Over the course of 61 episodes Earwolf and Midroll Media founder Jeff Ullrich has charted the maturation of the podcasting business on The Wolf Den podcast like no one else.
At the beginning of the show’s run three years ago Jeff talked with many of the medium’s rising stars, like Marc Maron, The Sklar Brothers, and Doug Benson. He also interviewed other entrepreneurs at the vanguard of this new media movement, like Jesse Thorn from Maximum Fun, Chris Harwick of Nerdist, Jack O’Brien at Cracked and Dick Glover from Funny or Die.
What made the show particularly unique is that Jeff would check in with candid updates from the front lines of an entrepreneur’s life as he led two rapidly growing businesses. His blend of forthright honesty and curiosity about what makes for a successful and sustainable new media business has been the key driver of The Wolf Den. This made the show a must-listen for leading figures in online media like former Slate editor David Plotz and producer of This American Life and Planet Money, Alex Blumberg.
In June Jeff stepped aside from the CEO role to become the non-executive Chairman of Midroll Media, and Adam Sachs became the new chief executive. With this transition Jeff is also handing off The Wolf Den to Adam, who will be the new host.
Jeff recently recorded his last two episodes as host of the show. In episode #60 he is joined by Earwolf co-founder and Comedy Bang! Bang! creator Scott Aukerman. They talk about the early days of Earwolf and the growth of the company, and how they started developing shows like How Did This Get Made? and Professor Blastoff. They also share some fond memories as well as some of the challenges of bootstrapping a new business on a very low budget.
Adam is Jeff’s guest for episode #61, which is the figurative passing of the torch (if only podcast hosts had to hold actual flaming torches!). Jeff interviews him about his life before Midroll as the head of an online dating startup that got acquired, and they recall their first meeting before Adam came aboard. Adam is a long-time comedy nerd, so they talk about why he is excited to take the reins at Midroll, and take over The Wolf Den.
Jeff also offers some advice for Adam in taking over the show. He explains that producing the podcast, “started as a way to document things that were going, and then at some point it evolved to building relationships.” So, he recommends, “If there’s someone that you wish that you could have a have a meaningful conversation with,” then, “invite them to be a guest on your podcast.”
Both episodes should not be missed. Together they tell a story of how a founder makes the crucial determination that the company he started and nurtured is ready to be entrusted wholly to the team he worked so hard to assemble. It’s a valuable story for any entrepreneur.
Speaking personally, it was a privilege to serve as the producer of The Wolf Den with Jeff beginning episode 54, and to work with him on other projects since joining the company a half-year ago. Although it was a pretty short time, I found his passion for and belief in podcasting exciting to be around. His willingness to ask hard questions about how and why we do what we do is a much welcome challenge. That he does it all with a strong integrity is encouraging and inspiring.
It’s been a fun ride so far, especially since my first time talking with Jeff was as guest for episode 53 back in December of last year. I never would have predicted then that I would end up working here at Midroll and becoming the show’s producer just a couple of months later.
Like everyone at Earwolf and Midroll I will miss working with Jeff, and wish him the best in the next stage of his life and career. I am also looking forward to working with Adam in this next chapter of The Wolf Den. It’s great to work for a company that walks the walk, and talks the talk, by making it a priority to share openly experiences, insights and questions about the business, in the very same medium it specializes in. I am enthusiastic about the future of the show, and the company.