'The Most Irresponsible and Ridiculous Thing You Could Ever Do!': The $2 Million Bet That Skyrocketed Success for This Entrepreneur

Key Points

• Scott and Missy Tannen founded Boll & Branch after a simple search for quality sheets revealed no premium bedding brand, inspiring them to launch a direct-to-consumer organic bedding company.
• Scott personally guaranteed $2 million in debt to underwrite a year of advertising on Howard Stern’s radio show—a move he calls “irresponsible” but that ultimately broke open their business.
• Boll & Branch differentiates itself as an affordable luxury brand by using certified organic materials and fair labor practices.
• Today, Scott defines success not just by sales but by the freedom to enjoy family life, while still seeing “lots of green space” ahead for further growth.

Every week on How Success Happens, I get to talk to awesome people who do awesome things and ask the simple question: how on earth did you do that?

This time around, I put Scott Tannen in the "awesome person" hot seat. About 14 years ago, he and his wife Missy were switching from a queen-size bed to a king, and Scott was faced with a seemingly small problem: Where do I go for sheets?

That little question eventually turned into a big business — Boll & Branch, an affordable luxury bedding company that prides itself on using organic materials and fair labor practices.

I met Scott and Missy at an event in New York City not too long ago, and was wowed by their origin story (ditching careers to pursue something that they admittedly didn't know much about) and how a combination of determination and fearlessness (betting $2 million on a radio campaign with Howard Stern!) put them on the map.

Following the event, I spoke with Scott for How Success Happens, which you can listen to here or on the platform of your choice. And check out some highlights of our conversation below, which have been edited for length and clarity.

Subscribe to How Success Happens: Apple | Spotify | YouTube

How do you define success for yourself?
That's a question I struggle with. It's something a little bit elusive, dangling out there that you never quite reach. If 14 years ago, when Missy and I first started working on Boll & Branch, you told me where the company would be today, I wouldn't have believed you. And I would've defined our success as beyond our wildest dreams. But today I sit here still pretty hungry because I think there's a lot of green space in front of us. But when I pull back, I have three daughters, and so when I really think about what success looks like, it's the fact that I'm at a place in my life where I can enjoy them and enjoy where they're going with a little less of the pressure that I felt 10 years ago when I was wondering how we're gonna handle the electric bill.

What's the origin story of the company?
I was at an interesting place in my life, to be honest with you. I had sold my last company, which was in the video game space, so it couldn't be a more different industry. But it wasn't like, "I sold the company, come visit me on my yacht in the Mediterranean!" It was more like, "Okay, let's go find another job." I was also caring for my mother, who was diagnosed with pancreatic cancer, and then she passed a year later. I was in a bit of a crossroads in my life. Missy and I knew we needed to find jobs. At that time, I was just particularly attracted to the first generation of direct-to-consumer businesses. Things like Shopify were just popping up, and the bar to get a product to market and get a company to market selling online was really, really low. I knew I could market, but I needed to find a category that nobody was playing in. And when it came time to buy sheets for our bed, I realized that I didn't know the difference between what I was buying at Bloomingdale's vs. Bed, Bath and Beyond. And I stayed up all night on Google researching and digging into the New York Times archives and I realized that even though everyone uses sheets, no one knows about them. There's no Olympic brand in this space. So the story gets longer, but Missy got involved in creating our own company, and we quickly found our roles: she would develop the products, and I would create a brand people were excited about.

Related: Barbara Corcoran Reveals Who the Cheapest Shark Really Is — And Explains the True Passion That Drives Her Success

I remember your voice quite vividly from early radio spots. Can you talk about your decision to go the radio route and the lengths you went to in order to get on one particular show?
When we started, we were playing the exact same playbook as other companies — running a ton of Facebook ads — and we were struggling. We couldn't get performance out of it because we weren't selling a cheap product. We were actually selling a luxury product. This was the time before influencers. So I was looking for advertising venues where people are attentive. We started doing a little bit of experimentation with advertising on the radio and going into channels like politics, where people listen intently. I was a big Howard Stern fan, and he is sort of the original influencer. I bought so much stuff because of Howard. He's a curmudgeon, right? He doesn't like anything. And the very few things in the world he likes, I usually realize they're pretty darn good. So we sent him custom-made sheets. And it turned out that he loved them. So I got in touch with SiriusXM and I was like, "Hey, wanna buy some spots.." And they were like, "Yeah, we'd love for you to advertise on Howard Stern. Here are the terms: you gotta guarantee us a year. The minimum spend is $2 million." We didn't have that, but I was convinced he would break open our business. So I started getting SBA loans and I ended up raising $2 million in debt — all personally guaranteed. And I sent it all to SiriusXM, which is the most illogical, irresponsible, ridiculous thing you could ever possibly do! You know when they say, "Don't put all your eggs in one basket"? I actually bought the basket, put all my eggs in it, and then just said, "Let's see what happens." And it worked! Years later, Howard heard the story, and his response was, "Man, Scott is an idiot."

Related: How Rescuing Chihuahuas with Kaley Cuoco Led to Katie Hunt's Big Success

Since you deal in bedding, do you have a recurring nightmare?
Yes, I have a recurring nightmare. I think it means something. I've Googled it, but then I forgot. In the dream, I'm back in college at Vanderbilt and I realize I forgot to go to a class for an entire semester, and I'm gonna fail it. I don't know why it's a nightmare because I actually did fail some classes in college!

Be sure to subscribe to How Success Happens: Apple | Spotify | YouTube