Comedy Industry Insights: Crafting a Legacy of Laughter, Community, and Lasting Success

This month’s Small Business, Big Lessons is all about SF Sketchfest , San Francisco’s iconic comedy festival that’s been bringing laughter to the Bay Area—and beyond—for over two decades. What started as a humble passion project among three college friends—David Owen, Cole Stratton, and Janet Varney— has blossomed into the longest-running comedy festival in the U.S., uniting comedy legends and rising stars for two unforgettable weeks of sketch, stand-up, improv, and more.

Now celebrating its 22nd year, Sketchfest has grown into an internationally celebrated event. The 2025 season (January 16-February 2) will feature over 180 shows across San Francisco’s most iconic venues. The lineup is a testament to its incredible journey—from intimate club shows to grand tributes to comedy icons like Albert Brooks and Tim Curry, plus anniversary celebrations of cult classics like Napoleon Dynamite and Airplane!.

SF Sketchfest’s evolution from a grassroots idea to a beloved cultural institution offers powerful lessons for any entrepreneur. It’s proof that with the right blend of artistic integrity, smart growth, and a commitment to the original vision, you can scale without losing the magic that made your project unique.

Below, David shares his personal journey of building SF Sketchfest from the ground up, along with the invaluable business lessons he's learned along the way.

Fresh out of college, you and your friends found a business together based on a shared passion. Did any of you have a background in business?

Learn by doing, grow by trying. We knew nothing about it - we were just a group of friends who discovered a shared passion. There was this amazing program at our school called Brown Bag Theater where students had to handle everything themselves. We selected the material, acted, directed, managed the tech, did the marketing - basically the entire production from start to finish. While there wasn't any money involved, it taught us the fundamentals of bringing a creative project to life. That experience gave us the confidence to just dive in and figure things out as we went along. None of us went to business school or sought professional guidance at first - we learned everything through hands-on experience. We just sort of figured it out as we went and we're still kind of doing that today. 

What’s the key to building a successful business with friends?

Trust as the Foundation for Success. Make sure they're friends that you really get along with and are willing to fight like brothers and sisters with. There needs to be a full trust – if you fall, they're going to catch you. 

How did you initially build your network and develop your approach to programming? 

Authentic Connections and Intuition. It was completely grassroots and driven by intuition. As performers ourselves, we naturally connected with other performers. The first year, we booked six local sketch comedy groups, and through word of mouth, we started building relationships with performers in cities like New York, LA, Austin, and Seattle. Our network grew organically, focused more on artists and the audience than on industry connections. We weren’t thinking, “What would a major network want to see?” We were thinking, “What do we want to see, and what does San Francisco want to see?”

How has your approach to dividing responsibilities among founders evolved as your organization has grown?

Natural Evolution and Intentional Growth. There’s a lot of overlap, but each of us tends to take the lead in certain areas. Overall, it’s always been all hands on deck, and we’re always ready to jump in and help each other out when needed. 

As the festival grew, we knew we needed more people to handle all the shows at different venues. If you add a show, yes, it's gonna add more revenue if it sells well, but it's also adding a ton more expenses. After 22 years, we know how it all works, and we have a great team. Many of our seasonal employees have been with us for years, and they know the festival inside and out. We’ve built a strong production and artist services team who take exceptional care of our artists—managing their hotels, transportation, flights, and making sure they feel welcomed. We have an incredible team of people who ensure everything runs smoothly and all the plates keep spinning at once.

For anyone looking to scale their passion, but lacking business experience, what advice do you have?

Don’t wait for permission. If we had known how difficult it would be, or tried to learn all the business stuff upfront, we probably never would have gotten started. My advice is simple: don’t wait for permission. We didn’t wait—we just did it ourselves. We didn’t go out and try to get financing; we kept it DIY because we wanted to be our own bosses. It wasn’t easy, and we definitely made a lot of mistakes, but each year we treated it as a chance to learn from what went wrong.

Start Small: You’ll figure things out along the way, but start small. Don’t put all your eggs in one basket right away. Keep your overhead low and your risk manageable. That’s the approach we took early on. We kept our model sustainable, so we didn’t have to sell out to succeed.

Write your own rulebook: Another key lesson: don’t feel pressured to follow the industry’s rules. We never went to agencies to ask how much comedians cost. We simply said, "Here’s what we can pay—do you want to come?" And we built a reputation with people who saw our event as something fun, like a summer camp where they could hang out with friends and perform. We played by our own rules, and if people wanted to join, great; if not, that was fine too.

How do you know when and how to scale?

Grow boldly, pivot quickly. There’s no perfect formula—it’s really intuitive. Sometimes we’ve scaled too far and bitten off more than we could chew. Ultimately, it’s about analyzing the numbers and seeing what works for your business. We’re constantly making adjustments. For instance, we introduced the SF Sketchfest Tribute in our third and fourth year, initially honoring just one performer each year. Now, we honor five or six people each year. The key is to honor as many as we can without overextending ourselves. We only have a finite amount of time on this planet, so, let's do as much as we can without doing too much.

Click here to purchase tickets to next month’s festival and here to learn more about SF Sketchfest.

This interview has been edited and condensed for clarity.