Icebreakers with entrepreneur and reality TV star Bethenny Frankel

Tonight, Bethenny Frankel will receive the Reality Royalty Award at the 2022 MTV Movie & TV Awards: Unscripted for her legendary reality TV career, which was highlighted by a long run on The Real Housewives of New York City.

But Frankel isn’t just a TV star—she’s also a super savvy businessperson. She sold her Skinnygirl cocktail brand for a reported $120 million and has ventured into TV production, philanthropy, and authoring multiple NYT bestselling books.

We chatted with Frankel about her entrepreneurial journey on the Imposters podcast. Here are some choice excerpts.

What was your childhood like?

My childhood was adventurous and filled with uncertainty. I think I went to 13 schools. I had a family all embedded in the thoroughbred horse racing world, which is about highs and lows, having and not having, gambling, action, odds, racetracks all over the country. I had a crazy childhood, but it was fun because there was a lot of action. My personality is a reflection of that journey. I like winning on my own terms, in my own way. Nobody cares about who comes in second in the Kentucky Derby.

Have you had any failed business experiences prior to your Skinnygirl breakthrough?

Well, BethennyBakes was a wheat-, egg-, and dairy-free, low-fat cookie business. We’re talking plant-based 20 years ago. That was ahead of its time, but I also didn’t have the infrastructure or the right packaging partner. I couldn’t get the consistency. I had to fold it.

How did you deal with that failure?

I don’t consider winning to be hitting a home run every time you get up to the plate. I consider winning how you handle it. Or how do you survive and how do you thrive? And I always turn a loss into a win. My first time trying to get on The Apprentice, I think, “I’ve made it” and they tell me, "You didn’t make it.” But then I connected with that same casting director, and went on the Martha Stewart Apprentice. I consider those losses to be case law for my $100 million business now.

How did you end up on Real Housewives of New York?

I was at polo, the sport in the Hamptons. It’s just a place to schmooze, and I was trying to hawk those cookies, the BethennyBakes cookies, and I ran into a woman who was excited about the show and had brought casting directors. The production company was happy with the four women they had; Bravo said they needed a fifth woman. It wasn’t a proven show. It was called Manhattan Moms. They just were like, “Let's pick her,” which makes no sense because they were looking for a mom and someone wealthy. I was broke. I wasn’t a mom.

How have your motivations changed now that you basically have enough money to never work again if you don’t want to?

I want to do the things that I love, that I’m passionate about, that I think are interesting, that I think are in line with who I am as a person, not doing things for alternative goals. Meaning, when I was on reality television, I was having disputes and talking about things that I don’t necessarily care about and in a lot of unnecessary drama that is created by a circumstance on television. That’s not in line with who I am and I don’t have to do that anymore.

This interview has been edited for clarity. Definitely check out the full podcast episode here.