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What Entrepreneurs Can Learn From the World's Best In Comedy Hiring strategies, like setting up a festival, include bringing in people you like to be around.

By Rebekah Iliff Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


We tend to picture bootstrapped startups or corporate-kingpin success stories when we think of entrepreneurship, but there are so many non-traditional, creative career paths that are built upon taking risks too. Event-based business SF Sketchfest (also known as The San Francisco Comedy Festival) was founded in 2002 by Bay Area actor-comedians Cole Stratton, David Owen, and Janet Varney.

With little more than a hankering to create something new, a whole lot of wit and a bit of business-savvy, the trio turned a mini comedy fest into a 15-year running, nationally recognized festival that's drawn the likes of more than 700 performers including Conan O'Brien, Gene Wilder, Neil Patrick Harris and Nick Kroll, to name a few. At one point, Fred Armisen said the festival was like "coming to summer camp," a feeling Cole, David, and Janet believe to be due to the event's inclusive nature.

Related: 4 Ways to Engage Your Audience Like a Comedian

I sat down with the co-founding team to get their take on why the festival's been so successful and what it took to get there. Listen to the podcast, and check out their advice for making it as an entrepreneur, regardless of your field.

Let yourself learn as you go.

"It's still trial by error. It's been 15 years of not knowing what we're doing and trying to figure it out at the same time," says David. Cole adds, "We initially called it a festival to have an angle for it, really." From learning how to market an event to handling their own event production, David, Janet, and Cole got their hands dirty and learned the ropes through hard work and with the help of trusted mentors.

Be tirelessly optimistic.

Janet jokes, "A lack of comfort with conflict turns you into a tireless optimist. I would so much rather feel like something's going to be okay then it's not, and I don't know if that's what makes an optimist versus a pessimist but if i'm going to assume something's going in a certain direction, it just feels better and safer to assume it's going to be okay." When people call Janet ambitious, she laughs. She wonders whether what she possesses is truly ambition or if she's just doing what she knows.

Related: What a Comedian Can Teach You About Running a Business

Surround yourself with good people.

"One of the smartest things we've done is try to keep great people around us." says David. Other that its co-founders, SF Sketchfest has zero full-time employees. However, when the festival takes place in January and February they bring on a ton of contractors. David adds, "We've been really lucky to get people to come back year after year." When hiring, their strategy is simple: They look for people they'd like to be around, and have hence considered the event a "good-vibes festival" because of it.

Remain calm and don't play the blame game.

When things go wrong (which as any event producer/entrepreneur will tell you, they always do), David suggests, "Being confident, remaining calm … and just coming together to work the problem and find a solution." Also, don't play the blame game. Decide upon next steps and work together to put the fire out.

Be patient.

The trio advises, "It's so important when starting out." Whether it's with each other (your partners), prospective sponsors, or anyone you're working with on a regular basis, know that good partnerships and outcomes take time.

Related: Improv and Comedy Can Infuse Companies With an Inventive Spirit

Janet adds, "I think that there are creative people who have difficulty being professional and there are professional people who have difficulty opening up the creative side. Whether we knew it or not (when starting out), we have a really nice combination of both." Cole, David, and Janet may not be the ones chauffeuring talent to SFO anymore, but they do still find themselves running last-minute errands like picking up a case of wine or working on graphic design. They think it's a good thing; it keeps them connected.

"I think we got lucky in the sense that we came at it from two sides, quips Cole: "One: Being performers -- we wanted it to be a great experience for other performers. And two: I think we all have pretty good business minds and we're very organized. I think those two things together made it succeed."

Rebekah Iliff

Chief Strategy Officer for AirPR

Rebekah Iliff is the chief strategy officer for AirPR, a technology platform to increase public-relations performance that serves Fortune 500 and fast growing technology companies. Previously, she was the CEO of talkTECH Communications, where she created an industry-first methodology for emerging technology companies which positioned talkTECH as one of the fastest growing, launch-only PR firms in the U.S. Iliff holds a B.A. in philosophy from Loyola University Chicago, and an M.A. in organizational management and applied community psychology from Antioch University at Los Angeles (AULA).

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