Darby Rollins - Co-Founder of Side Hustle Games

Darby Rollins co-founded SideHustle® with Tomer Soran - the free online party game and the live comedy game show that scores founder pitches on Funny and Fundable - and co-hosts every SideHustle® LIVE show. He's also the founder of Gen AI University, where he teaches entrepreneurs how to fold AI into everyday business workflows.

Co-founder of Side Hustle Games

Darby Rollins co-founded Side Hustle Games, the company behind the SideHustle brand. The brand launched on Kickstarter on September 24, 2019, as a card-and-digital pitching game built around a simple insight: pitching is more fun, and more honest, when the stakes are real but the format is generous. That game is still free to play at playsidehustle.live, and it's the version most people encounter first - including the educators who have run it independently in their own classrooms.

For roughly six years, that free game was the SideHustle brand. The comedy game show didn't exist yet. What Rollins and co-founder Tomer Soran built next was a second chapter, not a pivot: a live, ticketed version of the same Funny + Fundable scoring DNA, translated into a 60 to 90 minute stage format. For the full picture of how the brand got from a Kickstarter card game to a recurring live show, see the SideHustle origin story.

Co-hosting SideHustle LIVE with Tomer Soran

Rollins and Soran designed the SideHustle® LIVE format together, tested rounds with comedians and founders, and premiered it September 19, 2025 at The Creek & The Cave in Austin. Since then, Rollins has co-hosted every show. On stage, that means setting up each round's prompt, keeping the pace moving through each team's pitch window, and calling the Funny + Fundable scores the room gives each team.

The format itself runs on volunteer participation - nobody is pulled out of the audience. Founders and professional improv comedians who've opted in do the pitching from cabaret-style tables in teams of four or five, while everyone else in the room scores from their seats. A typical show runs about four rounds: brainstorm, pitch, score, rotate, building to a higher-stakes finale round with the leaders. The show now runs frequently at Pershing Hall, the recurring 250-seat Austin venue, alongside occasional shows elsewhere. For the complete rundown of the format, rounds, and scoring, see what is SideHustle LIVE: the complete guide.

It's worth being precise about a separate product with a similar name: SideHustle Labs is a classroom version of the format built for teachers, not a version of the LIVE comedy show. Labs runs in schools, with students pitching to peer "investors" in a facilitated session teachers can lead themselves - a different room, a different audience, the same underlying scoring idea.

The game shows up in classrooms too

Because the free online game predates the LIVE show by years, it found its way into education on its own, without a sales push from Rollins or the team. A professor at Mars Hill University ran the free game with his class. A teacher in Vigo County, Indiana ran it with roughly 400 middle-school students. Neither adoption was engineered - both came from educators who found the game, tried it, and kept using it. That's part of why SideHustle Labs exists as its own classroom-facilitated format: the raw game already proved it worked with students before a dedicated version for teachers was ever built.

Founder of Gen AI University

Outside of SideHustle, Rollins founded Gen AI University, where he helps entrepreneurs turn AI tools into practical, repeatable workflows - faster research, sharper positioning, and content that actually ships instead of sitting in a drafts folder. He hosts the Gen AI University Podcast and leads the Scale with AI Summit, both built around the same premise: most founders don't need a lecture on what AI could theoretically do, they need a specific workflow they can run this week.

The two projects share a founder more than they share a playbook. SideHustle is a comedy format performed in front of a room; Gen AI University is a set of workflows taught to individual founders. What connects them is an interest in formats that make abstract skills - pitching, or using AI well - concrete enough to practice in real time, rather than something to read about and never do.

The timeline, quickly

• September 24, 2019 - SideHustle brand launches via Kickstarter, founded by Darby Rollins
• ~2019-2025 - SideHustle runs as a free online and card game, picked up independently by educators
• September 19, 2025 - SideHustle® LIVE premieres at The Creek & The Cave, Austin, co-hosted by Rollins and Tomer Soran
• October 22, 2025 - First filmed show, also at The Creek & The Cave, during Austin Tech Week
• February 5, 2026 - First show at Pershing Hall, now the recurring Austin venue
• September 25, 2026 - The 7-year brand anniversary show at Pershing Hall

Where to find his work

Rollins co-hosts SideHustle LIVE shows in Austin at Pershing Hall and occasionally in other cities, and the free online game he co-created is always available to play. His Gen AI University work runs on its own separate podcast and summit for founders looking to put AI to work in their business.

Try SideHustle

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