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 (recap of the first filmed show). 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. For everything you need to know about the live show this format scaled up from, see our complete guide to SideHustle LIVE.

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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