Michael Bosstick arrives at our interview in a crisp white tee and polished blue blazer, confident and right on time. Minutes later, Lauryn Bosstick follows, looking as though she stepped straight out of the glossy pages of Vogue, her long brunette hair falling over a soft white top.

From the outset, the husband-and-wife duo’s rhythm is unmistakable. They finish each other’s thoughts and shift effortlessly between big-picture strategy and instinctive storytelling. One moment they’re talking about rebranding their decade-old podcast. The next, they’re unpacking audience behavior, product design and the future of media.

At one point, Lauryn captures their shared mindset in a single phrase.

“The words that keep coming up for me are ‘level up’,” she tells The CEO Magazine.

“It’d be very easy for us to just be comfortable with where we are, but we want to make ourselves uncomfortable.”

The rebrand

While millions of listeners know them as the hosts of The Bossticks – the podcast formerly known as The Skinny Confidential Him & Her Show – what’s less visible is everything happening behind it. The podcast, despite its scale and cultural impact, is only a fraction of what they’ve built.

Michael is the Founder and CEO of Dear Media, a modern media company generating more than US$50 million in revenue and reshaping how creator-led businesses scale. Lauryn is the Founder and CEO of The Skinny Confidential, a beauty and lifestyle brand that has turned everyday rituals into high-performing, design-led products with global reach.

The podcast, meanwhile, is recorded just once a week.

“The show is our side hustle,” Michael explains with a smile.

After a decade of building businesses behind the scenes, the Bossticks have stepped forward under their own name, rebranding their show to reflect who they are today: not just hosts, but founders, operators and architects of something much bigger.

“We feel that after a decade of really building our companies and brands first, it’s time to step into our own identities and our own name. It’s time to really highlight those,” Michael says.

For Lauryn, the shift is both personal and hard earned.

“To me, this 10-year rebrand feels like us stepping into our own narrative and owning all the work we’ve done,” she says.

Indeed, it’s a transition from student to teacher, from platform to authority – and it has been years in the making.

From blog to brand ecosystem

Long before Dear Media, before the product lines, before the podcast charts and sold-out launches, Lauryn was just a college student in 2011 with a blog – The Skinny Confidential. But even then, she never thought small.

“I launched the blog as a brand,” she reflects. “I knew intuitively going into it that I was building a brand, and I think that shift for me was really helpful because I didn’t make it all about ‘Lauryn Bosstick’. It wasn’t just about me.”

That framing allowed the brand to grow beyond a single voice. Lauryn spotlighted other women, shared what was inside their routines, built trust through recommendations and created something that felt expansive.

Eventually, what started as a blog became a book, then a podcast, then a product line. Each extension was a natural next step because it was entirely anchored in a clear understanding of her audience and what they valued.

Michael saw that early on.

“She built a ton of value for the people that were listening,” he says. “And so, they kind of became marketers for her.”

The idea that the audience carries the brand forward remains central to how they think today. It’s also what separates their approach from much of the creator economy, where attention is often mistaken for sustainability.

“Virality has never been my goal,” Lauryn insists. “For me, it’s always been, if I can get just one girl to go out on happy hour and tell 15 of her friends about my blog, then that’s success.

“It has always been about having people authentically and organically talking about my blog in their day-to-day lives where they’re actually excited about my brand. It’s not me pushing anything on them – they’re the hero.”

It’s a deliberately human approach to growth.

“A lot of creators these days are too focused on virality,” Michael says. “It’s great to get a bunch of eyeballs on your content, but if they don’t consistently come back, then where’s your business?”

Rewriting the media playbook

By the time Lauryn and Michael launched their podcast in 2016, the medium was still largely shaped by male hosts and traditional media thinking. Audio was treated as the product, and everything else was secondary.

The Bossticks knew it could be so much more.

“We wanted to be able to use the other platforms,” Michael says. “We wanted to marry it all together and not have it live separately.”

That instinct became Dear Media. Launched in 2018, the company was built on a simple but powerful premise – a podcast should be the starting point, not the ceiling. From day one, Dear Media was designed to help talent expand beyond audio into video, live events, products, books and brand partnerships.

“Dear Media is a modern media company that leverages the full opportunity of every channel at our disposal,” Michael explains. “Wherever media lives is where we like to play.”

Today, the company includes more than 100 shows, a combined social reach of more than 700 million and a growth trajectory that reflects both timing and strategy.

In 2025 alone, 26 new shows were launched, while existing shows typically see 25–50 percent growth, both in audience and revenue, after joining the network.

The couple with their children Bond, Zaza and Townes

But scale is only part of the story.

“We’re not a podcast company,” Michael insists. “We’re building talents’ entire brands, and podcasts happen to be one vehicle.”

The shift from content to brand building is what sets Dear Media apart. It’s also what has allowed it to turn shows into something more substantial. The Toast, for example, expanded into a multimillion-dollar beverage brand.

Pretty Basic became a sold-out national tour. And Raising Good Humans turned into a New York Times bestseller.

Each example reflects the same underlying idea – attention is only valuable if you know how to build around it.

“The creators that look at themselves as their own brand are the ones that we’ve seen have staying power,” Michael says.

It’s a lesson learned through observation as much as experience. The Bossticks have watched waves of creators rise quickly, monetize aggressively and then struggle when attention fades.

“The ones that start to struggle chase the brand dollars, and they never diversify,” Michael points out.

That’s why Dear Media was built – to offer a different path where creators can turn audiences into assets, not just impressions, he says.

Designing and refining products

While Michael has been building infrastructure for creators, Lauryn has been doing something equally strategic on the consumer side. The Skinny Confidential beauty brand launched in 2021, but its success is rooted in the same thinking that shaped the blog.

“It’s a mixture of staying extremely close to the audience while also studying behavior and culture at a macro level,” Lauryn explains.

This combination has led to products that feel both familiar and fresh. The Ice Roller, for example, was born out of frustration with what was already on the market.

Existing products didn’t stay cold long enough, so Lauryn got to work on one that would. The result? A best-in-market ice roller crafted with thick, custom-made silicone specifically designed to hold its chill longer.

Mouth tape, by contrast, introduced a relatively niche concept to a broader audience, backed by education and strong branding.

Both approaches require conviction.

“I’ve never viewed a market as too saturated,” Lauryn explains. “Saturation simply signals demand – and that’s a fabulous thing.”

At the same time, she’s not interested in launching products for the sake of it. Every decision is filtered through a clear perspective.

“I’m looking to refine, elevate and reposition it with a distinct point of view,” she says.

That point of view shows up in the details – the packaging, the functionality, the aesthetic. It’s why the brand has been able to turn simple tools into premium categories and built a loyal customer base that returns repeatedly.

The results speak for themselves. The brand has seen 50 percent year-over-year revenue growth, with subscription revenue up 72 percent. More than 300,000 beauty tools were sold last year alone.

Mouth tape, in particular, became a breakout success.

“The mouth tape was a risk,” Lauryn admits. “But it was a risk I was very prepared to take.”

At launch, the market wasn’t widely educated on the benefits of nasal breathing or sleep optimization.

The category was niche, even slightly controversial. But the response was immediate, with the product selling out within 48 hours, building a 20,000-person waiting list within a week and going on to sell 200,000 units in its first year.

For Lauryn, the success comes back to trust.

“The reason they keep coming back to our brand is because we’ve built the trust,” she says. “I make sure that everything we put out is a 10 out of 10.”

Building through chaos, not comfort

Spend enough time talking to Michael and Lauryn and one thing becomes clear – they’re not interested in ease.

“There’s fires we’re putting out all day long,” Lauryn says.

Their approach to those moments is what defines them. Where others might pause or retreat, they find energy, even enjoyment.

“What’s the opportunity?” Michael says. “That’s what I focus on and chase.

“Sometimes, it can be easier to focus on the ‘doom and gloom’ – and there’s plenty of that in the world – but the great entrepreneurs are the ones that see an opportunity to spin that and turn it into a success.”

For Lauryn, it’s equally about resourcefulness.

“If I’m not coming through the front door, the side door, the back door or the window, then I’m coming down the chimney,” she says.

“You can find a way to figure it out. And that resourcefulness is really important as you become a CEO or set out on your entrepreneurial journey.”

This mindset has carried them through everything from early podcast struggles – recording in closets, making no money for years – to high-stakes business moments, including financial miscalculations and industry disruption.

It also shapes how they operate as partners. Working together, running separate companies, raising a family and sharing a public platform is, by their own admission, not simple.

“It’s not for everyone,” Lauryn acknowledges.

She describes it as ‘potpourri’ – everything blended together, constantly shifting. There’s no clean separation between work and life, no neat boundary where one ends and the other begins.

“Everything’s a little bit messy,” she admits. “We are talking about things as they come up. As much as I would like to say that we can keep our personal and professional lives separate, I can’t.”

But within that, there is structure and intentionality. Even more, there’s a deep understanding of where their time goes and what matters most.

“My time is my most cherished asset,” Lauryn says. “I don’t mess around with it.”

This discipline has become essential as both businesses scale and as the Bossticks step into a more visible leadership role. It also reflects a broader shift happening across business.

“The landscape is changing of what CEOs look like,” Lauryn says. “They don’t all look the same anymore.”

For years, media, beauty and lifestyle were often dismissed as secondary industries. Today, they’re some of the most influential forces shaping consumer behavior, brand building and global culture.

The Bossticks haven’t just adapted to that shift, they’ve built within it. And they’re still building. Because if there’s one thing that comes through clearly – whether you’re listening to their podcast or sitting across from them in conversation – it’s that they’re not interested in maintaining what they’ve created.

They’re interested in what’s next.

“Longevity requires discomfort,” Lauryn says. “I never want to get too comfortable repeating what worked yesterday.”