SideHustle® LIVE #1 Recap · The First Filmed Show at The Creek & The Cave

What was the first filmed SideHustle® LIVE show?

On October 22, 2025, the second SideHustle® LIVE show — and the first one ever produced for the YouTube channel — happened at The Creek & The Cave in Austin during Austin Tech Week. Five rounds, three comedians, two business owners, one absurd Antarctica pitch, and the line that closed the room: "More shows next year. Time flies, doesn't it? If you want to freeze yourself, I know a place."

The setup

Austin Tech Week brings the kind of crowd that has sat through more pitch decks than is medically advisable. The Creek & The Cave was the right venue to break the pattern: a real comedy room with a stage built for setups and punchlines, not slide builds. Darby Rollins and Tomer Soran co-hosted. Cameras were rolling for the first time, which meant the show had to actually hold together end-to-end — no resets, no stops, no "can we do that again." The audience walked in expecting to watch. They left having played. The running joke that landed early and held all night: "no bad ideas zone — except for Darby's."

What happened on stage

Five rounds, five product names, five categories, and a steadily rising room.

Round 1 — "Trixie" — Fashion & Retail. The first pitch on camera in SideHustle® LIVE history. The room calibrated to the format fast: pitch lands, comedians and audience teams score Funny and Fundable as separate one-point votes, totals matter.

Round 2 — "Snow Monsters" — Health & Wellness. The breakout moment of the night and the pitch that wrote the closing line of the show. The Snow Monsters concept went somewhere between cryogenic freezing and Antarctica rehab — exactly the kind of swing the format rewards. The audience locked in.

Round 3 — "Skyhop" — Media & Entertainment. Audience volunteers got to pitch with the mic in hand, which is when the room realized this is not a show you watch, it's a show you can end up in. Energy spiked.

Round 4 — "Bright Side" — Fashion & Retail. First Investor's Choice round of the night — the audience picked the category, the entrepreneur had to deliver against it. The format flexes here. It stops being a script and starts being a game.

Round 5 (final) — "Cloud Hat" — Toys & Games. Second Investor's Choice round, audience-selected category, and the closer. Cloud Hat sent the room out laughing and gave the founders the runway to tee up what was next: the new compact game format that fits on the shelf with other party games, teased to the room as a pre-sale.

The theme song — "Unicorn state of mind, pitching madness, one of a kind, funny fundable, side hustle players" — got its first filmed callback. It now opens every recap.

The cast

Comedians on stage: Allison Veovich, La Mer Lee, and Destiny Lain. Business owners on stage pitching gloriously fake business ideas: Amanda Orman and Jordan Bonic. Co-hosts: Darby Rollins and Tomer Soran. That five-person stage cast plus two co-hosts is the template every filmed SideHustle® LIVE show now follows — three comedians, two founders, two hosts, one format.

What it means for SideHustle® LIVE going forward

October 22, 2025 was the proof that the format films well, holds the room for five full rounds, and produces clip-worthy moments without a script. It cleared the runway for the recurring Austin shows at Pershing Hall, the first 9.25 anniversary show, and every show that has followed. The closing tease — more shows, the compact party game format, the line about freezing yourself — was the founders saying out loud what was already in motion.

Watch it

Full episode: youtube.com/watch?v=rmFpulE454E. The 77-second sizzle: youtube.com/watch?v=yl11O6x0CEI.

Try it

• Play free at playsidehustle.com
• See us live: Oct 1 at Pershing Hall in Austin. playsidehustle.com
• Email team@playsidehustle.com