Founder’s Story: From Radio Obsession to Wall Street – The Untold Story of PodcastOne | Ep 217 with Kit Gray

Release Date: May 9, 2025
Host: IBH Media
Guest: Kit Gray, Co-Founder and President of PodcastOne

Introduction

In Episode 217 of Founder’s Story, IBH Media delves deep into the entrepreneurial journey of Kit Gray, the co-founder and president of PodcastOne. Kit shares his passion for the audio medium, the inception and evolution of PodcastOne, strategies behind its growth, and the intricate process of taking the company public. This episode is a treasure trove for aspiring entrepreneurs and podcast enthusiasts alike, offering candid insights into the resilience and creativity that define entrepreneurial success.

Early Passion for Audio and the Spark to Entrepreneurship

Host 2 kicks off the conversation by asking Kit about the initial spark that led him to entrepreneurship, particularly in the audio industry.

Kit Gray reflects on his early fascination with audio:

“Audio has always had a special place in my heart. Back when I was a kid living in Boston, listening to sports talk radio with my dad during matches was our bonding time.”
[02:56]

His admiration for Howard Stern played a pivotal role in shaping his vision:

“Howard Stern built brands into both his show and his radio network. He was a thought leader in that space.”
[03:20]

Kit’s academic background in finance and his initial career in national security provided him with a solid foundation in business principles, which he later applied to the burgeoning podcast industry.

Building PodcastOne: From Concept to Reality

Transitioning from his role at Katz Media Group, Kit identifies the potential of podcasts early on. He recounts his first interaction with Adam Carolla, a move that would prove instrumental:

“I reached out to Adam Carolla about integrating advertisers like Proflowers and LegalZoom into his podcast. This was back in 2012, and it laid the groundwork for PodcastOne’s business model.”
[05:10]

Kit explains how PodcastOne leveraged the transition from traditional radio to podcasts, capitalizing on the flexibility and targeted reach of the new medium. By representing high-profile talents like Mark Maron and Bill Burr, PodcastOne quickly established itself as a leading podcast network.

Navigating the Changing Landscape: Timing and Adaptability

Host 2 brings up the critical role of timing in entrepreneurial success, prompting Kit to elaborate on how PodcastOne navigated industry shifts:

“Timing is a lot to it—hard work, perseverance, and believing in the medium. We got lucky when COVID-19 happened; people were stuck at home consuming more content, which boosted podcast listenership.”
[10:24]

Kit highlights the significance of adapting to technological advancements and market demands:

“With the iPhone revolutionizing on-demand content and YouTube entering the podcasting space, we adapted by enhancing our offerings and integrating video, audio, and social media strategies.”
[11:15]

He emphasizes the importance of community-focused advertising over mass impressions, a strategy that set PodcastOne apart from traditional advertising agencies.

The Growth and Expansion of PodcastOne

As PodcastOne grew, Kit details the diversification of revenue streams and the expansion into various forms of media:

“We do IP sales where our shows become TV programs, movies, or books. We also handle merchandise, live shows, and comprehensive marketing services to help podcasters monetize their content effectively.”
[12:40]

With $51 million in revenue and over 200 shows, PodcastOne's model showcases a blend of creativity and business acumen, ensuring sustained growth and industry relevance.

Taking PodcastOne Public: Challenges and Insights

The conversation shifts to the complexities of taking PodcastOne public. Kit shares his unconventional approach to leadership:

“I try to live differently as a CEO—wearing flip-flops and shorts, bringing a relaxed demeanor to a publicly traded company.”
[22:49]

He discusses the strategic decision to go public under the NASDAQ symbol PODC, aiming to create an inclusive environment where talent is invested in the company's success through stock options:

“Offering stock to talent ensures they have a stake in the company’s growth, aligning everyone's interests and fostering loyalty.”
[27:44]

Kit also touches upon ongoing mergers and acquisitions, seeking synergistic opportunities to enhance PodcastOne's market position without overburdening the existing infrastructure.

Advice for Aspiring Entrepreneurs

Towards the end of the episode, Kit offers invaluable advice for those looking to embark on their entrepreneurial journey:

“Never have any regrets in life. If you have an idea and you believe in it, go for it. You only live once.”
[20:40]

He underscores the importance of timing, perseverance, and surrounding oneself with a supportive network—highlighted by his wife's unwavering support during the early challenging phases of PodcastOne.

Kit encourages entrepreneurs to take calculated risks, emphasizing that groundbreaking successes often stem from bold moves and genuine belief in one's vision.

Conclusion

Episode 217 of Founder’s Story unveils the intricate tapestry of Kit Gray’s journey with PodcastOne, blending personal passion with strategic business maneuvers. Kit's transparent recounting of his experiences—from initial challenges to orchestrating a successful public offering—serves as both inspiration and a roadmap for aspiring entrepreneurs. His emphasis on community, adaptability, and authentic leadership encapsulates the essence of modern entrepreneurship in the digital age.

For those looking to explore the dynamic world of podcasting and entrepreneurship, Kit Gray’s story is a testament to the power of passion, timing, and relentless drive.

Notable Quotes with Timestamps

• Kit Gray on His Early Passion for Audio:
  “Audio has always had a special place in my heart... We would listen to sports talk radio to break up the awkward silence.”
  [02:56]

• On Leveraging Howard Stern’s Influence:
  “Howard Stern built brands into both his show and his radio network. He was a thought leader in that space.”
  [03:20]

• Discussing the Impact of COVID-19 on Podcasting:
  “Covid happened, and while it was horrible, it actually helped the medium quite a bit because people were consuming more content.”
  [10:24]

• On Offering Stock to Talent:
  “Offering stock to talent ensures they have a stake in the company’s growth, aligning everyone's interests and fostering loyalty.”
  [27:44]

• Advice for Entrepreneurs:
  “Never have any regrets in life. If you have an idea and you believe in it, go for it. You only live once.”
  [20:40]

Connect with Kit Gray

For listeners interested in learning more or connecting with Kit Gray, reach out via email at Kit@PodcastOne.com or visit PodcastOne.com to explore their extensive network of shows and opportunities.

This summary captures the essence of Episode 217, focusing on the substantive conversation between Kit Gray and IBH Media hosts, while excluding advertisements and non-content segments.