The Power Couple

Lauryn & Michael Bosstick Rule the Modern Airwaves

By Hailey Bethke | Photography by Arielle Levy

“I enjoy the art of making nothing into something; there’s something about it that’s so romantic, you know? When you build a brand, the sky’s the limit. You can become anything you want.”

These are the wise words of Lauryn Bosstick, founder of The Skinny Confidential. She cohosts the widely popular podcast, The Skinny Confidential HIM & HER show, with her husband, Michael Bosstick, CEO and founder of the Dear Media podcast network. The husband-wife duo are individualists and trailblazers known for doing things their way. Whether behind the mic or in a business meeting, you can expect both to state what they believe fearlessly—a respectable trait in a world so overly consumed with being likable and appealing to the masses.

Paving their own lane has yielded massive rewards: The Skinny Confidential HIM & HER show’s devoted audience has downloaded the podcast over 200 million times. The Skinny Confidential brand, which began as a blog run by Lauryn thirteen years ago, has launched instant-sell-out wellness products ranging from the Hot Mess Ice Roller to chic pink mouth tape. Dear Media is a leading network that has produced over one hundred shows, many of which consistently rank in the top charts on Apple Podcasts and Spotify. On top of these awe-inspiring feats, they balance being present parents to their two children, Townes and Zaza, while prioritizing their relationship and personal well-being.

Michael and Lauryn Bosstick have been interviewed hundreds of times. Still, we feel this holistic and honest feature offers fresh insights into how they do it all—from building a modern media empire to owning who you are and their favorite hacks for success and optimized living. Like Michael and Lauryn, we don’t run by a script: we believe in telling stories with heart and soul. Today, we are honored to share theirs.

When Lauryn started The Skinny Confidential blog in 2011, she was never concerned with making money. Instead, she focused on perfecting her craft and stayed patient for her big break. “From the beginning, my intention was to build a brand,” she says. “One of the best business tips is to think big and start small, like an upside-down triangle. When I began The Skinny Confidential, that looked like blogging seven days a week, becoming my own photographer, staying organized, and always engaging with and listening to my community.”

Lauryn is visibly confident and secure in her own skin; her style and eye for on-point aesthetics certainly shape her success in launching game-changing, elevated versions of your favorite wellness products through the TSC brand. “Without The Skinny Confidential, I’d be the same person, although it’s important to note that The Skinny Confidential has given me invaluable skills,” she expresses. “The business and brand have allowed me space to refine and edit my people skills, become more comfortable on camera, and become a strong leader. It’s enhanced my abilities in the best ways.”

Although Lauryn says these traits have been amplified through her work, each traces back to her childhood. “When I was little, I’d make scrapbooks for my friends that matched their personalities. I built cookie stands that were aesthetically pleasing, and in sixth grade, I created a magazine that was the brand of my life at that point. I found it the other day—it was hilarious, like a blog on paper,” she reminisces.

“At the dinner table, my dad likes to tell stories about how I loved being on camera and oversharing from a young age—what you see is what you get, with or without my business. When it comes to confidence, my parents instilled it in me from a young age. They did a nice job of caveating that with the importance of a strong work ethic. Both those skills have enabled me to feel comfortable putting myself out there with an intense awareness of the fact that not everyone is going to like me. When you know that, it makes it much easier to show up as exactly who you are.”

Lauryn shares that many experiences shaped her need for independence—something every true entrepreneur can relate to. “Some examples are getting my first job at age fourteen, my parents making sure that I had to go out and get it if I wanted it (car, material items, college), and losing my mom at a young age. Basically, I quickly realized that no one was going to do it for me. Every day, I still think about that—no one is going to do it for you. Go kill the tiger yourself. Your confidence will soar.”

In 2016, Lauryn and Michael launched the HIM & HER show. It was an opportunity for the couple to create together, says Michael. “A common misconception about us is that we work on everything together,” he explains. “Many don’t realize we operate completely separate businesses with separate teams and manage those teams individually based on our personal management styles.”

The HIM & HER show is a natural complement to The Skinny Confidential blog, allowing readers to listen on the go. “We’re in the audience’s ear while they get their nails done, drive their kids to soccer, fold laundry—they’re saving time because they can do two things at once. The evolution from a blog to a podcast was a totally natural way to grow,” says Lauryn.

We have been disruptors in our space because we pay very little attention to what legacy media companies of the past have done and try to offer services and content on any medium or channel where our creators reach their audiences.

One of the most refreshing aspects of the show is how the Bossticks are not afraid to share their unfiltered opinions. “When you try to appeal to everyone, you appeal to no one,” Lauryn emphasizes. “By nature, I overshare. I am bold with my opinion. It all feels natural to me. On that note, I also give myself space to change and evolve; people can see that evolution process through the podcast. It’s a waste of energy to be afraid of what people think, and I am not afraid to say it how it is. The audience can smell someone constantly trying to appease everyone; it comes off as inauthentic.”

“We aren’t actors,” Michael adds. “We don’t want to spend a ton of effort or time trying to curate a voice that isn’t ours or reach an audience we know won’t like us as we are. We are fine not being liked by everyone as long as it means we can always be ourselves. We would rather share our voices authentically and be disliked than be mistrusted.”

He continues, “With the success of the show and after joining another media company that we felt didn’t bring enough to the table, we decided to create a media business of our own that would be ‘by talent for talent’ and provide all the capabilities we believe a modern media company should offer to media personalities and talent. So we created Dear Media, and the rest is history,” he explains. “We have been disruptors in our space because we pay very little attention to what legacy media companies of the past have done and try to offer services and content on any medium or channel where our creators reach their audiences. This could look like audio-only shows, audio and video shows, live events, publishing deals, commerce brands, merchandise, fast channel opportunities, and social syndication across all relevant platforms. We are platform agnostic and look to build great content on any relevant channel our audiences care about.”

Another differentiating factor of how the Bossticks operate is their innovative creative process. For Lauryn, it’s chaotic—in her own words. “I’m the type of person who has to think of an idea, sit on it, stew on it, think about it, walk on it, meditate on it, blend it up, cut it up, try it on, and then refine and edit it,” she shares. “This process is annoying to a lot of people. But the process is the best part and my favorite part. Sometimes, I need to get to the other side to see if something isn’t a good fit, but that’s also where the magic happens.”

For example, she says, “Taking a product I use every day or that the community uses every day and trying to make it better with a lot of edits and fluffing is what excites me most. When a consumer opens something from The Skinny Confidential, I want them to think, ‘Wow, this is way better than I thought it would be.’ That’s the goal, from the shipping box to the packaging to the product. Each touch point is thought out.”

Lauryn admits that expanding from a blog to a line of products has been a challenging and educational experience. “The product line has taught me a lot about scaling, which I had no clue about before building a business. The creative process can be romantic, but I realized to become successful, you have to pair the romance and creativity with the business side. Currently, I consume a lot of business-oriented content: podcasts, audiobooks, books, and newsletters. It’s vital to stay curious and never think you know it all. A big mistake entrepreneurs make is that they drink their own Kool-Aid. I always want to step away from the big picture and look at things from a consumer or competitor’s perspective. I guess you could say I’m good at checking myself. I always feel I have a lot to learn.”

She adds, “The wellness space is rewarding because you can make people feel good. People need to understand it’s not selfish to practice self-care, and we want to give people the tools to do quick rituals throughout their day whenever they can. Discovering old-world tips has been a fun part of the process, too. So many wellness practices have been around for hundreds of years. Cold therapy, shaving a woman’s face, facial manipulation—these are all things that have been in front of us for so long, and rediscovering them has made sense for the trajectory of the brand. Old Hollywood books are my favorite, so I love reading about Marilyn Monroe, Zsa Zsa Gabor, and Elizabeth Taylor. Between the lines, there are mentions of beauty tips and hacks, and we like to pull that nostalgia into our products but make them fresh for today.”

One of the best business tips is to think big and start small, like an upside-down triangle.

Lauryn’s most recently launched product is her take on mouth tape, which arrives in a branded storage box and is complete with her signature pink. If mouth taping is unfamiliar to you, it’s not only a beauty hack but a wellness upgrade. “After reading the books Breathe, Jaws: The Story of a Hidden Epidemic and Shut Your Mouth and Save Your Life and then talking to Dr. Andrew Huberman on the HIM & HER show, I became so interested,” Lauryn says. “And it’s an easy habit to stick with (no pun intended, haha!) because the results and benefits are insane.”

Mouth taping helps strengthen and sculpt your jaw, improves sleep, and leaves you with more energy upon waking to carry you throughout the day. “Of every product we’ve done, the mouth tape is the most life-changing,” Lauryn expounds. “What it’s done for my face and energy levels after using it every night for ten months is out of this world. And I was a big mouth breather. I was a snorer, which did get better with my double jaw surgery, but still. Now, I’m neither of those things. I’m extremely passionate about recommending this to everyone because it’s enhanced my life beyond what I ever thought a little piece of tape could.”

Despite these major wins, Lauryn reminds us she is still human and encounters daily struggles. “When it comes to business, struggle is just part of the game. I have yet to hear of one business owner who didn’t struggle.”

The intense double corrective jaw surgery is a struggle that stands out to her, Lauryn shares. “I suffered a genuine identity crisis for two years. It was one of the hardest periods of my life to look in the mirror for two years and not recognize who was staring back at me. People were coming at me online and asking what happened to my face when I had just had serious surgery. It added a different layer to my life. Looking back, I’m grateful for the experience because the ice roller was born from that, and my husband became more comfortable in front of the camera (because I turned it on him). I also never lead with looks—I try to be interesting and interested. Engaging and engaged. Looks are lower down the list after that experience.”

She continues, “Another struggle I had was gaining sixty pounds while pregnant with both my kids. It’s another form of an identity crisis to be so out of your body and not feeling like yourself. Through that experience, I discovered the importance of eating tons of protein and weightlifting, which has changed my life. Now I have twenty times more confidence, my clothes feel amazing, my whole body composition has shrunk, the dopamine hit gives me something I can’t shut up about, and I show up as a better mother. My hope is that other women struggling with their weight see the importance of weightlifting, which is why I talk about it so much.”

Her other daily struggles include staying present, managing her time, growing her team of fourteen, and showing up the way she wants. She says, “There’s a quote I love by Robert Greene on overcoming adversity: ‘Everything that happens to you is a form of instruction if you pay attention.’”

The Bossticks recently gave an entrepreneurship-focused lecture to students at Columbia University. They incorporated this theme of conquering setbacks and doing things your way into the ethos of the talk. “We both loved it, especially given that it is very likely our applications for that school would have been tossed in the trash when we were applying to college!” Michael shares.

Lauryn continues, “I hope they learned there are many ways to skin a cat, and it’s not just one straight line. You don’t just get a degree and you’re good. You need to constantly challenge yourself, learn, read, and absorb information. As an entrepreneur, you have to throw yourself out there, then edit and adjust as you iterate. It’s a massive exercise in not giving a **** what anyone thinks about you, but it’s necessary. If you’re a content creator, you should always make a list of what makes you special and unique and lean into those things. What makes you stand out? Show up and do that every single day online.”

Sharing a tool that has helped her, Lauryn adds, “There’s a book I highly recommend called The 38 Letters From J.D. Rockefeller to His Son, and one of the things he says is ‘Second place is still losing. If you want to be the best at something, you have to show up every day and do it.’ If you want to be the best, you need to have persistence and patience. Patience is a vital part of the equation. Taste is, too, when it comes to an aesthetic, knowing what the consumer wants, or a particular marketing strategy. Stay curious and realize that you don’t know everything. I like to get all the information I can get my hands on.”

The couple’s advice for creating the best work-life balance and dynamic is to get crystal clear on your vision to ensure you’re on the same path. “Michael and I have gotten laser-focused on the vision for our life and how it’s laid out. Sometimes, couples can get disjointed from that vision. We are committed to exactly what we want out of life and building it together. We map out how we want the next two months to look, the next year, and what life looks like when we’re older,” Lauryn says. “We have a mutual respect for each other’s strengths. I know when he is the better person to ask for something, he knows when I’m the better person for something, and we lean into those strengths. Michael is also very quietly confident, which is helpful to me and the key to our relationship. My advice is to set a map of where you want to be in six months as a couple, in a business, and as parents, and where you want to be in one year and ten years. We spend a lot of time planning, and that goes for all aspects of our life.”

What’s next for this multifaceted, ever-evolving duo? According to Lauryn, the ultimate business goal has yet to be wholly envisioned. “Michael and I have a massive vision, and it’s something we work on every day. I feel like we haven’t even fully penetrated the potential—we have a lot of work to do. On a daily basis, we aim to create value, whether through a book, product, or live event. We want the community to leave feeling like it was worth their time. We’re going to continue to put out the best content we can in every single arena. This is only the beginning.”

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To connect with Michael and Lauryn Bosstick, follow along on social media @theskinnyconfidential, @tscpodcast,@dearmediastudio, @laurynbosstick, and @michaelbosstick, and stream The Skinny Confidential HIM & HER show on all listening platforms. Plus, check out TheSkinnyConfidential.com for all of your wellness and beauty needs.

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VIE: Michael, tell us about your vision for Dear Media to be the “Netflix of podcasts.” How do you plan on achieving this goal, and what changes would you like to see within the network over the next few years?

Michael Bosstick: My vision for Dear Media has always been to build a modern media presence that would have its arms in more than just podcasts. I don’t even like to call Dear Media a podcast business, as we are so much more than that. We used podcasts as our entry point to prove ourselves in media but have always had the ambition to go far beyond audio. To date, we have produced over one hundred shows that stretch into audio and video. We have curated billions of social and video impressions, both in short-form and long-form content, against all of the biggest social platforms; we have incubated two commerce brands that are now venture-backed, including Lauryn’s business, The Skinny Confidential (product line); we have invested in eight commerce brands, such as Arrae, Deux, Canopy, and more; we have produced multiple live events and our first summit; and we co-published our first book, which landed on The New York Times Best Seller list.

I say all this to point out that our ambition and capabilities stretch far beyond a typical podcast business. It’s why I also don’t participate very often in whatever is going on in the podcast industry. No shade to anyone there; I just think focusing solely on audio is limited in opportunity and personal interest.

VIE: Lauryn, we know you both do lots of interviews, but is there something you never get asked about that you wish you could highlight?

Lauryn Bosstick: Sometimes I get asked how I “do it all,” and I always want to be very transparent. I love being asked this question because I want everyone to know that I have a lot of help. I have a nanny and a house manager. I have help cleaning our house, assistants, and an entire team. That’s really important for me to let other women know—I am not an octopus.

On that note, I have balanced a business all on my own, which I’m proud of, but throw kids, a husband, and dogs into the equation, and it’s OK to need, ask for, and accept help.

I’m also very methodical about the calendar. When my daughter is at school, I will pack the calendar so that when she’s home, I can show up, be present, and be there for her 100 percent. We do crafts, bake cookies, and do things together that make memories. I don’t get it right every day. There are many nights where I lay my head down and think I could’ve done better, but for the most part, this works.

Meditation helps me have inner harmony. It’s been powerful and allows me to be stoic and not lose my sh*t.

Another thing: I pay for my time, too. That means getting hair and makeup done so I can be on phone calls and working, taking Ubers so I can think or post on social, and taking walks during conference calls. Getting creative with your time can free some up and help you stay more present for other things.

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