Inside This Booming Plug-and-Play Network for Comedy Podcasters


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“Teamwork makes sleep work,” says Marty Michael as she sits behind a professional microphone in her podcast studio at Headgum’s LA office. In the age of Zoom interviews, it’s refreshing to hear someone speak with quality audio!



Marty Michael

Founded in 2015 as a network of independent comedy podcasts, Headgum was Marty Michael’s first foray into entrepreneurship. His biggest achievement was the co-founder of Headgum and its sister organization Gumball, a tech-read host advertising market that recently closed a $ 10 million round of funding. His career in entrepreneurship began when he worked in advertising sales. She credited her first job in ad sales with honing her digital advertising skills, preparing her for a major role that came in a few years when she joined CollegeHumor. He helped married brands like Frito-Lay and Turner with talent from the platform to tell their stories through creators that the public knew, loved and trusted. Finally, Michael became close friends with some of the creators and together they took the opportunity to expand the creator-brand relationship outside of traditional digital media into the growing audio space.

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Collaborating with creators Jake Hurwitz and Amir Blumenfeld, Michael began selling read ads from the host on his first hit podcast, “If I Were You.” The company was successful. “If I Were You” earned several hundred thousand dollars in revenue during their first year working together. This first success illuminated the financial and creative opportunity of podcasting. In 2015, the trio decided they wanted to make the leap and start their own network called Headgum.

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“Starting a business is difficult. One of the most difficult was finding the financial seeds to plant. I had to convince friends and family about the missed opportunities in podcasting, “said Michael, explaining the humble beginnings of the journey as the trio prepared to release Headgum with a list of 9 original shows. Two years after the release, Headgum had grown to become the home of more than 30 shows, including hit hits like “Doughboys” and “Why Won’t You Date Me?” The trio has managed to create shows with a following.

For Michael, who was primarily responsible for the business side of things, success has gradually revealed to him the clouds that cluster away: growing the business. While the host’s ad is the signature of the relatively nascent podcast medium, booking them is still an archaic manual process. Most of the booking was done back and forth between creators and advertisers in Excel and by email.

“I can say this with confidence: everyone hates emails.”

Michael thought there was a better way to send an email to scale. He had an idea for an automated marketplace where algorithms would do the job instead of 12-point Caliber font words. Together with his friend Andrew Pile, a former CTO of Vimeo, a sister company of CollegeHumor, they both threw Gumball hand in hand with Headgum. Gumball, a technology-enabled host-read ad marketplace, was designed from the ground up to connect podcast hosts with advertisers without the need for more email and spreadsheets.

Related: Top Advantages of Podcasting for Entrepreneurs

For the next two years, Michael purposely kept Gumball inside Headgum. He focused his efforts on perfecting Gumball until it could really become a plug and play for any podcast on the Internet. Although the decision meant that some early financial gains would be lost, he believed in laying a solid foundation. Together with the team, they would use the content and involvement of the Headgum listener to evaluate the success of the Gumball platform and make the appropriate corrections and improvements.

“As the saying goes, rubbish goes in, rubbish goes out. Without the quality content of the team, there is no way we could have launched Gumball properly, “added Michael. As Gumball approached maturity, a venture capital fund realized. In early 2020, Michael went received a surprise call from a former colleague of his at CollegeHumor who later switched to a different role at Union Square Ventures. “I thought I just wanted to have a beer and catch up!” It turned out that Union Square Ventures he wanted to capitalize on the growing podcast advertising market and was looking to invest in Gumball.

“The enthusiasm of the people who want to invest in us was really inspiring. With that kind of money, we could build on the dreams that the original team had in the early days of Headgum,” Michael knew the next step was to create a team that knew the industry inside and out. “We dreamed big; now is the time to build big.” At 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 Headgum Network talent.

Today, Gumball is proud to be the platform for independent creators of all shapes and sizes. In the second quarter of 2022, more than 150 independent creators joined Gumball. The company’s revenue is already tripling that of 2021. Gumball’s algorithm seems to have solved the archaic problems of podcast advertising. For Michael, however, the ultimate ingredient for success was not the algorithms. Rather, they were the creators, the programmers, the marketers, the marketers, all of them joining forces.

“The success happened because the right people came together and decided to work together.”



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