Serial entrepreneur Evan Williams spoke onstage at Wired’s Business Conference, about going from Pyra Labs to Blogger to Obvious to Odeo to Obvious to Twitter to Obvious to Medium. Whew! “Turns out I’m bad at parallel entrepreneurialism,” Williams laughed, joking about why he just can’t stop focusing when a particular startup takes off within one of his many umbrella companies.
The most recent bright, shiny object in Williams’ purview is Medium, the publishing platform that’s focused on “ideas and stories with a longer shelf life.” Williams is now spending most of his time helming the 30 person team of former Obvious and now Medium employees. Curiously, the still invite-only publishing company is paying freelance writers to write for it, much like a traditional media organization.
When asked by Wired senior writer Steven Levy when the time was right to pull the plug on a company or when to stick with a project like Blogger, Williams said it was basically a gut check every time: “There’s something about just hanging in there, on the Internet. If you don’t die, then you win sometimes.” Google acquired Pyra Labs and Blogger for a rumored eight figures in 2003. You probably first started blogging on a Blogger blog. I sure did. And it is still around.
Twitter is another one of the wins. When asked what surprised him the most about Twitter’s hanging in there (seriously), to an eventual IPO in 2014, Williams, who still is on the Twitter board, said, “Everything.”
“I’m impressed and amazed every time I have a board meeting there. You zoom out and you think it’s pretty much the same as it was two years ago, but in other ways it’s just more and more indoctrinated into the culture. And everywhere you go, at least things I pay attention to, it’s like Twitter’s built into everything … It’s been really educational for me to see the evolution of a company that I was involved in from the very beginning now grow to be almost 2000 people. When I stepped down as CEO [two and a half years ago] it was 300 people, which felt like a big company.”
Eventually if you stick around enough, the wins will add up. To close the talk, Levy brought up one of Evan’s recent tweets, a quote from Nassim N. Taleb’s ANTIFRAGILE, a book that Williams is “obsessed” with, “Success brings an asymmetry: you now have a lot more to lose than to gain.”