Brainstorming Games to Play With Your Cofounder When You're Stuck

How do you break a stuck cofounder brainstorm?

Change the rhythm. The fastest fix is a constraint-based round (Random Constraint Pitch), a Bad Idea Brainstorm where only bad ideas are allowed, or one round of SideHustle on a fake business. The point is to disable your real-time editor so the actual best ideas can surface.

The story

Tomer and I have been cofounders since 2019, which means we've been on the same problem for three hours more times than I can count. The pattern is always the same: the whiteboard fills up, two of you are now arguing about whether the problem you're trying to solve is even the real problem, and somewhere around hour three you stop writing things down.

The fix isn't more analysis. It's a rhythm change. We built a few moves into our routine that reliably reset the conversation:

(1) Random Constraint Pitch. Take whatever problem you're stuck on. Add a constraint — "What if we had to ship this in 7 days?" or "What if we couldn't use email at all?" The constraint forces your brain off the trail it was stuck on.

(2) Bad Idea Brainstorm. Set a 15-min timer. You can only suggest bad ideas. The worse the better. By minute 8, the best ideas of the day come out, dressed up as bad ones.

(3) One round of SideHustle. Open the free game at playsidehustle.com. Play one round on a fake business. The pattern transfers when you go back to your real problem.

(4) Steal From Three Industries. Pick three industries unrelated to yours. How do they acquire customers? How do they price? Which moves could you steal?

(5) Pitch Each Other's Bad Idea. Trade your worst ideas. Now pitch your cofounder's bad idea — for real — for 60 seconds. You'll find what's actually good about it.

What it means

The best cofounder brainstorming sessions aren't the longest ones. They're the ones with the most rhythm changes. Built-in resets prevent the cognitive ruts that kill four-hour sessions. Carmen G., an Amazon reviewer, called it "the perfect way to flex your creative muscle and practice improv." That's what these are. Improv reps for your operating brain.

Try it

• Play SideHustle free at playsidehustle.com for the rhythm-reset round
• Live show: Sept 25 at Pershing Hall in Austin. luma.com/playsidehustle
• Email me at team@playsidehustle.com for cofounder retreat formats