Lauryn and Michael Bosstick, the wife and husband co-founders of The Skinny Confidential beauty, media and lifestyle brand, recently joined Entrepreneur+ members for an intimate Subscribers-Only Call. You can join in future live Q&As with some of the biggest names in business by signing up here.
Following their amazing talk. Lauryn and Michael shared the following insights into how they grew their side hustle into a media and commerce empire, and offer their advice for anyone looking to launch and grow a passion project. (Answers have been edited for length and clarity.)
Tell us about your roles.
Michael Bosstick: I am the founder and CEO of Dear Media. We not only produce podcasts in audio and video format but also invest directly into creator-led commerce brands, live events, and merchandise. My side hustle is being the co-host with my wife Lauryn of a popular show called The Skinny Confidential Him & Her. We recently surpassed 200 million downloads.
Lauryn Bosstick: The Skinny Confidential started as a blog 12 years ago and has evolved into a resource that’s focused on wellness and beauty. We speak to all kinds of high performers who share their stories and tips when it comes to life, business, relationships, sex, supplements — nothing is off limits. I’ve also authored two books and I am a mom to two kids.
What inspired you to create this business?
LB: The Skinny Confidential community was 100% the reason behind the product line. Through the blog and social media, reading DM’s and comments, I knew that a line of preventative beauty tools specializing in high quality, aesthetically pleasing (we’re so sick of sterile, white eyesores), efficient and classic but innovative would be welcomed. There was never an “aha” moment. Everything with The Skinny Confidential was steady-paced and strategic. We made sure we were thoughtful about every single product we launched, which is why it took four years to launch the HOT MESS Ice Roller. Saying that, whenever I get comments or emails about how much The Skinny Confidential product line has helped our community, it gives me a little aha feeling, because we’re just so proud of what we’ve created with the help of our readership.
MB: When Lauryn started creating content online in 2010, the term influencer didn’t even exist. She was primarily creating content on her blog at the time. As the brand evolved and social channels started to emerge, we decided to work on something together. That resulted in the podcast. After self-producing for about a year we joined a prominent podcast network thinking they would take care of the major pain points. We quickly realized that they had very little understanding of how to marry an audio platform to other digital platforms, so we went back to self-producing. That experience led me to the realization that there was a more effective and more lucrative way to produce audio content. After analyzing the market and seeing that there was very little female representation, we decided to create Dear Media which now hosts over 80 shows and growing.
How did you know it was time to turn your side hustle into your main hustle?
LB: I was a bartender while building the brand and there was this moment when I realized to scale the business, I needed to focus on it full-time. So I quit. I never looked back. Looking back wasn’t an option. The only option was The Skinny Confidential, full speed ahead. I had big plans for the brand.
MB: After about two years of producing our podcast, we started to see a ton of traction. The audience on that platform was growing faster than any other platform and the revenue started to become meaningful. I had a feeling that we would also be able to bring that kind of success to other creators in our space and felt the moment to go all in on audio was there.
What has been your biggest challenge and how did you pivot to overcome it?
MB: The hardest part for me personally running a company like Dear Media was learning how to deal with talent, talent agencies, managers, and lawyers who come from the media/talent world. As a former commerce executive, this was all foreign to me. I had to learn about a whole new world that I wasn’t familiar with. I think this ended up becoming a superpower in the end because I was able to put my own spin on things. I also think it enabled Dear Media to operate the way it needs to operate without having to worry about “how things have been done traditionally.”
LB: The biggest challenge has been delegating and having a team. It’s a work in progress, but the team is so incredible, it’s getting easier to let go of things. When you’re a solo entrepreneur, you’re used to doing everything yourself. It’s one thing to ask for help when you realize you need it, but to actually give it up and not have your hand in every cookie jar is a real challenge. But like I said, everyone on the team is so damn effective at what they do, it’s just getting easier and easier to let them take over certain things. That being said, I still have my finger on the pulse. I am a detailed person by nature and I am always listening to the audience. They’re the hero.
What advice would you give entrepreneurs looking for funding?
LB: Know your investor demographic. Check out their social media, look at what other brands they invested in, see if your product is one they would actually use & love, or at least find a way to make your product/brand a part of their lives. Knowing your ‘audience’ will give you a better shot. Also, be bold. Desperate or nervous energy turns people off.
MB: Investors are very savvy, and their entire job depends on finding great companies. Get loud with what you are doing and create enough noise that it grabs the attention of the right investors. It’s also easier to close a deal when the fund or venture has pursued you. This doesn’t mean you won’t have to pitch them like hell after, it just creates a different dynamic where you have more leverage than if you were the one pursuing from the start.
What does the word “entrepreneur” mean to you?
MB: Someone without a safety net or backup plan. Their only plan is to go all in on their idea and there is nothing stopping them from executing on their vision. They are also probably a little crazy.
LB: Working on your business, not in your business. A true entrepreneur is always evolving and creating and moving the needle of the business.
What is something many aspiring business owners think they need that they really don’t?
MB: A lot of capital. We started our podcast with 100 dollars in equipment and no funding. We then started Dear Media ourselves without any outside capital. We slowly bootstrapped the business and optimized our model all the way to series A. I think glorifying capital raises for the sake of raising has been a big mistake that we are all seeing now. Bring capital on when you need it. It will also be cheaper capital once you’ve executed well without it.
LB: Besides thinking they need lots of money, they’re what I call a “forever student.” They’re putting off launching because they feel they need to read or go to school or have a mentor. They don’t. They need to execute and learn as they go.
What is a book you always recommend?
MB: Lonesome Dove by Larry McMurtry. It has nothing to do with business and everything to do with the fragility and simplicity of life. It’s a good reminder to live life to the fullest and enjoy the time you have here.
LB: The Slight Edge by Jeff Olson. Essentially it’s about always coming back to what made you popular in the first place. For me, that’s the blog — it’s the mothership. Another one I like is The Daily Stoic by Ryan Holiday Stephen Hanselman. It is especially a good one for women in business. It really strengthens your emotional intelligence and helps you move on from what you cannot control.
Is there a particular quote or saying that you use as personal motivation?
LB: “Protect your peace.” Say no, carve out time for what makes you happy and what’s important to you, recharge, read, read more, meditate. Thinking time is essential to building a massive business.
MB: “The coyotes howl, and the caravan keeps moving” I can’t remember who said it but I’ve always loved it. I think as entrepreneurs and content creators we will always be met with moments of self-doubt. There will always be people who say things we don’t like, who doubt us or dislike us. It’s critical to find a way to keep pushing forward while blocking out the noise. If you start reading your own press clippings or reviews, it can really slow you down and make you doubt yourself. So onward! And with no regard for what the coyotes are howling about.
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