Lauryn and Michael Bosstick Talk Social Media, Leadership and Putting Authenticity Over Algorithms

When it comes to cultivating an online audience, few are as savvy as Dear Media and The Skinny Confidential founders Lauryn and Michael Bosstick.

The couple began their internet ascension by growing a college blog into a successful entertainment and lifestyle media network and a cult-favorite beauty brand over 15 years, building their ever-expanding empire on a foundation of authenticity, rather than chasing algorithms. Today, Dear Media is home to more than 100 podcasts hosted by major names, including Khloé Kardashian’s Khloé in Wonder Land, Amanda Hirsch’s Not Skinny But Not Fat and Claudia and Jackie Oshry’s The Toast.

Their journey started in 2011, when Lauryn launched her blog, The Skinny Confidential, sharing her top career, beauty and wellness tips with equal parts excitement and education. The blog steadily gained popularity, growing her following and creating a community of equally passionate fans. In 2021, the site expanded into a go-to brand for beauty lovers looking for their next obsession, regularly selling out products with Lauryn leading the charge as a trusted source.

While the world of blogging has certainly changed since the early 2010s, the founders note one factor has remained more important than ever: trust between a content creator and their audience. “Creating content has become incredibly accessible, but building trust has become far more valuable,” Lauryn tells SI Swimsuit. “Anyone can publish something online, which is exciting ... At the same time, audiences have become even more in tune and intuitive. They can tell when someone is creating from genuine experience versus trying to keep up with an algorithm or a trend.”

This conscious choice to prioritize their audience over algorithms remains at the core of their overall operation. Following the success of The Skinny Confidential, the couple launched their podcast The Bossticks—formerly known as The Skinny Confidential Him & Her Show—in 2016, where they continue to interview high-profile guests through an entrepreneurial lens. Over the years, they’ve chatted with Jessica Alba, Paris Hilton, Martha Stewart and more, and at the SI Swimsuit Social Club in May, they presented a live version of the show with a very special guest: 2026 SI Swimsuit cover star, Alix Earle.

Still, with so many looking to break into the social media and podcasting space over the last decade, the Bossticks maintain that individual perspective is precisely what sets those who succeed in their industry apart. “There is always room for someone with a genuine perspective and a clear point of view,” Lauryn adds. “Your perspective is your advantage. No one has your experiences, your curiosity or your way of seeing the world. When you lean into that instead of trying to sound like someone else, people remember you. THAT is what resonates.”

This passion for perspectives also colors the pair’s leadership approach. With the skills they acquired through The Bossticks, Michael founded Dear Media in 2018. There, the company embraces a “360 model” with podcasts, noting on the official website that they view their shows as “springboards” to expand their hosting talent beyond a single medium. The network has become a go-to hub for some of the most popular creators online.

When asked about the biggest leadership lesson learned at Dear Media, Michael tells SI Swimsuit, “Leadership starts with accountability. As a leader, you have to look at every challenge as an opportunity to continue improving. When things go wrong, you get a lot more out of the people you work with by asking questions and working with them to figure out what they need. It puts you on the same side of the table to find a solution together.”

Looking ahead, the future of Dear Media is bright, as the founders remain steadfast in their mission to entertain, empower and educate their audience by delivering content that highlights important industry players. They also host live events through their Dear Media IRL series, bringing their podcast hosts from behind the microphone and into the world to engage directly with their communities.

“We’ve never thought of Dear Media as a podcast network. We’ve always thought of it as a culturally relevant media and entertainment company that will be in audio, video, short-form, long-form, live events and consumer brands,” Michael says. “Our vision has always been to build a place where people can discover the voices and stories they care about. As we look ahead, we’re focused on continuing to expand that ecosystem and create more ways for our audience to engage with the people, brands and ideas they love.”

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