Inside This Booming Plug-and-Play Network for Comedy Podcasters How Marty Michael and the team at Headgum built a tech-enabled podcast network.

By Robert Tuchman

Marty Michael

"Teamwork makes the dream work," Marty Michael remarks as he sits behind a professional microphone in his podcast studio in the Headgum office in LA. In the age of Zoom interviews, it is refreshing to hear someone speaking with quality audio!

Founded in 2015 as an independent comedy podcast network, Headgum was Marty Michael's first foray into entrepreneurship. Co-founding Headgum and its sister organization Gumball, a tech-enabled host-read ad marketplace that recently closed a $10million-dollar funding round, was his biggest achievement. His journey in entrepreneurship started when he was working in advertising sales. He credited his first job in ad sales for honing his skills in digital advertising, preparing him for a major role which came in a few years when he joined CollegeHumor. He helped married brands like Frito-Lay and Turner with talent from the platform to tell their stories through creators who the audience knew, loved, and trusted. Eventually, Michael became close friends with some of the creators and together they seized on an opportunity to expand on the creator-brand relationship outside of traditional digital media into the burgeoning audio space.

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Teaming up with creators Jake Hurwitz and Amir Blumenfeld, Michael began selling host-read ads on their first hit podcast, "If I Were You". The venture was successful. "If I Were You" went on to pull in several hundred thousand dollars in revenue in their first year working together. This early success shined a light on the financial and creative opportunity within podcasting. In 2015, the trio decided they wanted to take the leap and start their own network that would be called Headgum.

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"Starting a business is hard. Among the hardest was finding the financial seeds to plant. I had to convince friends and family of untapped opportunities within podcasting," reflects Michael, recounting the humble beginnings of the journey as the trio prepared to launch Headgum with a roster of 9 original shows. Two years after launch, Headgum had grown to be the home of over 30 shows, including breakout hits like "Doughboys" and "Why Won't You Date Me?". The trio has succeeded in creating shows with a following.

For Michael, who was mainly responsible for the business side of things, the success has gradually revealed to him the gathering clouds afar – scaling the business. While the host-read ad is the signature of the relatively nascent podcast medium, booking them remains an archaic, manual process. Most of the booking took place back and forth between creators and advertisers in excel and on emails.

"I can say this with confidence: everybody hates emails."

Michael thought there was a better way than emailing to scale. He came up with an idea for an automated marketplace where algorithms do the work rather than words in 12-point Calibri font. Together with his friend Andrew Pile, the former CTO of Vimeo, a sister company of CollegeHumor, the two launched Gumball hand-in-hand with Headgum. A tech-enabled host-read ad marketplace, Gumball was designed from the ground up to connect podcast hosts with advertisers, no more back and forth emailing and spreadsheets.

Related: Top Podcasting Benefits for Entrepreneurs

Over the next two years, Michael purposefully kept Gumball within Headgum. He focused his efforts on refining Gumball until it could truly become a plug and play for any podcasts that exist on the internet. Although the decision meant that he would miss out on some early financial gains, he believed in laying a solid foundation. Together with the team, they would use Headgum's content and listener engagement to gauge the success of the Gumball platform and make corresponding corrections and improvements.

"As the saying goes: garbage in, garbage out. Without the quality content from the team, there's no way we could have launched Gumball properly," Michael adds. As Gumball approached maturity, a venture capital fund took notice. In early 2020, Michael got a surprise call from a former co-worker of his at CollegeHumor who then moved on to a different role at Union Square Ventures. "I thought he just wanted to grab a beer and catch up!" It turned out, Union Square Ventures wanted to capitalize on the growing podcast ad market and was looking to invest in Gumball.

"The enthusiasm from the people who want to invest in us was really inspiring. With that kind of money, we could actually build upon the dreams the original team had in the early days of Headgum," Michael knew the next step was to build out a team who knew the industry inside and out. "We dreamed big — now it's time to build big." By the end of 2021, they closed $10 million in Series A funding, led by Union Square Ventures, Good Friends, Craft Ventures, Vertical Partners, as well as talent from the Headgum network.

Today, Gumball prides itself as the platform for independent creators of all shapes and sizes. As of early Q2 2022, over 150 independent creators have joined Gumball. The company's revenue is already pacing to triple that of 2021. Gumball's algorithm seems to have solved podcast advertising's archaic problems. For Michael, however, the ultimate ingredient for success was not the algorithms. Rather, it was the creators, the coders, the salespeople, the marketing people – all of them joining forces.

"Success happened because the right people came together and decided to work together."

Wavy Line
Robert Tuchman

Entrepreneur Staff

Host of How Success Happens

Robert Tuchman is the host of Entrepreneur's How Success Happens podcast and founder of Amaze Media Labs the largest business creating podcasts for companies and brands. He built and sold two Inc.500 companies: TSE Sports and Entertainment and Goviva acquired by Creative Artists Agency (CAA).

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