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 with real ideas to defend: 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 9.25 anniversary tradition, 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: Sept 25 at Pershing Hall in Austin. luma.com/playsidehustle
• Email team@playsidehustle.com