This Austin Board Game Turned Into a Live Comedy Show

Howdy, Austin.

Welcome to Austin Founders Feed, your weekly glance behind the scenes at the fastest growing entrepreneurship community in the country.

We’re proud to announce the launch of our Friday edition. Every Friday expect an exclusive interview from an Austin founder delivered straight to your inbox.

This week we interviewed Austin’s Darby Rollins from SideHustle Live.

Let’s get to it.

— Ken

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If “networking” makes you think name tags, forced small talk, and pitch-slap energy… this is the antidote.

SideHustle Live is a live comedy game show for entrepreneurs where the point isn’t to pitch your startup — it’s to pitch ridiculous business ideas, collaborate in real time, and laugh with strangers until they feel like friends.

Founder Darby Rollins came up with the idea in a goofy bar riff back in 2019, but it quickly transformed into a very real board game, funding the Kickstarter campaign within the first 12 hours.

Since then the SideHustle Live has transformed into something truly special.

In this interview, Darby breaks down:

Here’s the full conversation…

SideHustle Live is a live comedy game show built for entrepreneurs, based here in Austin, Texas.

The idea goes back to the summer of 2019. A group of friends and I were hanging out at a bar when someone noticed our table was unstable. We started joking around and pitching business ideas for a company called “Stable Table.” We were entrepreneurs, there was a problem in front of us, and we just started riffing.

We realized how much fun we were having just coming up with ideas together, and that sparked a bigger question. What if this could be a game we could play with anyone? As entrepreneurs, this is something we naturally do.

That led to a 90-day sprint to launch a Kickstarter campaign within the Austin entrepreneur community to create a board game. We launched the campaign, funded it in the first 12 hours, and delivered on it the following year after production.

From there, between 2020 and 2025, we hosted dozens of game nights and had thousands of people play the game in classrooms, at home, at company offsites, and at events around the world. After all of that, we realized there was another evolution of the game that felt exciting to explore. Turning it into a live show to really level up the entertainment aspect.

We pitched a pilot to a comedy club here in Austin in 2025 and did two shows at The Creek and the Cave. Both were a big hit with our audience, and that’s when we knew we were onto something with the comedy show format. Now we’re continuing to build that into 2026 and beyond.

Austin has always felt like a special place for entrepreneurs to gather and build together. When I officially moved here in 2017, I didn’t have many entrepreneur friends, but I knew I wanted to keep building businesses and connect with others doing the same.

There’s just a certain energy in Austin that attracts a specific type of entrepreneur. People working on interesting things who are open to connecting. The city’s density helps too. You can get from east to west, north to south, within a few miles. Compared to places like LA or New York, people here are physically closer, which makes a difference.

It’s hard to fully put into words, but there’s a collective entrepreneurial spirit here that feels unique.

Word of mouth, without a doubt. People play the game, they love it, and they tell their friends.

It hasn’t been viral in the way you sometimes see online where you suddenly have millions of followers, but the people who do play the game, attend the shows, and experience it firsthand are deeply impacted. They come back to shows multiple times.

We host a lot of game nights within our friend group, and it’s just genuinely fun. What’s really cool to me is seeing teachers sign up to use the game to facilitate entrepreneurship conversations in classrooms. People hear about it through friends or stumble across it online and then pass it along.

The growth might be slower, but it’s real. That kind of traction is important because it tells you you’re on the right track.

The shows. We had a hunch that turning the game into a live show, where the show itself is the product, would work. But seeing how much fun people actually have has exceeded expectations.

Watching people laugh, play, and connect is exactly what we hoped for. What’s especially exciting is seeing real relationships form. People are building friendships and business connections in a way that feels more meaningful than just swapping startup pitches or having surface-level conversations.

It’s really sparked something special. It’s working the way we hoped, and we’re incredibly excited about the response so far.

I’m seeing a big increase in founder-centric, in-person meetups. They’re popping up all over the city, which shows that the Austin founder energy is alive and well.

People want to get out, connect, and spend time together away from screens. There are more events where founders and creatives are meeting face to face, and it feels like a big uptick compared to just a few years ago. That’s really exciting to see.

There’s an incredible amount of opportunity here to meet and talk to your potential customers directly. You don’t need to look to other cities to make meaningful connections that could change the trajectory of your business.

Your first customer could be in the zip code next door or sitting in a coffee shop downtown. Don’t be afraid to talk to people, attend local meetups, and connect with other founders.

If you come from a genuine place, truly building something and willing to put in the work, people here are incredibly open and generous with their time and knowledge. You can learn a lot from just a few in-person conversations.

LinkedIn and Instagram are great for making initial connections, but meeting up at a coffee shop, a comedy show, or a local founder event can open doors to opportunities you wouldn’t find online.

You can learn more at playsidehustle.com. You can sign up to play the online version for free on your phone anywhere you have internet. You can also see tickets for upcoming shows.

Our next show is March 18th at Pershing. It’s the last night of South by Southwest. If you’re looking for a fun time, come out, bring your friends, and be ready to pitch some wild and ridiculous business ideas.

Use our exclusive discount code “AFF5” for $5 off at the next event.