Seattle tech investor Ben Gilbert is transitioning to a new role at Pioneer Square Labs, the startup studio and venture firm he helped co-found, to focus more attention on “Acquired,” the wildly popular podcast that he co-hosts.
Gilbert, who has been a managing director and general partner at PSL, is moving to the role of venture partner beginning Jan. 1, about eight years after PSL and “Acquired” both got started.
“At some point earlier this year, I became certain that two extremely demanding jobs was going to be too many,” Gilbert told GeekWire. “‘Acquired’ feels like one of those once-in-a-lifetime opportunities that you just have to pursue.”
The podcast was initially a side hobby. But along with co-host David Rosenthal, Gilbert has helped build “Acquired” into one of the world’s leading technology and business podcasts. The listener base has doubled each year since inception and “Acquired” now attracts more than 450,000 monthly listeners. It’s currently the No. 1 tech show on Apple Podcasts and Spotify.
“Acquired” tells in-depth stories and strategies of companies, with episodes typically three to four hours in length. That means plenty of behind-the-scenes production work. Gilbert admits to obsessing over every sentence, editing each five times.
For a deep-dive episode on Nike or Costco, for instance, Gilbert and Rosenthal are each spending about 100 hours a month on research — reading books, watching conference talks, taking notes, etc. Another 20 hours is spent listening to and editing an episode before release.
Gilbert said the pressure he and Rosenthal put on themselves to create the episodes is “at odds with doing good work as a general partner.”
Rosenthal, a former principal at Seattle-based Madrona Venture Group, has been working on “Acquired” full time for the last four years. He’s also an angel investor at San Francisco-based Kindergarten Ventures.
Gilbert credits part of the success of “Acquired” to the fact that both hosts are active participants in the entrepreneurial ecosystem, rather than just trying to glean what they can from the sidelines.
Gilbert said his views and analysis on “Acquired” have been sharpened by sitting in startup board meetings or talking daily or weekly with founders. PSL has spun out 34 startups and invested in more than a dozen via its venture arm.
And the lessons go both ways. He said the podcast also helps him in his investor role.
“There’s no doubt that I’m able to help founders think through issues where I can say, ‘Hey, I’ve just done 100 hours of research on a company that had a similar problem in the past and here’s how they solved it,” Gilbert said.
He added that the success of ‘Acquired’ also helps with lead generation for PSL.
“There’s a lot of folks in the ‘Acquired’ community that, when they’re raising capital, think of me and PSL,” Gilbert said.
As a venture partner, Gilbert will serve on boards of existing PSL portfolio companies and continue to play an active role in helping to source talent and companies in the Seattle startup ecosystem on behalf of PSL.
PSL co-founder and managing director Greg Gottesman said the firm is proud of Gilbert and Rosenthal’s success, and that everyone is excited to continue working with Gilbert in his new role at PSL.
“It is in our DNA here at PSL to work with obsessed founders,” Gottesman said. “‘Acquired’ is Ben’s baby in the same way that many PSL portfolio founders feel about their companies.”
