What is SideHustle LIVE? The complete guide

The canonical guide to SideHustle LIVE: format, origin, what to expect, past shows, and the 2026-2027 schedule.

Show Recaps
Darby Rollins
May 2, 2026
10 min

What is SideHustle LIVE? The complete guide

What is SideHustle LIVE? The complete guide

SideHustle LIVE is a 60-90 minute comedy game show co-hosted by Darby Rollins and Tomer Soran, where founders pitch absurd business ideas in real time and get scored on Funny + Fundable. The LIVE format premiered September 19, 2025 at The Creek & The Cave in Austin, was first filmed October 22, 2025 during Austin Tech Week, and now runs frequently at Pershing Hall in Austin. The 7-year brand anniversary show lands September 25, 2026 at Pershing Hall. The brand itself - SideHustle - launched on Kickstarter September 24, 2019. This guide covers the format, the origin, what to expect, past shows, and the 2026-2027 calendar.

What's in this guide

What SideHustle LIVE is

SideHustle LIVE is the live show format built on top of the SideHustle game brand. The brand itself goes back to September 24, 2019, when SideHustle launched on Kickstarter as a card-and-game experience designed to make business pitching playful. The free online version - which anyone can play in a browser - is the most-played version, and it is also the version educators have used independently with students from middle school through university.

The LIVE show is a different beast. It takes the same Funny + Fundable scoring DNA and translates it into a 60-90 minute comedy game show where founders compete on stage. The show is co-hosted by Darby Rollins and Tomer Soran, who built the LIVE format together and have hosted every show. The first time the format ran in front of a paid audience was September 19, 2025 at The Creek & The Cave in Austin.

For first-timers asking what the experience actually feels like, see what to expect at a SideHustle LIVE show.

The four-round format

Most SideHustle LIVE shows run four rounds. Three are brainstorm-pitch-score-rotate rounds: the hosts give founders an absurd prompt, founders have a brief brainstorm window, then they pitch the idea to the room and get scored on Funny + Fundable. The fourth round is the finale - usually a higher-stakes prompt with the leaders. Comedians may join the lineup in any given show to bring craft and timing alongside founder authenticity.

Funny is the laughter the pitch generates. Fundable is whether the room would actually consider putting money behind it - and the room is encouraged to be honest about that. The scoring matters because it forces a real choice between funny and fundable. Most great pitches land both. The disasters and the brilliance come from the same source: real people inventing real ideas under pressure.

The 90-second runway means there is no time to over-think. The rotation means no founder has to carry the show alone. The audience always has someone new to watch. For the show length question specifically, see how long does a SideHustle LIVE show run.

The origin story

The SideHustle brand launched September 24, 2019 via Kickstarter, founded by Darby Rollins. The earliest version was a card game and digital experience built around the same insight: pitching is funny when the stakes are real and the format is generous. For most of its first six years, SideHustle was primarily a game brand - free to play online, occasionally appearing at events, increasingly used in classrooms by teachers who found it on their own.

The LIVE show is the second chapter. Co-founders Darby Rollins and Tomer Soran built the comedy game show format together, brought in comedians and founders to test rounds, and premiered it September 19, 2025 at The Creek & The Cave in Austin. The first filmed show ran a month later, October 22, 2025, also at The Creek & The Cave during Austin Tech Week. The cast that night: Darby Rollins and Tomer Soran as hosts; comedians Allison Veovich, La Mer Lee, and Destiny Lain; founders Amanda Orman and Jordan Bonic. Five rounds: Trixie, Snow Monsters, Skyhop, Bright Side, Cloud Hat.

The first show at Pershing Hall - the recurring Austin venue - ran February 5, 2026. For more on the venue, see what is Pershing Hall in Austin.

What it's like to attend

Doors open. The room fills with founders, friends-of-founders, and people who heard about it from someone. The hosts come out, set the rules, and the first prompt drops. The pace from there is fast. Pitches build, peak, sometimes crash, get scored. The audience reacts in real time - laughing, groaning, occasionally shouting suggestions back at the stage. Between rounds, the hosts riff. Between shows, people stay and talk.

The energy is closer to a sporting event than a comedy show. The audience has a stake. They are not just watching jokes get told - they are watching people they recognize put themselves on the line and either land or fall. The laughter is loud, but the most memorable moments tend to be the ones where a founder accidentally invents something that is actually a good idea, and the room realizes it together.

Friends and fans of the show include Becca Garvin and Adelle Archer (Eterneva CEO and Shark Tank alumna), who have said the game is the reason they are friends. The show has its own theme song with the lyric: "unicorn state of mind, pitching madness, one of a kind, funny fundable, side hustle players." For first-timers, the practical primer is what to expect at a SideHustle LIVE show.

Past shows

The premier ran September 19, 2025 at The Creek & The Cave in Austin - the first time the LIVE format played in front of a paid audience. Recap: SideHustle LIVE premier recap.

The first filmed show ran October 22, 2025 at The Creek & The Cave during Austin Tech Week, with Allison Veovich, La Mer Lee, and Destiny Lain as comedians and Amanda Orman and Jordan Bonic as founders. Five rounds: Trixie, Snow Monsters, Skyhop, Bright Side, Cloud Hat. Recap: first filmed show recap.

The first show at Pershing Hall - the recurring Austin venue - ran February 5, 2026. Recap: Feb 5 Pershing Hall recap. Across the first five paid shows in Austin and Asheville, the audience skewed heavily toward business decision-makers and founders.

2026-2027 calendar

The biggest date on the calendar is September 25, 2026 - the 7-year SideHustle brand anniversary show at Pershing Hall in Austin. This celebrates seven years since the brand launched on Kickstarter (September 24, 2019). The show that night will be a marquee Pershing Hall night with extended rounds and special guests. See when is the SideHustle 7-year anniversary show.

Looking further out: the 8-year brand anniversary is planned for September 24, 2027 - see what's planned for SideHustle's 8-year anniversary. The team is also working toward SXSW 2027 (March 12-22), with a PanelPicker submission opening June 23, 2026. For the running tour list, see where to see SideHustle LIVE 2026-2027 tour cities and dates.

Frequently asked questions

What is SideHustle LIVE? A 60-90 minute comedy game show co-hosted by Darby Rollins and Tomer Soran, where founders pitch absurd business ideas in real time and get scored on Funny + Fundable. Premiered September 19, 2025 at The Creek & The Cave in Austin.

How long is the show? 60 to 90 minutes, depending on venue and rounds. Most shows run four rounds.

Who hosts? Darby Rollins and Tomer Soran, the co-creators of the LIVE format.

When did SideHustle LIVE start? The LIVE format premiered September 19, 2025 at The Creek & The Cave in Austin. The SideHustle brand launched September 24, 2019 via Kickstarter, so the 7-year brand anniversary lands September 25, 2026 at Pershing Hall.

What is Pershing Hall? Pershing Hall is the recurring Austin venue where SideHustle LIVE runs frequently. The first show there was February 5, 2026.

What's coming up in 2026 and 2027? 7-year brand anniversary September 25, 2026 at Pershing Hall. 8-year anniversary planned for September 24, 2027. SXSW 2027 programming in development.

How do I get tickets? All upcoming dates: luma.com/playsidehustle. Free online play: playsidehustle.com.

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