Now, two years later, she considers her podcast, “Everything is Best” — where she offers conversations on issues such as parenting, pregnancy, financial planning, entertaining — a big success. She credits her partnership with Dear Media.
Since its launch in 2018, Dear Media has quietly become one of the most prominent names in women’s media. The podcast network’s social media channels reach a combined audience of more than 120 million. Dear Media’s shows were downloaded more than 200 million times in 2022, and the company has launched over 50 lines of influencer merchandise and doubled its annual revenue in each of the past four years.
The brand has become ubiquitous in women’s spaces online. It’s hard to scroll through TikTok or Instagram without seeing a Dear Media podcast video clip. “You see a clip on TikTok and you know immediately it’s Dear Media,” said the TikTok star Corporate Natalie, who has nearly half a million followers on the app.
Podcasting is forecast to be a $94.88 billion industry by 2028, and big players including Spotify and Apple have acquired or commissioned a slew of high-profile, exclusive shows. And the growth of platforms such as Anchor, which allows anyone to create a podcast, has led to a tidal wave of homegrown shows. But, as the economy contracts and this media sector enters what the podcast critic and analyst Nicholas Quah calls a “podcast winter,” competition is becoming fierce. That’s where Dear Media comes in.
“[There’s] generally a feeling of pessimism in the podcast business,” he said. “I haven’t seen that many attempts at building out a women’s focused multimedia lifestyle brand that has a distinct podcast presence like Dear Media. The big question of a network of that scale is whether they have the downloads.” Meaning, for Dear Media to survive, it must continue to churn out shows and expand its audience.
Dear Media seems to have tapped into a winning formula: leveraging podcasts as a springboard for female influencers to build multimillion-dollar brands. The Dear Media network hosts 63 shows, primarily chat shows (where hosts and guests have freewheeling conversations) with dozens more in development, and is constantly bringing on new talent. Its popular slate of shows includes “Not Skinny But Not Fat,” a pop culture show hosted by the influencer Amanda Hirsch, “Back to the Beach,” which is hosted by the reality TV stars Kristin Cavallari and Stephen Colletti, both of whom starred on the MTV show “Laguna Beach,” and “Absolutely Not,” a comedy podcast hosted by the actress and comedian Heather McMahan.
“They’ve created this network of powerful women that all have really interesting channels,” Baroncini said. “…We’re all constantly doing pod swaps with each other.”
Last year, Dear Media launched its first limited series, “Summer of Gold,” hosted by the retired figure skater Michelle Kwan and co-produced with Togethxr, a women’s sports media company. It tells the oral history of the 1996 Olympics, when the women’s sports teams swept gold. And this year, the network also introduced its first fiction show, called “Bone, Marry, Bury,” with Sarah Hyland, about romance and murder. Dear Media also has announced a show with the “Black-ish” star Tracee Ellis Ross called “I Am America.” It features stories that spotlight everyday Americans and “transcend[s] all the divisions we have in this country,” an announcement for the show reads.
Although Dear Media itself has managed to stay out of the online drama that is often synonymous with the influencer industry, it has not shied away from controversial talent. In October, the company recruited Claudia Oshry and Jackie Oshry Weinreb, daughters of far-right extremist Pamela Geller, to host a show, despite Claudia Oshry’s being mired in backlash for espousing views similar to her mother’s, such as repeatedly making racist comments and downplaying the coronavirus pandemic.
Dear Media was founded as a joint venture between the entrepreneur Michael Bosstick, who serves as the company’s chief executive, and Raina Penchansky, the founder of Digital Brand Architects (DBA), the leading lifestyle influencer management company, which helps social media creators monetize and expand their brands. DBA’s primacy in the field was cemented when the management company was acquired by United Talent Agency in 2019.
The business came to fruition after Michael Bosstick and his wife, Lauryn Bosstick, a massively popular lifestyle influencer known by her handle, @theskinnyconfidential, produced a successful podcast built off her brand called “The Skinny Confidential Him & Her.” The show featured frank conversations with entrepreneurs, content creators and authors.
Although their show was a success — the Bossticks have produced more than 500 episodes, never missing an episode a week in six years and garnering over 150 million downloads — they had trouble finding a podcast network. They didn’t feel that any of the leading networks took them seriously or were interested in serving a primarily female audience.
The Bossticks recognized that countless influential women with huge online followings, including lifestyle content creators, reality stars and entrepreneurs, wanted to start podcasts but were dismissed or were greatly undervalued by the male-dominated podcast industry. So, they partnered with Penchansky, whose company had a record of working with major female content creators, and Dear Media was born.
“It was at this time we realized how many other female-focused shows were also not getting the attention or resources they deserved,” Michael Bosstick said. “The top charts of major podcast platforms were all male-dominated, and there were very few women being represented in the way we both felt was appropriate. We had been collaborating with and speaking to so many incredible women and thought it was time to even out the charts a bit.”
What Dear Media recognized before most was that the media industry was shifting away from traditional brands and toward online creators. “The idea of building a platform by creators, for creators, that caters to female audiences looking into opportunities beyond just audio was born,” Michael Bosstick said.
Each Dear Media brand speaks to a specific type of woman or interest. Dear Media shows cover topics including fashion, entertainment and pop culture news, dating, marriage, pregnancy, the challenges of being a woman in the workplace, and more. The network does include men, but they largely speak to the company’s predominantly female audience.
“Consumers view Dear Media podcasts as a resource for real life,” said Siffat Haider, an influencer and the founder of the wellness brand Arrae, who hosts “The Dream Bigger Podcast.” “The [listener] finds a lot of Dear Media shows relatable, no matter where they are in their life. Whether it’s a parenting podcast or career podcasts, there’s a lot of genuine, real-life applications.”
“The hope is that you may come to Dear Media for a comedy show but then decide you also want to hear a parenting show. Or you may come in to listen to a business show and discover that you also like a pop culture show,” Michael Bosstick said. “Our goal is to create a wide enough offering that can appeal to anyone as they go through their weeks and days as well as through different moods throughout the week.”
Unlike other podcast companies that have generic equipment and bland studio spaces, Dear Media has constructed Instagram and YouTube-ready studio spaces in West Hollywood and Austin. The spaces have become a hub for influencers and celebrities who come in as guests or to host their own shows, simply to sit in front of the Dear Media branded microphones. Dear Media branding is affixed to the thumbnail of every show, and the Dear Media name is shouted out in the beginning of every episode of every show on the network. That branding has allowed Dear Media to achieve a level of name recognition that other networks have struggled to attain.
“Branding is something that has been on the forefront of every business conversation,” said Paige Port, Dear Media’s president. “What does the brand look like on cover art, in the studio, when it comes to distribution. It’s something that’s become really recognizable, and when you see content on other platforms, it’s like, ‘Oh, that’s a Dear Media show.’”
While Dear Media uses podcasts as a launchpad for the talent with which it works, the network’s success comes from its ability to help influencers build mini media empires around themselves. “We look at all the shows as brands within themselves, and when you look at them as brands instead of just audio channels, you can do so much more,” Michael Bosstick said, mentioning opportunities that include merchandise, live events, touring, product lines, streaming and IP. “This is a focus many of our competitors can’t or won’t entertain.”
For the talent, working with Dear Media opens up monetization opportunities not often available in traditional podcasting. “Why should I have a random advertiser on the podcast that I don’t really use?” Baroncini said. “I wanted to work with brands that are a part of my life and can seamlessly integrate with my other social media channels.”
Michael Bosstick has championed sponsored episodes, where guests pay thousands of dollars to be featured on a show, similar to the way influencers would produce sponsored content for brands on their social feeds. The practice is common in the online creator space, but in podcasting, it has traditionally happened only behind the scenes. Bosstick puts it out in the open. “The Skinny Confidential Him & Her Podcast” charges between $20,000 and $40,000 per sponsored interview, according to Bloomberg News. “We always frame it as: There’s no talking points; you don’t get to submit questions; the only thing is it’s just your brand being featured,” he told Bloomberg. And sponsored episodes account for only 1 to 3 percent of Dear Media’s total programming, he said.
The company also spins out consumer products. Dear Media has incubated The Skinny Confidential, Bosstick’s original lifestyle brand, and Woo More Play, a sexual-wellness toy company. The company also has invested in and helped to grow a supplement brand, a line of vegan and gluten-free cookie dough, a humidifier company, a line of sparkling wine cocktails and a line of natural remedies. It also runs a thriving merchandise business.
Chat shows remain Dear Media’s bread and butter, but the company is rapidly expanding into new formats. In 2020, Dear Media raised $8 million Series A investment, telling Forbes that the company planned to use that money to broaden its slate of programming. “We’re focusing on adding more diversity, not only in the types of women we represent, but also the type of content,” Bosstick said at the time.
In November, Dear Media introduced “dailys,” which are five- to 10-minute pieces aimed at the Dear Media audience. Port calls them “digestible, snackable episodes people can start or end their day with.” The company hired a team to focus on the product.
“You can listen while doing the dishes, folding the laundry, you can be on a walk, or working,” Port said. “It’s content that doesn’t take up a huge portion of your day and can be added onto shows you’re already listening to.”
Correction: The name of the women’s sports media company Togethxr was misspelled in a previous version of this story.
