Week 44: Ben Gilbert, Pioneer Square Labs

Crissy Costa
52 Founders
Published in
3 min readOct 3, 2017

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Most startups begin when the founder(s) come up with an idea. The proverbial lightbulb that goes off signifies the beginning of a company’s journey, and indeed, most of the founders I’ve already interviewed told such a story. People who dream up the ideas usually want to be the ones to execute them, at least initially, and more often than not, hope to do so for the long term as well. There are times, however, when startups diverge from this path, as is this case with this week’s podcast. Ben Gilbert is the cofounder of Pioneer Square Labs, a startup studio that brings together bold entrepreneurs, big ideas, and its own team of builders, to rapidly create companies. While it may first sound as though the studio just imagines an idea before handing it off, a lot of rigorous testing is done to ensure that the idea in question is viable. Thus far, PSL actually has ended up killing 9 ideas for every 10 created, leaving only the tried and true remaining.

Once the decisions are made, PSL then finds the right people to execute the vision and obtain external financing. Yet it’s sometimes the case where a PSL team member steps up in the interim to lead, as Ben recently has with Taunt. Esports is, as Ben puts it, the “art of watching other people play video games,” and has already become a global phenomenon while still in its infancy as an industry. It’s estimated that over 300 million people will tune in to watch esports in 2017 alone. Taunt is capitalizing on this trend by building the social competition layer for fans to make watching games more fun and engaging. While Ben may only be acting as the CEO for a short while — he prefers the aforementioned idea creation phase of things — I couldn’t think of a better person who embodies the qualities that make a great founder. Not only did he cofound PSL, but he also ran Microsoft’s Garage, the place for grassroots innovation at the large tech firm. Ben is wise well beyond his years, extremely willing to help others, and introspective enough to know that the companies he and the PSL team dream up require people with deep industry expertise to ensure their success.

💥💥 Bonus💥💥 Be sure to check out Ben’s podcast, Acquired, that he hosts with David Rosenthal, to learn about the stories behind the (in)famous deals in tech M&A.

Featured Company 👉 Taunt
Location 👉 Seattle
Total Startups Created 👉 6 (since September ‘16)

“There’s this inherent thrill for serial entrepreneurs of feeling like you found ‘it.’ It’s the thing we keep chasing every time we work on a new project.”

In this episode, you’ll hear about:

  • How the Pioneer Square Labs model works, and why the team views the people that eventually run the company as the true founders
  • What qualities PSL looks for in these founders, and why domain knowledge is key
  • The startup ecosystem in Seattle, and why the big tech incumbents are largely to thank for it
  • How Taunt currently operates, and the future monetization strategy the company sees playing out
  • How Startup Weekend played a pivotal role in both Ben and his father’s careers
  • Ben’s advice to budding entrepreneurs about working for a large tech company before starting something of your own
  • Why accountability is critical to having a great career, and the best thing Ben’s ever read on the topic

Check out Ben’s Seattle startup pick (outside of PSL companies) at the end of the episode, in addition to hearing us both geek out about Amazon.

P.S. Thanks to 52 Founders alumn Andy Sparks for the introduction! And a BIG thank you to Ben for helping me originally get set up when I reached out to you with nothing but an idea for this show.

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