The Big 2-0-0: Highlights, Hits, and Hot Takes from the Playbook Archives

In this milestone 200th episode, host Heather Osgood takes a look back at some of the most defining conversations and insights shared over the years on The Podcast Advertising Playbook. From the early days of educating marketers on podcast ad basics to tackling today’s complex issues around distribution, targeting, and ROI, this episode reflects on how far the industry (and this podcast) has come. Like raising a child, podcasting changes in small, almost imperceptible ways, until you look back and realize just how far it’s evolved. We revisit key themes and takeaways from standout episodes, including: Foundational best practices for getting started in podcast advertising How censorship, piracy, and platform policies are shaping the industry The importance of testing and targeting in successful direct response campaigns Emerging trends in programmatic, consolidation, and content growth Smart strategies for reaching broad audiences and building emotional connection through ads Whether you’ve been with us since episode one or you’re tuning in for the first time, this retrospective offers valuable perspective on the evolution of podcast advertising, and what marketers should be thinking about next. Thank you for being part of our journey to 200 episodes!

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Chris Norton, Founder and Managing Director of Prohibition PR and host of Embracing Marketing Mistakes. With a deep background in public relations and brand strategy, Chris brings a unique perspective on how podcasting fits into a successful marketing mix. Chris shares the journey behind building his award-winning agency and what led him to launch a podcast focused on marketing missteps. He explores the power of earned media in the podcast space and why podcasting offers brand storytelling opportunities that traditional channels often miss. Here’s what we cover in this episode: How podcasting enhances brand storytelling in a cluttered media landscape Why earned media matters in audio and how brands can tap into it The connection between podcast advertising and PR strategy A marketing mistake that led to surprising insights Where creative growth is headed in podcast advertising Whether you're a brand looking to build trust or a marketer eager to refine your podcast strategy, this conversation is full of actionable insights from both the PR and podcasting worlds.

In this special episode swap, Heather Osgood joins Sam Brake Guia on the Mics to Millions podcast for an insightful conversation about what it really takes to monetize a podcast through advertising. As the founder of True Native Media, Heather brings a wealth of experience to the discussion, breaking down the evolving landscape of podcast monetization—from programmatic ads to host-read endorsements and everything in between. Key topics covered in this episode: The pros and cons of programmatic vs. host-read ads Why mid-sized health podcasts are becoming increasingly attractive to advertisers How to build long-term, authentic sponsor relationships Choosing between baked-in and dynamic ad formats What advertisers are truly looking for when they invest in podcasts Smart monetization strategies for shows with fewer than 5,000 downloads per episode Whether you're a seasoned podcaster or just starting to explore ad revenue opportunities, this episode offers clear, practical advice to help you build a sustainable and values-aligned monetization strategy.

In this episode of The Podcast Advertising Playbook, host Heather Osgood is joined by Mark Pafume, Vice President of Sales and Customer Success at Podbean. With years of experience guiding creators and brands through the evolving podcast landscape, Mark brings a fresh perspective on why combining video and audio is no longer just a nice-to-have, it’s a must for growth-minded podcasters. Mark dives into the current media environment and explains why now is a pivotal moment for creators to expand their reach across multiple formats. He offers insights on the unique discoverability challenges (and opportunities) of video-first versus audio-first platforms, as well as actionable tips for podcasters looking to streamline production without sacrificing quality. In this episode, Heather and Mark discuss: Why creators can no longer ignore the power of video The pros and cons of video-first vs. audio-first platforms for discoverability Workflow strategies to reduce burnout when producing in both formats What metrics matter most when tracking multiformat success Common pitfalls creators face when venturing into video Whether you're an audio purist or already dabbling in video, this episode will help you build a sustainable strategy that grows your audience and multiplies your impact.

In this episode of The Podcast Advertising Playbook, host Heather Osgood is joined by Angela Hollowell, Podcast Host and Producer of Honey and Hustle. Angela shares how her podcast centers stories of creative entrepreneurs and changemakers, and why building a vibrant, engaged community around that content has been key to its growth. Fresh off her session at Podcast Movement Evolutions, Angela dives into why community-building isn't just a nice-to-have in today's podcast landscape—it's essential. She explains what it means to create a “thriving ecosystem” around a podcast and how this ecosystem can become a powerful value-add for both creators and advertisers. Key discussion points include: How Honey and Hustle connects storytelling with community-building Common pitfalls podcasters face when trying to build community Why advertisers are paying more attention to audience engagement metrics If you're looking to elevate your podcast's impact—not just through downloads, but through deep listener relationships that attract brands—this episode offers practical strategies and fresh insights from the front lines.

Join Heather Osgood as she sits down with Joe Cilio, CEO and Co-Founder of Forever Dog Productions, to explore how the network has evolved over the past decade—most recently with a bold pivot into video podcasting. Joe takes us behind the curtain on the logistical and strategic challenges of adding video to an audio-first operation, the monetization opportunities (and limits) across YouTube and Spotify, and why visual storytelling matters now more than ever. He also dives into Forever Dog’s innovative approach to talent development, including their groundbreaking work with drag icons through Moguls of Media. In this episode, we cover: What Forever Dog’s transition to video really looked like behind the scenes The monetization model for video podcasts—CPMs, simulcasts, and platform payouts How Forever Dog approaches YouTube packaging, set design, and branding Building successful partnerships with creators What a ten-year-old podcast network is doing to stay fresh in 2025 Whether you’re a podcast creator, advertiser, or strategist, this episode offers a smart, forward-thinking look at where the industry is headed.

On this solo episode of The Podcast Advertising Playbook, Heather Osgood dives into the world of podcast advertising through the lens of reality TV’s favorite matchmaking experiment—Love Is Blind. Spoiler alert: when it comes to ads, love at first listen isn’t always guaranteed. Just like the hopeful couples in the pods, advertisers sometimes enter the podcast space with high hopes but no clear strategy. Heather shares why going in blind can lead to unmet expectations and why partnering with podcast ad experts can help you find your perfect match. This episode is all about setting realistic expectations, embracing the testing process, and building strong, data-driven relationships with your audience. Key discussion points: Why advertisers shouldn’t “go in blind” when launching podcast campaigns The importance of working with experts to guide your strategy How testing and iteration lead to long-term success What to do when your campaign doesn’t go as planned Why every brand should run a test campaign before committing to long-term partnerships Whether you're new to podcast advertising or trying to figure out why your last campaign didn’t work, this episode is a reminder that finding the right fit—just like love—takes time, patience, and a smart strategy.

This week on The Podcast Advertising Playbook, host Heather Osgood sits down with Hetal Patel, President of Ad Intelligence at iHeartMedia, to unpack how data, technology, and strategy are shaping the next era of podcast advertising. With deep expertise in media measurement and a front-row seat at one of the industry's biggest players, Hetal shares how iHeartMedia is harnessing ad intelligence to deliver smarter, more effective campaigns—and what that means for brands looking to make an impact. In this episode, Heather and Hetal discuss: How ad intelligence is driving innovation in podcast advertising. The trends shaping how brands approach podcast ad campaigns today. How iHeartMedia uses data to enhance targeting and performance measurement. Advice for brands new to podcasting and measuring ad success. How leaders can stay ahead of fast-moving industry shifts, and more! Whether you're a brand, an agency, or an audio insider, this conversation offers valuable insight into the future of podcast advertising—and how to use intelligence to stay ahead of the curve.

This week on The Podcast Advertising Playbook, host Heather Osgood sits down with Matt Shapo, Director of Digital Audio and Video at the IAB, to explore the evolving landscape of podcast advertising—from emerging tech to evolving standards. With podcasting in the spotlight and video on the rise, Matt shares how the IAB is helping guide the industry forward while keeping trust, scalability, and innovation at the center of it all. In this episode, Heather and Matt discuss: The limitations and opportunities of video podcast advertising. How host-read ads are evolving—and where they still shine. What the IAB is doing to improve transparency in programmatic. Whether DAI is helping or hurting the listener experience. Ad load best practices and where the industry can improve. The future of AI in podcast advertising. If you're looking to stay ahead of where podcast advertising is headed—or better understand the standards shaping the space—this episode is packed with insight you won’t want to miss!

This week on The Podcast Advertising Playbook, host Heather Osgood sits down with Kirk Martin, host of The Calm Parenting Podcast, to pull back the curtain on what it takes to build a successful show while staying true to your mission. With millions of downloads and a dedicated audience, Kirk shares how he’s grown Calm Parenting into a go-to resource for parents—and why he decided to bring advertisers into the mix. In this episode, Heather and Kirk discuss: The inspiration behind The Calm Parenting Podcast and its evolution. Why Kirk started accepting advertisers and what makes a great brand partnership. How he balances authenticity with sponsorships. Strategies he’s used to grow his audience. What he wishes he had known before starting his podcast. If you’re a podcaster looking to grow your show while staying true to your voice—or an advertiser wondering what makes a podcast partnership successful—this episode is a must-listen!