How to Book SideHustle® LIVE for Your Company: The Full Process

How do you actually book SideHustle® LIVE for a company event?

Booking SideHustle® LIVE for a company event is a five-step process: you share your date, audience, and venue; we quote based on those specifics; you confirm and the date locks; we run a short pre-show call to calibrate the prompts to your industry and audience; then the show travels to you (or you come to us) and runs. There's no application, no waitlist mystery, and no per-seat ticketing to manage on your end — it's a single flat booking.

Step 1: Share the basics

The fastest way to start is an email to team@playsidehustle.com or a 15-minute call with four things: the date you're targeting, roughly how many people and what kind (all-engineers, mixed sales and marketing, a founder-only dinner, whatever it is), the venue or city, and what you want the event to accomplish. That last one matters more than people expect — "we want the team to actually talk to each other" and "we want this to feel like a headline moment at our conference" lead to different calibrations of the same format.

Step 2: Get a real quote

Once we have those four inputs, we can quote against them specifically instead of giving you a generic number. Group size, whether the show has to travel outside its regular route, and how much you want the prompts customized to your business are the biggest levers. For the full breakdown of what drives the number, see how much does it cost to book SideHustle® LIVE.

Step 3: Lock the date

4-6 weeks of lead time is the comfortable zone — enough runway to calibrate the show without rushing it, not so far out that your event details are still in flux. Shorter timelines are workable when the date and cast line up, but the earlier you can confirm, the more room there is to get the prompts right for your specific room.

Step 4: Calibrate the show to your audience

This is the step most corporate entertainment vendors skip, and it's the one that determines whether the show lands. Before show day, we talk through your audience's actual makeup — technical or non-technical, senior or junior-heavy, founder-dense or general staff — and adjust the pitch prompts accordingly. The four-round format (three brainstorm-pitch-score-rotate rounds plus a finale) stays constant; what changes is the flavor of the prompts so the jokes land for the room you actually have. Audience size matters less here than audience composition — a room that's all one department is easier to calibrate than a mixed one, but the format works for both.

Step 5: Show day

The format travels. Theaters are the easiest venue to run the show in because the room is already built for a stage and an audience. Hotel ballrooms work well. Conference rooms work fine as long as the AV can handle a mic and some basic staging. Outdoor spaces and standing-room-only setups are harder — the show depends on the audience being able to see and hear the stage clearly, and standing crowds lose that focus faster than seated ones. If your venue is unusual, flag it early so we can plan around it instead of discovering it show week.

What you don't have to bring

You don't need to source hosts, cast, or a scoring system — that's the whole show, and it comes with us. What you're responsible for is the venue, basic AV (or confirming ours works with your space), and getting your people in the room at the right time.

Frequently asked questions

How far in advance should we book?

4-6 weeks is comfortable. Tighter is possible but leaves less room to calibrate the prompts to your specific audience.

What information do you need from us to quote a show?

Date, audience size and makeup, venue or city, and what you want the room to walk away feeling.

Can the show travel to our office or venue?

Yes — theaters are easiest, ballrooms work well, and conference rooms work with decent AV. Outdoor and standing-only spaces are the hardest fit.

Ready to start? Book a 15-minute call with your date, audience, and venue and we'll walk the rest of the process with you.