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Thought Leadership Dear Media CEO, Michael Bosstick Knows How to Make Podcasts Work For Advertisers

Serial entrepreneur Michael Bosstick has done it all. He’s sold beds for private jets and overcame his fear of public speaking to launch a hit podcast with his superstar wife, Lauryn Evarts Bosstick. But the reason we asked him to join us on the Media Roundtable is because of his tireless work as CEO of the podcast network, Dear Media, where he has created a platform for female podcasters to dominate the landscape.

“Launch fast and adjust. Anytime that you want to do any kind of venture… stop waiting for perfection, get it out there, start, and adjust along the way.” –Michael Bosstick

In our humble opinion, Dear Media (Life with Marianna, Lipstick on the Rim, Breaking Beauty, and many, many more) is quite possibly the leading female-focused podcast network out there. We’re talking dozens of shows reaching over 10 million rabidly loyal listeners each month. In addition, as advertising partners, Bosstick’s team consistently goes the extra mile to put together integrated partnership solutions, complete with thoughtful customizations from their talented hosts.

Dear Media “gets it”  because Bosstick has one of the most complete understandings of the entire podcast ad space. How could he not when he’s held every single role? In addition to his role as CEO, Bosstick’s been in sales, operations, talent, and marketing. Plus, he’s been on all sides of the table; brand, agency, and client. It’s that insight, his desire to expand his perspectives continually, and his willingness to get started, get feedback, and make critical adjustments that make him a marketing role model from whom we can all learn.

Tune in to hear:

  • The secret to being in business with a famous spouse.
  • How to “keep your side of the street clean” amidst a wave of criticism.
  • How to build the confidence to talk to anyone.
  • What you need to do once third-party tracking gets obliterated.

You’re not going to want to miss this week’s episode. Click below to hear the entire conversation. 

Listen to the interview

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Find out as we look back on all the major news stories of 2025 in a new Media Roundtable: Industry Edition.

Dan Granger (CEO & Founder, Oxford Road) breaks down the stories that shaped the year with fellow audio luminaries:

The team is talking: Video Everything, Critical Mass, and Radio’s Next Act. Let’s dig in.

“ Video is definitely the big story for 2025.” – Neal Lucey (EVP, Strategy & Product, Oxford Road)

Video Podcast Wars – While YouTube still holds the crown, Spotify and Netflix came for it in 2025. We don’t know who will rule video next year (okay, probably still YouTube), but advertisers can’t ignore the video part of podcasts. Measurement is messier, but 100% doable. It’s time to get off the sidelines, and for the industry, we need to count impressions the same way. No more random combinations of views/downloads/instant plays/vibes. Standardize measurements to create confidence and growth.

Critical Mass – 73% of Americans have consumed a podcast. This is proof that our little industry’s all grown up. But James says the important number is 773, as in 773 million podcast hours consumed each week. Going from 73% to 100% is harder and less fruitful than increasing consumption. In 2026, industry expansion will come from both deepening relationships with existing deals, while expanding reach.

Radio’s Reckoning – Radio remains a contradiction. It’s still shrinking (~1% a year), and it’s still big (74% of audio use in cars). It has a massive reach, but the median age is ~59. This year saw Nielsen juicing ratings, local radio scoring in trust, and Tesla planning to drop FM from lower-priced models. Still, we think Radio is more overlooked than overrated, making it a smart channel for advertisers to invest in.

Want more insights from what was a wild year for the industry? Tune in to the full episode by clicking the link below.

Ad Infinitum S3E15 - Human Hacks

Marketers have been trying to predict how consumers will behave with statistics and studies for decades. But what if there’s a chance that science could help you understand consumers? Would you take it?

The world’s only podcast solely dedicated to audio ads is back with those answers and more! Presenting Ad Infinitum Season 3, Episode 15: “Human Hacks.”

Host Stew Redwine (Executive Creative Director, Oxford Road) welcomes best-selling behavioral science author Richard Shotton (The Choice Factory, Hacking the Human Mind). They’re looking at some of the most relevant behavioral studies in marketing and applying that formula to top-spending podcast ads from  McAfee, AmBev, Tide Pods, and  IBM

Stew and Richard talk Simplicity, Big Ladles, Concrete, and more. Let’s dig in…

“[It’s] always easier to work with human nature than against it.” – Richard Shotton (Author, Hacking the Human Mind)

Simple is Smart – To sound smart, keep it simple. In a study with simple and complex versions of the same text, readers said the simple version’s author sounded smarter. Why?  Big words confuse the audience, and they blame the writer. So make your talking points simple. Hosts will love you, and you’ll sound smarter, too.

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Words like Concrete – Studies show people remember concrete phrases (“white horse”) 4 times more than intangible ones (“subtle fault”). Look over your copy. If you want it to stick in people’s minds, skip the floating abstract words and firm up the copy with sturdy, concrete words and phrases.

Want more research-backed insights to make stronger audio ads? Tune in to the full episode here:

Protecting Human Connection: Audio’s ROI, AI Slop, & Netflix Moves

How will the industry shift with 200k AI episodes? Or with Netflix’s $400M podcast push? How do audio and video podcasts actually stack up for attention? Find out on a new Media Roundtable: Industry Edition, sponsored by our friends at ALLCITY Network.

Dan Granger (CEO & Founder, Oxford Road) breaks down the biggest stories and their potential impacts on the industry with fellow audiophiles:

• James Cridland (Editor, Podnews & Podcast Business Journal)
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The team is talking: Cheap TV, Video vs. Audio Attention, and Wading Past AI Slop. Let’s dig in.


“How do we make sure that we don’t get run over, for those of us that really care about the human connection piece?”
– Dan Granger (CEO & Founder, Oxford Road)

 

Netflix’s $8M Question – Netflix is offering 50+ podcasts to leave YouTube for $8M. If Netflix thinks podcasts are just cheaper TV, this move makes sense. But most podcasters don’t think about themselves that way. They build audience connection in a wildly powerful and efficient way. Leaving open platforms for closed ones diminishes that power. Todd’s hot take: Podcasters looking for a fast payday should take the exit and leave the others to grow their audiences.

Attention Increases ROI – A new study found that video podcasts cost 77% more to produce than audio, but audio beats video for completion rates (66% vs 61%). Audio’s an incredibly efficient way to grab and hold attention. That said, adding a video component actually increases plays for the audio version. The TLDR for CAOs: audio and video both help your campaigns. Measurement’s going to be harder, but it’s worth it. And in the meantime, keep asking for better measurement tools to anyone who’ll listen.

Protecting Human Connection – Ashley Carman’s Podcast Business Summit encapsulated the fight for the soul of podcasting. Inception Point boasts +200k AI episodes (all without QC). Netflix hopes to entice shows to take the sure money, and creators want to stay in control and help build brands (their own and their partners). While there’s money to be made in all directions, trying to protect the heart of podcasting, the authentic human connection, is only possible from some paths. CAOs: Uncertainty creates opportunity–for your shows that work, start conversations that can deepen your partnerships. If you value the connection between your creators and their audiences, continue to invest in them, and they’ll continue to invest in you.

 

Want more insights from the forces shaping the industry? Tune in to the full episode by clicking the link below.

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