In this episode of Clover, I get to catch up with my longtime friend and powerhouse media executive, Tracy Kaplan, and her “hodgepodge” career that turned out to be a masterclass in building a bold, non-linear path in media, tech, and podcasts.

Tracy walks us through her journey from WGBH and ABC News to CBS Interactive, SnappyTV, Twitter, TuneIn, Patreon, Tenderfoot TV, and now Courier Newsroom, all while launching her own company, Small But Mighty Media, and creating The 10 News, an award-winning news podcast for kids. Along the way, she shares how she spots the real inflection points in media (from mobile video to podcast subscriptions to now AI), builds durable partnerships with platforms like Apple and Spotify, and refuses to let imposter syndrome keep her from jumping into the next big thing.

We also dig into the business side: subscription models, monetization beyond ads, what actually grows a podcast audience, and how to lead high-pressure teams through constant change without burning everyone out.

In this episode, you’ll learn:

• How to turn a “hodgepodge” career into a strategic advantage and deliberately collect the skills and experiences you’re missing instead of chasing a straight line.
• How to spot the next wave in media and tech by staying curious, observing real people’s behavior (hello, commuters watching video in Japan), and forcing yourself to experiment with new tools like AI before you feel “ready.”
• Practical ways to move into a new lane—before you’re an expert, including how Tracy taps her network, asks smart questions, and leverages subject-matter experts to fill her own gaps.
• A clear breakdown of podcast monetization today—ads, Apple/Spotify subscription channels, Patreon-style membership, and even donations and fiscal sponsorship—and how to think about diversifying your revenue so you’re not at the mercy of one market.
• How Tracy built and scaled The 10 News for kids, including the real origin story (NPR in the school pickup line + political ads on YouTube) and the tactics she used to secure high-caliber guests like Dr. Fauci.
• What makes a partnership last in a fickle industry, from being radically responsive and direct, to making every deal a “win-win” instead of a zero-sum transaction.
• Tracy’s leadership philosophy in high-pressure environments—how she pushes her team to grow while still rolling up her sleeves, taking on grunt work when needed, and making sure no one is left to fail alone.
• Hard-won career advice for women in media and podcasting, including why allies inside and outside your company matter, how to recognize when it’s time to leave a role you once loved, and why tearing other women down is a long-term losing strategy.
• Her big blue-sky vision for helping kids and families better understand the world—and why she dreams of a “domestic Peace Corps” style program that gets people outside their bubbles and into each other’s communities.

If you’ve ever worried that your career looks “messy” on paper, or felt behind on the latest shifts in media, this conversation will give you both a roadmap and a serious permission slip to build something beautifully non-traditional.