are most likely to change behaviors, get in shape, lose weight, stop smoking, stop drinking, whatever it is. Most fitness apps are just one-to-one, app-to-user; here’s a training program, here’s a workout, do this 15-week program. There’s no social motivation or social accountability, so when people inevitably have a motivation dip, or get sick, or are traveling for work, or are too tired, or run out of time in the day, they just fall off the bus. And there’s nothing to pull them back in.

In the real world, people solve this with personal trainers, running a half marathon together, the Turkey Trot 5k, the Spartan Race, or SoulCycle on Friday mornings. Social motivation and social accountability are what keep them going, and the idea behind Chorus is small teams of people all connected to each other, helping each other achieve some common goal.  

Describe the transition from Twitter to a startup.

When I left, Twitter was over 4,000 people, well over $2 billion in annual run rate from zero when I got there. We went from dozens of offices around the world, to literally 10 to 12 people at Chorus.

This is the fourth or fifth company I’ve started, and I knew what I was getting into. It’s always hard. Even if you’re doing stuff you’ve done before, in a new space with new challenges, you’ll have things like, “Why is it that research says X and we’re experiencing Y?” or “Hey, we prototyped this and it worked great, but now that it’s in the app, it’s only working for 50% of the user population.”

You’re always walking uphill. Like, always. The thing that’s the same is you’re always walking uphill.

The thing that’s different is when you’re over 4,000 people, everyone’s roles are really specialized. You’re sort of like cells in an adult body. All the cells are fully specialized—this is a liver cell, this is a cell in a pancreas that does this specific thing. When you’re a startup, much like when you’ve got 12 cells when the body’s first being created, you’re all doing everything. Every cell has a lot of responsibilities.

Right now I’m the janitor, the next minute I’m the office supplies person, and the next I’m the BD person, and the next minute I’m the product person. So that’s a really fun part of getting started when everything’s not highly specialized and everyone’s wearing a lot of hats, doing different things and pitching in in different ways.

What hat have you been wearing the most?

The thing I’m most excited about is getting to spend most of my time on the product. When you’re a CEO, you want to spend your time on the highest-leverage thing. Occasionally, getting really into the details on something is needed, either to make a point or a decision, or to help people understand something. But for the most part, you want to be spending your time on the highest-leverage things. What are the things and decisions that only the CEO needs to make?

The reality, though, is when you’re at a 4,000-person public company, you get dragged into things that are not the highest-leverage use of your time, but the required legal use of your time. I didn’t love that part of it.

I remember hearing you talk about the Twitter Roadshow before its IPO.

It was two weeks of literally answering the same question every hour for 70 different meetings. It’s the most broken process, but it’s that way because that’s the way the financial system is set up.

You’re building a company around fitness and health, but you’re still a startup—how are you able to balance work and health?

Generally speaking, because we made a policy that it’s okay to leave for yoga at noon, or CrossFit at 2 p.m., that stuff is going to be tolerated. We’re also telling everybody, “Hey, this is an intense time and it’s going to be a big commitment, and everyone has to put lots of extra hours in because we shouldn’t assume we’re smarter than anyone else.”

We’re going to get where we need to go by working hard, but we’ll make time for physical exercise knowing that has great results on your mental energy as well. So, with a few exceptions—today being one of them—I’m able to work out with some regularity.

Growing Up in Michigan

Let’s take a step back. What was your childhood like? How did it play a role on your work ethic?

My childhood was super-comfortable. I have a younger brother and a younger sister. We didn’t have a bunch of money, but we were perfectly comfortable because even if I have a bad credit score, I still grant for loans . You can visit this site more info here. I had jobs growing up, but my parents helped me pay for school. I didn’t need to get out of student loan default.

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My parents instilled a work ethic in me. I’ve been working since I was 12. The job you could get when you were 11 or 12 was caddying, so I caddied from 5 a.m. to 4 p.m., went to bed, and did it again.

I had jobs throughout college, during school, over the summer. During the school year in college, I ran the IT department of the student union. It was just in me from early on to work hard.

Did you see that work ethic around you as a kid through mentors or your parents?

My dad worked super-hard, and would come home and work harder. We didn’t have people who came in and did everything. My dad and mom painted the house, replaced the roof, redid the gutters—they did all that. It wasn’t like, “Bob’s coming over to do XYZ,” they did it. So I was brought up around that.

Did you have a big extended family? What were some of your traditions?

Totally. Aunts, uncles, cousins were all in the Detroit area. Grand Rapids was the farthest away anyone was. My grandparents on both sides all ended up in the Detroit area, so everyone was there.

My parents are still around. They’re in Northern Michigan. Lots of the extended family is still in that area around Detroit. My cousin still lives in Ferndale. It’s kind of the gathering place for Thanksgiving.

You ended up at the University of Michigan doing comedy. How’d that happen?

I was always kind of the funny guy in high school, but at Michigan, I decided to do standup at the student union. They would have the big standup comedian who was in town playing at Birmingham or Detroit on Thursday, Friday, Saturday; on Wednesday night they would come into Ann Arbor and perform at the University of Michigan, and you could sign up as a student to do warm-up acts.

Four or five students would go up before the big headline act, and I started doing that and loved it. So when I graduated from Michigan, I just decided to try to go get into Second City, and eventually audition for Saturday Night Live. I spent a bunch of time at Second City and the Annoyance Theater in Chicago, and eventually auditioned for Saturday Night Live and didn’t get it, and decided, Well, I better go back to CS.

Did you keep some computer science going on the side, or were you all-in on improv and standup?

I was all-in until I had auditions and didn’t get them. Then it was like, It’s time to go put that computer science degree to work and make some money. I was very hand to mouth for a good four, five years, when I only had odd jobs that allowed me to do Second City and the Annoyance during the day and at night. You’re rehearsing during the day and performing at night, so you’ve got to have random odd jobs—working at a nightclub as the door person, random stuff.

Fast-forward a few decades and you’re giving the commencement speech at the University of Michigan. What was that like?

It was amazing. Giving the commencement speech—for those who haven’t been to the football stadium, there are about 45,000 people in there for commencement. For football games with a comprehensive review like the one here, there are 110,000 people. For commencement you’re at the 50-yard line and half of the stadium is filled. The center is filled with the 5-6,000 graduating seniors in their caps and gowns. Around them are 40,000 more people, friends, family, extended family.

It’s just crazy. You’re walking out of the tunnel that the football players walk out of. I remember Mary Sue Collon, the president of the university when I gave the speech in 2013—Mary Sue is 5’1”, and she was standing in front of me very calm, and said, “So, have you ever spoken in front of this many people before?” I was like, “Yeah, for the invasion of Normandy. Nobody has spoken in front of this many people before except you last year when you did this, so when would I have spoken in front of this many people?” No, by like 44,000 people, I hadn’t spoken in front of that many people. That was a crazy experience.

You learned to be comfortable on stage through improv and standup. How’d you keep it together?

I did three things: two things intentionally, and one thing that sort of happened. The first thing was I rehearsed my speech more than I’ve rehearsed any other speech. I said, “I want to know this backward and forward.” And I reminded myself of something I always tell other people who are nervous about speaking—the more informal and less rigid you are, the more comfortable the audience is going to be. If you’re formal and stiff and sound like you’re reading from a script, people are going to be nervous for you. And if you’re not, and you’re relaxed and just let go, the audience is going to be more comfortable.

By telling myself those two things and being comfortable with the speech, I was able to improvise a little bit, which is what I wanted to do. I remember rehearsing it, and the assistant who was helping me at the time was like, “Don’t improvise too much. The more comfortable you’re getting, the more you’ll want to go off-book, and don’t do it.” She was right.

Living in the Moment

You’ve discussed being present and being bold and following your passions. Being present is something everyone talks about, but it’s really hard to do. What have you learned?

You really learn to listen in improv, and that’s a very pragmatic approach to being in the moment. Really listening, not just nodding and being quiet when other people are talking and waiting for your turn to talk.

Frankly, I’ve always tried to build off of that. I’ve tried not to worry about what comes next and pay more attention to what comes now, irrespective of what it is. In fact, it even extends to—I work out on Wednesday and Thursday nights with a guy who I’m doing a gymnastics strength-training thing with. It’s a combination of flexibility and strength—rings, handstands, all kinds of stuff. When he tells me what we’re going to be doing next, I’m always, like, “I want to focus on what we’re doing, not the future or past. I want to focus on this.”

It’s taking some simple, practical things like listening and trying to extend them to everything else. As I’ve gotten older, I notice a lot more when people have the sense that there’s always someplace better to be than where they are right now. We’ll be at a restaurant and people will say, “Do you think we can go to so and so? That might be better than this.” I really detect that now, and when I hear it, I think, Wow, what a miserable way to go through life. This is great, we are where we are, let’s do what we’re doing.

That must have served you well in the growth environment at Twitter. You have too many meetings, too many priorities, and being able to context-shift from one meeting to the next is hard.

That’s fair, with the caveat that there are moments when the thing hiding in the corner is so overwhelming that you can’t block it from the mind. To be perfectly frank, there are times when you’re running a company and you’re in meeting number four, but all you can think about is something from meeting number two. The repercussions or implications of that become overwhelming.

What do you do in that situation?

I never came up with a perfect coping mechanism. The bigger Twitter got—and I did this intentionally—the less I tried to have my schedule filled. When I took over as CEO in October 2010, in those first couple months, it was meetings. One would end, and the next would start. By the time I left in July 2015, I tried to have two hours free in the morning and two hours free in the afternoon every day. I wouldn’t go on email during that time. I’d go try to solve whatever pressing problem was weighing on me, or try to get ahead of whatever pressing problem I needed to be thinking about.

Having my morning and afternoon clear helped me see, Okay I gotta go think about XYX before I go to this metrics meeting at noon, or I’m not going to hear a word anyone says.

That was helpful, but there are times when something comes up where you’re like, This is what we’re going to be thinking about for the next three days. An investor thing, a metrics thing, some external event.

Did you hit a breaking point before you realized you needed those two hours?

No, I just felt like if you’re the CEO of a big company, you can always get pulled into things, but then you never stop to think, What should we do about this bigger issue? So you have to be religious about those hours. People can’t book that time. You’re not going to use that time for busy work like email.

If I didn’t have pressing issues in those hours, I would go talk to those people. If I hadn’t talked to direct sales in a while, I’d go see what they were doing. Or I’d go down to the Ads API team or the Android team to see about the new release and what was happening with the load time.

Those are great things to figure out—what’s going on in the company versus what you hear from your direct reports. You quickly learn whether everyone is saying the same thing when you just walk by and talk to people.

Are you able to carve out time at Chorus?

At this point, I have one-on-ones with everyone on the team. We’ll see how long that lasts as we grow.

What are your habits outside of work that allow you to be successful?

Exercise, for sure. I have way more positive mental energy when I exercise. Not even because I like exercising so much. I just have more positive thoughts and mental energy and a better ability to focus when I get an hour workout in four, five, or six days a week.

If I can work out in the afternoon or evening, I’m ecstatic. On Friday, I have to work out at 7 a.m. because of my schedule, and I dread getting up in the morning and going to work out. Especially as I get older (laugh), I need to move around for a while before I start working out. That’s probably the most common thread.

Even though we’re a smaller company now, I’ve also tried to stick to not having days where I’m in meetings all day, or all afternoon. It’s just not great for your mental focus and ability to think about things.

What about things like reading, music, and meditation? What grounds you?

Fiction. I’m an avid consumer of fiction. I believe reading fiction is one of the best things leaders can do. I think it builds empathy for how other people view the world, which in turn helps you motivate people, inspire people, and build resilience. It helps you understand what it means to be resilient and helps you understand mental toughness.

I think that combination of being able to look at the world through other people’s characters and perspectives, and intensive physical exercise, are great ways to build resilience and focus.

Any favorite books right now?

So many. I was just talking about this last night. I happened to glance across the bookshelves, and was thinking a lot more about Ken Kesey’s Sometimes a Great Notion, which changed the way I thought. In many ways for me, it’s the great American novel. A lot of people would say Norman Maclean’s A River Runs Through It; other people would say Hemingway or Fitzgerald. Sometimes a Great Notion changed the way I thought about America in a lot of ways, and it’s one of my favorite books.

Which parts of your day, or week, matter most to you?

I feel like it just takes me out of what’s happening to be in a routine. The things I have that are routine are physical exercise. I box on Monday afternoon; I do this gymnastics, strength, and CrossFit stuff on Wednesday and Thursday night; I do plyometrics on Friday morning; I run or mountain bike on Saturday (on Mount Tamalpais in Marin); and I do weight stuff on Sunday. That’s my one routine.

Spotlight on Parenthood

Let’s discuss you as a CEO versus you as a parent.

One of the reasons I left—no, the reason I left Twitter was, I remember telling Peter Curry, a lead independent director, “Listen, we moved out here when Rose, my daughter, was in sixth grade. I started working at Twitter that fall. She’s a senior in high school this year, and I haven’t seen Rose since sixth grade. I literally, not figuratively, have missed everything. The dance rehearsals, the birthday parties, the you-name-it, I missed it. She’s here for one more year; you guys pick between this date and this date, but once we get together and tell the whole board about it and vote on it, that’s it for me.”  

Where is Rose in school?

She’s in Michigan—in Ann Arbor, where I went, which is great. She loves it and is having a ball.

Would you talk about parenting before Twitter, when you were starting companies?

I had time to spend with the family, and I would always cut out to go see the dance recital, take Rose to brunch, or something like that. There was just zero time for that at Twitter. The notion that you could run a company and have balance—there was zero work-life balance.

How did your daughter react to that?

Well, I don’t know, because I didn’t see her at the time. Both my kids and my wife, Lorin, were very understanding that this was going to be super-high-volume, high-stress, until it was over, and then that would be that. They could tell there was enough going on not to expect things like my leaving work at 2 p.m. to get to something.

You know the family photos I hold at home—it’s zero to sixth grade, and twelfth grade. There’s no sixth through eleventh. That was when I decided, I’ve got to go spend time with Rose. I’m not going to miss the last year she’s home with us.

And here it is, Dick’s 2013 commencement speech. Don’t forget to visit direct payday loan company to get some idea about financial tools that you can use to have extra cash onhand. 

Also published on Medium.

About The Author

David Swain

David Swain is the founder of Common Threads Media. Swain was the head of communications at Instagram and director of technology communications at Facebook. He is an advisory board member of Strava.

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