“Dear Media,” Dara Treseder, and the future of advertising

This week’s episode of “Fast Break” looks at how COVID-19 has affected the advertising business and what’s next for Dara Treseder’s company, Carbon. We also spoke to Dear Media cofounder and CEO Michael Bosstick about how he started a podcasting network without having had any audio broadcast training. Check out the podcast below, and keep reading for an additional interview with Bosstick.

Fast Company: How did you get into the podcasting business and how did that lead to creating Dear Media?

Michael Bosstick: Nobody should take my advice, because if you had asked me five years ago if I would be doing anything in this space, I would have looked at you strangely. Traditionally, I’m a commerce executive who had built retail, direct-to-consumer brands. Prior to this, I was running a company called Jetbed, selling beds for private and corporate aircrafts.

But 10 years ago, back when they still called influencers bloggers, my wife (Lauryn Evarts) started a blog called The Skinny Confidential that covered beauty, health, and wellness tips. My expertise at the time was marketing online businesses and she asked me to start writing on the blog and I said that’s not necessarily for me but what about a podcast?

The company’s mission is to help people create customized podcasts with an emphasis on female hosts and voices. Can you talk a little bit more about this decision?

My wife had been speaking to a 95% female audience, and when we looked at the charts, it was very male dominant. I realized there’s obviously a huge appetite from female consumers and there’s an appetite from female hosts, but why is there not more amplification of the female-focused shows? Females make a lot of the household purchasing decisions, so why is there not a concentrated place where brands can come and connect and feel confident that they’re reaching their target audience?

Back at the end of April, you received a rather large amount of money in Series A funding. How do you see your company changing as a result of such an investment?

In the beginning, we were running on a really lean team, doing everything in-house, from sales to distribution to production to marketing, which was a lot to manage. With the Series A funding, we’re going to invest in our infrastructure, diversify content, in both voices and formats. It’s not about the podcast ad revenue; it’s really about what can these channels turn into.

How does Dear Media stand out in such a crowded field?

We’re not focused on the singular channel of podcasting. This is a platform for creators who want to do more than just create a podcast channel. Our talent is open to creating a podcast collaboration; maybe it includes a blog recap or a social recap, a live event, or something on YouTube.

Some might say we’re living in the “golden age of podcasting,” but ever since the pandemic hit, and many people stopped commuting to work, there’s been a decline in podcast listenership. How have you tackled this at Dear Media?

We’re actually up about 25-30% in listenership. Because we had started out in our living room and been working so lean for so long, we knew what it meant to self -produce a show at home. For the past few months, we’ve seen an increase; it’s more of a flat listening curve as opposed to a spike. People are taking more time to listen on home devices. It’s like on-demand television—you would never go back to just typical cable television once you knew you could fast forward and pause.

What is some advice you would give to women just getting into this space?

Make sure you’re really excited about podcasting and talking on a mic. I call it the Rule of 25 where I believe every individual can get on a mic 25 times and have a unique episode, but what does it look like after that? Are you still excited? Are you diversifying the content? Are you talking about something new? Are you passionate about the space, are you evolving the show? Go into it like it’s a long-term thing. Now, more than ever, think about how you can stand out in a unique way and then over time you can broaden out. Think of it like an upside down triangle.

What do you tell people who push back on the idea that this is a project for expanding female voices that’s headed by a guy?

I realized I have worked with strong women my entire career. My first example of a strong woman was my mother; she’s run a company for a very long time. If we could get to a place in this country where men and women are working together to amplify these voices, that’s ultimately where we want to get to. From an outside perspective, sometimes it looks strange, but to me and to the women I’ve worked with, it’s been a very natural collaboration.

Diversity is more important than ever right now—we’re seeing the Black Lives Matter protests going on—and there’s been a call to include more voices from people of color. How is Dear Media addressing this?

The beginning was to amplify female voices—we could have done a better job at amplifying more diverse female voices, but it’s been a conversation we’ve been having internally for a long time. With the rise of this movement, I’m not so interested in words; I’m really interested in actions. I think that’s what we’ll be judged for, and I think Dear Media takes these conversations very seriously. Hopefully, we will pave the way for men and women from all walks of life who will at least see some version of themselves represented here in some way.

Can you give us a taste of what we should expect to hear from Dear Media in the future?

Those are still TBD as we’re working on some really exciting new shows with new talent jumping in. A lot of these women have brand ideas for themselves, and we’re getting ready to invest and make a couple of announcements in some of those brands. We’re just excited to build new and unique projects to continue to move the podcast space forward.