Rising from e-commerce executive to head of a women’s podcast network may not be an obvious career path. But for Michael Bosstick, the former CEO of a company that provided beds for private jets who now heads up the Dear Media podcast network, a background building brands in retail almost directly translated to the way he’s helping members of Dear Media build their brands.

“When we went into the space, I didn't really look at what other networks were doing because I didn't want to recreate something that is, in my opinion, an outdated model,” Bosstick says. While Dear Media, like other podcast networks, primarily earns money from ads, it ultimately aims to act more like an incubator for talent. It’s not just promoting its 32 podcasts, which are branded almost every shade of millennial pink. It’s also plugging those podcast hosts’ other platforms and products.

“These creators are going to become brands within themselves,” Bosstick says. “They're going to have their own products.” An April influx of $8 million in Series A funding for Dear Media will go partially toward “customer service, shipping, and contract manufacturing” for those products, he adds.


"It's an exponential growth model. If some of these listeners love a show, they're going to go tell 10 friends, who are going to tell 10 of their friends."


Podcasters on Dear Media range from well-known influencers, like “The Hills” reality TV star Whitney Port, to foodies, career coaches, and the former SiriusXM radio personality Taylor Strecker. Those with celebrity pedigrees also make an appearance, like Katherine Schwarzenegger, who interviews other celebs about their adopted rescue dogs. The hosts’ overlapping audiences skew overwhelmingly female, creating a shared target demographic.

Bosstick originally entered the world of influencer women through his wife, Lauryn Evarts Bosstick, longtime author of the popular blog, “The Skinny Confidential.” After a night drinking margaritas in Cabo, the couple decided to start a podcast that would feature them both under TSC branding. They grew the podcast, Him & Her, independently, learned podcasting’s “pain points,” and realized they could help others grow their shows, too. Bosstick founded Dear Media in 2018 with Raina Penchansky, CEO of influencer management agency Digital Brand Architects, and now he oversees day-to-day Dear Media operations as the CEO.

Since Dear Media’s launch, the podcasting space has gotten increasingly crowded. Every influencer and media outlet seems required to start their own audio show. Here Bosstick talks about what sets Dear Media apart from other podcast networks, how it can be “confusing” for people that he’s a man running a women-focused company, and why COVID might expand the audience for audio.


With the coronavirus lockdown, there was initially a small drop in podcast listening that many attributed to listeners no longer commuting. Do you think that’s what led to that drop, and if so, why did people come back?
In the first week or so at Dear Media, we saw a decline because people were trying to figure out what to do. Probably every medium saw that, because most of us were tuned into the news cycle to figure out what the hell was going on in the country. We obviously lost the commute, but I believe traditional AM/FM radio was more hurt by that. We've seen a 25 to 30 percent increase in listenership since March from new listeners. We’ve also been doing more media lately and marketing ourselves more. 

Because of COVID, podcasting is going to see a much faster increase than it would have without COVID. Many of us have realized that AM/FM radio is an outdated business model. I compare it to how we used to watch cable television before we had on-demand. You wouldn't necessarily jump back into cable television now, and I think the same thing will happen to radio. With an increased listenership, you'll also see a lot of new dollars flow into the podcast space from [the radio] space.

That’s a good analogy. But at the same time, the podcast space has gotten increasingly crowded in the past several years. How do you ensure that Dear Media podcasts stand out?
Content. It has to be good content. I've been in the digital space for a long time, and we heard the same thing about bloggers, influencers, and YouTubers. Content is king and queen. [Him & Her] started four years ago when the space wasn't as crowded, so it was easier to stand out. Now, we have a dedicated listenership across all the shows and a lot of visibility because our shows are cross promoting. 

How effective is that cross promotion? I would imagine at some point you’re just cycling through the same listeners.
I would agree with that, but Lauryn and I found early on that it wasn't as easy to convert people from [other media] channels to podcasts. When we launched our show, we figured the majority of her [TSC] audience would jump in, but it required a lot of education about podcasting to make that happen. Over time, we found that guesting on other shows, having other shows cross promoting and sharing audiences was—and still is—the most effective way to build a show. It's an exponential growth model. If some of these listeners love a show, they're going to go tell 10 friends, who are going to tell 10 of their friends. 


"I'm not going to participate in cancel culture. I'm not going to participate in a long apology tour. What’s so much more important to me at Dear Media is what we do, not what we say."


You and Lauryn did a recent short titled, “We understand that we’ll never understand,” which addresses being white podcasters processing racism, police brutality, and Black Lives Matter. How else have Dear Media podcasts addressed, or not addressed, this moment?
We leave the narratives and tones to talent themselves. That’s built into our contracts. It’s their voice, their narrative, and their platform. If it’s something the network vehemently disagrees with, we can make decisions internally. 

I'm not going to participate in cancel culture. I'm not going to participate in a long apology tour. What’s so much more important to me at Dear Media is what we do, not what we say. We have been taking actions to add more diverse voices to the platform on the internal team, the executive team and the talent team. Over time, that's what we're going to be judged on. 

Are you looking at any specific podcasts that would add diversity to the network?
Yeah. There are about five or six conversations we're having. Right now, we’re in the throes of the world I hate to be in, which is negotiating with agents and managers. Hopefully once we get that done, we can make some exciting announcements, but I want to make sure the talent has the chance to announce first.

How do you determine whether someone who’s an influencer but not previously a podcaster will make a good podcaster? Is there a minimum number of followers that person should have for you to consider them as a member of the network?
No. We work with a lot of influencers, but we also work with entrepreneurs and other creators. It doesn't need to be an influencer-driven podcast. That's just where we started because of the relationships we had. 

We're less interested in the typical influencer or celebrity talent who’s looking to do a quick seasonal show and then jump into another medium. I'm looking for people that really want to engage in this space and be in it for the long haul, who realize that audio could be the cornerstone of a much larger brand conversation, whether that's products, live events, or a series that gets sold upstream. 


"We've passed on some big-name talent because their business models didn't align with ours. I'll pass on what would be considered bigger name talent at the expense of short-term gains."


What questions do you get asked most about being a man who runs a women-focused podcast network?
For a lot of people, it’s a little bit confusing. It was something that I had to tackle with my wife, my cofounder, and myself to figure out the optics. What it came down to was, I've worked with strong women my entire career. I’ve spoken to a large, female demographic for four years [through Him & Her]. It feels very natural. Where I maybe get in trouble as a male in the space is I don't necessarily see gender. I just see smart, talented people. 

What is an example of a tricky conversation you’ve had to have with a creator in your network?
The podcast space is focused on one subset of the brand—the podcast channel. That becomes limiting. With Dear Media contracts, we have the ability and the right to bring opportunity to the entire brand, whether you have a huge YouTube channel, blog—whatever makes sense. A lot of times we get into hard conversations when agents, managers, and talent come in and say, we’re carving this piece and not that piece. For me, that doesn't always work. We've passed on some big-name talent because their business models didn't align with ours. I'll pass on what would be considered bigger name talent at the expense of short-term gains. 

It seems like podcasts have been a media craze for awhile. TikTok has gotten popular since, but that’s different because it’s very short-form content. What’s coming next to replace the podcast? 
New mediums will always exist. But one thing that's not going away is spoken word and audio. We're starting to see an even bigger audio renaissance with home devices like Alexa. We are going to get to a place where voice and audio are a huge element in the way we engage with the world around us. Audio is going to be a very protected medium. What podcasting evolves to, I don't know, but I'm also not so interested in that because for me, I go where consumer attention goes. Blogs were big, then you had to cater to the rise of social. For me, it's not always about figuring out the next thing. It's about moving fast when the next thing presents itself