Podcast Advertising Playbook

Heather Osgood
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  • MARKETING
  • UPDATED TWICE MONTHLY

This podcast is dedicated to helping listeners better understand podcast advertising. Whether you're in advertising, marketing, or simply a podcaster interested in learning more about the podcast advertising world this show is for you. We'll provide techniques for implementing your ad campaigns, setting budgets, and expectations giving you the knowledge and expertise to become a podcast advertising expert.

  1. 1 DAY AGO

    Live from SXSW: How AI Agents Are Reshaping Podcast Operations with Podstock

    In this special live episode of The Podcast Advertising Playbook, recorded at Podcast Movement Evolutions during SXSW, host Heather Osgood sits down with the team behind Podstock to explore how AI is beginning to transform the way podcast businesses operate. From the origin story of Podstock to the development of their new AI-powered “Agent,” this conversation dives into the real operational challenges podcast teams face today and where automation can actually make a meaningful impact. Rather than replacing teams, tools like Podstock Agent are designed to streamline workflows, reduce manual tasks, and unlock more strategic thinking across podcast networks, studios, and sales organizations. In this episode, we cover: The problem Podstock set out to solve and why AI became the answer What Podstock Agent actually does and how it changes day-to-day workflows The most time-consuming podcast tasks that can now be automated How AI is shifting the economics and scalability of podcast businesses Where podcast teams should start when adopting AI tools If you’re thinking about how to scale your podcast business more efficiently, or want a clearer understanding of where AI fits into the industry, this episode offers a grounded, practical look at what’s already possible. This episode was recorded during Podcast Movement Evolutions at SXSW with the support of Nomono, SimpleCast, and The Podcast Academy.

    28 min

  2. 18 MAR

    Beyond Downloads: Rethinking Podcast Measurement

    In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Jonas Woost, Co-Founder of Bumper, to explore how podcast measurement is evolving beyond traditional metrics. Jonas shares how shifting from downloads to deeper consumption data can unlock more accurate insights, helping advertisers and publishers make smarter decisions and build stronger campaigns. In this episode, we cover: Why downloads alone fall short and how consumption data provides a clearer view of performance Where impressions fit and what better reporting should look like for advertisers today Why podcast retention and ad engagement are still undervalued and under-communicated What’s ahead for the industry, including collaboration, video integration, and AI’s impact on creative If you’re looking to better understand how measurement is evolving and what it means for your podcast advertising strategy, this episode offers a clear and practical perspective on where the industry is headed.

    51 min

  3. 4 MAR

    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.

    33 min

  4. 18 FEB

    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.

    44 min

  5. 4 FEB

    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.

    36 min

  6. 14 JAN

    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.

    28 min

  7. 17/12/2025

    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.

    42 min

  8. 03/12/2025

    Guesting, Booking, and Brand Awareness, Oh My!

    In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Sam Brake Guia, Co-Founder of Podwritten and host of Mics to Millions. Sam works at the center of podcast guesting, booking, and creator strategy, bringing a unique view into how brands and personalities can use interviews to increase visibility and connect with targeted audiences. Together, Heather and Sam explore: Why certain industries, especially health and wellness, lean toward podcasts What makes for successful guest pitching, including timing and seasonality How brands can use guesting to build authority and increase brand awareness

    39 min
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This podcast is dedicated to helping listeners better understand podcast advertising. Whether you're in advertising, marketing, or simply a podcaster interested in learning more about the podcast advertising world this show is for you. We'll provide techniques for implementing your ad campaigns, setting budgets, and expectations giving you the knowledge and expertise to become a podcast advertising expert.

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