Podcast Advertising Playbook

The Power of the Middle

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Brian Conlan, President of DAX US, to explore how programmatic buying is reshaping the podcast advertising landscape and why mid-tier and long-tail podcasts may represent one of the most overlooked opportunities in the medium. Brian shares how he entered the podcast space and offers insight into the role DAX US plays in helping advertisers access podcast inventory at scale. Together, he and Heather unpack the assumptions that often drive media planning decisions, why advertisers tend to focus on top-ranked shows, and what brands may be missing when they overlook mid-tier creators and niche audiences. In this episode, we discuss: • Why mid-tier and long-tail podcasts are often undervalued in media plans despite strong audience alignment • How programmatic buying is making it easier for advertisers to scale across a broader range of podcasts • Whether the concept of “mid-tier” podcasts will evolve as buying and execution become more automated If you are looking for smarter ways to scale podcast campaigns while maintaining strong audience alignment, this episode offers a thoughtful look at how expanding beyond the top charts could unlock meaningful performance and reach.

Attribution in the Age of Audio and Video

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Bryan Barletta, Founder of Sounds Profitable, to discuss how podcast attribution has evolved and what measurement really looks like in a world where audio and video are converging. Attribution in podcasting has come a long way, but it is still widely misunderstood. Bryan shares where measurement is genuinely improving, why some reporting may appear lower than expected, and how advertisers can think more strategically about evaluating performance across platforms like Spotify Video, YouTube, and traditional audio. In this episode, we discuss: * How podcast attribution has improved and what is driving greater advertiser confidence * What advertisers often misunderstand about podcast measurement and performance data * The tradeoffs that come with video podcasting and how it impacts reporting * How to think about attribution when campaigns run across audio, Spotify Video, and YouTube * What “good enough” attribution looks like and what the future of measurement may hold If you are trying to better understand podcast performance and make smarter decisions with attribution data, this episode offers practical guidance and a clear view of where the industry is headed.

Is There a Place for AI-Generated Host Reads?

On this episode of the Podcast Advertising Playbook, Heather Osgood sits down with Marty Avallone, CEO of Ekoz AI, to explore the growing conversation around AI-generated, voice-cloned host-read ads in podcast advertising. Marty shares his background and what inspired him to build Ekoz AI, along with a look at how voice cloning is currently being used in live campaigns. Together, they discuss where this emerging format fits within today’s monetization landscape, positioned between traditional host reads and programmatic, and why advertisers and sellers are paying close attention. In this episode, Heather and Marty discuss: * How voice-cloned host-read ads work and where demand is coming from * Who is selling this type of inventory and how it’s being priced * Industry reaction to AI-generated content and ads * Where authenticity, trust, and scalability intersect Heather brings a thoughtful seller’s lens to the conversation, acknowledging the efficiency and creative support AI can offer while also raising important questions about authenticity and whether voice cloning truly addresses the challenges most podcasters face today. The episode offers a balanced, practical look at the potential and the open questions surrounding AI’s role in podcast advertising.

True Native Media: 10 Years of Building Trust and Scaling Podcast Advertising

To mark 10 years of True Native Media, VP Nick Gryniewicz steps in as guest host to sit down with founder and CEO Heather Osgood for an honest conversation about what it really takes to build a company in podcast advertising from the ground up. Together, they reflect on the lessons learned over a decade in business, the pivotal moments that shaped True Native Media’s growth, and the decisions that changed everything along the way. Heather shares the turning points that mattered most, what surprised her about entrepreneurship, and the things she wishes someone had told her before she ever got started. This episode is part reflection, part reality check, and part roadmap for anyone building in podcasting, media, or entrepreneurship. Whether you’re just starting out or deep in the work, there’s no shortcut here, just hard-earned insight from ten years in the business.

Why Focus Wins

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Jason Fishman, Co-Founder and CEO of Digital Niche Agency (DNA), to explore how specialization, podcasting, and thoughtful marketing strategy can drive sustainable growth. Jason shares how building a focused niche helped DNA stand out in a crowded digital landscape and why clarity matters more than ever as AI and automation reshape the industry. Together, Heather and Jason discuss how brands can prioritize their marketing efforts today, from underutilized digital tactics to the role podcasting plays in long-term credibility and thought leadership. Jason also offers practical advice for founders considering launching a podcast and highlights the most common mistakes brands make when advertising in the podcast space. In this episode, you will learn: * Underused digital marketing tactics brands should be testing right now * How podcasting fits into a modern thought leadership strategy * Where new brands should focus first: content, paid ads, or community * Common podcast advertising missteps and how to avoid them * And more This episode is a must-listen for marketers, founders, and agency leaders looking to build authority, make smarter marketing decisions, and use podcasting as a powerful growth lever.