Case Study: Michael & Lauryn Bosstick

Michael and Lauryn (Evarts) Bosstick are massively successful entrepreneurs and investors with a knack for growth in the digital space. Michael is the Founder and CEO of Dear Media, a podcast network hosting over 60 shows. Lauryn is an author and the creator of the health and wellness resource, The Skinny Confidential, which boasts a robust community of like-minded women, as well as a storefront featuring various beauty products. Together, the couple also hosts The Skinny Confidential HIM & HER Podcast, which has more than 600 episodes, and 200 million downloads. Their businesses combined are said to generate more than $10,000,000 in revenue every year (Forbes.com). Their portfolios run deep, so we could spend days exploring all the avenues the Bossticks lay claim on. But for now, let’s dig into the background of their most lucrative endeavor: The Skinny Confidential HIM & HER podcast.

Lauryn Evarts Bosstick was born and raised in California, and attended San Diego State University, where she earned a degree in TV Broadcasting and Journalism. In her words, however, college was “boring the f*** out of her,” and she set out in pursuit of a side hustle–not in order to make money, though. Working as a bartender and PureBarre instructor at the time, she began to explore the blogging space. For context, this was 2010: blogging was not “cool,” and the term “influencer” was yet to be coined. She hustled anyway, writing blog posts daily for three years without making a dime. When asked how she consistently produced so much content with no reward, she replied, “I’ve never been in it for the money.” She continued, “when you go into any career with your main intention of monetization, it taints it. I think that you should go in with an intention of purpose, or providing value, or something more and bigger than money and yourself.”

Lauryn went into The Skinny Confidential blog with a passion for health and the desire to build a community around it. She came up with the idea, claimed it as her career, and paid no attention to the time or effort it would take to monetize it. She’s said in numerous interviews that building a strong community, prior to reaching for opportunities to turn a profit, was surely the foundation for her success. She just wanted a girls’ club of sorts; a network of resources, and a community of women that supported one another. And that, she did. Just a few years following TSC’s first profitable year, it was named the top health and fitness blog in the world by Bloglovin’. To this day, Lauryn blogs regularly and has over 100,000 followers. However, blogging was only the beginning for The Skinny Confidential empire.

Lauryn often says that Michael was her #1 supporter from the start, seeing her brand vision before anyone else did. Michael, also born and raised in California, earned a Business Administration degree from the University of Arizona. He spent his childhood performing an assortment of odd jobs, and he later applied that spirit of versatility as he entered the workforce. In 2008, after unsuccessfully dabbling in Real Estate investment, he pivoted; co-founding a highly successful company called JetBed… which started off far from prosperous. Michael, now having done business with massive corporations and celebrities such as Oprah and Taylor Swift, recounts years selling only one or two products a month.

Through this experience, and various others in his professional life, he adopted the “launch quickly, adjust later” frame of mind we see in so many successful entrepreneurs today. Michael is a visionary; he sees potential, and loves the process of cultivation it takes to exploit it. So it is no surprise that, after over five years of examining and supporting his then-fiancée’s blogging hustle, he saw an opportunity for expansion.

In 2016, The Skinny Confidential HIM & HER podcast was born. Starting with cheap mics, no editing, and an overall low-budget feel, they did just that–they started. Not the slightest bit concerned about the numbers or the money, they pumped out episodes weekly (often even twice weekly). Lauryn defines herself as a “natural-born oversharer,” and that trait proved to be an asset. Listeners seemed to multiply, growing to love the couple’s candor— nothing was off-limits. If you’ve ever listened to a HIM & HER episode, you would know that the Bossticks interview boldly, with no reservation, and they do not discriminate when it comes to choosing guests on the show. This raw, no BS approach to podcasting is what ultimately drove such extensive growth for the brand.

The rest of the Bosstick portfolio is a series of solutions to gaps the couple observed in their own lives. For instance, they signed with a podcast network and were unimpressed, so Dear Media was created. Lauryn was unsatisfied with the beauty products and tools on the market, so she spent years developing her own. Sub-par media consulting firms? Bosstick Media launched. A lack of skin health resources? Lauryn became a published author. The list goes on, and on, and on. How are they so successful with everything they launch?

Analysis

Many people would probably chalk Lauryn and Michael’s success up to fate, or luck of the draw. While some of it may be, I can’t help but think of Roman philosopher Seneca’s idea that “luck is what happens when preparation meets opportunity." Chance can only take you so far, before intelligence and skill must kick in to replace it.

Either way, the couple’s business literacy is undeniable, and they have the numbers and community to prove it. Below are a few immense learning opportunities that I’ve distilled from their practices:

Launch quickly, adjust later. Rather than ruminating on a concept and getting lost in logistics, they utilize time as an asset and correct their mistakes as they go. This ultimately tailors the customer experience far more precisely than if they were to construct the details without that public feedback. Never let your excuse be “I’m not ready.” You’ll never be ready.
Think like an investor. The Bossticks (under Dear Media) now have their own portfolio of startup investments, but even before that, they presented their concepts to investors a) concisely, and b) asking for advice over money. Lauryn and Michael are firm believers that if you present well and your investor is confident and excited in your business, the money will come. What is of more importance upfront, is to not only gain valuable insight, but to signal that you value your investor and the resources they may offer (monetarily and intellectually).
Passion > profit. Whether you are a founder, entry-level employee, or a CEO, this one always applies. Pursuing something you love and that creates unique value for others will always trump a soulless job that may have a higher starting salary. Not only is it more enjoyable, but it likely will take you further, professionally. Passion is the best motivator to work hard.
“No” just means “hustle harder.” Throughout the course of their careers, Lauryn and Michael have received countless “no’s.” Lauryn has spoken extensively about the rejection she received when it came to funding The Skinny Confidential, and she and Michael, both, have told tales of their humbling experiences. But rather than taking it as discouragement, they utilized it as a catalyst for improvement. This is not to say you shouldn’t accept criticism–in fact, you should get pretty friendly with negative feedback– just don’t let it beat you down. Use it to figure out a better way.
Do it tired— and with kids! Lauryn and Michael did not let their widespread success hinder them from pursuing their dream to expand their family. They now have two kids, and Lauryn says that motherhood is “the best job [she’s] ever had.”