Best games to play at a founder meetup

Founder meetups are awkward by default. The right game flips that in 15 minutes.

Entrepreneurship
Darby Rollins
May 2, 2026
3 min

Q: What are the best games to play at a founder meetup?

Quick competitive games that reward pitching. Most founder meetups default to a happy hour with name tags and awkward circles. A game changes the social contract because everyone is doing the same thing on the same timer, which makes connection automatic.

The story

SideHustle is a comedy game show built specifically for this audience. Across 5 paid shows in Austin and Asheville, we have hosted 262 unique paid buyers; 73 percent are business decision-makers and 42 percent are Founder or Owner. The format scales down too. At a meetup of 30 to 50 founders, we run a compressed version: each small group brainstorms an absurd-but-plausible business idea, pitches it in 60 seconds, and the room scores on Funny + Fundable. The competitive structure handles the awkwardness. By the second round, founders who had never met are arguing about whether a startup that delivers ice to other ice deliveries would actually work. That is the kind of conversation a normal meetup never gets to.

What it means

Founder meetups should be designed, not just hosted. A 15-minute structured game in the middle of the night turns the room from passive networking into active conversation. People remember the game; the connections happen as a side effect.

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