It's hard to believe now, but when we met Bethenny Frankel on The Apprentice: Martha Stewart in 2005 and got to know her better on The Real Housewives of New York City in 2008, she had very little money. Actually, it's hard to remember a time before Frankel, period - that's how ingrained in the culture she's become: first on TV, then in business and now on social media and in our collective consciousness. For almost two decades, Frankel, 54, has shared her no-nonsense, warp speed takes on everything from the best chicken salad in the Hamptons to why it's important for everyday citizens to chip in when communities are suffering. Through it all, she's been working her tush off and making bank - and headlines. She sold off the Skinnygirl Cocktails arm of her corporation in 2011 for a reported $100 million, and to date, Skinnygirl's other categories (including shapewear, popcorn, salad dressings and coffee) have generated $1 billion in retail sales. She has 3.3 million followers on TikTok and 4 million on Instagram. She walked the L'Oréal runway in Paris in 2024 and the Sports Illustrated Swimsuit show in May. Life is very, very good. Us Weekly's Entrepreneur of the Year - who recently left Connecticut for Florida with her 15-year-old daughter, Bryn, and their dogs - caught up with Us about finding her greatest success in her 50s, her dating status and what she really thinks about having so much cold, hard cash. Alexander Tamargo/Getty Images Let's go back to the beginning. Where do you credit your motivation? I went to 13 schools. I was always the new kid. I wasn't really a child, I was more like an adult as a child, being at the racetrack [with my dad] for my summers, living in Vegas for several weeks. I didn't have a lot of parental involvement, so I was kind of raising myself. I grew up in a very gritty lifestyle, so I think sometimes I miss a sensitivity chip. I don't get really tired, and pros play hurt. That's my life mantra. Do you ever wish it weren't? That you could flip to a less intense way of being? I would love to be like that. It's not the body, it's the mind. I have so many ideas that it's really hard to turn them off, but I'm so grateful for that. I've dated a lot of men who either have money from families or have made money on their own or have sold companies, but they'll be like, "Wait, you have so much going on that it makes me feel like I have nothing going on." Or they'll try to overcompensate and find things to do, because they used to feel happy, and being around me, they feel like they're not doing enough. So I feel grateful that I can execute ideas all the time, that I can connect with people - I have 15-year-old fans and I have 70-year-old fans. Inside Bethenny Frankel's Life in Florida: Everything We Know Is there someone you relate to most, or do you feel like you've created your own lane? I've heard Martha [Stewart]. I think there are some similarities because Martha is a hard worker, but I've heard from people who worked with her that she doesn't have as much energy as I do, and I know she's much older, but... it's a different style. Ellen [DeGeneres] did that one powerhouse thing so well, which was a beast, but that was one thing. I'm just doing so many different things that I don't know. I can't think of many women that are doing so many different things. Do you remember your earliest business deal or something you did early on that gave you that first big adrenaline rush? The first thing that was really successful for me was being on the New York Times bestseller list [with 2009's Naturally Thin: Unleash Your SkinnyGirl and Free Yourself From a Lifetime of Dieting]. Being there for five months as a fairly unknown was a big deal. Then Skinnygirl was the fastest-growing cocktail in history at the time, and it was the first-ever low-calorie ready-to-drink cocktail. I mean, I invented the skinny margarita. I was the first person to use the word "skinny" before items like lattes and pizza. The ready-to-drink space was dead. So knowing we were the fastest-growing liquor brand in history, that says something. And then when I did my spinoff to the Housewives [Bethenny Ever After], it was the highest-rated series premiere in Bravo history at the time. Or, like, the Forbes cover was amazing, my leaving Housewives and the ratings going from 3.2 million to 1.6 million. The numbers don't lie. And then [returning], and [the ratings] going back to over 3 million. It was like, "Oh, wait, I have value." These were signs that things were going well. You need those in life. For people who are entrepreneurs, you need that data, those stats - they keep you going. Have you ever worried about seeming too intimidating or powerful? I don't really care about celebrities, but I've been called by much more successful and well-known people than myself to try to get me to, like, say something positive about them, or take their side in something that's going on. This is all more recent, though, because I'm op