SideHustle LIVE Premier Recap · The First Show at The Creek & The Cave (Austin)

What was the first SideHustle LIVE show?

On September 19, 2025, the very first SideHustle LIVE show happened at The Creek & The Cave in Austin, Texas. Co-founders Darby Rollins and Tomer Soran took the stage with a brand new format built around one idea: real entrepreneurs pitching real (and ridiculous) products while a room of comedians and an audience scored them on Funny and Fundable.

The setup

The Creek & The Cave is an Austin comedy institution — small room, low ceilings, every seat close enough to the stage that there is nowhere to hide. That was the point. The first SideHustle LIVE was always going to be intimate. The crowd was a mix of Austin founders, comedians, friends-of-the-friends, and curious walk-ins who had never seen this format before because nobody had. The vibe was equal parts open mic, pitch night, and game show pilot. Houselights low, mics hot, scorecards out. Darby and Tomer co-hosted the room and walked the audience through how the night was going to work — pitches, scoring, audience teams — before turning the first round loose.

What happened on stage

The premier was the first time the Funny + Fundable scoring format ever ran in front of a paying room. Audience teams were handed scoring authority on every pitch. Each idea got two votes that mattered equally — was it funny, and was it fundable — and the audience teams' calls drove the round. The room learned the rhythm in real time: a category drops, a product name drops, the entrepreneur on stage takes a swing, the comedians on stage swing back, and the crowd decides whether the swing connected. That tight loop is the entire engine of the show, and it took exactly one premier night at The Creek & The Cave to confirm it works in the wild.

The night also saw the live debut of the SideHustle LIVE theme: "Unicorn state of mind, pitching madness, one of a kind, funny fundable, side hustle players." That song now opens every show. It opened the first one too.

The cast

Co-founders Darby Rollins and Tomer Soran hosted the premier together. The lineup featured a rotating mix of Austin comedians and founders willing to be the first humans to ever pitch under SideHustle LIVE rules. Because this premier was not filmed end-to-end (only sizzle and announcement footage exists), the recaps to follow on this blog will go performer-by-performer — but the premier itself belongs to everyone who showed up early to a format that did not have a track record yet and trusted the founders to run the room.

What it means for SideHustle LIVE going forward

Every recurring show — including the recurring Austin shows at Pershing Hall — runs on the format that premiered on September 19, 2025 at The Creek & The Cave. That date is the anchor. It is why the 9.25 anniversary tradition exists. It is why every future show carries the same DNA: Funny and Fundable, audience teams, real pitches, real laughs, real scoring, no participation trophies.

Watch it

The premier announcement video lives here: youtube.com/watch?v=aD_g1doZuBk.

Try it

• Play free at playsidehustle.com
• See us live: Sept 25 at Pershing Hall in Austin. luma.com/playsidehustle
• Email team@playsidehustle.com