From Business Failure To Podcast Star

One entrepreneur found accidental fame in a podcast series, but couldn't spin it into a successful business. There's a lot you can learn from his mistakes.
Writer and Public Speaker, Freelance
November 20, 2013

In 2006, Dan Repperger of St. Louis started a podcast dedicated to one of his hobbies with the sole intention of having fun. This year, Fear the Boot is the most recognized podcast on tabletop role-playing games, with approximately 20,000 downloads per episode and an annual fan convention—Fear the Con.

Meanwhile, years after beginning the podcast, Repperger started a computer consulting business. Though he worked for multimillion-dollar startups, he ended up closing his business less than three years later.

The parallel experiences of success and failure taught Repperger these important lessons about how to run a business.

Lesson 1: Follow Your Passion

Repperger loves role-playing games, and merely likes computer programming. Because of this, one of his projects got far more time, attention and energy than the other. Furthermore, podcast listeners experienced—and were themselves energized by—Repperger's passion for the hobby.

Takeaway: If you can get excited about a product or service, start a business offering it. If you're merely good at something, find somebody to hire you to do that work on a contract basis.

Lesson 2: Product Before Promotion

Part of the success of Fear the Boot comes from the professional quality of the podcast. The team uses high-level recording equipment and editing software, and approach each episode with a plan. This alone makes the podcast stand out among most free downloads. While running his consulting business, he found that many clients had their marketing plan laid out—and sometimes even active—before they had created a quality product. Those businesses are no longer around.

Takeaway: Don't promote your product at the expense of quality. All that does is show lots of people that your offerings are substandard.

Lesson 3: Listen To Your People

Fear the Boot RPG Podcast


When he began consulting, Repperger had already developed several years' experience of promoting and running a successful podcast. He had ideas to offer about how to run and promote the businesses he had been hired to help succeed. However, because Repperger was a technician instead of a C-level executive, his ideas were roundly ignored. Repperger credits much of Fear the Boot's success to his willingness to listen to fellow hosts and listeners, and to be outvoted.

Takeaway: Judge ideas and suggestions based on the merit of the suggestion, not on the person who brings the idea to your attention.

Lesson 4: Pick The Occasional Fight

In 2007, Fear the Boot was nominated for an ENnie award—a major award in the role-playing game industry. They were removed from the running because a joke in one podcast episode seemed to give listeners instructions to cheat on the votes for the award. Although Repperger stresses that Fear the Boot worked hard to keep discussion of this decision civil, the resulting debate got heated in forums and social media across the Internet with the end result of several thousand new listeners for the podcast.

Takeaway: A little controversy now and then increases people's engagement around your brand. Make sure that engagement is positive by staying classy.

Seven years into its run, Fear the Boot is still a free podcast with proceeds from projects generally going to charity. However, Repperger has received gigs for his fiction based entirely on connections made on the podcast.

Do you have a similar story of accidental success? Tell us about it in the comments and join the conversation.

Jason has contributed over 2,000 blog and magazine articles to publications local, regional and national. He speaks regularly at writing and business conferences. You can find out more about Jason at his website.

Read more articles on leadership.

Photos: Getty Images, Courtesy Fear the Boot RPG Podcast

Writer and Public Speaker, Freelance