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:

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.

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.

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

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.

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.

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.

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.

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.

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:

This week, host Heather Osgood sits down with Steve Rock, a leader in the influencer and creator marketing space, for a conversation that bridges two worlds advertisers often treat as separate: podcasting and influencer marketing. With deep experience across both industries, Steve brings a grounded, strategic perspective on how brands can think more holistically about creator-led media.

In this episode, Heather and Steve explore why podcast advertising is still misunderstood, how brands can unlock more value from host-read creative, and what it really looks like to pair brand-building and direct response within a single campaign. Steve also shares his thoughts on the future of creator marketing, and how intelligent automation is reshaping the way teams plan, measure, and optimize spend.

They discuss:

Why podcasts aren’t categorized as influencer marketing—even though many of the same dynamics apply

How brands can guide creative without stifling authenticity

The role of creativity and strategy in generating true brand advocacy

When direct response vs. brand marketing makes the most sense

How today’s tools and emerging IA capabilities could streamline campaign planning and measurement

Whether you’re evaluating where podcasts fit within your 2026 media mix or looking to better integrate creator strategies across channels, this episode offers clear, practical insight into how to make your campaigns more effective. Steve’s experience helps demystify the overlap between podcasting and influencer marketing, giving advertisers the clarity they need to plan smarter and grow faster.

In this episode of The Podcast Advertising Playbook, host Heather Osgood sits down with Matt Drengler, Head of Partnerships at Podscribe, to explore one of the hottest questions in the industry today: how video is changing podcast advertising.

Together, they unpack what the data says about video ad performance versus traditional audio-only campaigns, how engagement and attribution differ between the two formats, and what advertisers need to know about tracking conversions when pixels aren’t available. Matt also shares insights on how video can expand reach across platforms like YouTube and social media, and whether audiences truly prefer seeing their favorite hosts, or still favor an audio-first experience.

If you’re curious about where podcast advertising is headed and how to make sense of video’s growing role in the space, this is an episode you won’t want to miss.