Latest Episode

The Rise of the Creator Entrepreneur

What happens when a podcast becomes bigger than the podcast itself?

Heather Osgood sits down with Christiana Brenton, Chief Business Officer at Steven.com, to explore the rise of the “creator entrepreneur” and what it means for the future of podcast advertising. Christiana breaks down the FlightStory ecosystem, why ownership and control of monetization matter, and how her team approaches selling creators across audio, video, social and beyond.

They also dig into what traditional podcast moneti

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The Rise of the Creator Entrepreneur
234
Oct. 7, 2026

The Rise of the Creator Entrepreneur

What happens when a podcast becomes bigger than the podcast itself? Heather Osgood sits down with Christiana Brenton, Chief Business Officer at Steven.com, to explore the rise of the “creator entrepreneur” and what it means for the future of podcast advertising. Christiana breaks down the FlightStory ecosystem, why ownership and control of monetization matter, and how her team approaches selling creators across audio, video, social and beyond. They also dig into what traditional podcast moneti
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Live from Podcast Movement
233
Sept. 25, 2026

Live from Podcast Movement

We’re live from Podcast Movement with Norma Jean Belenky for a candid conversation about where podcasting is right now, and where it’s headed. Together, Heather and Norma Jean dig into some of the challenges facing the industry, the conversations podcasting needs to keep having, and why, despite all the doom and gloom, there’s still so much to be excited about. They also talk about Norma Jean’s work with PodBiz, what she’s seeing from creators and businesses across the space, and why podcasting
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Who Controls the Podcast? Navigating Reach, Video & the Future of the Format
232
Sept. 23, 2026

Who Controls the Podcast? Navigating Reach, Video & the Future of the Format

As podcasting expands beyond the traditional RSS feed, creators and publishers have more opportunities than ever to reach audiences, but what are they giving up in exchange? In this episode of The Podcast Advertising Playbook, Heather Osgood sits down with Andy Slater, Head of Partnerships & Strategy at ART19, to unpack what “control” really means in today’s increasingly distributed podcast ecosystem. They explore the rise of video, the trade-offs between reach and ownership, whether creators r
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Are We Trying Too Hard? Laura Mayer on Podcasting’s Next Chapter
231
Sept. 2, 2026

Are We Trying Too Hard? Laura Mayer on Podcasting’s Next Chapter

Laura Mayer has spent her career inside some of podcasting’s most influential companies. Now, she’s looking back at the ambition, anxiety, and relentless drive that came with building a career in a fast-moving industry. In this episode, Heather sits down with Laura, podcast executive and author of Tryhard: A Cautionary Tale of Clocking In and Spinning Out, to talk about what happens when professional ambition becomes impossible to turn off, and what she learned when she finally did. They also
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Who Defines the Future of Podcast Advertising?
230
Aug. 20, 2026

Who Defines the Future of Podcast Advertising?

Podcasting is evolving faster than the systems built to measure it. Audiences are moving between audio and video, consumption is increasingly happening across closed platforms, and advertisers are being asked to make sense of performance without always having access to the full picture. In this episode of The Podcast Advertising Playbook, Heather Osgood sits down with Dan Granger, CEO and Founder of Oxford Road, to unpack the newly released AMP Accords (Alliance for Measurement in Podcasting) a
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How Smart Advertisers Actually Measure Podcast Performance
229
Aug. 5, 2026

How Smart Advertisers Actually Measure Podcast Performance

Podcast advertising has matured, but measurement is still one of the most misunderstood aspects of the industry. In this episode of The Podcast Advertising Playbook, Heather Osgood sits down with Jason Fialkov, Vice President of Sales at Claritas, to unpack how marketers should really be evaluating podcast performance in today's privacy-first landscape. Together, they explore the biggest misconceptions surrounding podcast attribution, the difference between downloads, conversions, and true bus
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About the Host

HEATHER OSGOOD Profile Photo
HEATHER OSGOOD

Founder

Heather Osgood is the founder of True Native Media, a boutique podcast representation agency specializing in podcast advertising. With an extensive background in radio advertising and a love for podcasting, Heather was uniquely positioned to start an agency that could help advertisers get better results and assist podcasters in finding sponsors.

She is an influential voice in the podcast advertising space and has sold over 60K ads in six years. Heather is also the Podcast Moneymaker's creator, a course designed for podcasters who want the formula, tools, and tactics to get advertisers in 6 weeks.

Heather can be credited for contributing her expertise to major podcasting events like Podcast Movement, PodFest, and more. She is the host of The Podcast Advertising Playbook, a show dedicated to educating anyone interested in podcast advertising.

When Heather is not playing matchmaker to brands and podcasts, you will find her hiking and spending time with her family at the beach.