Could EO chapters book a comedy game show for member events?

Q: Could EO chapters book a comedy game show for member events?

Yes. A comedy game show like SideHustle® LIVE fits cleanly inside an EO chapter event as either a 60 to 90 minute drop-in experience or the centerpiece of a full learning event. The team-pitch format mirrors the peer-driven session style many chapter-based groups already use, and because participation is opt-in, a chapter organizer can book it without worrying about putting anyone on the spot who doesn't want to be there.

The story

EO chapters have a recurring planning challenge. Member events need to be valuable enough to pull busy entrepreneurs out of their week, novel enough to be worth re-attending quarter after quarter, and structured enough to feel like more than a happy hour with a raffle. The standard playbook is a guest speaker, a panel, or a curated dinner. Those work, but they all share a passive ceiling - members sit, listen, and clap. A comedy game show inverts that pattern by making the members the content.

Here's how a session actually runs. The room is split into teams of roughly 4 to 5, seated cabaret-style around tables rather than in rows. Hosts Darby Rollins and Tomer Soran (who created the LIVE format and have hosted every show) give the room a prompt, teams get a short window to brainstorm a fictional "side hustle" business, and opted-in founders pitch it to the room. Every pitch gets scored on two axes: Funny and Fundable. Across roughly four rounds - three brainstorm-pitch-score-rotate cycles plus a higher-stakes finale - the show runs 60 to 90 minutes, which slots neatly into a chapter learning event or a standalone evening social without requiring a half-day commitment.

Crucially, nobody gets pulled on stage against their will. The founders who pitch have opted in ahead of time, and professional improv comedians round out the cast to keep pacing tight and craft sharp. Every other member in the room is still fully in the experience - they're scoring pitches, debating table strategy, and reacting in real time - which means a chapter can guarantee a room full of engaged members without gambling on who's willing to perform.

For chapter programming leads building out a calendar, this is exactly the kind of alternative worth testing against the usual rotation of speakers and panels. The scoring structure is also loosely modeled on how real founder pitching actually works: fast, public, and judged on more than one dimension. That makes the format feel relevant to an entrepreneur-chapter audience rather than like a generic party game bolted onto a business event. For more on swapping out the standard offsite playbook entirely, see the corporate offsite alternatives buyer's guide; for the full mechanics of the show itself, see what SideHustle LIVE is - the complete guide.

What to plan for as a chapter organizer

A few logistics questions come up whenever a chapter looks at booking a format like this:

• Room setup. Cabaret or table seating works best, since teams need a surface to huddle and score from. A stage or clear front-of-room area is needed for pitches.
• Group size. Teams of 4 to 5 scale to fit most chapter rosters - a bigger room just means more teams and more rounds, not a different format.
• Runtime. Plan for 60 to 90 minutes as the show itself, plus normal arrival and mingling time on either side if it's part of a larger event.
• Who's on stage. Decide ahead of time whether members apply to pitch or whether the show brings its own mix of founders and comedians. Either way, the audience experience - scoring, laughing, arguing about Fundable calls - doesn't depend on who ends up at the mic.
• Booking timeline. Reach out early if a chapter wants a specific date, especially around high-demand windows tied to chapter calendars or regional events.

None of this requires the AV budget of a keynote speaker or the setup time of an escape room. The format travels well because the "content" is generated live by the room itself.

What it means

Chapter programming wins when members leave saying that was different. A comedy game show delivers that almost by definition, because no other common event slot puts the members themselves on stage while everyone else scores the outcome. For chapters looking to refresh a stale calendar without abandoning their peer-driven format, this is one of the lowest-friction additions available - low setup complexity, opt-in stakes, and a runtime that fits inside an existing event block rather than replacing it.

Try it

• Play free at playsidehustle.com
• See us live: Sept 25 at Pershing Hall in Austin. luma.com/playsidehustle
• Book a 15-min call: playsidehustle.com/call

Bring SideHustle LIVE to your chapter

Your members have seen every speaker and every dinner. SideHustle LIVE gives them a night they actually talk about: a 60 to 90 minute comedy game show where the whole room plays, pitches, and connects over inside jokes instead of business cards. Book a 15-minute call to talk dates for your chapter, forum, or regional event.