How SideHustle Works · The 4-Round Game Loop in Plain English

How does SideHustle work?

SideHustle gives players a random business name and industry. Teams have 90 seconds to brainstorm what that business could be, then pitch it in under 60 seconds. The audience scores each pitch on Funny plus Fundable. Three or four rounds per session. Plays free on mobile at playsidehustle.com.

The story

If you've heard about SideHustle but haven't played, the explanations online are usually some version of "Shark Tank meets Whose Line Is It Anyway." That's accurate but it doesn't tell you what actually happens. Here's the loop, in plain English.

Setup: Open playsidehustle.com. Players sit in a circle (or around a table, or in a Zoom window). 2 to 8 people works best.

Round 1 · The prompt drops. The game shows a random business name (like "Velvet Mango") and a random industry (like "logistics"). Yes, those don't go together. That's the point.

Round 2 · Brainstorm fast. Players have 90 seconds to come up with what Velvet Mango could possibly be as a logistics company. Solo or in teams of 2-3.

Round 3 · Pitch. Each person or team pitches their business in under 60 seconds. What is it? Who's it for? Why now?

Round 4 · Vote on Funny + Fundable. The audience scores each pitch on two axes: Funny (did it crack you up?) and Fundable (would you actually invest?). Highest combined score wins the round. Then the prompt rolls and you do it again.

What it means

The game does two things at once. It's actually funny because the random-prompt mechanic produces situations no one could plan, and the room runs with it. And it builds a real founder skill. Every round you pitch, defend, and think on your feet. Not because the game told you to learn. Because the game made it fun.

Try it

• Open SideHustle free at playsidehustle.com on any phone
• Catch us live: Sept 25 at Pershing Hall in Austin. luma.com/playsidehustle
• Email team@playsidehustle.com for the physical card deck or corporate event bookings