Corporate Entertainment Ideas for Company Events That Actually Engage

Why Most Corporate Entertainment Falls Flat

Corporate entertainment has a reputation problem. Somewhere between the motivational speaker and the acoustic guitarist in the corner, most company events lose their audience. People eat, they network politely, and they leave without a story to tell.

The events that break through that pattern share one thing: entertainment that demands attention and delivers genuine reactions. For the broader landscape of options, see the corporate offsite alternatives buyer's guide.

SideHustle® LIVE: A New Category of Corporate Entertainment

SideHustle LIVE is a live comedy game show where founders pitch gloriously fake businesses to professional comedians. For corporate events, it delivers something traditional entertainment can't: a room full of people genuinely laughing, engaged, and sharing a memorable experience.

The format works because it's inherently unpredictable. No two shows are the same. Every pitch is different. Every comedian reacts differently. And the audience is part of the show — voting, reacting, and becoming invested in whether each side hustle is "Funny or Fundable."

Where SideHustle LIVE Fits in Your Event

• Holiday parties — Replace the DJ with a 60 to 90 minute show that becomes the highlight of the year
• Sales kickoffs — Energize your team with entrepreneurial entertainment before the strategy sessions
• Client appreciation events — Give your clients an experience, not just a dinner
• Conference entertainment blocks — Fill the evening session with something people actually attend
• Team offsites — Bond your team through shared laughter, not shared awkwardness

SideHustle LIVE travels to cities across the US for corporate events. book a 15-minute call.

Inside the Format: What Event Planners Should Know

"Comedy game show" is a category most corporate planners haven't booked before, so here's the format in the detail that actually matters for a run of show.

A standard booking runs 60 to 90 minutes across roughly four rounds. Three are brainstorm-pitch-score-rotate rounds: the host drops an absurd prompt, teams of about four or five get a short window to invent a fictional business, then pitch it to the room. The fourth round is the finale, usually raising the stakes for whoever's leading heading into it. Every pitch gets scored on two axes — Funny and Fundable — so a team can win the room's laughter without winning its money, or the reverse. That tension is what keeps a corporate crowd leaning forward instead of checking phones under the table.

The room itself is built for this kind of night: cabaret or table seating rather than rows facing a stage, so the audience is scoring and reacting from where they're sitting, not just watching. And participation is opt-in at every level. Nobody gets pulled out of their seat to perform. The people on their feet pitching are founders and professionals who signed up in advance, working alongside professional improv comedians who round out the cast — everyone else plays from the table. That distinction is what makes the format safe to book for a mixed audience: clients, executives, and new hires can all sit back and enjoy it, while the handful of people performing know exactly what they signed up for.

Co-hosts Darby Rollins and Tomer Soran, who created the format together, run every show, which keeps the pacing and tone consistent whether it's an intimate client dinner or a large-scale kickoff. For a full walkthrough of the format and how it developed, see the complete guide to SideHustle LIVE.

Teams that want a preview before committing budget can try the free browser version of the game on their own time — same Funny + Fundable scoring, no travel required, and no commitment to bring it to your event.

Cities We Travel To

SideHustle LIVE is a touring show — we bring the format to your venue, wherever your team is. Home base is Austin, TX, with Pershing Hall as the recurring 250-seat venue, and the show has also traveled to markets like Asheville, NC.

Don't see your city? SideHustle LIVE tours nationwide — book a 15-minute call to check dates for your market.

FAQ

What size room does SideHustle LIVE work for? The format scales from an intimate team dinner (a shorter icebreaker version) up to a full company event of several hundred people.

How long is the show? A standard SideHustle LIVE show runs 60 to 90 minutes, timed to replace or anchor an evening entertainment block.

Do you travel to our city? Yes. SideHustle LIVE is based in Austin, TX and tours nationwide — the show has also traveled to markets like Asheville, NC — and we regularly book new markets — book a 15-minute call to check dates for your city.

What kind of venue do we need? Any indoor space with room for an audience works — hotel ballrooms, event spaces, restaurant private dining rooms, and rooftop venues have all hosted the show.

Is this appropriate for a mixed audience, like clients and employees? Yes. The comedy is professional and workplace-appropriate, and the game show format — founders pitching gloriously fake businesses to comedians who decide "Funny or Fundable" — plays equally well for internal teams and client-facing events.

Ready to bring SideHustle LIVE to your team?

Nametag networking does not pull people out anymore. SideHustle LIVE drops in as a 60 to 90 minute headline experience that gets your whole room playing, laughing, and actually connecting. Book a 15-minute call to check dates and see if your event fits: corporate offsites, conferences, sales kickoffs, and private founder nights.