Q&A: Dick Costolo on Life After Twitter and Why He’s on Board With 2 Ambitious Startups

He's focusing for now on IfOnly and Patreon

Since his high-profile parting of ways with Twitter, former CEO Dick Costolo has kept a low profile—and that's just the way he wants it.

But recently, Costolo has resurfaced to lend his expertise to two companies he feels could become major players in the future: experience sharing site IfOnly and art crowdfunding platform Patreon. He recently joined the board of directors for both startups and is considering launching his own venture someday.

Costolo chatted with Adweek about what he's been up to since leaving Twitter, how he feels about current CEO Jack Dorsey and the lessons learned from scaling companies.

Adweek: What is it that drew your interest in IfOnly?
Dick Costolo:
(CEO of IfOnly Trevor Traina) and I have known each other for a while. I'd say several different things brought me to the company. I've had a lot of requests to help out in the past few months, and I've only done two things: this and the Patreon board. Mostly because I need to keep my time free if I start something myself in the spring.

Specifically, the things that turned me to IfOnly were, one, I think Trevor is really onto something with this notion of experiences being of growing importance over material things and possessions. I thought that was a really interesting insight.

Secondly, I thought I'd be able to help Trevor out with my operating experience. Thirdly, I like the way that a significant part, and in fact I think the majority, of his VPs are women. Having women in technology is something that is very important to me, and Trevor is really putting his money where his mouth is there.

All those things coupled together, on top of which, Trevor is just a really good person, and it's worth it for me to work with people I think are good people, led me to this being something I want to do.

What do you want to bring to the company as a member of its board of directors?
I would say operating experience and things that I've learned doing with other companies—both my own and Twitter. (Trevor) is at the point where he's growing the company, he's done the zero to 50, now he needs to take it to the next level.

As it is in most startups, lots of the other folks on the board are investors and maybe they have some operating experience, maybe they don't, but it's always helpful to have someone else on the board—it certainly was for me at Twitter—that had been a CEO or was a CEO and scaled organizations. Those are the types of people I decided to add to my board at Twitter. I thought they were helpful and important, and that's what I hope to help out with at IfOnly.

You've joined the board of IfOnly and Patreon, so what kinds of things are really gaining your attention now, in terms of what you want to get involved with?
I'm not really basing my decisions specifically on my personal interest. That's going to be an area where I go and attack that on my own and start my own company. This has been more of a combination of people I thought were good people—Trevor and (Patreon CEO) Jack Conte are really good people—and there were aspects of the companies that were important and interesting to the future and the kind of economies that are going to be created. In Trevor's case, the experience economy and in Patreon's case, patrons of the arts. So those are two folks I've decied to help out. On the personal-interest side, I'd go after that on my own.

Who do you feel are some of the blossoming superstars of tech nowadays? Who's really impressing you?
The first half of the year, I was with Twitter. Then the second half of the year, I've really been sort of disengaged from keeping up with everything going on in the industry, and I did that intentionally as I did some traveling and so forth. So I'll probably be in a better position to think about that next year when I dive back into things, but I've been trying to intentionally give myself some time and create some distance there over the past six months.

Have you been keeping in contact with (Twitter CEO) Jack Dorsey and other main people from Twitter in the meantime?
Jack, yes. Jack and I are mostly just socially [communicating]. But, no, not really with other folks in the company. I've been doing a bunch of travel and trying to do some things outside of work for the last six months, so to be perfectly frank, I've been pretty disconnected.

How do you feel Twitter has been doing recently?
I think the world of Jack. I think he is real cheerful and deep product thinker. He's a great editor of the product. I think he's great at doing that, listening to ideas from all over the company and then editing those ideas. From my admitted distance from the company, I think that people react really well to that.

Looking back on your time at Twitter, were there things you wished you would've done differently, or any other reflections you have about your time at Twitter?
No, I loved it. It's one of the best things I've ever done. It was like the best job you could ever have. It was in the middle of so many things going on in the world. I scaled the company up. I joined the company when it was 50 or 60 people, and when I left, it was about 4,500. When I joined, there was one office on Bryant Street in San Francisco and when I left, there were dozens of offices around the world.

It was amazing. It was exciting, and it was in the eye of the hurricane. What else can you say except, "That was awesome." So I don't have any regrets about it or anything like that. I do think that one of the fantastic things about it was all of the lessons learned about trying to build a company of that size and that magnitude and scaling. That's invaluable, and I'm sure will be helpful later on. Hopefully, it'll be helpful in working with Trevor and seeing patterns and recognizing those patterns and seeing what works and what doesn't work, and bringing that to IfOnly.

So what are the big lessons learned from Twitter that you'd like to use to help IfOnly?
They're just too numerable to mention. Everything from the proper way to think about prioritization and budgets to the proper way of thinking about reordering groups to the proper way of thinking about building teams and the kinds of people you want to work with … I could go on and on and on about it.