Kelly Bensimon on The Golden Life, Reinventing Herself & Why She Embraces Being Misunderstood

Summary

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Podcast Summary: Kelly Bensimon on The Golden Life, Reinventing Herself & Why She Embraces Being Misunderstood

Podcast: Miss Understood with Rachel Uchitel
Host: Rachel Uchitel
Guest: Kelly Killoren Bensimon
Date: May 19, 2026

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Episode Overview

Rachel Uchitel sits down with model, author, editor, and reality TV icon Kelly Bensimon to discuss her new reality show on E!, her journey from modeling to real estate, her philosophy on reinvention, and her willingness to be “misunderstood.” Throughout the candid conversation, Kelly opens up about her career pivots, relationships, being a single mother, her infamous reality TV moments, and the human stories beneath the headlines.

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Key Discussion Points & Insights

Returning to Reality TV and Differences from the Past

• Why Return Now?
  Kelly was drawn back to television by E!’s modern storytelling and focus on authentic women’s voices. She feels this project differs from her time on “Housewives.”

  • “The way that they think is just so modern and cool, and I just was like, they’re just real storytellers, and I think it’s really important to hear women’s actual stories.” (Kelly, 01:33)

• Bravo vs. E!
  Shooting for E! contrasts sharply with Bravo's earlier days, which Kelly describes as being more fixated on fame than real stories.

  • “When I was on Housewives, it was 2009, Rachel. It was like the Ice Age…everyone was just like, I’m famous. I’m like, okay, great. Congratulations.” (Kelly, 02:18)

• On Reality TV Fame:
  Both Rachel and Kelly reflect on the superficiality of fame and the importance of being genuine.

  • “I’m like a show me who you are kind of person. I’m like, don’t tell me.” (Kelly, 04:24)
  • “When I’m impressed by somebody, they don’t have to be famous…there’s something about them that impresses me.” (Rachel, 04:02)

The Jill Zarin Incident & Group Dynamics

• Jill Zarin Drama:
  Kelly candidly discusses the fallout with castmate Jill Zarin, who she believes self-sabotaged a great opportunity.

  • “I called her and I was like, what did you do?...We could have had the best time talking about what a great mother you are...She basically self sabotaged.” (Kelly, 07:33)
  • She expresses disappointment but reiterates her love and high regard for Jill.

• What to Expect from the Show:
  The upcoming season promises strong dynamics and the depiction of women thriving in their 50s and 60s.

  • “It is mass chaos. But it is just like a beautiful dance of chaos and love.” (Kelly, 09:31)

Being Misunderstood & Reinvention

• ‘Scary Island’ Legacy:
  Kelly speaks about being cast as “unhinged” on “Housewives,” reflecting on how the real narrative of her life was missed.

  • “They were just trying to reenact that, and they were just like, well, she’s not scary...I’m a badass, right? I am a mama bear...But I’m not unhinged, and I’m definitely not crazy.” (Kelly, 10:32)
  • “They missed the real story, which was the heartbreak and the fear that I had during that time...You didn’t see the real story.” (Kelly, 12:59)

• On Reinvention:
  Both Rachel and Kelly discuss the journey of reinventing themselves post-divorce and the lack of space once given to women’s real challenges and successes.

  • “Now I feel like to reinvent yourself is such a big deal. Everyone’s trying to do it, and we all want the secret code on how to do it.” (Rachel, 13:18)
  • “They tried to make me crazy, but not crazy enough because…coal eyeshadow is not my vibe. So this is all, like, not good, right?” (Kelly, 14:47)

From Modeling to Writing & Editing

• Modeling Beginnings:
  Kelly recounts being scouted at 14 and being the runner-up to Cindy Crawford in a modeling contest.

  • “Cindy Crawford won, and I was the runner up.” (Kelly, 17:29)

• Modeling Industry Reflections:
  Kelly feels she had a generally positive experience, crediting strong family support, but acknowledges the industry’s impact on many others and her own struggles with eating disorders.

  • “A lot of these girls that start modeling come from absolutely nowhere…the modeling industry is their hug.” (Kelly, 23:19)

• Transition to Editing/Writing:
  Encouraged by professors and contacts, Kelly became one of the first bloggers for Elle.com, wrote columns, and authored seven books.

  • “There’s something to be said about higher education. I mean, it is not for the faint heart.” (Kelly, 30:12)
  • On her book ideas: “My first book called In the Spirit of the Hamptons...Then I was asked by Anna Wintour to write American Style...” (Kelly, 29:43–33:15)

Real Estate Pivot

• Origin Story:
  Kelly’s shift into real estate was triggered by a personal need to sell her family’s homes after her mother’s illness.

  • “My mother fell ill and I had to sell my family’s homes. And so I got my license, like, literally immediately.” (Kelly, 38:54)

• Approach to Real Estate:
  Kelly differentiates her business by selling “lifestyle,” focusing on the ultra-high-net-worth market and using her network, but discourages the “bad habits” of stereotypical brokers.

  • “I sell to the masters of the universe, and I sell the most illustrious properties in the world.” (Kelly, 43:33)
  • “I don’t sell real estate. I sell lifestyle...my enthusiasm is so infectious.” (Kelly, 44:04)

• On Real Estate Reality Shows:
  She shares “tea” about big names in the industry and the unreality of real estate reality TV.

  • “You can’t. You don’t have no properties. People don’t want their properties on the market on the shows. And number two, real buyers don’t want to be on the show.” (Kelly, 61:53)
  • “I think of real estate as the ultimate luxury and the genesis of your generational wealth.” (Kelly, 62:44)

Fashion, Style, and Consulting

• Fashion Rules & Iconic Looks:
  Kelly learns “the rules” of fashion from modeling — practical tips, not just trends. She wrote a book on being “hot” and the bikini book.
  • “When people see me, they’re like, oh, that looks good. I’m like, because I follow the rules, right?” (Kelly, 36:27)
  • “I wrote a book called I can make you hot in 2011, which was healthy options today.” (Kelly, 36:32)
  • On swimsuits: “I wrote the bikini book, so I know a lot about bathing suits.” (Kelly, 47:23)

Relationships, Prenups, and Single Life

• On Love and Prenups:
  Kelly discusses the end of her recent engagement, emphasizing the importance of legal protection and putting her kids first.

  • “As a single mother, like, I’ve been protecting my girls all their lives, and I will continue to do that. And I just was like, you know, I make money. You make money. I probably will make more money. You know, I have a little money, and I’m just not going to give it to you.” (Kelly, 49:57)

• Modern Dating:
  Kelly admits to using dating apps like Hinge and Raya but finds most meaningful connections come in person.

  • “I was on Hinge for a little bit... but I’ve never really met anyone on, like, real dating apps that were, like, real.” (Kelly, 55:16)

• What She Wants in Love:
  She wants to be seen for who she is, not as a “show pony” or arm candy.

  • “I want someone that just genuinely loves Kelly Kaloren from Rockford, Illinois.” (Kelly, 53:40)
  • “I just want a partner in crime. I just want someone who wants to dream big like me. I am a dreamer.” (Kelly, 73:15)

Reflections on Being Misunderstood

• Owning Complexity:
  Kelly embraces confusion about her public persona.

  • “I think that people are just so confused why. And I think that is the most amazing thing ever.” (Kelly, 71:06)
  • “I don’t want them to know who I really am. I just want them to know that if I’m working for you in business, I am an absolute animal.” (Kelly, 71:23)

• On Old Drama with Bethenny Frankel:
  Kelly is unbothered and wishes her well, believing the era of tearing others down for the spotlight is over.

  • “There is so much room in this world for success. And I just feel like trying to break someone down to make you better is so dated.” (Kelly, 68:48)

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Memorable Quotes & Moments

• “Show me who you are. …But don’t tell me, because I can already smell that a mile away.” (Kelly, 04:24)
• “You want to see crazy and scary? Come into my real life and watch me make money to provide for my kids so they have the education that no one can take away from them.” (Kelly, 12:43)
• “If you need to get something done, get it done.” (Kelly, 39:16)
• “The world is so fucked up, and people need to protect other people. They need to really start doing that.” (Kelly, 49:57)
• “I just want someone that, like, just genuinely loves Kelly Kaloren from Rockford, Illinois.” (Kelly, 53:40)
• “There is so much room in this world for success…If you’re not a part of a community and you’re not creating a community, like, you should really put social down. I just, you know, talk to your cat.” (Kelly, 68:48)
• “Make as many mistakes as you can. Because if you don’t make mistakes, you’re never, ever gonna learn.” (Kelly, 74:28)

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Timestamps of Important Segments

• Kelly returns to reality TV; differences from Bravo: 01:06–04:42
• Jill Zarin drama & expectations for the new show: 06:55–09:31
• ‘Scary Island’ & the cost of being misunderstood: 10:32–12:59
• Modeling beginnings; Cindy Crawford story: 17:14–19:03
• Transition from modeling to writing, first blogging for Elle: 27:31–31:29
• Real estate origins and philosophy: 38:54–46:07
• Fashion rules and style advice: 35:46–36:49, 47:04–48:23
• Prenups, relationships, dating after 50: 49:39–55:16
• Reflections on reality TV, old drama, being “misunderstood”: 66:14–71:23
• Final bucket list and what’s next: 72:01–73:54

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Tone & Style

The conversation is warm, humorous, and direct—matching the candor and wit of both Rachel and Kelly. Kelly gives honest, sometimes blunt, answers and combines vulnerability about her struggles with an unapologetic embrace of her strengths and ambitions.

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Key Takeaway

“Misunderstood” is not a label Kelly shies away from—it’s a space she inhabits powerfully. From high fashion to reality TV to luxury real estate, Kelly’s story is about resilience, reinvention, and candidly speaking the truth behind the headlines. For aspiring women, anyone facing a major life reinvention, or those who’ve felt boxed in by others’ perceptions, this episode offers both inspiration and sage advice.

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Transcript

[DSW Announcer]

You know that thing where you get an amazing pair of shoes at a really great price and want to tell everyone about it?

[Kelly Killoren Bensimon]

Yeah.

[DSW Announcer]

So do we here at Designer Shoe Warehouse. We'll give you something to brag about, like the latest styles from brands you love or the trends everyone's obsessing over or shoes that make you feel like, well, you. So go ahead, show off a little. Buying shoes that get you at prices that get your budget. Head to your DSW store or dsw.com today. DSW. Let us surprise you.

[Rachel Yucate]

Kelly. I'm so happy to finally meet you and have you here on Misunderstood. Welcome to the show.

[Kelly Killoren Bensimon]

Thank you so much, Rachel. This is so cool. We should have met so many years

[Rachel Yucate]

ago, by the way. I know. And we were just talking about it. You finally have gone back to New York. You were here for a while. I wish I had met you when you were down in Palm Beach. But I'm so excited for your new show to be coming out. The trailer just dropped, and everybody's super excited about it. So I guess my first question would obviously be, what made you decide to come back to reality tv.

[Kelly Killoren Bensimon]

You know, first of all, it was E. And just everything that, you know, E represents and all the great, great brands that they've built, I just love them so much. So I was really excited to work with E. And also the producers just, like, the way that they think is just so modern and cool, and I just was like, they're just real storytellers, and I think it's really important to hear women's actual stories, and if you want to fight about it, you can. But, like, I really love stories.

[Rachel Yucate]

Right. Was there a difference in shooting for a Bravo show versus an E Show? I mean, it's the same cast, essentially. So did you feel like it was completely different this time?

[Kelly Killoren Bensimon]

Completely different.

[Rachel Yucate]

Wow.

[Kelly Killoren Bensimon]

Because of that point about really, you know, highlighting people's real stories and hearing their voices and, you know, their fears and their accomplishments. And, you know, I think sometimes we get like, you know, when I was on. When I was on Housewives, it was 2009, Rachel. It was like the Ice Age. Like.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

And it was just like, everyone was just like, I'm famous. I'm like, okay, great. Congratulations. Be famous all day. Like, everyone's just like, but I'm more famous than you. I'm like, that is so fantastic. Like, I'm like, that is Congratulations. I love that for you. I was like, who are these people?

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

And why do they want to be famous?

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

I just wanted to be on a show and talk to women and, you know, kind of see where women were in New York and, you know, see what was going on and take a leap of faith and try something totally different.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

I'd recently gotten divorced, and I had two young kids at the time. And, you know, I really needed to get out of the shell of this, you know, quiet world in New York and just explore and celebrate, you know, whatever was going to happen. I mean, I've been modeling since 14 years old. This is not like I didn't just start working yesterday. Yeah. And so I was just excited to do that. And honestly, I was just like. Literally, I was like, two scenes in, they're like, don't you know who I am? And I'm like, no idea. And I literally didn't know.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

I mean, like, you and I have met a lot of people.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

I mean, we meet people all the time, every single day. I mean, have you ever heard anyone be like, do you know who I am?

[Rachel Yucate]

Well, yes, I've heard people say that, and it's such a gross comment.

[Kelly Killoren Bensimon]

And no one ever says that to me.

[Rachel Yucate]

I'm like, no, but you know what I mean? But people say it thinking it's like, you know, that they are putting themselves on a pedestal, and it's so embarrassing, and they don't realize how embarrassing it is. We've met a ton of people. We're not that impressed by people. Do you know what I mean? And that's how I know the true people that I really love. Because when I'm impressed by somebody, they don't have to be famous. That's not. But there's something about them that impresses me, that says a lot to me because I've met so many people just like you.

[Kelly Killoren Bensimon]

I mean, I'm like a show me who you are kind of person. I'm like, don't tell me.

[Rachel Yucate]

Right, Totally.

[Kelly Killoren Bensimon]

Tell me who you are. Don't tell me how famous you are. Show me how great you are as a human. Show me how great you are as a mother. Show me how great you are as a business person. But don't tell me, because I can already smell that a mile away.

[Rachel Yucate]

Right, exactly. So how did you feel about Palm Beach? Had you spent a lot of time down here?

[Kelly Killoren Bensimon]

So I grew up going to Palm beach, so my dad was a lawyer, and a lot of his clients were in Palm beach, so we used to go there as children. And then I spent Covid there, which was so nice. And so, like, I know Palm beach so well. A lot of my friends live there. And it just was really, really easy. I mean, I was literally filming and then hanging out with my friends. And I loved it. I loved being down there. Riding every day, running every morning. It just was a really. It was great. It was really fun.

[Rachel Yucate]

Do you think that you'll ever come down here or get a place down here?

[Kelly Killoren Bensimon]

You know, I really. Rachel, I really like it down there.

[Rachel Yucate]

Yeah, it's so fun. I just moved three years ago from New York. And like, I know that you love New York. Like, you are a New Yorker through and through. Like inside of you, I can tell that about you. Your style, the way you are, the fast pace. Like, I think you really like that. But Palm beach has something that, like, once you're down here, it's so. What is the word? You feel kind of at peace. Do you know what I mean? And you feel seen, but also you can be part of that fast crowd and then you don't have to be, but you don't feel like you're missing out on anything. It's very peaceful.

[Kelly Killoren Bensimon]

Well, I love what I love about Florida so much. It's like, it seems like it's all these little hamlets. So it's like, you know, West Palm is one, Soso is another. You know, obviously the island is one. There's all sorts of different groups on the island. And then you have like Jupiter and all that. It's like, it's just so vast. And I have so many. Again, I have so many friends there. It's funny that you say that I'm such a New Yorker because I'm from Rockford, Illinois. And so the New York is where I work. You know, it's where I've done most of my. Is my work life. But I mean, I raised my kids as much as I could in the Hamptons. Like, I really need to touch grass. Like, I'm a. You know, I am not. And you know, I mean, I love to wear high heels, but I mean, it's either high heels or barefoot. Like, that's like I'm that wild juxtaposition.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

And so I love New York and I love everything it has to offer, but I'm not a fast paced kind of person. I do my work, I get it done, and then I go and hang out with my friends and touch grass. Right.

[Rachel Yucate]

I love that. I wanna hear more about that. So. But before we get to that, I wanna just ask you a few more questions. I know that this show got off to a rocky start because of what happened with Jill Zarin. So. And I listen, I'm friends with Jill. I love her. I was there when the whole thing happened, you know, so. But I saw all the press, obviously, as we all did. I mean, it was made fun of on Saturday Night Live. I mean, it became the biggest story of the moment after the Super Bow. So did you go into this feeling like, oh, God, this is a problem, or were you like, this is great press, or how did you feel going into it with the group? Because the group now changed?

[Kelly Killoren Bensimon]

No, I called her and I was like, what did you do? Yeah, I was like, what did you just do? She's like, I know, I know, I know, I know, I know. And I said, no, no, you don't know. What did you do? We could have had the best time, you know, talking about, like, what a great mother you are, doing all these amazing. How incredible you are, creative. And she, you, like, she's such a. She's such a beautiful human. And it's just like. I was just like, what did you do? Why did you do that? Like, why did you. She basically self sabotaged.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

I'm like, can't you just enjoy, like, your new life? Which is. Which is fantastic. And let me celebrate that with you. So. I was so disappointed.

[Rachel Yucate]

I know.

[Kelly Killoren Bensimon]

So disappointed.

[Rachel Yucate]

I know.

[Kelly Killoren Bensimon]

So I love her so much and I, you know, it's just like, you know, people just don't realize. And I think this is just like something in. In this world where, you know, everybody just thinks that just because there's a camera that followed them around at one point or another, that they just have the liberty to just chat up a storm. And it's like, know your audience.

[Rachel Yucate]

Very good point. Very good point. So is there anything we can expect? Because I know you probably can't say a lot about the show, but we've heard little to, you know, tidbits here and there. I know Dorinda was pissed about some people being late. There's all sorts of things that I heard from being on the island of how the filming went. But all in all, can you give us a little tidbit of what we should expect from this season?

[Kelly Killoren Bensimon]

I think that people are gonna be surprised. I think they're gonna be surprised. I think that there is so much going on, the dynamics are so strong. And one thing that I loved about the show is that there's always talking about 50 being a new 30 and 60 being the new 40. Well, it's true. And we're all just living our best lives and doing so many different things. And it is mass chaos.

[Rachel Yucate]

Wow.

[Kelly Killoren Bensimon]

But it is just like a beautiful dance of chaos and love. And chaos and love. It's amazing. It's amazing.

[Rachel Yucate]

So you're glad you did it?

[Kelly Killoren Bensimon]

Oh, 100%.

[Rachel Yucate]

Oh, good. I love hearing 100%.

[Kelly Killoren Bensimon]

So much more than Ultimate. I mean, so much more than Ultimate.

[Rachel Yucate]

Oh, yeah, tell me about that.

[Kelly Killoren Bensimon]

I mean, ultimate was only seven days. Yeah.

[Rachel Yucate]

Who was on the cast?

[Kelly Killoren Bensimon]

It was me, Dorinda Luann, Ramona Sonia, and Kristin Tapin.

[Rachel Yucate]

Oh, okay.

[Kelly Killoren Bensimon]

And I just feel like ultimate was just too short, and I felt like a lot of the women had watched or were watching Scary island while we were filming. I'm like, you guys, you do realize you're, like, giving me air time, don't you? I'm like, hello.

[DSW Announcer]

Oh, wow.

[Rachel Yucate]

Okay.

[Kelly Killoren Bensimon]

Can I say that? What are you doing? Right? But I think they were just trying to reenact that, and they were just like, well, she's not scary.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Yeah. You know, I'm like, I'm not. I'm really not. Like, you know, she's not unhinged. I'm like, I'm not unhinged. Well, I'm a badass, right? I'm. I am a mama bear. I will protect you. I will make sure you're safe. But I'm not unhinged, and I'm definitely not crazy.

[Rachel Yucate]

Do you feel like.

[Kelly Killoren Bensimon]

I wish I were, though, because it would give me a vibe. Rachel.

[Rachel Yucate]

Yeah, no, I know what you mean.

[Kelly Killoren Bensimon]

I could be sexy. I could be cool.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

My dark makeup.

[Rachel Yucate]

Right, right. But do you think people be like, how are you?

[Kelly Killoren Bensimon]

I'd be like, I don't know. I don't know.

[Rachel Yucate]

Right, right.

[Kelly Killoren Bensimon]

But do you feel like it could be, like, alluring?

[Rachel Yucate]

People froze you in one moment in time in Housewives for a little bit.

[Kelly Killoren Bensimon]

They did.

[Rachel Yucate]

But did you feel misunderstood about it? Were you upset about it? Or were you like, okay, this got me a lot of airtime. Whatever.

[Kelly Killoren Bensimon]

Well, you know, it was hard because at the time, I was working for three magazines at the time, raising my kids, and no one wanted to hear about my work life. No one wanted to hear that I was recently divorced. No one wanted to hear anything about that. They just wanted me to be a socialite and an it girl and for the women to be upset. So I'm like, okay, fine, I get that.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

But then when I. Then I realized that they had a show to another show to produce and that I was going to be the scapegoat to make that other show better, I was like, you guys like, don't. You don't. Can't you produce something better than this? Like, I'm going to be your scapegoat.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

You do realize that people do know who I am and that they do know what I've done. And the way that you're trying to make me look doesn't resonate.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

And then you put me on another season, and I'm having the time of my life. How does that work? The math doesn't math.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

So I think it was fun and spirited and congratulations for those big memes. I'm up here, you're down there, and scary island. Boo. So congratulations on that. But at the end of the day, like, they could have celebrated or explored a woman in her early 40s who was going through this very, very, very difficult time of trying to reinvent herself again after getting divorced. And really, like, how do people. How do women after you get divorced actually make money?

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

Like, that would have been a story you wanted to see. You didn't see the real story. You want to see crazy and scary come into my real life and watch me make money to provide for my kids so they have the education that no one can take away from them. And that was frightening. Yeah.

[Rachel Yucate]

No, that's such a good point.

[Kelly Killoren Bensimon]

I'm like, you guys didn't even. You're like. You're so busy trying to, like, make gummy bears a thing that you missed the real story, which was the heartbreak and the fear that I had during that time and later on. Yeah, like, you missed the boat. You didn't know what you were doing.

[Rachel Yucate]

I mean, I totally agree, and I hear what you're saying. I feel like production way back when, like, you were ahead of your time, almost, like, in terms of. That wouldn't have been a storyline. Cause it was almost like, too traumatic for people that would be watching it because so many people were going through it, but no one wanted to talk about it. Now I feel like no one. Yeah. I feel like now to reinvent yourself is such a big deal. Everyone's trying to do it, and we all want the secret code on how to do it. Right. Thank God we're. I'm 51, you know? Like, I feel like. Thank God we've been through it because now we know how to do it. If, God forbid, anything happened in your life, in my life, like, we know how to climb out of that hole. So I really, you know, appreciate those times that I've been at the other end of the pendulum of, like, being in the worst time. Ever. Because to that same extent, I can be in the best time ever. If you don't experience it, you don't know how to get out of it. So.

[Kelly Killoren Bensimon]

We should write a book together.

[Rachel Yucate]

I know. We should.

[Kelly Killoren Bensimon]

We should. Rachel. Rachel Kelly. Right? Yeah. I mean, that's the truth. And I think that people were scared at the time. I think that talking about divorce, talking about reinventing yourself was something that was very. I mean, like, that's what I did as an. As an editor is I was constantly looking to the past to see how that was gonna forecast the future.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

So that was always something that I always. How I always think. And television isn't like that. Television is, like, right now. Well, they missed the boat. Like, because they missed. They missed. I mean, I have amazing children.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Like, unbelievable children that I raised on my own. And it just. It's like. It. You know, it just. It's a disservice. And. But anyway, they tried to make me crazy, but not crazy enough because I don't get to wear the dark sunglasses and, you know, coal eyeshadow is not my vibe. So this is all, like, not good, right?

[Rachel Yucate]

Well, it's funny because you. You're stuck in the middle. You're way too pretty to be that, like, edgy, you know, person. I feel like. So it's like, people don't know if to hate you or love. I think people are probably threatened by you because of the way you look. And so they'll grab onto anything, whether it's the crazy story because it makes you, to them, less threatening because they're so threatened. I mean, that's. To me, as an outsider, what it looked like, you know.

[Kelly Killoren Bensimon]

Well, it was interesting that you. It's interesting you say that because, like, on Ultimate, I, you know, so I sell real estate. I'm licensed in three states, and I was doing this major deal with Josh Rubin in Encinitas, California. And so I'm sitting, you know, they're. They're off chatting about whatever, and I'm sitting in the. In the. In my. Bathing in a bikini, and I. My sunglasses, and I'm like, what are you doing over there? I'm like, mama's got to make some money. And one of the girls goes. And I'm just like, do you even know what it takes to make money? Do you even know how to make money? Like, real money? Like, real cash in the bank money for yourself? I've been doing it all my life, so I know how to do it. But, like, I'm not sitting here. You Know, telling everyone how to do it. Like, I'm not like, here's the ABCs on how to make money. But if I need to make money and I'm filming, you better believe that I will excuse myself and make some money, because that's for my kids, right?

[Rachel Yucate]

100%. All right, well, let's talk about that. So let's go back. You said you were from Illinois, which I didn't know. Okay, so what did you want to be when you grew up, when you were little?

[Kelly Killoren Bensimon]

I don't know. I started modeling when I was so young.

[Rachel Yucate]

Did you feel like that was what you wanted to do?

[Kelly Killoren Bensimon]

I don't. I know. I wanted to be a doctor. I wanted to be a surgeon.

[Rachel Yucate]

Oh, you guys.

[Kelly Killoren Bensimon]

Like, I really go with my hands. Like, I don't know. I'm just. And that sounds really creepy, Rachel. I'm so good with the hands.

[Rachel Yucate]

Did you play that little game when you were a little operation? Do you remember that game?

[Kelly Killoren Bensimon]

Yes. But I used to do, like, all creepy things, like dissect animals from the creek and, like, all sorts of weird stuff. I was awful. I'd be like, look what I brought to school. I'd be like, where'd you get that? I'm like, the creep. They're like, ew. Oh, my God.

[Rachel Yucate]

Hysterical. So how were you? How did you become a model?

[Kelly Killoren Bensimon]

So my dad told you was a lawyer. And one of his clients we were in, I was picking him up from a club in Chicago, and one of his clients was like, that's your daughter? And my dad's like, yeah. And he's like, she should be a model. My dad's like, no, thanks.

[Rachel Yucate]

How old were you?

[Kelly Killoren Bensimon]

And then I was 14. And then I entered this contest, and Cindy Crawford won, and I was the runner up.

[Rachel Yucate]

Stop.

[DSW Announcer]

You know that thing where you get an amazing pair of shoes at a really great price and want to tell everyone about it?

[Kelly Killoren Bensimon]

Yeah. So do we.

[DSW Announcer]

Here at Designer Shoe Warehouse. We'll give you something to brag about. Like the latest styles from brands you love or the trends everyone's obsessing over or shoes that make you feel like, well, you. So go ahead, show off a little. Find shoes that get you and prices that get your budget. Head to your DSW store or dsw.com today. DSW. Let us surprise you.

[Rachel Yucate]

Wow.

[Kelly Killoren Bensimon]

Yeah. I mean, she's older than I am, but I was like. I was like, God, she's so pretty. And I had literally. Rachel, remember, like, I know you're almost 10 years younger than me, but back then There was, like, this. Everyone was, like, cutting their hair bi level.

[DSW Announcer]

Oh.

[Kelly Killoren Bensimon]

So right before the contest, I had hair like this. Yeah. And I went, whoop. Literally days before. Oh, my God.

[Rachel Yucate]

Well, obviously, it must've looked great if you came in second.

[Kelly Killoren Bensimon]

I thought it was so cool.

[Rachel Yucate]

Oh, my gosh. All right.

[Kelly Killoren Bensimon]

We didn't have extensions back then.

[Rachel Yucate]

Right. God, I don't know how anyone survived. I mean, Jesus.

[Kelly Killoren Bensimon]

All the photographers were like, put your hand like this. So there's all these photos of me. Oh, no.

[Rachel Yucate]

I love it. Okay, so, well, how was Cindy Crawford? Was she nice?

[Kelly Killoren Bensimon]

Amazing? Brilliant? Beautiful? Kind? Fantastic.

[Rachel Yucate]

Beautiful. I love hearing that.

[Kelly Killoren Bensimon]

Yeah.

[Rachel Yucate]

So then you win runner up. And then how does this blow into a career for you?

[Kelly Killoren Bensimon]

Then they just are like, basically, like, you have to come to New York. And so I moved to New. I mean, I went. I didn't move. I went to New York and Stephanie Seymour and I lived together, and I started. You know, I worked for Vogue the next day.

[Rachel Yucate]

Wait, was she famous back then, or she just.

[Kelly Killoren Bensimon]

She was. Yeah.

[Rachel Yucate]

Okay, so everyone.

[Kelly Killoren Bensimon]

She was already starting to be famous. She was 15. We were all 15.

[Rachel Yucate]

Oh, my God.

[Kelly Killoren Bensimon]

Yeah.

[Rachel Yucate]

I didn't realize that all of you guys were that young. Jesus.

[Kelly Killoren Bensimon]

Yes.

[Rachel Yucate]

Wow. Okay.

[Kelly Killoren Bensimon]

We lived next door to John Casablancas wife. And. Yeah.

[Rachel Yucate]

Wow. You know, I've done some interviews with some interesting people that were in that industry, and they absolutely hated it and regret it and have all these bad things to say. But when you're talking about it, you have a smile on your face. Was it good for you?

[Kelly Killoren Bensimon]

Well, because, you know, I'm from Illinois, so I would go and have fun. And all my friends from my sister. My sister went to. My sister went to college at Trinity and Hartford, so all of her friends were in New York, and they're, like, two years older than me, so I was hanging out with them. And then I was, like, running, you know, running around, going to these castings, meeting all these people that were so bizarre.

[Rachel Yucate]

Right?

[Kelly Killoren Bensimon]

And then I was going home and, like, playing tennis. Like, I was like, this is wild. This is so fun.

[Rachel Yucate]

I mean, and then.

[Kelly Killoren Bensimon]

And then I ended up going to Trinity as well. And then we really, really modeling a lot, and it was very, very stressful, just being, like, back and forth. But I have to be honest with you, like, I had a really. I had a really, really good experience with the modeling industry. I also have great parents who, you know, I'm like, mom and dad. I'm going to wherever my dad would be, like, okay, we're coming. And they Would hang out and they'd be like, okay, go have a tennis lesson. And then I would go off and you know, do whatever. The only bad thing that I can say is about, you know, my eating issues that were just awful.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

I mean, I had to come back. I had to come back from Europe when I was 19 just because it was just so bad.

[Rachel Yucate]

Oh, wow. Okay. Did you end up watching the documentary that came out recently about Tyra Banks and that whole thing?

[Kelly Killoren Bensimon]

I haven't seen the whole documentary, but I know Tyra from, you know, forever.

[Rachel Yucate]

Right. And I had Nigel on. Did you ever work with Nigel, the photographer worker?

[Kelly Killoren Bensimon]

Yeah, I know him as well.

[Rachel Yucate]

Yeah. So I had him on a couple weeks ago and he was talking about it and he didn't feel as terribly about Tyra that most people talked about her in the documentary. What did you think about that whole process? Maybe not just about her, but that kind of reality show was such a big reality show and really changed lives for these young girls. Mostly. It sounds like, in a terrible way.

[Kelly Killoren Bensimon]

I mean, I think what's different about my experiences versus being on a reality show is when you're on a reality show, you're under a microscope.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

I mean, I was going to castings. Nobody knew if I got the job or not. Like, nobody really knew. But on a reality show there's a narrative and there is an arc. So you have to, like, something bad has to happen. There has to be a reinvention. There has, you know, there's all these different things. And when you're really modeling, it doesn't really happen like that. You can be a one hit wonder like that or you can be a slow and steady, like, it just, it's not the same situation. I mean, we don't have that. You know, after being a model and then being an editor, you know, I started L Accessories, so I would hire all these models. You know, I, I, it just doesn't, it really is not like that. Yeah, I mean, I was a real, I was a big model and so was Tyra. And, you know, yeah, the photographers were skeevy. But like, I'm from Rockford, Illinois. Like, if you can't play tennis or golf, I don't want to be around you. I don't want to be around some guy wearing black tight jeans. Like, what?

[Rachel Yucate]

Right, right, right. I love that.

[Kelly Killoren Bensimon]

Like that. Do you have any pants with like whales on them or like, you know, something like that? Question mark.

[DSW Announcer]

Oh, my God.

[Rachel Yucate]

That's my take.

[Kelly Killoren Bensimon]

I was just like, I don't know who you are. I'm like, we are not the same.

[Rachel Yucate]

So you were able to turn it off. You were able to be in the moment, be a model, and then you were able to go home, be with your family, appreciate life, and be away from that.

[Kelly Killoren Bensimon]

Yeah. And, you know, but Rachel, I mean. And I'm a unicorn. Like, that is not normal. A lot of these girls that start modeling come from absolutely nowhere.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Come from broken homes, and the modeling industry is their hug. And, you know, I have friends who have been, you know, who I've met, you have, you know, known through that process. And it's also a very, very. People think it's super insular, and it's like the 90s supermodel crowd. It is not that at all. It's wildly transient. You meet some. Like, you and I would be on a job together for two weeks. We'd get along, we'd be best friends, and I would never see you again. And that was how it was. And so it was just. It was just, you know, the. The insecurity that is bred from that environment is just wild. And I also think that's one reason why I do well on reality TV is because even though I have insecurities about, you know, being able to provide for my kids and being the best mom and doing things, you know, being a good role model, those are my. Those are my core insecurities. I have a lot of confidence because I've done a lot of things, and I have experienced a lot of things. So it's like this weird juxtaposition, and a lot of these girls are just wildly insecure, and one guy takes advantage of them or one agent takes advantage of them, or, you know, whatever. You know, whatever it is that happens. And, you know, it's not easy for a lot of people.

[Rachel Yucate]

It also sounds like you learn to be good about not getting attached and being able to move from, you know, job to job, person to person, befriend the people in the moment, and then move to the next thing and not get so attached that you're missing and longing for something else, which I personally think is a skill. That's something that I learned to do just from, like, being sent to boarding school and never living at home past the age of 12 and having to figure it out, you know, and you grow up faster, but you also really can count on yourself. You learn to count on yourself, and it might take you a while to get that, but other people go in the other direction. Do you know what I mean? And get really attached to things and almost lose themselves and their vision for their career because they just want to be with the person that makes them feel loved or hugged, as you like to say, you know.

[Kelly Killoren Bensimon]

Yeah, I mean, I agree with that. I think that's also, I think it's a double edged sword. I think on the one hand it's great to be able to have that skill set where you can navigate different worlds. On the other hand, it makes, like work, you know, filming housewives difficult because, you know, we want the viewer. And me as a person, like, I want to make, I want to create connecting connections, real connections. And so, you know, it's sometimes hard for me because I'm just like, we film and then we're gone. And like, I'm just like, oh, okay, we're. I'm back to being 19 again, where we were in Mauritius for 12 days and then I don't see you ever again. And then, you know.

[Rachel Yucate]

Yeah, I can understand that. Wait, so now talk about.

[Kelly Killoren Bensimon]

It's just like hard because you don't have real, you don't have real friends.

[Rachel Yucate]

Yeah, no, I totally can see that. Yeah.

[Kelly Killoren Bensimon]

And like, your friends are from your world, you know, and for your, from your kids. And that's, and that's really, like, my friends are from my kids and from horses. Like, those are my true core friends. I mean, I would wish I could say that, you know, I, you know, I see Jill Zarin all the time, or I see this person or I see that person all the time, but I just don't. And it's hard. It's hard.

[Rachel Yucate]

But it is nice to know that you have people that have been through different things with you so you can call on Jill or people you've kind of trauma bonded, so to speak, because, you know, they've been through those things that not a lot of people have. I think that's good that you have that.

[Kelly Killoren Bensimon]

Yes, 100%.

[Rachel Yucate]

So now talk about.

[Kelly Killoren Bensimon]

I mean, I think that trauma bonding is like a real thing. Yeah. And yeah, I mean, it really, really there is like that baseline of like, okay, you were, you were in that. I was in that. We can be friends.

[Rachel Yucate]

Yeah. I want to hear more about how you got into like the second part of your career because you were a model and then all of a sudden you're working with Elle. Right. Is that what came next? How did, how did that happen?

[Kelly Killoren Bensimon]

So my, one of my, one of my professors at Columbia was like, your mom. He's like most people in this business and you know, this. There they were like, you're either one or the other. Yeah, you're either a model or you're an academic. And my professor was like, I'm a poet. He's like, let's have you start writing. And a woman by the name of Jean Guthrie June started this, the first blog called Elle.com. and she, you know, I was modeling for Elle and everything and she's just like, you know, we would, I would go and meet her all the time. And she was like, you're just, you know, you have a really interesting perspective on things. Would you ever consider writing? And I was like, it's funny that you say that because I'm at Columbia and I'm a writer and I would love to do something for you. And so I became one of the literally not self, I guess, self proclaimed first bloggers for ELLE.com and she really nurtured me and taught me how to write well. And also in like magazine speak, like, you know, writers can write novels, but writing for a magazine is very short, like fun, charming, engaging. It's a totally different kind of way of writing. And she taught me how to do that. And you know, I love her for it.

[Rachel Yucate]

Wait, does anyone like, stop you and say, wait a minute, you went to Trinity? You went to Columbia? Like, yeah.

[Kelly Killoren Bensimon]

What? At my mba?

[Rachel Yucate]

Yeah, like, hello, License in three states.

[Kelly Killoren Bensimon]

Yeah, I know, but I'm like, crazy and stupid. Rachel, don't blow my cover. Come on.

[Rachel Yucate]

But I love that about you people. This is like, this is super hard. These are super hard schools to get into, not the podcast. Wait, were people like, you're too pretty to be here? Like, what?

[Kelly Killoren Bensimon]

I don't know, were they saying that about you?

[Rachel Yucate]

No, stop. I didn't go to those colleges and I'm definitely not a model, so.

[Kelly Killoren Bensimon]

You're amazing. Thank you. And you've been through a lot.

[Rachel Yucate]

Thank you. All right, so I wanna go back to.

[Kelly Killoren Bensimon]

All right, wait, what's so funny?

[Rachel Yucate]

Hold on. What was your favorite job that you had? I mean, forget real estate. Cause I know you're in that and you're having a moment and this is great, but like leading up to this and changing all these different things, like, and you worked for. Didn't you like help write for Aslene or something?

[Kelly Killoren Bensimon]

Oh, yeah, I've written seven books.

[Rachel Yucate]

I mean, hello. How did you do that? I don't get it. Is this from your education or it's just stuff you got passionate about and met the right people at the right time?

[Kelly Killoren Bensimon]

Well, I mean, both. So I was at Columbia and it's like they Just teach you this formula of like, just. This is what you do. You just put it in the formula and just spits it right out and just keep doing it over and over and over and over again. I mean, there's something to be said about higher education. I mean, it is not. It is not for the faint heart. Yeah.

[Rachel Yucate]

And do they give you the contacts, like, because you went there, do you think it opened more doors?

[Kelly Killoren Bensimon]

No, I just knew how to plug it into the formula.

[Rachel Yucate]

Got it. Okay.

[Kelly Killoren Bensimon]

Like, if you ask me to do something, I'll be like, rachel, I got it. No problem.

[Rachel Yucate]

Right, right, right.

[Kelly Killoren Bensimon]

And it's not that I'm so great. I just know the formula. Yeah. I mean, it's not, you know, it's just like. So anyway, as ellene where they were coming to the US And I had. I wanted to write for. I got an opportunity to write for Hamptons magazine. And the one of the editors was a friend of mine and she was like, I'm just gonna give you everything. So I was responsible for like 80% of this magazine. In my early 20s, I'm like, what? But I would call my friend. I would, like, be like, working with Calvin. I'd be like, calvin, can you give me a quote on like, summer means to you? And I was just like writing, asking all my friends and then writing them down and putting them in the magazine. Everyone's like, where'd you get that quote? I was like, oh, I, you know, just was with that person. So I asked them the question, then I just wrote it down and then I wrote a column. Cause I wanted to do something that would. It's one thing to be to color the pages and make them pretty, but it's another thing to create where the money is. Like, where is the money, Rachel? That's all. I like, I'm like, I'm a money person. So I'm like, okay, this is a great magazine, but we need to make more money. And so my publisher was like, okay, what do you want to do? And I was like, I'm going to create this magazine called in the spirit of. And I'm going to bring in everything from New York and everything from the Hamptons. And I'm going to put it together and I'm going to like, spit it out. It's going to be called in the spirit of it, and it's going to be a list. And he's like, kelly, what? It became this wildly well known article. And then I wrote another article which was the opposite of the list, which was like, 25 of the best of the best. It was the one thing. The one thing that no one else could have. So I had these two columns, and I was in charge of all the beauty and the fashion, which is, you know, which I. What I knew. But these columns really thrust me into, like, superstardom, because in the spirit of When Aslan came, they were like, well, you've already been doing this. You know so much about the area. You've been interviewing the landscaper, the pharmacist, the old guard Bonicker, the socialite, the nail color, you know, the. The. This person, the equestrian, all these different people. So I had been literally meeting everybody and interviewing them. So he's like, write a book. And so that was the. My first book called in the Spirit of the Hamptons. So it was really, really fun and just was so nice to celebrate an area that I love so much. And for people to really see the. You've been to the Hamptons many times, but just to see how the Hamptons. The Hamptons is. There's so many different Hamptons. Do you know what I mean? Yeah. And so it was just really. It was a great, great book. And then I was asked by Anna Wintour to write American Style, and that really, like, threw me into a whole different stratosphere.

[Rachel Yucate]

Wow.

[Kelly Killoren Bensimon]

I wrote it for the Met at the beginning. This is like the genesis of Costume Institute. When Anna Wintour was at Vogue and she had this group of eight women, you had to be invited. And it wasn't because you were the best designer or whomever. It was like, you were just a very curious human that loved fashion. And so they invited. I was one of the youngest, one of the eight. And I was like, I want to write this book. And she gave me all the archives. And then Harper's Bazaar gave me all their archives for free.

[Rachel Yucate]

Wow.

[Kelly Killoren Bensimon]

And I wrote this book called American Style, which is. Instead of doing this narration of, like, this is where we started and this is who we are. And this is your history lesson with Kelly. I, like, put, like, Madonna next to, like, you know, a 1970s designer. And I, like. I juxtaposed all these different images, and the images are so wildly fantastic. And then Bergdorf Goodman took all the photos and wrapped the store. And then I got Elle.

[Rachel Yucate]

Wow. That is insane. That is insane. Wait a minute. Speaking of Anna Wintour, do you have a feeling about all the conversation pieces around what's going on with the Met gala and the fact that people don't want to go, it's too expensive, and the whole Jeff Bezos and Lauren Bezos situation.

[Kelly Killoren Bensimon]

I just think that she's so fantastic, and she's just. She's such a pioneer in the real, you know, nature of the word. She is such a game changer. She doesn't care what you think. She just wants you to be successful. And that is so unique. You know, so many people are so concerned and consumed by what other people think, and she's just like, you're not doing it right. Do it this way. And then all of a sudden, you're like, oh, yeah, she's just a mastermind. She really is. And she was so clever to make the Costume Institute something that people could dream about. So whether you like it or not, you're dreaming when you watch. And I think that's something that's so incredible.

[Rachel Yucate]

Do you think the style has gotten weird? Like, what did you think of this style? Last week's, you know, Met Gala?

[Kelly Killoren Bensimon]

I mean, I think that, you know, it was based on the best of the best dresses that the designers could make. And I think that designers are just having a moment of creativity. And, you know, whether you like it or not, you're watching it.

[Rachel Yucate]

Yeah, that's a good point.

[Kelly Killoren Bensimon]

So it's making an impact.

[Rachel Yucate]

Yeah. Where do you get your fashion ideas from? Like, when somebody's looking down your Instagram or they see all the stuff that you've done, you're clear, clearly fashionable in. On an everyday sense, but you have a sense of style in general. Where do you think you got that from?

[Kelly Killoren Bensimon]

I got that from being a model.

[Rachel Yucate]

You did?

[Kelly Killoren Bensimon]

100%. Because they would say, like, wear capris with flats. Wear a turtleneck with capris with flats. Wear a black mini skirt and a black turtleneck and black tights and heels. Don't wear too high of a shoe if you're gonna wear a high shoe. Only wear bare legs. Like, it's like, all. There's, like, rules. Wow, you like that? So when people see me, they're like, oh, that looks good. I'm like, because I follow the rules, right?

[Rachel Yucate]

Oh, my God, that's so interesting. Have you written book on that?

[Kelly Killoren Bensimon]

They're just rules.

[Rachel Yucate]

Oh, see, that's.

[Kelly Killoren Bensimon]

So I wrote a book called I can make you hot in 2011, which was healthy options today. Everyone's like, you can make me hot. I was like, damn straight I can.

[Rachel Yucate]

Yeah. Oh, my God.

[Kelly Killoren Bensimon]

I mean, I can make you healthy. I don't know if I can make you, like, smoking hot, but I can make you hot.

[Rachel Yucate]

Right?

[Kelly Killoren Bensimon]

And that was just basically, like. It was instead of doing. Writing another one of these books that was, you know, how fabulous and amazing I am. It was Monday through Sunday.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

So this is like your Monday through Sunday. What you're going to do, how you're going to do it. Your, you know, food narrative, your, you know, your clothing uniform. And then Sunday is your fun day, and you're going to enjoy your life. And it was kind of like the tricks from my fashion and my fashion days and then just like, my mom's recipe. So it was a really fun book to write.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

But it was also something that really forecasted body shaming. And I was just like, there is no way that that anyone on my watch is gonna be shamed about their weight.

[Rachel Yucate]

Yeah. Oh, I love that. Did you notice how the world completely went nuts over the Carolyn Bessette and John Kennedy Jr. Documentary or docu series? And now everybody is trying to dress like her.

[Kelly Killoren Bensimon]

He was in my. Well, he was in office above me, so I would see him all the time.

[Rachel Yucate]

Oh, no way.

[Kelly Killoren Bensimon]

And, like. Cause we were an Elle. We were in a shed. So it'd be like, John's coming in, and he would, like, zip in on his bike. And she's like, a very nice person and.

[Rachel Yucate]

Right, right. For sure. Did you ever meet her?

[Kelly Killoren Bensimon]

Yes. Yeah. Because she worked with Calvin, right? Yeah. She was just like, you know, girl from Connecticut, easy. You know, just like, you know, she was a VIP dresser. So it's just like, made people feel good, which is not easy. You know what I mean? Like, at the time, you have to remember, the VIPs were like, Meryl Streep and, you know, Annette Benning and, you know, it was like, iconic women.

[Rachel Yucate]

And they're just like real VIPs, not, like influencers. Windsor VIPs. Yeah, yeah.

[Kelly Killoren Bensimon]

They're not like, you know, whoever it is today, they're like these major, major, major stars or actors.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

And they're just like, I'm not wearing that. Whatever that is.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

And I'm like, I wouldn't wear it either.

[Rachel Yucate]

Right, right, right. Exactly. Okay, now, how did you get into real estate? Because again, it's like, you. I understand the changes in things up until this point. What made you pick Real Estate Date?

[Kelly Killoren Bensimon]

Okay, so that's like, everything has from from now on. Before, it was like these little pivots. Micro pivots. Right. But then it was like this major, major pivot. My mother fell ill and I had to sell my family's homes. And so I got my license, like, literally immediately. I mean, to everyone's like, it takes all this time. I was like, well, if you need to get something done, get it done.

[Rachel Yucate]

And was the intention just to help your family sell this, or were you like, oh, I'm gonna make a career this.

[Kelly Killoren Bensimon]

Oh, no, no, no. I was. I had no interest in real estate. Like, I was like, whatever. I mean, I built a home. I bought and sold apartments before. Like, real estate was like, the land of the bad shoes. I was like, no, thank you. Like, this is not my vibe. Like, no, thank you. And so I got my license, and I sold one of my family's properties. And then Covid hit and that. And I was in Florida, and one of my clients was like, I need an apartment for my son. Like, 30 million downtown. So I'm like, okay. So I texted a couple of my friends, and I was like, you guys, I need something in New York. And he's like. One of my friends is like, oh, what about mine? And I said, what about yours? He's like, I just. Kelly, I just redid my apartment. I'm like, I don't know everything about everything. Like, you know. And so he's like, go and see mine when you come back. So I came back to New York and went to go see it. It. My. The client came, and they're like, okay, I'll take it. And I was like, okay. And they're like, how much? I'm like, you tell me. And they're like, no, no, you tell me. I'm like, no, you tell me. So it's just like, back and forth, which is not real estate. It's always like, it's 49.95.

[Rachel Yucate]

I'm like, oh, God, yuck.

[Kelly Killoren Bensimon]

Stop talking like that.

[DSW Announcer]

You know that thing where you get an amazing pair of shoes at a really great price and want to tell everyone about it?

[Kelly Killoren Bensimon]

Yeah. So do we.

[DSW Announcer]

Here at Designer Shoe Warehouse, we'll give you something to brag about. Like the latest styles from brands you love or the trends everyone's obsessing over, or shoes that make you feel like, well, you. So go ahead, show off a little. Find shoes that get you and prices that get your budget. Head to your DSW store or dsw.com today. DSW. Let us surprise you.

[Kelly Killoren Bensimon]

And so I just was like, didn't respond. Totally ghosted this guy.

[Rachel Yucate]

Wow.

[Kelly Killoren Bensimon]

And he's like, kelly. I'm like, yes. He's like, okay, how about 42? I was like, okay, I'll take it. So I call my client. I'm like, I just got you 42. He goes, okay. He Goes. You did. I was like, yeah, I just got you $12 million more.

[Rachel Yucate]

Right? Right.

[Kelly Killoren Bensimon]

12.

[Rachel Yucate]

Timeout, timeout. $12 million more than the ask. So. But up until this point, had you been doing little deals here and there besides your family? Like, did you feel like you were involved in real estate and kind of.

[Kelly Killoren Bensimon]

But I. You know, kind. I mean, a little bit. Like, I was doing, like, some influencing. I would go and see. Cause I'm, like, curious. So I would go and, like, I went to all the new developments, and I would take video content of everything. And so I became, like, the new development queen. Because people are like, no one. No one. No one goes to see these places. You know, I was like, no one even, like, knows anything about what's available out there. And I was just. Let me go see. Let me see their swimming pool. Let me go see their golf simulators, yada, yada, yada, because this is something new. It was like, the new bright and shiny thing, and I wanted to be a part. I wanted to see it. That's my nature is to, like, be educated. And so, yeah, that happened.

[Rachel Yucate]

Wait, was it hard for you to pass the test? I feel like so many people are like, oh, I can't do it. I have to hire someone to pass the test. Clearly you're very smart, but did you find it hard?

[Kelly Killoren Bensimon]

Okay, New York. I passed immediately because I had to. Florida, I think it took me like, five times, six times.

[Rachel Yucate]

Really?

[Kelly Killoren Bensimon]

I mean, I was just like, oh, can I live again? California, I had no choice. Like, you have to pass. I had. Because I literally flew in. I had to pass. And I had this really, really gorgeous Harry Geisner home in Malibu, and I literally needed to get my name. I need to get my license, like, like, right now. And so that was, like, mandatory.

[Rachel Yucate]

So do you. Do you think that this was a case of you had developed the skills where you knew how to monetize your list of names in your phone and it. And it worked out well for you? I feel like during COVID so many people were like, okay, I'm gonna be a real estate agent. Or obviously, as you know, you come down to Florida, every woman says she's a real estate agent. I mean, she doesn't have a job, and she has a rich boyfriend. So, like, how did you turn it into a real career? Because this was a big different move for you.

[Kelly Killoren Bensimon]

Because, you know, I sell. I sell to the masters of the universe, and I sell the most illustrious properties in the world, right? Like, I sell, like, Wallace Cunningham, Harry Geisner. I represent the police building. Like, I sell.

[Rachel Yucate]

I love that building.

[Kelly Killoren Bensimon]

I sell properties that I am so obsessed with. So when you walk through. Rachel, if you walk through the police building with me, you'd be like, I'm buying this right now.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Like, because I. Because my enthusiasm is so infectious, and

[Rachel Yucate]

your knowledge of what you're selling is probably.

[Kelly Killoren Bensimon]

I know where I am, and I know the environment, and, you know, it's not. I'm not like, I don't. It's. It's like everyone's like, the. Out of the deal. I'm like, if you stop talking like that, you will actually make money. And. And it's like the whole mining of the database. No, do not mind your database. Know your business. Know your business, and then people will come to you. So I don't sell real estate. I sell lifestyle because my clients are like. And, you know, it's funny because you said, like, you're pretty, and I. That's such a nice compliment, but women love me. They're like, where'd you get your jacket? Where do you get your hair done? Who does your nails? Like, who does your Botox? Like, what shoes are those? Like, they just want all the stuff that I have.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Where do you live? In the Hamptons. Where do you like to go to eat? And they just want all the intel. So I am selling my lifestyle to the women, and then the men are like, my wife's so happy. They get to. Kelly's, giving me their new best friend. We're moving in.

[Rachel Yucate]

Right. So do you think it helped you, though, from being on TV and people knowing you? Do you think you got more phone calls than the average person because they wanted to meet you, or you think it didn't have anything to do with it?

[Kelly Killoren Bensimon]

You know, it's bittersweet because on the one hand, I meet a lot of people from that, but on the other hand, people just want to be. They want to, like, housewife. I'm like, this is not a verb. I actually am making money right now, and that's part of my life. That's just one of the hats that I wear. But my love of all loves is. I love beautiful things. I'm the ultimate hedonist. I love beautiful things, and I will find the most beautiful whatever you want. Not, I will find you the best of the best. Like, I love that everyone else can be like, you know, oh, I sold, you know. You know, $500,000. Whatever. I'm like, that is so great for you, and you should continue to doing that. That Is not my business. My business is ultra high net worth. The best of the best. I love it. Just love it.

[Rachel Yucate]

And do you do, like, interior decorating with it too? I mean, you seem to have such a little knack for that. I saw what you were doing in Florida.

[Kelly Killoren Bensimon]

I mean, I don't. I mean, I've learned a lot from my life, and so I just plug and play. But I wouldn't say I'm an interior decker. I know the best of the best. So if you are looking for something, whatever it is, that's the other thing too, is I'm like, such a vessel for the best of the best. So if it's like, you're looking for an iconic shoe, I know that person. If you're looking for an iconic home, I know that person. If you're looking for an iconic yacht, I know that person. If you want the. The coolest new car, I know that person. Like, I just know a lot of people. We're very similar in that way where we just know the best of the best and they like working with us and it's easy.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Wait, there's no drama and there's no sensationalism and there's no craziness. Yeah.

[Rachel Yucate]

You brought up before something that when I was looking at your Instagram, I was like, I need to fucking ask her this. You always wear the best, best simple bathing suits. What are they?

[Kelly Killoren Bensimon]

Melissa Otaposh.

[Rachel Yucate]

She's the best. Yeah. Okay. All right. Good to know. Because you always have the tie side, the little triangle, and it looks amazing on you. And I can never find these. So now you know what the thing

[Kelly Killoren Bensimon]

is, too, is, like, that's not like another thing. Like, when you're looking for a bathing suit, like, you have to wear the right bathing suit.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

You can't just walk in and put it. Put a bikini on. How many women do you see walking around the bikini? And I wrote the bikini book, so I know a lot about bathing suits. You like, I'll look on the beach and I'm just like, why is that. Why is that triangle so big on that girl? Like, she needs a smaller size. I love it. I'm like, why doesn't she, you know, pull that up so we can show. See more of that butt.

[Rachel Yucate]

See, this is business for you.

[Kelly Killoren Bensimon]

I feel, I think, I don't think, like, oh, my God, she's hotter than me. I'm like, she's not hot enough.

[Rachel Yucate]

Yeah. I think that people should be hiring you as a consultant. A personal consultant. Consultant to come in, stand there Naked in front of you and be like, what do I do? Here's where I live. Fix it. I need a man. Introduce me. Like, you're good at that. I feel like this. This. If all else fails and you can't be a real estate agent anymore, this is what you got to do. Because this.

[Kelly Killoren Bensimon]

Oh, my God. Well, that's. That is what I do all day long. Like, it is my job. I sell them. I sell them where they want to live, and then they sell them how to live.

[Rachel Yucate]

That's what I do. I love that. I love that.

[Kelly Killoren Bensimon]

But, you know, it's interesting what you said about finding a man. Like that is. That is, like, the most difficult thing I can.

[Rachel Yucate]

I agree with you. Yeah. Let's talk about love.

[Kelly Killoren Bensimon]

Most difficult thing.

[Rachel Yucate]

Okay, so you have a podcast, and you talk about relationships. In a lot of it, you talk about relationships on your Instagram. Your relationship girl, we all know from the news. A couple years ago now, at this point, a year, year and a half, you ended an engagement. I'm sorry to hear that. Can you talk a little bit about it? Because I know that you've made it public that the prenup was a big part of why it didn't happen. I don't know if you know this about me. I just got married on New Year's Eve. Yeah, it was awesome. Because I've been waiting for 51 years to find the right person, and you don't realize who it is until you're really with them. Because. Because beyond that, it's like, there's a lot of anxiety. You think you have a type. You think this. You think that when you finally find the right person, it's great. The one issue that took us eight months was the prenup, and it is very important, and I love that you talk about it, because people need to be more savvy about the prenup, and it is absolutely important. So just tell me your experience, if you don't mind.

[Kelly Killoren Bensimon]

No, no. I'm the daughter of a lawyer, and I think that the prenup, you know, acts in two ways. Number one, I think that it kind of solidifies the future of your. How you're going to. How you're. How either one of you are going to live your life.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

So whether that. If you're. If you unfortunately something happens to you or unfortunately something happens to the other person, like how that is going to. How that's going to solidify that. And I think that's. I think to me, that's probably one of the Most important things, because is, if you have children, and it's your second chapter, if you have children, like, protecting other people, like, it's just like, the world is so fucked up, and people need to protect other people. They need to really start doing that. And, you know, as a single mother, like, I've been protecting my girls all their lives, and I will continue to do that. And I just was like, you know, I make money. You make money. I probably will make more money. You know, I have a little money, and I'm just not going to give it to you.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

In case something happens. Because if I died, he would have gotten. So. He would have gotten my daughter's money. And I just was like, this is not going to happen.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

It's not going to happen.

[Rachel Yucate]

And he was not willing to let that go. He was dying on that bridge or.

[Kelly Killoren Bensimon]

And I had a great lawyer who, you know, she's a. She's a fantastic lawyer. Her name is Marilyn Chen.

[Rachel Yucate]

I love Marilyn. She did the show. And by the way, I use. Because I'm in Florida, she found me my lawyer, so that's who I used.

[Kelly Killoren Bensimon]

Yeah, she's fantastic. And actually, I found her through a guy that I went to Trinity College with. My freshman seminar is my entertainment lawyer today.

[Rachel Yucate]

Oh, wow.

[Kelly Killoren Bensimon]

And he was like, I want you to make sure that everything's okay. So Marilyn was just like, listen, Kelly, she's like, like, you've been through a lot. You've been, like, providing for everyone. Like, come on. Like, just don't. Like, just be careful. Right. So I gave it to him, you know, whatever. And it's like, you know, he's not a bad person. He's not a bad person. He's just not the right person for me.

[Rachel Yucate]

Sure.

[Kelly Killoren Bensimon]

So, you know, as sad as I am that we couldn't make that work, I am happy that I protected myself and my family, of course.

[Rachel Yucate]

And was there a conversation that you guys would remain dating and just not get married or that anything.

[Kelly Killoren Bensimon]

I said that. I said, we can go through the whole thing and we just don't have to get married. And he was like, no. And I just was like, I can't do this. I just can't do this. If you're not gonna make sure that I'm safe, I can't do it. Yeah. I just can't. And it's interesting because before him and his mom, I was in love with his mom. You know, both my parents were deceased. I was in love with his mother. In love with her. She was just the most Beautiful, human. And, you know, he was such a nice guy. I just was like, but it doesn't matter how nice you are. I have to protect myself. And I've just been through too much, Rachel, to be like, let me just try something nice, right?

[Rachel Yucate]

And it's not a time to, like, trust that in the moment, later it's gonna work itself out. Because God forbid something does happen and you do decide to get a divorce or he does die or you do die. People are not in the right frame of mind to be kind and be nice. Right?

[Kelly Killoren Bensimon]

I already got.

[Rachel Yucate]

Course. Yeah, exactly.

[Kelly Killoren Bensimon]

I already. I already. You know, I left SHIELD and then I introduced him to my best friend. I was like, okay, I'm gonna leave you, and here's your new girlfriend, and you guys are going to be great, and she's fantastic, and you're fantastic, and everyone's gonna be great and over there. And then I am going to take care of my children. My father is going to now nurture my children, and we are going to raise these kids in a different way. And that's what I did. And I just was like, I want. Honestly, I just want someone that, like, just genuinely loves Kelly Kaloren from Rockford, Illinois. It's like,

[Rachel Yucate]

I hear you.

[Kelly Killoren Bensimon]

Is that too much to ask for?

[Rachel Yucate]

No, but it's very hard because people see you before they see you. Do you know what I mean? And you, obviously, there's plenty of people, I'm sure, that have gotten that side of you, but they have to get over all the stuff that they get to see with you, which is all good stuff, too. But, I mean, there's more to you than that, right? Your kids, you as a mom, all the things you've done, the hard work you've done. And you don't need someone to just want you on their arm. You want someone who you wanna sit with on the couch and watch ID Network with or whatever the things are that you like, right? Or. And things that are important to you as opposed to show you off. And so I think.

[Kelly Killoren Bensimon]

I mean, do you know how many times I tell a guy I'm not a show pony?

[Rachel Yucate]

Yeah, I'm.

[Kelly Killoren Bensimon]

I can. And what's interesting is that, like, recently I've noticed that, like, I. You know, when I was in Florida, I went on a couple of dates with some guys, and I just was like. From day one, I was like, just want you to know, I'm only here for two months. I'm filming a show. I'm here for two months. Rachel, you would have thought That I was telling them that I was madly in love with them and I wanted to get married to them. Like the fact that I was like, I am not available. They went so nuts to the point where I was like, this is, you're, you're, you're, you're, I'm filming a show. Like, you need to get off.

[Rachel Yucate]

Like, wow. Well, do you think it was because they loved the fame?

[Kelly Killoren Bensimon]

No, I think they loved the distance. I think they loved that I was unavailable.

[Rachel Yucate]

Got it.

[Kelly Killoren Bensimon]

And they were just like, she's not available. I want her.

[Rachel Yucate]

So now does. How does someone like you meet men? Like, are you on Bumble?

[Kelly Killoren Bensimon]

I mean, I was on Hinge for a little bit. That's when I met my ex fiance, my assistant, and was like, I'm putting you on Hinge and you're going to meet a Jewish guy. And he made my age 10 years younger, which was actually funny but hideous. He's like, no, you read, you read

[Rachel Yucate]

as so much younger than your age. So I mean, I think it's fine.

[Kelly Killoren Bensimon]

Thank you. Well, thank you. But I mean, I am 57. Or no, I'm 58. Like, how old am I? But I just was like, okay, that was fine. But you know, it's so, you know, obviously like I've been on Raya forever. Like when it first started out, they were just like, just go on and say hi to people. Like, I've never really met anyone on like real dating apps that were like, real.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

I mean, that's always been some kind of issue. Yeah. If I go out with them, there's always an issue. There's always something.

[Rachel Yucate]

Right. So how did you meet these guys in Florida? Just by being out.

[Kelly Killoren Bensimon]

Oh, one guy just was at dinner and he just came up to me.

[Rachel Yucate]

Don't you love when I got the

[Kelly Killoren Bensimon]

wine, I was like, sure.

[Rachel Yucate]

I love when they have the self esteem to do that because that rarely happens happens, don't you think?

[Kelly Killoren Bensimon]

Rarely, yeah. But I'm a very like bubbly, friendly. I mean, I walk into a room, if you, if you walked into a room with me, I'm like, how are you? Nice to see you. Oh my God, how are you? And I genuinely mean it. I'm not just saying hi to people to shoot the sugs. I'm like, hi, how are you?

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

And so I think I'm just very approachable in that way. And so the people are like, oh. And then they're like, you're not all that. You're gonna be 60 and alone. I'm gonna be Like, I know some hot six year olds. Let me name some.

[Rachel Yucate]

Exactly. I mean, I get it. My husband is turning 59 in a week, and I think he's hot. And I feel lucky to have him. So I know that there are a lot of men out there that are great men that are looking for great women. Do you know what I mean?

[Kelly Killoren Bensimon]

I think so.

[Rachel Yucate]

Very hard to find. Find them. I spent many years looking, and that, to me, ended up being the problem. Right? Like, when you're least expecting it, you're going to find someone or someone that is a friend that you don't even, like, think that that's an option. And then all of a sudden, you look at them one day and you're like, oh, my God, I love this person. I don't want to be without them. And that becomes the thing. It's like, not who you want to be with, but, like, who you can't live without. And to me, that's what got me.

[Kelly Killoren Bensimon]

Okay, so I'm gonna tell you a little secret, okay. Because even though we're on a podcast, I'm like, I'm just, I'm loving this moment with you. You're so fantastic. I love you. So I broke up with this. I was dating this really, really nice guy who, like, I was just crazy about. And I broke up with him in December because I was going on the show. And so for some reason on my TikTok, the algorithm changed and it was like, all these psychics, like, you know, he's going to come back. You're so great, good things are happening to you. And so I became, I have, I am obsessed from, like, let's say, I'm going to say January 1st to me, I listen to these psychics like a couple times a day. And what I'm listening to is not like they're, you know, what they're, you know, whatever it is, like, what's going to happen. I'm listening to these positive affirmations from them. And it has really, really, really changed me so much because instead of being like, oh, my God, like, am I going to meet a guy? And even on my podcast, like, I mean, that's what I talk about. I talk about. I do part two. I talk to people about their second chapters all day long.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

And so I was like, I just don't want to be, you know, the cobbler with the bad shoes. And I'm just like, if I'm learning from all these people, I want to keep the positivity. And so I literally listen to, like, A person's gonna come into your life. You're gonna be so great.

[Rachel Yucate]

So where are we at with it? So have you. But are you dating someone now? Can you talk about that?

[Kelly Killoren Bensimon]

I mean, I'm going on dates.

[Rachel Yucate]

Okay.

[Kelly Killoren Bensimon]

But I just moved back to New York. I mean, I sold my apartment in the apartment I was living in in New York.

[Rachel Yucate]

Move.

[Kelly Killoren Bensimon]

Put everything in storage, moved to fl. Florida. And then I came back four days ago and I moved into another apartment.

[Rachel Yucate]

Oh, wow.

[Kelly Killoren Bensimon]

And so it's been a lot. So I'm just kind of like in this kind of state of emergency. But I. I don't feel good.

[Rachel Yucate]

Good. Okay. So no big love affairs going on at the moment, but you're open to it, right?

[Kelly Killoren Bensimon]

And I did have to cut the guys off in Florida. The ones that were like, I love you. I hate you. I love you. I hate. I'm like. And everyone at Florida is like, you're the best thing. You're gonna be old. I'm like, which one is it? Can you just tell me which? Cause I just, like, just tell me which one it is. So. I know.

[Rachel Yucate]

Listen. It's just as hard to find a good woman down here. The women here are, let's just say, difficult as you, I'm sure, saw. There's not a lot going on. There's. I mean, there seems like a lot of competition. Looks wise. Cause there's a lot of young girls, beautiful girls, but when you really get down to it, there's nothing. Not a lot of competition. So, you know. All right, wait. I do want to ask you a question about real estate that I just thought of because there's so many real estate shows out there.

[Kelly Killoren Bensimon]

Yes.

[Rachel Yucate]

And I want your opinion on them. Like, I know the Altman brothers very well. I actually met Matt. I don't talk about this often. I met Matt Altman. He wrote me on Facebook, and we started dating, like, over the phone. Like, I lived in New York and he lived in LA or whatever.

[Kelly Killoren Bensimon]

I love him.

[Rachel Yucate]

Flew out to meet him. His personality, I will say, is one of the best. Like, it made him the most handsome guy ever. Do you know what I mean? Once love him. He is.

[Kelly Killoren Bensimon]

I mean, we have a very love hate relationship. Because he's like, you're not all that. I'm like. He goes, you're not a supermodel. I'm like, I'm a reality star, right?

[Rachel Yucate]

Oh, God, I hate that he said that to you. What a jerk. But he. Anyway, so it's just funny because as. And then, of course, I know Ryan and I know all these guys, but do you think that these are real? Are these real people in the real estate market, in your opinion?

[Kelly Killoren Bensimon]

Okay, so I'm gonna give you some tea. You ready? So Freddie and John have known them forever, like, way, way, way, way before I was even on television. And I love them. And I always loved Frederick. I just loved his personality. And I thought that he's very warm, and John is amazing. Brian Serhant went on a date with me on Housewives.

[Rachel Yucate]

Okay.

[Kelly Killoren Bensimon]

That's how we got into television with, like, reality.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

Steve Gold. I put him on TV as well. I called Andy and I was like, this guy is hot. Like, you have to work with him, and he's great. I'm not saying that I'm responsible for them, but I am. You know, I was part of their beginning, parts of their reality lives. I. You know, I've been on a couple of the shows in real estate, and I think one of the biggest problems with these shows is that, number one, you can't. You don't have no properties. People don't want their properties on the market on the. On the shows. And number two, real buyers don't want to be on the show. So that's like, okay, so what are you going to do? Have real estate brokers fighting about real estate brokers?

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

You know, again, like, I think of real estate in such a different way. I mean, I think of real estate as the ultimate luxury.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

And the genesis of your generational wealth. I think of buying a property, your first property, where you put 10% down of whatever that is. That is your first step to creating a future for yourself and for your family. It is the most powerful thing you can do. So I think of it. I have such an emotional and such a protective and such a hugely vast difference, different perspective on real estate. Like, I don't think of it like we told about before, it was like, the land of the bad shoes. Like, I don't think of it like anyone else does. I think of it as the genesis of generational wealth.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

And how you're going to build that and provide and protect for your family. Because you move to Florida, no one can take anything from you.

[Rachel Yucate]

Right. That's very true. But, like, how selling that way, I

[Kelly Killoren Bensimon]

don't see it as, like, throwing. You know, I'm always like, guys, I don't just jump into pools. Okay. I was a model. Yes. I wear bathing suits. I do. I do wear bathing suits.

[Rachel Yucate]

Yes.

[Kelly Killoren Bensimon]

And I do go to the beach. Correct. But I don't think of real estate as, like, sensationalistic. I'm very. I'm very, very specific. I'm super buttoned up. My. My partner and I are like, we do it right the first time. There's no mistakes.

[Rachel Yucate]

Yeah.

[Kelly Killoren Bensimon]

I have the best lawyers. Like, I just don't fool around. Like, if I'm going to do the. I do these big deals because I'm super serious.

[Rachel Yucate]

Yeah.

[DSW Announcer]

You know that thing where you get an amazing pair of shoes at a really great price and want to tell everyone about it?

[Kelly Killoren Bensimon]

Yeah. So do we.

[DSW Announcer]

Here at Designer Shoe Warehouse. We'll give you something to brag about. Like the latest styles from brands you love or the trends everyone's obsessing over or shoes that make you feel like, well, you. So go ahead, show off a little. Buying shoes that get you. You at prices that get your budget. Head to your DSW store or dsw.com today. DSW. Let us surprise you.

[Rachel Yucate]

And it's because I have a bigger reality. It's not reality tv. Like, do you ever watch Selling Sunset?

[Kelly Killoren Bensimon]

You and I are having drinks on a Tuesday. And like, dancing does not mean that I am not wildly buttoned up.

[Rachel Yucate]

Right. You know what I mean? Like, no, I love that. But like, you know how Selling Sunset became so popular because it's. It became so over the top and the girls are so pretty and they're dressing a certain way and it's ultra high net worth stuff. Do you. Do you watch it and do you think that's reality or that's all?

[Kelly Killoren Bensimon]

I mean, first of all, no one. I mean, I represent 240 Central street and I'm their broker specialist. So if you come into. It's like the problem with me is that all these buildings I represent, I am the gatekeeper.

[Rachel Yucate]

Right? Right.

[Kelly Killoren Bensimon]

So, like, you come into me and you're like in a hot pink dress. I'm gonna be like, we have nothing else available.

[Rachel Yucate]

Right. And we have nothing else in common.

[Kelly Killoren Bensimon]

Yeah.

[Rachel Yucate]

Right.

[Kelly Killoren Bensimon]

And we're never gonna see each other again.

[Rachel Yucate]

Right. I got it.

[Kelly Killoren Bensimon]

I just. I'm not gonna do it. Like, I'm not. Like, if you don't have, you know, you don't have proof of funds and your client isn't real, and you don't come, like, prepared and ready to go. And by the way, I'm not. This isn't Disney World and I'm not your tour guide. You know, you have to be responsible for your client, and I'm responsible for my client. I need you to be professional.

[Rachel Yucate]

Yeah. Yeah.

[Kelly Killoren Bensimon]

So, I mean, I Love it. I think it's so my. My. To answer the question, I want people to be successful, and I want them to have a good time. Just don't come on my properties.

[Rachel Yucate]

Right, right. Exactly. Okay. All right. I can't let a conversation with you go without asking about your dynamic with Bethany Frankel, because obviously that was such a big moment in. And she is so vocal and always out there every day, posting about her thoughts. You were talking about earlier about. Just because you had a platform doesn't mean you should be posting your thoughts every day. What is your current state of your relationship with her, and what do you think of how she's turned out? Like, the stuff she's doing now?

[Kelly Killoren Bensimon]

You know, a lot of people ask me this question. I really should be more educated and I should be more professional in what she's doing. I really don't know that much. I mean, I hear some little things from people. My. You know, originally when we met, you know, she was, you know, a girl that wanted to be someone great, and she thought that I was great. And instead of just being like, hey, my name's Bethany. What's yours? She was like, I'm gonna go after you. And I'm like, go after who? Yeah, who are you going after? I'm confused. I was like, I don't understand. I don't understand who you are, and I understand what you want from me.

[Rachel Yucate]

So it was almost like she didn't feel like there was space for both of you to be great and both of you to be liked.

[Kelly Killoren Bensimon]

Right. I think that she was intimidated that I had a very, like, easygoing way. You know, she comes from a good family. I come from a good family. She has a great education. I have a graduation education. She comes from money. I come from some money. You know, it's like, we are very similar people. Like, she had a great upbringing. I had a great idea upbringing. Like, she has a lot of friends. I have a lot of friends. Like, it's not that much of a disconnect. But I. I affected her narrative. I. I was the person that I. I made her narrative, like, unhinged. And the only person that was unhinged was her. Like, I was just like, do you. Like, Right. I'm over here eating candy. You just enjoy yourself.

[Rachel Yucate]

So I guess you guys don't speak anymore.

[Kelly Killoren Bensimon]

Well, it's not that. We just don't need to. There's no. There's no. Like. I mean, we filmed. We didn't even film that many scenes together. It's not like we Were together every single day. It's not like, you know, like, on Golden. We were together, like, for two months. I think all in all, we filmed maybe, like, maybe seven or eight scenes together. Like, we didn't really interact that much together. But, you know, she's one of those kind of things. It's like, you know, he who barks the loudest gets the bone. And I'm just like, keep on barking. Like, I'm over here, like, drinking coffee. Like, you're like, good.

[Rachel Yucate]

Right? Right. All right, in closing, let's just.

[Kelly Killoren Bensimon]

I wish her. I wish her and I and anyone who wants to be my nemesis, I wish you all the best. Like, I could not. I just want everyone to do well. And, like, there's. There is so much room in this world for success. Yeah. And I just feel like trying to break someone down to make you better is so dated, and it doesn't land well anymore. It's just like, if you're not a part of a community and you're not creating a community, like, you should really put social down. I just, you know, talk to your cat. I don't know.

[Rachel Yucate]

I love that you just said that. It's so true. And, like, as you get older, you realize, what. What do you want to fight like that for? It's just so, you know, there's no need for it. And it's gross. It's gross. If you behave that way. You clearly don't want to be around people that act that way, so. And you choose your community. Like, my community is. Listen, I know a lot of people. We talked about this before, before, but. But my community is very small. I keep it that way on purpose, and I don't like those interactions at all. And now it's very easy for me to just pick myself up and be like, I don't want to be around this, and I'm good in the area that I want to be in. You know, I don't need that interaction.

[Kelly Killoren Bensimon]

So, I mean, I guess, too. I guess just to, like, hop on that, you know, I. In my business, because I do work in the transaction business, there's so much at stake. And so if. If we're talking, if I'm representing you and I'm trying to figure out how to put, you know, an extra $500,000 in your pocket, I will go. I will be an animal to do that for you. But when it comes to my personal life, if you're trying to attack me, like, I have. I just. I'm like, I don't even know what you're talking about. And by the way, I have such selective hearing from, like, listening to people scream and yell at me all day long. I'm like, if it is not like, you're the nicest person on the planet, I want to, like, hang out with you and eat sh. Chinese food. I'm not listening to you.

[Rachel Yucate]

Right. I love that. That's a good point. A lot of people only see the negative, you know, and it's good. It's. That's a good piece of advice. Listen to the positive and just drown out the rest of it.

[Kelly Killoren Bensimon]

Right? Like, just be positive and have a good time.

[Rachel Yucate]

What do you think? My final question. What do you think people finally understand about you today that they didn't 15 years ago or whenever you started doing the.

[Kelly Killoren Bensimon]

I think that people are just so confused why. And I think that is the most amazing thing ever.

[Rachel Yucate]

I love that. So you've made yourself complicated, even though you're not.

[Kelly Killoren Bensimon]

I don't want them to know who I really am. I just want them to know that if I'm working for you in business, I am an absolute animal. And if I am your friend, I will do everything to protect you and to be a great friend to you. Like, that's all. But I mean, everything else. I mean, I like it. The people are confused. Well, you're like this. Okay, tell me more about me.

[Rachel Yucate]

Right? Right. Oh, my God.

[Kelly Killoren Bensimon]

It's like you can't fight it. Do you know what I mean?

[Rachel Yucate]

Yeah. It's so true. What's on your bucket list? Is there anything you want to do in the future that is way out there that you're like, one day. One day.

[Kelly Killoren Bensimon]

Day. I mean, I don't really think like that. I just, like, I want to go to Couture. I want to go sit and, like, watch my beautiful friends make the most beautiful clothes in the world. It's not a bucket list, but it's just like a. A tomorrow thing. Can't wait to have. See my kids. Have. Get married and have children. Like, I can't wait for that.

[Rachel Yucate]

How old are they now?

[Kelly Killoren Bensimon]

They're 25 and 27.

[Rachel Yucate]

Okay.

[Kelly Killoren Bensimon]

Okay.

[Rachel Yucate]

Is anyone.

[Kelly Killoren Bensimon]

I can't wait for that.

[Rachel Yucate]

Is anyone close to getting married or anything?

[Kelly Killoren Bensimon]

They will be. They're just, you know, they're such great girls. You would love them. They're just so smart and cute and feisty and.

[Rachel Yucate]

And do you get to see them all the time?

[Kelly Killoren Bensimon]

All the time, yeah. They live really close to me, and we spend a lot of time together, so just that. But that's really just like, for me personally, I just want to go to couture. I just want to dream. Like, I'm a dreamer. I just want to dream and just like look at beautiful things. I don't need to. To do any. I mean, I'm already doing. Not worried about what I'm working on. I just want to dream bigger and then, you know, to see what happens in my life.

[Rachel Yucate]

And is marriage on your list of things that you are dying to do in your future or you'll be okay if that doesn't happen?

[Kelly Killoren Bensimon]

You know, I used to think it was. I used to think it was like, Rachel, like when after I got divorced from my ex husband because I was like, you are amazing at what you're doing do. But I want a family for my family, and I always wanted the family for my family and I just never found it. And so now I'm just kind of like, what? I just want like a. I just want a partner. I want like a partner in crime. I just want someone who wants to like, dream big like me. I am a dreamer. I cannot tell you. I mean, I'm. I'm pragmatic. Yeah, but I'm a dreamer. I just want to, like, make things better.

[Rachel Yucate]

And yeah, just.

[Kelly Killoren Bensimon]

I don't know. I just am a big dreamer.

[Rachel Yucate]

My wish for you is that you find a witness to your life. Like someone who can, like, be around, watch you do your thing. And then someone. I always love the idea, like, to go through life, you want someone at the end of the day to call and be like, okay, well, here's who I met at the bus stop. Not that I take the bus, but you know what I mean? Like, here's what I did, and here's what I ate, and here's who I saw. Someone who can be a witness to what I see and feel. And I wish that from. I think you're amazing. I'm so honored that I got to spend the last hour with you. I really hope the next time you're down here or I'm in New York, we'll. I'll text you, we'll get together, we'll have dinner. I would love that.

[Kelly Killoren Bensimon]

And I'm gonna tell Michael that we spoke and had so much fun and I appreciate you so much. And I, you know, it's like, it's just so interesting to, you know, talk to you about, you know, the lives that we're leading and then just like, it's okay to make mistakes. It really is. And make as many mistakes as you can. Because if you don't make mistakes, you're never, ever gonna learn. Y just going to go through life

[Rachel Yucate]

being a like, it's the only way to learn. It's the only way to get a little bit of tough skin so that you're not depending on others for your own happiness. And that, to me, is something I had to learn. I have to figure out the happiness with me.

[Kelly Killoren Bensimon]

Exactly. Yes.

[Rachel Yucate]

All right. Thank you. Thank you so much for listening to Misunderstood. I'm your host, Rachel Yucate. Please be sure to subscribe to the show and give us a five star rating and review. You can support the show by joining our [e-mail] misunderstood with Rachel Ukitel. Do you have ideas for the show or want to reach out? Email [e-mail] that's spelled M I S S. Understood. Thank you so much and I'll see you next.

[DSW Announcer]

You know that thing where you get an amazing pair of shoes at a really great price and want to tell everyone about it?

[Kelly Killoren Bensimon]

Yeah. So do we.

[DSW Announcer]

Here at Designer Shoe Warehouse. We'll give you something to brag about, like the latest styles from brands you love or the trends everyone's obsessing over or shoes that make you feel like, well, you. So go ahead, show off a little. Find shoes that get you and prices that get you your budget. Head to your DSW store or dsw.com today. DSW. Let us surprise you.