Previously in this column, I have shared the progress of my own startup, Shyndyg. While there are still more stories to tell, we’ve enlisted the help of another start-up founder, Jeff Ullrich, President of Earwolf Media (and host of the “Love, Dad” podcast with David Koechner) to discuss his experiences.

Earwolf produces the most highly rated comedy podcasts online, and has recently expanded to television (with IFC’s Comedy Bang Bang) and comedy album production (James Adomian’s recent album “Low Hangin’ Fruit” was released earlier this week.)

Two years ago, Jeff Ullrich was a business manager for entertainers in Los Angeles. One of his clients was asked to fill in as the host of Comedy Death Ray Radio on Indie 103.1, and Jeff tagged along. What happened next changed his life.

Shortly after meeting the regular host, Scott Aukerman, Jeff was putting together a 14-page deck to propose his vision of the future of digital comedy: Earwolf Podcasting Network. Since they were building an infrastructure to record and promote one show (the incredibly popular Comedy Bang Bang), they might as well leverage this infrastructure to help grow the audience for other talented comedians. Scott immediately jumped on the idea, and Jeff got to work.

There was only one problem: Jeff had never built a website before. Knowing enough that it was an expensive proposition best left to people who knew more than he did, Jeff decided to crowdsource the development of the page and issue a call to action for fans of the show. They announced on the show for interested people to fill out a Google form, and then jump on a Skype call to ensure that they were covering off the immediate needs.

Karen: How did you take the initial interest and form it into something which would produce results?

Leveraging a large testing pool and rapidly iterating was a key to the early success of the site. To scale the network, Jeff and his creative partner, Scott Aukerman (Mr. Show, Comedy Death Ray) approached other performers who already had a base and name recognition.

Karen: One of the hurdles new start ups face is pitching and business development. When you were building the podcasting network, how did that work for you?

Karen: People will think that because your start-up was related to comedy, you could easily become successful because people love to laugh. Is that true?

As Earwolf grew, they had many bumps in the road, including engineer turnover, a studio space on a flight path (to which the Comedy Bang Bang team created a theme song, “Plane Break”) and self-doubt. Jeff admits there were times he wanted to exit the company, but those feelings would pass in between 10 minutes and 24 hours. “It’s definitely a rollercoaster. There were times when I was an emotional wreck,” he said.

Karen: Were there any decisions you made earlier on which you regretted?

There was another pitfall along the way: the same people who were so passionate about Earwolf were sometimes a stumbling block to change when it came to disagreements. “People care so much, but they don’t agree on how it should be handled.”

Jeff admits that through different management styles and changing the staff has helped fix this problem. The hurdle which still exists for Earwolf is one which affects most startups: how to effectively monetize. At the time of Earwolf’s inception,two of the three leading podcasts in this area charged the listener.

“[Charging listeners] was never something that was on my radar. I didn’t think that the model of truncating growth when you’re growing by 100 per cent every three months made any sense. But, now the problem is how do you monetize? It’s a problem we’re still working on today.”

Earwolf’s store sells premium podcasts, (usually coinciding with a live event — Bridgetown Comedy Festival, for instance) T-shirts, collector’s items and also patronage: similar to the public television model in the U.S.

It has worked for them. Earwolf’s now 13 podcasts get an average of 800,000 downloads per week. They have attracted blue chip sponsors such as Pepsi and Stamps.com who have helped Earwolf reinvest in what Scott and Jeff look at as “an incubator of comedy talent.”

Jeff previously spoke to us on the importance of listening to your gut as a business owner.

On hindsight, Jeff says, “I’ve never looked back on something we did and said, ‘I’m glad I listened to that other person who told me it was a bad idea.'”