Determined Society with Shawn French | Adversity & Mindset - Kelly Bensimon: From Controversial Reality TV Star to Real-Life Powerhouse

Episode Date: October 27, 2025

In this sharp, high-energy episode of The Determined Society, host Shawn French sits down with the iconic Kelly Killoren Bensimon — model, author, Real Housewives of New York alum, and powerhouse lu...xury real-estate broker — for a raw conversation about mental toughness, authenticity, and legacy. Kelly opens up about the lessons learned after fame, how she rebuilt her identity beyond reality TV, and why music and curiosity still fuel her every move. From embracing “minnow vs shark” mindset shifts to navigating public perception, Kelly shares what it really takes to evolve in the spotlight while staying grounded in family and purpose. The two dive into double standards, resilience, and the underrated power of healthy coping mechanisms — from horses and polo to parenting and purpose. Kelly reveals how she transformed criticism into clarity, leveraged her Midwest roots for grit, and turned chaos into creativity through focus, curiosity, and real work. By the end, you’ll see that behind the headlines and the high-rises is a woman defined not by fame, but by fearless reinvention. Key Takeaways: -Music fuels mindset — every success story starts with a rhythm. -Minnows can become sharks through curiosity and work ethic. -Public perception ≠ personal truth — redefine yourself through action. -Mental toughness and self-awareness outlast hype. -Curiosity is the secret weapon in business and life. -Authenticity wins — people feel what’s real. -Family and legacy matter more than fame or followers. Connect with me : https://link.me/theshawnfrench?fbclid=PAZXh0bgNhZW0CMTEAAaY2s9TipS1cPaEZZ9h692pnV-rlsO-lzvK6LSFGtkKZ53WvtCAYTKY7lmQ_aem_OY08g381oa759QqTr7iPGA Kelly Bensimon https://www.instagram.com/kellybensimon/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

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Starting point is 00:00:33 The keyboard warriors and the armchair quarterbacks, they make fun of people like me. Even today, 15 years later, after being on Housewives, people are constantly telling me how ugly I am, how stupid I am, how awful I am, how what a terrible person I am, how self-centered I am, you met me. Wow.
Starting point is 00:00:54 You know, I went on Housewives because I recently got divorced. I was very young and I had to raise two children. And when you're a financial provider, you're not like, I'm just going to like sit home and just provide and wait for someone to provide. I didn't have that luxury. There are two types of people in this world, Kelly. In your opinion, what are they? Sharks and bottom feeders or sharks and minnows. Now give me the explanation.
Starting point is 00:01:30 because I think there's a good explanation behind this. So minors can become sharks. I mean, not in the obvious world, but in the business world, and minnow can learn all the tricks of the trade and become a shark. But there are problems. Sometimes minnows, there's problems
Starting point is 00:01:52 because there are a lot of them. And they're trying so hard. And the sharks are just the ones that rise to the top. and just take over the universe. I completely resonate with this, right? Because the reason why this question is so impactful is because we all start in this specific instance,
Starting point is 00:02:12 we all start as a minnow. And we can grow and grow and expand. And so as you're giving that explanation, I'm going through my own journey. I'm like, ooh, I really like that breakdown. I mean, we have to understand that minnows are not going to be sharks. Like, let's just make that. Yeah, especially in today's landscape.
Starting point is 00:02:29 if we got to make sure that everybody knows that a minnow can't turn into a shark. Right. Just about to make sure that's clear. But for the sake of my metaphor. Before the sleuth come out. Oh, is like I'd explain everything? Okay. Yes.
Starting point is 00:02:44 No, now you do. You know, because that. Correct. But for the sake of my metaphor, I'm up here and you're down there. I just want to clarify, this is for entertainment purposes only. But I think that one of the most important things about minnows and sharks is that there are a lot, like we said before, there are a ton of minnows, and there are very few sharks. And you can become a shark, 100%. You just have to get out of the middle mindset.
Starting point is 00:03:16 So you can be one of many, or you can be one of one. That's not my choice. That's your choice. I love the one of one because everybody, as they're a minnow, thinks they have to be like somebody else. And I was guilty of that, right? I thought I had to be, you know, somebody else or talk a certain way or give a certain energy or opinion based on what was working for somebody else. And as this thing kind of went on, I saw this massive roadblock. And I'm like, what is it?
Starting point is 00:03:48 And then for me, it was just about settling into myself and executing the gifts that I had. And I think that's a great point as people ascend to the next level in a different stage. Wait, Sean, that is a really, really astute. Tell me, like, can you give me an example of, like, a situation? Yeah, for sure. So when I started the, it turned out it started as a Facebook group. And when I started it is when I did 75 hard, you know, Andy Fricer, I don't know if you know who Andy Foresla is, but he's the CEO of First Form International, the biggest online
Starting point is 00:04:23 supplement company and he's viral. He has a lot of controversial things. So I thought I had to be that hustle culture that he was and speak loudly and energetically and in your face. And there's an aspect of me that can pull that off, but it's not my core beingness. And so at the very beginning, it was like I was a parrot. I was just echoing, right,
Starting point is 00:04:50 of what maybe how he would say it or what he felt was important. And after a while, when I started to settle in, I realized like, you know, this isn't me. This isn't hitting the right way. So when I got myself right and started double down on what my actual strengths were, then that's when I started to really experience some exponential growth. And I just think it's also, you know, everybody talks about, you know,
Starting point is 00:05:15 focusing on your weaknesses. I think there's some danger in that, right? So what I decided to do is like, I'm going to take what I'm really good at. I'm going to get it as good as humanly possible, and then I continue on that trend to really get better at what I do best. And that's all I can do. It's all I can control. I love that.
Starting point is 00:05:36 And I think that you're super correct about people focusing on weakness. For some reason, we are in a laser-focused weakness culture. And I have always, I was raised in the Midwest, corn fed, and raised by a father who, you know, came from nothing, education was paramount, and he would always tell us to be laser focused on what we were good at, or we are good at. And I raised my kids with that. As a single parent, there's only one voice. It's my voice.
Starting point is 00:06:12 And so I just was speaking to my youngest daughter today, and I said, you know, however you want to present yourself is how you want to present yourself. to present yourself as a leader? Do you want to present yourself as a solution-based person? Do you want to present yourself as someone who has innovative ideas? Do you want to present yourself as a game changer? Do you want to present yourself as the listener who can help move the needle? But these are all like positive, focused mindset totally different than, like, I don't think you should focus on your weaknesses because that's not going to move the needle. People aren't like, wow, you really,
Starting point is 00:06:56 really aren't good at baseball. Let's make you play baseball. Like, you're really good at football, but let's make you play baseball. It's not how it works. You know, Kelly, you make a great point, right? You're talking about laser focus, right? And being in a laser-focused society
Starting point is 00:07:14 that we're in because there's so much going on, you've done so many things. and you've been effective and brilliant at all of them. You were on season two through, hey, season two through four of Real Housewives in New York. You are a model. You have transitioned to being an ambassador and influencer for wellness products and companies of such. And you're a badass realtor that has also been featured on, you know, selling New York a couple different times. So like, there's a lot going, oh, and all your hobbies and being a mom.
Starting point is 00:07:47 Right. Let's be honest, there's been things that's gone on in your life over the last five, 10 years that could have derailed anybody that didn't have that focus. So what I really want to do right now is paint the picture for the audience that, you know, maybe some strategies on staying focused so that you can be so damn dynamic. I mean, I think like the operative word is derailed. You know, whatever has happened in my personal, professional life, I wasn't raised with the option of getting derailed. Like I've always said, like, I wasn't, I've never been, I was never raised that it's okay to not work hard, work smart, try to do better, be kinder, be more proactive.
Starting point is 00:08:33 I just wasn't raised like that. I wasn't raised to talk about how bad life was or the situations that were happening. I was raised to find the solutions not only for myself, but to help my friends, and people who I trust help them with solutions so we can work together. I believe in a team. No one person does envy.
Starting point is 00:08:56 Anyone that says that it's just one person on an island that's not true. You always have different people around you just choose to bring them along or not. So I think that being derailed is something that was just never in my vernacular, just never something that I was, I didn't have the luxury
Starting point is 00:09:17 of being able to have that or be like that or think like that. I love that. Because what we're talking about is mental toughness and grit and an amazing and unshakable mindset, right? We all have shit that goes down in our lives. Like we all do. We can have moments of being derailed. And I think at some point, you know, everybody has this moment. Like, okay, I got to take a step back and I got to evaluate this.
Starting point is 00:09:47 and maybe find a pivot. But what we cannot do is give up from the mission. I just think there's too many people right now that are giving up on what they want because of somebody else's voice saying that they can't do something. I had this conversation yesterday with Kathy Ireland. It was just she was saying that, you know, like there's people that are always going to tell you you can't do something. Always. Are you to do listen?
Starting point is 00:10:10 How many people made fun of me for doing this? I mean, are there any more dushy things than quitting an amazing sales career in the medical business to start a podcast. I don't know. I don't know. They make fun of people like me. First of all, it's amazing. Congratulations. And it takes a lot of confidence to make a big decision like that. So, I mean, that's awesome. I think that, you know, even today 15 years later, after being on Housewives, people are constantly telling me how ugly I am, how stupid I am, how awful I am, how what a terrible person I am. I am, how self-centered I am.
Starting point is 00:10:51 Have you met me? Wow. I've been on the, I've been on, all the things that I am not. I've literally, I know. It's so funny because I never judge anything based on what I see on reality TV, right? I know I have plenty of friends that were in, you know, reality shows that were produced to look like an absolute villain. And they're the kindest, most loyal individuals I've ever been friends with, right?
Starting point is 00:11:16 But it's so funny. Because, you know, when you look at all that, when you look at the exposure, how are some, because, because listen, let's be honest, there's people in this world that will have one person tell them one thing. Like, I don't think you can make it or you don't have what it takes. It could be a boss. But you literally have the keyboard warriors and the armchair quarterbacks telling you things about you that aren't true.
Starting point is 00:11:40 And after, you know, 10 minutes of this conversation, I can already tell you that, you know, Nick D's correct. and everybody who knows you, that is just you're an amazing person. And you're not, they don't know who the hell you are. No, they don't. But that's okay because that was a part of my life. That was really fun. And, you know, I went on housewives because I recently got divorced.
Starting point is 00:12:08 And I was very young. And I had to raise two children. and when you're a financial provider, you don't just, you're not like, I'm just going to, like, sit home and just provide and wait for someone to provide while I'm waiting to provide. It just doesn't work like that. And, I mean, I would love to be able to, again, like, I would love to have been able to, like, sit, regroup, figure out what I was going to do. I didn't have that luxury.
Starting point is 00:12:38 So I had to shift gears immediately. and I was offered an opportunity to be on Housewives. I was offered an opportunity to do something else, another show. And then the executive producer was like, we need to legitimize this brand. Like, we'd love to have you on. And I was like, why not? Yeah.
Starting point is 00:12:57 And normally, because I'm a writer, I'm always like checking things out. You know, I'm not like, I don't like die deep and find out people's deepest, darkest secrets. But I do like to have like an overall understanding of who they are. just as out of respect, like, hey, I saw you did this or I know you did that. And I didn't do that when I was on housewives because I was like, this is supposed to be reality. And I want people to see the real me.
Starting point is 00:13:26 And I thought people were going to be like, oh, my God, I can be like her too. I can come from Rockford, Illinois, and model and work hard and, you know, try to like make, hey, while the sun shines and, you know, explore and celebrate all these incredible people. But now, they were like, that's what you do? I'm like, yes, that's what I do. They're like, oh, my God, how awful. Can't believe you, like, are curious and want to do things to help other people. That's awful.
Starting point is 00:14:02 Yeah. It's amazing to me how people can be perceived, right? by watching a TV show. That is spoiler guys for entertainment purposes, right? I think too that they didn't like the fact that I was a single parent. The fans were not ready for that. I mean, I know that everyone, I know that they weren't ready for it. 2009, they weren't ready for a woman like me to be single and to be working hard.
Starting point is 00:14:34 It just didn't make sense. They're like, why is she working hard? Why doesn't she just marry someone rich? I'm like, well, why don't I, I come from the Midwest. I come from a core, strong value system. Why wouldn't I want to do well? Why wouldn't I want to be revered for the things that I do well and have a man around me and say, oh, my God, that's so great.
Starting point is 00:15:04 No, they were like, that's not how it works. just get married well they're forgetting that one size doesn't fit all and i want to ask you because there was an opportunity for me to comment on something in us weekly about this type of subject and um you know i think there's a double standard here i think it's a double standard and i and i want to hear your thought on that because do you feel that if it were you know the real you know how you know men of New York, would anybody give pushback on the man being single and being driven and successful and wanting to do it on their own? There's a double standard here. No, they would be like, he's a baller. Look at him. He's killing it. He's the Tom Brady of
Starting point is 00:15:55 housewives. He's the goat. But I'm like, they're like, oh my God, something must be wrong with her. Something really must be wrong with her that she's educated and works hard, looks like she does, raising two kids by herself. And by the way, like this whole idea of like marrying a billionaire, like if I were a billionaire, the last thing I'd want is some person who is like feeling, thinking they're like the shit. Like I want to be with someone who's an amazing human. Like I don't need to be with someone who's just like armed candy. Like that's not going to move the needle.
Starting point is 00:16:33 That's not going to like, you know, at the end of the day when the lights go down, Sean, Like, you know, you need someone that you can talk to and that you can, that has empathy and that is curious and that has genuine baseline kindness. Very well said. I mean, that's what everybody's shooting for. That's the real measuring stick of a relationship. I hope so. I mean, you would think, right? I hope so.
Starting point is 00:17:02 Yeah. So let me ask you a question. So when all this stuff came, you know, started coming out and seeing how Joe public or the viewers, you know, have their opinions of you, how did that impact you mentally? Because I would have to, I would have to think the first time, right? The first time that anything came out, there's this massive, you know, kick in the stomach. I want to tell a quick story. This is why I asked. So I was on, here's Morgan.
Starting point is 00:17:28 I think it was in February or March. And it was the first time I was on his show. and I got torched on X and YouTube that I was a covert feminist because, you know, I was happy that my wife was happy in her career in teaching. And, you know, I got completely blasted. I got called a SMP. I got called a bunch of different things, you know, basically like, your wife should be home raising the kids and you should be out doing this. I'm like, wait, hold on, what year is it? And why is it now that I actually support my part? in doing this. Yeah. In that moment, I called, I called vow. I said, what do I do about this? I'm getting torched. And she goes, welcome to fame. You just, you just deal with it. And I'm like, so I don't respond. I don't. She goes, no, don't do that. It's, but for me, like, that was my first time. I remember I was at a high school, I think a lacrosse game with my wife and my kids. And I was just, I was,
Starting point is 00:18:31 I mean, I was sweating already because it's Florida, but this internal heat, I'm like, oh my gosh, they hate me. They hate me. Yeah. Oh, Sean, I'm sorry. I'm sorry. You know, it's interesting because when I was on Housewives, I had this amazing publicist. I was working in the fashion business, so I obviously knew like the right tool for the right job. But when I was going on television, I wanted to have a great publicist that could really help move the needle. Didn't know what was going to go on, but I knew that you have to have a team, always have to have a great team with you. So I had this amazing publicist,
Starting point is 00:19:05 and they said, don't say anything. You're going to be on the cover of Playboy. You're not going to say anything because you are going to be doing all these different things. And I'm like, this is not the show. You're letting out these people have this narrative, and I'm not able to actually say anything.
Starting point is 00:19:23 So finally, I like, when I left the show, I just was like, I let everybody, they're on the talk shows, they're on all these, they're on their Instagrams, I'm like silent. Then I'm like, you know what, I'm going to go to this beautiful charity event. And I'm going to celebrate the charity. And I'll talk about it there.
Starting point is 00:19:47 And so, and everyone was like, why did you wait here? And I'm like, because I'm in a charity event. Let's talk about how great this charity is. And then we could talk about why I'm going to be moving on from housewives. And everyone was like, what? Here. You did it here. No, no, no.
Starting point is 00:20:06 I got this. I think it's better to celebrate, you know, the misfortune and to be able to talk about what I'm doing and celebrate them and package that than just to be randomly talking about myself, which was the total opposite of who they thought I was. They just didn't know. Yeah. Just didn't know. But I'm sorry you got torched, but I'm glad you spoke up. Hey, you know, it is what it is, right? And it was one of those things that, you know, I hadn't been yet.
Starting point is 00:20:37 And it was my first taste. And now it was a really good crash course. I'm going to tell you right now because now when things happen, I just go far for the course. Like I'm not everybody's flavor of ice cream. I'm never going to be. You know, it's so funny because we deal with these. things as creators, right? A lot of times we're measured by, you know, for me, how many show listens a month? What are my rankings and my ratings and everything? And I looked at my wife
Starting point is 00:21:04 the other day. I'm like, on Apple, I dropped from five stars to four point nine. Look at all these one stars. And there's no explanation. I'll go, this is crazy. And she goes, that comes with more listens, Sean. That's going to happen. Like, you are not going to be for everybody. And that's also very good. Because if there can start to be some discourse about you and things like, that and you're going to catch hate. You just got to be ready for it. And I'm starting to feel it. Like I really, really am. And I'm prepared finally. But, you know, but the haters are part, but the haters are part of the equation too. You can't have lovers without haters. Right. So the, and the haters are the ones that are going to fuel you to be better because they're going
Starting point is 00:21:49 to say, hey, Sean, here's a pop up of something that I didn't like. And then that's an opportunity for you to say, hey, you didn't like this. Let's explore that. Like, how would you have known about that before? So I never saw it like that. Maybe because, like, again, because I'm a writer. Like, I'm always looking at the whole story. Right.
Starting point is 00:22:11 And so I was always like, oh, my God, they got something there. There must be something in there. Let's see what they want. And then they were like, wait a minute, you're asking us questions. Like, you're asking me what you can do better? that's what we're supposed to be doing here. I'm like, no, no, no, that's what this is all about.
Starting point is 00:22:28 This is real life. This is real conversation. You're helping me grow. I know you don't want to. I know you want me to like, you know, be ugly and old in the corner, but we're going to grow together whether you like it or not. You know, it's funny when I always get these criticisms, you know, in a comment or something like that.
Starting point is 00:22:47 There was one recently. The girl had a great point because I really love this clip. This is all very true, but there's a lot of F bombs in it. And there's not a whole lot on my show like that any longer. The guest was going there. And I don't censor anybody. And I just said to her. I was like, I remember her name.
Starting point is 00:23:03 Her name was Angela. I said, Angela, thank you so much for your comment. I completely understand where you're coming from. And I do not disagree. I'll do my best to get better with that. I want you to be able to share this.
Starting point is 00:23:15 And it's disarming. Because you know what? There's multiple things that have gone on. Someone on my show commented, said, this guy says like too much. I just, I love his content. But if I hear the word like again, I said, you know what? Thank you for that. I didn't notice it.
Starting point is 00:23:34 But now that I do, I will work intensely on removing those. And I think I've done a good job with it. Sean, people say that to me as well. They would say, if you're so smart, why do you always say like? Well, we say like because we're giving ourselves a mental pause. to think. Instead of just having the space or the air, we're using a word. So there's nothing wrong with that.
Starting point is 00:24:02 You can use all the time. It doesn't make you less smart, doesn't make you less mindful, doesn't make you less talented. It just means that you are being respectful of other people and putting in a word so that they don't feel an awkward silence. I don't disagree with you. I got all the answers. You do. Gosh, I need you next to me all the time. I'm like, hey, Kelly, what do I say? I'm going to say, Sean, you're so great. My hype girl, let's go. Let's go.
Starting point is 00:24:33 No, I appreciate it. You last week, let's talk about some more crazy things that you're doing. Last week, you had modeling show, you were jamming, you were jet set, and you have a very busy life. Walk us through the modeling and everything that's going on with you right now. So I do a lot of, I used to say I wear many hats, but I think that's so tacky. It's like, I wear many hats. Well, it's cliche, but it's, yeah, you do a lot stuff. You're moving. I'm a curious person.
Starting point is 00:25:07 Yeah. But I'm also a prepared person. So when someone says to me, hey, I have a brand, what are your thoughts on our brand? I'm not just like throwing spaghetti at the wall and spewing out nonsense. I think to myself, that's such a great brand. Like there's so many things that resonate and what are those things? And I think that's one reason why I'm a good ambassador for a lot of these wellness companies is because I'm very, very real.
Starting point is 00:25:40 I may not be showing you my blood, but I'm very real about my experiences. and I think that's one reason why I resonate so well. And I'm just honest. You know, a lot of people just, they have this narrative, and I don't have a narrative. I'm ever-changing. I'm constantly at a state of learning, and I always want to be better,
Starting point is 00:26:06 and I don't want to be stuck with, like, my narrative is X, my narrative is Y, because I want to be able to evolve, and I want to be able to grow. And again, all of that authenticity, that genuine, real, not bullshit housewives authenticity, but that real core authenticity just resonates with people. So I've been able to do all these different things, talk about my psoriasis in on social media where something that I never wanted to talk about. I was always hiding it. When I was on the cover of Playboy, my ex-husband was my photographer
Starting point is 00:26:49 because I didn't want anyone else to see my psoriasis. And as much as I love and hate him, he's mine to love and hate, and I knew that he wouldn't exploit something that would make me feel really, really bad about myself. So it became a celebration of being 40 and not a cover-up of... Right. Having psoriasis. So I've just had a lot of, I've had a lot of unusual experiences. And I just, for me, social media has been a game changer because whether I'm showing the most
Starting point is 00:27:28 luxurious apartments in the world or whether I'm talking about something that's very heartfelt, I'm able to communicate in a way that resonates. And it's been really powerful. powerful. I mean, even on my, I have a podcast and I Heart Radio with, I do part two. And talking honestly about dating in your 50s and that next chapter and what that looks like has been, I've had such a really warm welcome because I'm real. I'm not trying to give you tricks, not trying to like show you how great I am. I'm just talking honestly about what's happening and how it's happening. And it's been great.
Starting point is 00:28:14 It's been great. And we're going to take a quick break to hear from our powered by sponsor. We're proud to announce a partnership between White Sands, treatment centers, and the Determined Society. With multiple locations across Florida, White Sands provides luxury, top-rated addiction treatment, from medical detox and inpatient care to outpatient support and long-term aftercare.
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Starting point is 00:28:57 like actual genuine authenticity. Everybody talks about it. You know, I'm very open as well. And I can only be me. And I would venture to say, you could only be you. And for me, it just happens to be a very real conversation. I'm always open with what I'm going through, whether it was my binge eating and my weight
Starting point is 00:29:16 issues, or there's certain times where if I didn't handle a conversation with my kids or my wife correctly the day before, I would always bring it up because I think those moments right there, the listener and the viewers, really want to grab onto because there's too many times where people in our positions or even above where I'm at that, you know, can come off really preaching and people think that they're not relatable any longer. And I never want to be the individual that is not relatable. I want people that have never met me to truly know me. And that's what I shoot for here. That's why these conversations are not scripted. They're not calculated. They're open conversations because when I have amazing guests on like yourself, I want the people that are listening
Starting point is 00:30:03 in Washington to truly get a feel for who you really are and what you have done and how you have done. how you focus on a day-to-day to do the many things that you do. Authenticity. It really is. And for anyone out there who thinks that there's a trick or just because sometimes we say like, here's one issue, two issues, three issues, everything isn't packaged in one, two, and three. You know, you really have to go through things and you have to be around people that you trust and you have to be able to talk to people that you trust
Starting point is 00:30:38 and whether that's your friend group or your social media platform, you have to be able to be open and personally available to be better and to make real change in your life. Very well said. Wise, my friend. You're so wise.
Starting point is 00:31:02 This is wild, Kelly. It's wild. Let me ask you another question. So you, I mean, again, we've talked about, you know, some of the properties that you show. You have some big luxury listings right now. And I think, I know as of six months ago, you were looking to sell your New York house. Did that sell? Are you still in it?
Starting point is 00:31:17 Like, what's going on? I rented that because the market just shifted. And so I decided to my whole mindset in real estate is all about generational wealth. And what is generational wealth? Putting money in your pocket. So sometimes if the market does not lend itself to sell. than renting an apartment or putting money into people's pockets is just a better and safer way for people to actually make astute decisions on what they want to do rather than just feeling
Starting point is 00:31:50 like they have to sell something. A little money goes a long way and money brings people a lot of freedom. And so, you know, you don't always have to just, I think that that's one, a big problem in the real estate market is that a lot of brokers feel like they have to sell. Well, if you have to sell, you're never going to be successful. You want to find that perfect place for that person. You want to listen to what their needs are. Hey, I need to put some money in my pocket.
Starting point is 00:32:20 Great. Let's rent it for a while. Let's put it at a higher price. Let's put it on the market for a short period of time. Let's make strategic decisions so that we can together build a relationship and a rapport where you can trust me. And that is one, that's one reason why I do well in this business.
Starting point is 00:32:39 It's not because I've got long hair, not because I smile, it's because I'm super strategic with my clients, and I listen to what their needs are, and I am able to manipulate certain things because I have a team of really good people that I defer to, like lawyers, and educated humans
Starting point is 00:33:05 that are making real decisions, everyday real decisions, and not just people that are just trying to sell something to somebody. So it's just a different kind of mindset. Like, I just, I operate on a different, I operate differently. Like, I'm not afraid. I'm not scared.
Starting point is 00:33:24 I know that I can do certain things in a certain way. It may not be the timeline that you want, but I know, can do things in the right way. I love that your solution oriented. I try to be. I mean, well, you, I mean, it's just, right? I mean, but that's the thing. You wanted to sell your property in New York. It wasn't selling because the market shifted so bad. You're like, okay, I'm going to rent it. There's solutions. Instead of being focused on what's not happening for you, focus on what you can do in the interim until you can get that ultimate, you know, situation to happen. But too many people,
Starting point is 00:34:02 let the lack of what's not, you know, or what's not happening control their mindset and, and, you know, quite honestly, how they impact their day and how they live and really how they, their quality of life. Let's be honest. I think, too, Sean, you know, working with, working with Anna Wintour at the Met, writing American style for her was a game changer for me. And the reason that it was a game changer, game changing moment for me is because I learned, who we are as Americans, why we're so successful, and where we're going in the future. So most people are just focused on this like this right now. Everyone's like, my boyfriend for right now, my life for right now, my partner for right now.
Starting point is 00:34:50 You know, I learned about the most innovative humans and what they did and how they did it. And so that's how I think. I think like there's going to be these bumps in the roads, but like there's been amazing icons in the past who took major risks. And they weren't like, wow, I'm not going to be able to do X right now. They just took those risks and they became the next masters of the universe. And so I'm okay with taking risks and working with the best of the best so that the risk. so that the risks that I'm taking are educated risks. They're not random risks.
Starting point is 00:35:35 I really like that because when- You're just like- I'm feeling gorgeous. You're like, I really like that. I really like that. You know, it's- You're getting a sign to be that no one ever hears. I love that.
Starting point is 00:35:48 No, and that's great. That means this is going well, right? It means that the conversation is open. And that's what I love bringing, you know, that's what I love selfishly about these, conversations is when I can do that because it provides a better connection, a better, you know, conversation, and then the audience can enjoy it better. But you're talking about speed bumps. It drives me up a freaking wall when someone has an idea or it could be something within the
Starting point is 00:36:21 family. It doesn't matter what the situation is. And a speed bump hits and everybody pushes the panic button, freaks the F out. It's like, wait a second, guys, did we not think that At any point in time, we were going to have any type of universal resistance or external resistance or some type of issue or landmine sitting right in front of us that we have to fix or disarm before we move forward. It drives me crazy. Those are opportunities to get better. Yes.
Starting point is 00:36:52 But those are weaknesses, Sean. Those are someone's opening a door and saying, I need help. What are your thoughts? that's not weakness no that's strength in my humble opinion yeah love that and i told my team before the call today i mean before our interview i go guys i need help i need more help i need help in xyz and let's go hire someone to do it and let's do it within the next 90 days but you also know who to ask you're not just randomly saying like hello yeah you know You have a team around your people that you trust who could help you make those decisions.
Starting point is 00:37:36 That's key. That's the fun thing about it because I look at it and you're talking about the team. I have a whole ass team. And it's not just my executive team. I have a great production team. I have a great publicist. Like all of these things. You have a great family.
Starting point is 00:37:51 I have a great family. Oh, my wife is backbone of this thing. Right? Without her belief in me, we wouldn't be here because she'd be like, you are not quitting your job. Like you, you are not retiring for corporate America,
Starting point is 00:38:04 dude, you're, you're 45 at the time, right? You're not doing that. But without that, this isn't where it's at right now. So again,
Starting point is 00:38:14 the risk factor, like, if it's out there, man, and you feel it, you got to take it. You know, and you got to take it in stages,
Starting point is 00:38:22 and I took it in stages. But, you know, speed bumps, man, those are something that, I think people need to start embracing instead of running from. It's interesting because like last year when I called off my wedding,
Starting point is 00:38:38 which I thought people were just going to slam me for, I had to move out immediately. And my friends were really nervous. Like what's going to happen? What are you going to do? And it's just going to affect your business, like all these different things. and I just packed up my things and I moved. And I will never forget the first night that I was in this new apartment and not this
Starting point is 00:39:09 apartment and other apartment. And I just thought to myself, this is the first day of the rest of my life. I am going to protect myself from now on. That was a really hard decision to make for you. I mean, that for anybody. I mean, I've been spending my life protecting everyone else, creating narratives for them, you know, writing about them, celebrating them, doing everything for everyone else. And it was the first time of my, you know, raising two children, educating them, making sure they had
Starting point is 00:39:43 every single thing from knowing how to ski to second languages to whatever it is that they wanted to do. It was the first time in my life when I was like, I, need to be laser focused on my actual self. And it was like, scary. I bet you it was scary. And by the way, I heard you, are you really fluent? Oh my God.
Starting point is 00:40:09 What did I just do? You first day of your, the first day of your life. That's what it was. First day of the rest of your life. Whatever the saying is. But you, is it true that you're fluent in French? Yeah. That's wild.
Starting point is 00:40:25 Yeah. How do that mean, go for it, go. It's a powerful mistake. What did you say? What did you say? The lesson one, the probably in Vectoire. Wow. Thank you for that.
Starting point is 00:40:39 That's amazing. It's amazing. It's amazing. You know, being bilingual is very important. My wife, you know, she grew up in Ecuador. That's where she's from. And we're really trying to get the kids to really, you know, really dive into Spanish.
Starting point is 00:40:54 It's something that I wish that I dove into further as a kid. I took, you know, three years of Spanish. I think, I don't know my biological father very well, but my grandmother full on 100% fluent in Spanish. So I'm, you know, I'm Hispanic somewhere, you know, so it's important. It's a segue, guys. It's called getting sidetracked, which happens in a conversation. I'm Hispanic somewhere.
Starting point is 00:41:22 I'm part of somewhere. I don't know what kind, but, you know, I always thought I was like, I want to do that DNA and me thing or 23 and me. No. But I think that was bad, right? I don't think that worked out very well for people. No, it did not work out well for people. And some people that worked out great. It's interesting because people are always like, are you from Brazil? I'm like, I'm from Rockford, Illinois. I'm Irish Catholic. Yeah, but no, no, no. I have a twin brother. He's blonde hair and blue-eyed and I am not. I'm from Rockwood, Illinois. Brazil, are you Brazilian? People are like, where are you from?
Starting point is 00:41:57 I'm like, where do you think I'm from? Oh my gosh. That's crazy, isn't it? I like, I like to think of moments in terms of takeaways. And so I was raised in the Midwest. It was raised in an environment where we learned about the land of Lincoln and where history was super important to us. and sports were really important to us
Starting point is 00:42:25 and independence of being able to ride our bikes places. And, you know, I was driving into Chicago to start modeling at 15 years old. And just there was a different kind of mindset. And I was never, one of my biggest takeaways from being raised in that environment is that I had this fearlessness, that everything was a possibility,
Starting point is 00:42:50 that there was something out there that was going to be bigger and different and more interesting and more evocative, more provocative. And I was just very, very curious about all of these interesting new things because I had this baseline. I had this baseline of love, culture, tradition, value. And so I could just go anywhere from there because I always knew if I fell back, it would just be this cloud of love, education,
Starting point is 00:43:26 value. And so that kind of, that's, that takes you a long way. And I think that when, you know, when we were on housewives, one thing that people didn't see, they didn't want to see me as a single mom. They didn't want to see
Starting point is 00:43:44 that I worked. They didn't want to see, that I was educated. But we were all doing the same things just in a different way. I mean, every single woman on that show is educated, comes from a good family, comes from money, has possibility. Every single woman on that show.
Starting point is 00:44:06 Not one of us is poor or from a, you know, dysfunctional family. I mean, just there was things that happened to people, but we all had a baseline. And I think that's one of the reasons why people really love to watch us is because there was an understanding and that we were all like in it together. We weren't trying to promote,
Starting point is 00:44:29 you know, one person was trying to promote, but we weren't trying to like, you know, it was more about how we felt what we were doing and, you know, how were we reacting to stuff. And that made major TV. Major TV. I just became a pop-up because they were like, there's no way that she works no way
Starting point is 00:44:52 come on what does she read comic books oh was that one of the comments comic books I bet you do though I bet you do comic books who doesn't yeah who doesn't come on Spider-Man but everyone comes from somewhere Sean
Starting point is 00:45:14 sure I mean 1,000 percent, you know, and you know, with that, you know, everything that you've, you know, the word curious to me is very impactful. And I want the audience to grab onto that word because that word can take you so far. And everything that I get involved in, it starts from a point of curiosity. And I would also say, for people listening, is when you about, when you're about to get into a heated conversation or you think it's going to be heated and you want to just attack somebody start out curious seek to understand what the point is and why they feel a certain way because what i've found is when we can be curious and explore we often agree on a lot more than we disagree on
Starting point is 00:46:04 and then we can get to different places and have a constructive conversation or a debate whatever it is I used to say all the time, since 2009, let's agree to disagree. Yeah, yeah. Like, I don't know where this is going. I don't know how valuable this conversation is going to be. Let's just agree to disagree. That's been like my tagline since like literally 2000. I mean, I've used to say it before because when you're raising kids, you're just like, okay, you're fine.
Starting point is 00:46:33 Everyone's good. Everyone's going to be great. Everyone's going to be great. Let's just move forward. And it's true. I mean, I think that I really, I appreciate you coming from a place of curiosity. I think that's incredible. And I think that a lot of people just don't listen.
Starting point is 00:46:54 Yeah. They're just desperate to chat and get their point out, like, or their story out, or that narrative that they've created for themselves. Again, like, I told this at the top. And for the listeners, I don't have a narrative. you know today i may be fearless tomorrow i may be petrified who knows what's going to happen but i'm but i will tell you i will be i will tell you about it i love it oh i like it's getting real today hey shit's hot it's hot right now i don't know how i feel i was good yesterday today not so much you know what today i am freezing cold i'm not leaving this kitchen i'm stuck right freaking here
Starting point is 00:47:38 and I'm going to have 17 cups of coffee today. That's all I'm doing. That's it. I have those days. You know, I love those days, though, because it gives us a chance to slow down a little bit. You know, okay, let's evaluate why I feel like shit today. You know, what did I do last night?
Starting point is 00:47:54 What did I eat last night? What did I consume? What did I read? What did I listen? It's all information. But listen, life's also about hobbies. And as we wind this down, I know you got a busy day. Wind us down.
Starting point is 00:48:07 I'm having the best time ever. I'm like ready to go. Okay, let's keep it going. Block out the rest of the afternoon, guys. Cancel everything. It sounds like I got hours of Kelly, hours, but hours. Hours with Kelly. That could be a spinoff show, Hours with Kelly.
Starting point is 00:48:24 All of the hours. You have some fun hobbies, though. I do. You know, you're an avid equestrian. Now, what's a polo enthusiast? Now, are you playing polo, or do you just like to go and rain? I learned. last year, because after the unwinding of my relationship, I was like, I need to do something.
Starting point is 00:48:46 And so it's interesting my executive producer at IHurt Radio, Amy Sugarman's like, you need to do something that is super challenging for you, that you just don't know if you can do. So I was like, okay, I'm going to try polo. Like, I know how to ride horses. And I know some of the guys that play polo, and it seems super. aggressive and I'm going to try just to do it. So I have been, it's called stick and ball. So you're on a horse and you're basically hitting the stick, the mallet with the ball.
Starting point is 00:49:22 And it's very challenging. It's like, think about like golf on a horse. And these horses are small and they're very feisty and it's been really, really fun. And it gave me, it's like, I just, I'm not. telling people, I'm not saying like, oh my God, like if you have an issue, something happens or like there's a speed bump in your life, play polo. That's like a, that's not like an every day. Ticking ball, baby, stick and ball. But maybe it's a metaphor. Maybe, yeah, maybe stick and ball is a
Starting point is 00:49:55 metaphor if we're doing something out of the normal, out of the ordinary, learning something new, whether that's a language, piano, you know, something that is out of your comfort zone to really redirect everything, whether that's your serotonin, whether that's your just general, general mindset. Whatever it is to bring new energy to something is going to help you move through all of, you know, whatever it is that you're feeling, you're thinking, you know, that the mind is a very, very, very, very powerful, powerful machine. And it can really do things that can be great. and it can do really do things that can really, really harm people. And so if we don't use that mind in the right way,
Starting point is 00:50:44 it can really, you know, turn people to do things that are not good for them. And I don't believe in self-sabotage. I believe in working through things the best way that I can. And sometimes I don't know a better way than to use my body and use my body. and use my brain to do something different. Those are called healthy coping mechanisms. Oh, really? Look at that.
Starting point is 00:51:14 I think they're healthy. I know. You're killing, dude. You're killing life. God, I don't even know this. I'm like, wow, I'm doing a great job. Hey, I'm doing good. It's good that you found out on a Tuesday.
Starting point is 00:51:24 Now you've got the rest of the week, you know, double down on that shit. Oh, I have a really healthy coping mechanisms. Yes, very, very good. good coping mechanisms. Very good. Just try to, you know, again, like, you know, when you're a father and I'm a mother and, you know, I'm just always trying to, like, I'm like my, at the end of the day, Sean, when, you
Starting point is 00:51:48 know, when I'm, when I passed, it's going to say she was a great human and a great mother. It's not going to say she was on housewife. It's not going to say she was a playboy. It's not going to say she sells hundreds of millions of dollars of real estate. It's just not. It's going to say she was a great human. And she handled herself well and she understood people. And like that's the good news.
Starting point is 00:52:14 That's the good news. There's a very hard line between something that you do and who you are. And I think we get lost in what we do and allowing that to label our identity instead of diving into who we are as people. And as long as we continue to focus on who we truly are, because those are the things, that matter to our families, to our children, to society. What are they going to say about you when you're gone? And if it's, she was a real estate mogul, she was a reality TV star, that's a fail. That is a fail.
Starting point is 00:52:46 If they say she showed up, she was there, she had empathy, she supported her family, she did X, Y, or Z things that are like about your value system. That's the good news. But people think that just because you're a shark doesn't mean you don't have to be, have to be valueless. You don't have to be a mean shark. You just got to be a shark, you know. I'm a shark.
Starting point is 00:53:16 Yeah, you are. I'm like a little shark. You're so cool. I'm so, I'm really impressed by you. I'm impressed by you. I'm impressed by your beautiful wife and your kids. I'm impressed. Like, it takes a lot to, first of all, you know, you were talking about like,
Starting point is 00:53:32 you're binge eating. I mean, no one would look at you and say, wow, he's a binge eater. I mean, you're the picture of health. So first of all, that is like so amazing that you opened up about that because men's health issues are real. Second of all, just talking about, you know, the ups and downs and the idiosyncrasies of family life. Like, it's just, it's never, you know, everyone's like, I'm such a great mom. It's like, it's not about being this great person. It's about being able to, like, go through what we're talking about before, those speed bumps and kind of saying, like, okay, this person needs a little space or maybe this person needs a little more encouragement.
Starting point is 00:54:12 Like, that's just all good news. And then to take the huge leap of faith, huge leap of faith. You're like, here you go, corporate world. Bye. Here you go insurance. Here you go life. Here you go security. I'm going to go and do something that is totally.
Starting point is 00:54:30 different and something that makes me feel like the best version of me and look where you are. Yeah, and it's run on air. It's run on fiber optic cable. Think about that shit. Like, like, creating something from nothing, right? But, but again, I do evaluate myself consistently in this show and in this business, but more so as how am I, how was I today, as, a father and a husband. Because those are the moments. Everybody else can think the world of you,
Starting point is 00:55:06 but if you walk through those doors and those people there don't see you in the best light and don't think you're leading the right way, nothing else freaking matters. You know how people are always like talking about their kids. My kids are so great. My kids are the greatest kids of all greatest kids, right? But what they're actually saying is they're not talking about their kids. They're talking about how great they were in parenting. And you know what? People should be heralded for that. Like, you've got a great child. They're a great student. They're a great athlete. They're, doing well. They're a doctor, whatever it is. That's like, that's not slow clap stuff. That's like, yeah, it's the 80s slow clap shit. Let's get it.
Starting point is 00:55:52 That's like real. Real. That's it. That's where the money is. Those kids, those brains. That's where everything is. Everything else means nothing. I love that perspective.
Starting point is 00:56:06 There are legacy. There are futures. They're the ones that are going to be the next game changers. And we have to put all of our time effort resources into them. Just like you're doing. Yes. Yes. Yes.
Starting point is 00:56:18 And like yourself. But thank you so much for coming on today and having this amazing conversation. I love that. One of my favorite conversations in a long time. Oh. Very open, fun, playful, informative, and engaging for the audience.
Starting point is 00:56:31 So thank you for bringing your absolute kick-ass A game. Thank you. Appreciate that. I appreciate that. So are there any other things that you want to, I mean, again, I want to make sure that the audience knows where to find you. There's a lot of local audience. I know you have some stuff going on in,
Starting point is 00:56:49 I think Sarasota, you have a house that may be, on the market. You want to talk about that briefly? Give them a place to find all this stuff. Sure. So you can find me on any social media, Kelly Ben-Simon, Instagram, TikTok, LinkedIn, Facebook. You guys know where to find me. And everything that I do is always online. So I work in real estate in three states in New York, California and Florida. I have a lot of beautiful properties in Florida right near you guys in Sarasota, Miami, Palm Beach. It's been so much fun celebrating this whole brave new world and I'm just getting started. Proud of you. And then you guys can find me on my podcast. I do part two if you're interested in learning about
Starting point is 00:57:43 finding love, falling out of love, falling back in love, making sure that you make the right decisions when you're looking for love. It's all goodness. Value, serving, just serving the people for your experience. I love that. Yes, yes.
Starting point is 00:58:04 Well, thank you again, Kelly. Make sure you hang out for a bit, but I'm going to tell the audience, I'm going to give them some instructions right now. And the instructions are, hey, if you love the show and you got something out of it and you know that you know somebody that would benefit from the conversation,
Starting point is 00:58:18 send it to them. Like, please, just that's the only, thing I want you to do is share this episode with everyone you know love and trust and take the words very deeply. Everything we spoke about, there's a lot of hidden meanings and a lot of outward meetings too that you can really take and apply to your life today. So until next time, guys, stay determined. Rinse takes your laundry and hand delivers it to your door, expertly cleaned and folded. So you could take the time once spent folding and sorting and waiting to finally pursue a whole new version of you. Like tea time you
Starting point is 00:58:54 Or this tea time you Or even this tea time you Said you hear about Dave Or even tea time, tea time, tea time you So update on Dave It's up to you We'll take the laundry Rinse, it's time to be great

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