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Kelly Calorin Bensimon
Lemonade? I don't like to talk about work.
Erica
Really?
Kelly Calorin Bensimon
Well, no. What do you want me to talk about? Real estate. You want me to tell you my strategy in real estate?
Erica
Yes.
Kelly Calorin Bensimon
No, I actually am super interested in that. Okay, you don't want to hear that because people are get very well.
Erica
You don't want to give other people your strategy, I would think.
Kelly Calorin Bensimon
Well, they couldn't do it anyway.
Erica
Now work. Welcome back to work. We have Kelly Calorin Bensimon with us today. She's fabulous. You may know her as a real housewife. She's a mom, she's an author. She seems to be a killer real estate broker, which is pretty awesome. We have a great conversation, so you'll like that. We're going to start with tips and tricks. I have a lot of thoughts on tips and tricks today. So I think there are a couple things to think about at work or that I'm thinking about anyway. So the first is we're having a problem right now. Many problems, to be honest. But one of the problems we're experiencing is I have a situation where we've made a commitment to a company. We're supposed to do a thing. How that came together was really fast. The team worked really hard on it. It was hard fought. It was like the nails in the mountain, like it was just like clawing our way there. And now there's a problem with how it's going to happen. And one of the things I've been thinking about at work is that which is I think also true in life is that when you're in a position of responsibility or you're in a managerial position or you're running a project, it's actually only going well if everybody's unhappy. And I think that's a funny thing to say. And it's a weird way to look at things, but it is, it's very real and I think it's very true. Because ultimately running a project and managing a team or leading people is really about compromise. And it was interesting where this whole situation has taken a whole bunch of meetings and a whole bunch of conversations and there's been a little bit of game of telephone tag and like finally I've gotten my hands on all the pieces and the reality is everybody's annoyed with me. And I think that's a hard thing for people managers and I think it's a hard thing for people in general that people annoyed at you. I think people are annoyed at me all the time in my life and at work. But I also think it's the nature of getting something done the right way, which is to say, hey, here's the situation we have. We have a problem at hand. Problems occur everywhere at work. Here's how we're going to resolve it. The resolution of that problem rarely, in my opinion, has a clear win and a clear loser or a clear person who's right and a clear person who's wrong. The reality is, hey, you're 70% right here and 100% wrong there and the other person is 50% right here and 40% wrong somewhere else. It's always nuance, there's always detail, there's always intricacy. There's always compromise in a solution or usually compromise in a solution. And being able to get to compromise is really important. And then also being strong enough to and forthright enough honestly to be able to say, hey, here's the deal. Like, you want this, they want that. The reality is we got to get something in the middle. This is what's right for the company. This is what's right for group one. This is what's right for group two. We're going to have to work together and we're also going to have to acknowledge that this could have been done differently or that could have been done better or this isn't going to be sustainable. So I think I'm going through this a lot at work right now and I think a lot of of people go through this at work and just being strong on being strong and being a steward of compromise is a really good, healthy way to think about leading. So that's kind of my opening thoughts today. All right, so our first current event comes from Complex and a survey is showing that 46% of Gen Z workers are already using retirement savings. Payroll Integrations has done a survey of Gen Z workers. So just as a reminder, the oldest Gen Z worker right now is around 28 years old, the Gen Z worker. So that would probably be people, I would say between 20. Are you working at 21? You're probably 23 and 28 have already tapped into their retirement savings. And of the group that has tapped into their retirement savings, 42% did so to pay down debt and another 25% used their retirement savings to cover an emergency. I have a lot of thought on this one, is their savings can't be that big. Like if you've been working for five years and on average you save, what do you save for retirement? Like 1% of your paycheck or 5% of your, let's say it's 10% of your paycheck. Let's actually, let's do a math problem real time Sarth. So let's ask GPT what the average salary of a Gen Z is. Okay.
Kelly Calorin Bensimon
In any particular field?
Erica
No, just aggregate. So we asked ChatGPT and the net net on this one is that if you're, if the Gen Z or so as a reminder, Gen Z ranges from ages 13 to 28. So most of them are not working full time. If you're working a gig, so you might be a student, you might have a part time gig, you're making like $23,000 a year. If you have entered the workforce post college, you're working full time, you're making $68,000 a year. All right, next question for what is the percentage of Gen Z's annual income? Do they save for retirement? This is fun. We're like doing a math problem in real time. This is how Erica does math. They save monthly, annually. It's probably like 0.000. Okay, so 25% of people in the Gen Z generation save between 20% of their income per month. Now that's just savings. That's not retirement. So let's pretend it's 7%. So like just for our case, let's pretend it's 7%. 7% of $68,000 is what it is. 4,006, 4,700. Okay. And let's assume you've been working three years. So you've saved like 12 grand. All right, so let's pretend 15.
Kelly Calorin Bensimon
Yeah.
Erica
Okay, so you've saved 15 grand and Gen Z is 10. Tapping into their 15 grand. Gen Z tapping into their 15 grand to pay for stuff. That actually doesn't surprise me. I mean, I think it's a bummer. I think, you know, you're always like taught like, don't touch the retirement. Don't touch the retirement. Don't touch the retirement. For good reason. When things compound, they grow faster. That's your nest egg. That's like the money you shouldn't touch. But we were having a chat actually in the work. Like a girl slack the other day about like, did your parents teach you financial literacy? And the large majority is people learn about their finances not from being taught by their parents, but watching their parents. So it was interesting. Like people who were raised by parents who were trying to make ends meet or who didn't do a good job making ends meet had a real life lesson around savings. And people who had it cushy and they never thought about money or didn't worry about money really didn't. And I actually, I think this is a good lesson for people of, like, how are, how are you thinking about the management of, I would argue like a top five asset, which is your money. But I don't think it's surprising that Gen Z is actually tapping into their retirement. I also think it indicates a bigger challenge, which is people aren't saving, there is a lot of debt, and that essentially there's some struggle, which is natural because you're in your 20s. I remember being in my 20s, living in Boston, and I went to the ATM at Citizens bank one day and had $5 in there and like a college loan payment due. I was like, fuck. And then I was like, can I bum beers off of you tonight? You know, like, that's just the reality. That's like working in your 20s. So that's my thought there. So this one comes from Fortune 500. Jamie Dimon back at it again. I love Jamie Dimon quotes. I'm like a Jamie Dimon stand. So anyways, his point is absolutely. Do not stay in your lane, is his quote. And what Fortune 500 writes is with workplace incivility and layoffs on the rise, incivility is a great word. It may be more tempting than ever to keep your head down, but according to Jamie Dimon, it's a bureaucratic, stupid decision and it's a mindset that won't get workers or their employers ahead in the current climate. In his 2025 shareholder letter, diamond urged shareholders to step outside their lane and challenge the status quo, advice he's long embodied for himself. I love this. I think that staying in your lane, what he's really. What he's really saying is accepting the status quo and staying quiet is really, really problematic. I am probably guilty of, like, poking, poking, poking. I'm not a big stay in a lane person. I'm not a big lane person in general. But I do see it. I see it a lot here, to be honest, in terms of, hey, we've always done it this way. This is how it was done before. I'm scared to do differently. Or people are held back because they don't want to grit through the shit you have to do to resolve something and to set it in a new way. And I think it's a good message, which is staying in your lane. Sure, it keeps you invisible and it keeps you safe for a short time, but I think ultimately it puts you at greater risk because one is you're replaceable, everybody's replaceable. And then the second piece is you don't see stand for anything. You haven't contributed anything. There's nothing standout about your approach, about your work ethic, about your output, about your thinking. And you haven't demonstrated a point of view. And I think having a point of view is actually becoming. For as much content as there is out there, and there's as much conversation there is about work, having a point of view is actually becoming quite rare. All right, so this isn't a current event topic, but it's something I read on Instagram. It came from Ogilvy. For folks who don't work in advertising, Ogilvy is one of the, I would say, most renowned, like, very highly renowned ad agencies. Started as a creative agency by a gentleman named David Ogilvie. Has been around forever, won a lot of awards, done a lot of campaigns you can recognize. But in 1979, on my birthday, actually November 6, 1979, David Ogilvie wrote a memo to some gentleman named David Weiss. We should look up who that is and what he. He titled it as my shortcomings. And he said, after you left our meeting on October 30, one of the trainees asked me, what are your shortcomings? And my answer was perfunctory. So, David, what I actually love about this is like, I love the afterthought of like, hey, I gave you an answer, but the answer wasn't great. And then he goes on to say, here's a better one about his weaknesses. He's intolerant of mediocrity. He fritters away too much time on things which aren't important. Like everyone of my age, I talk too much the past. I'm afraid of flying and go to ridiculous lengths to avoid it. When I was a creative head in New York, I wrote too much of the advertising myself. I know nothing about finance. I change my mind about advertising and people. I'm candid to the point of indiscretion. I see too many sides to every argument. I'm over impressed by physical beauty, and I have a low threshold of boredom. I loved this because one, I think just how great a couple things about it. How great to have done something and then rethought the way you should do it. Like, I had a date with my son last night and we're in the car. And I think the greatest time with your kids, if your kids are teenagers, are in the car, because it's just like the inhibitions drop and you just kind of have conversations. You don't necessarily have to look at each other. You can just talk more freely. And he was talking about how he plays football, and someone on the football line did something really stupid. And my son yelled at him and said he said something, and he kind of wished he didn't say it. And the kid responded poorly to it and was mad. And he's like, oh, I'm thinking about, I shouldn't have said that. I shouldn't have responded that way. I shouldn't have said that. And he's like, I'm thinking about if I should write him. And I was like, you should definitely. You should definitely acknowledge it. You should definitely say something. And then they ended up having. Which is, instead of talking to his mother, he was like, I'm just gonna text my friend. But they ended up having, like, a text conversation about it, which I thought was like a really good. Like, shit happens. You have an after review about it with yourself, and then you do something about it, which is a good way to think about when you mess up, because everybody messes up. But I also like the idea here of having a list of the things you don't tolerate. Like last week we talked about it, or a couple weeks ago we talked about it. Which is like, a leader is only as good as their weakest L or their most insufficient or least engaged person. And it's good to have a set of principles. I think just having principles about what you tolerate, what you don't tolerate, what's not great about yourself, David Ogilvy's writing, the things that are not great about himself. Two of these are things he could have done differently, but most are pretty great. And I think that's also a good way to look at your life, of even the things you don't tolerate or you're not good at or don't motivate you. They're motivating. And saying them gives clarity and honors them. So I really like that. I think it's a good use of time and a good thing to do, and you don't have to share it with anyone, but I think it's great to have it yourself. It's actually another one of these. If we look up on Instagram, the former Mickey Drexler, if you look at the former CEO of J. Crew, put a post out about an intern after a meeting, wrote him a note about what she learned from him in that meeting. And let's see if we can find it. Okay, so this is kind of related. So Mickey Drexler posts this. He said, avery, an intern on the team this summer, sent Me this note and what she said is, over the last 10 weeks of hearing you in action, here are some Mickey isms that I will take with me. So one, scarcity sell. Two, talk to customers and think like one. Three, Working at Alex Mill gives college a run for its money. While my professors may not agree, I learned a lot that I wouldn't get from any lecture and a few Yiddish words to boot. Four, obsess over the details. Five, trust your gut, even if you can't explain it. Six, the 8020 rule. Use it and know it. And seven, constantly edit, edit, edit. I thought these were great. You know, one, good for Avery the intern. I thought that's very thoughtful for her to write a note. But then the second piece is. These are. This is a masterclass from one of the best people in retail ever. But also, these are good rules of business, and they're also good rules for how you should think about yourself in business. Give us the Kelly story. I'm not doing a proper introduction. You seem like a woman who likes to work.
Kelly Calorin Bensimon
Not really. You don't think? I mean, people, you project work.
Erica
I do like working while leisuring.
Kelly Calorin Bensimon
Working while being casual. I mean, I guess I'm a just very curious human. And I, you know, I am a nerd at heart. I just was, you know, raised to work smart.
Erica
Okay.
Kelly Calorin Bensimon
And then enjoy your life. So my dad would be like, get your homework done and then go do whatever you want.
Erica
Okay.
Kelly Calorin Bensimon
So I'm really good at compartmentalizing things. I wouldn't say that I like to work, but I'm like, are you like.
Erica
Ugh, I gotta do that?
Kelly Calorin Bensimon
No, I'm just like, I'm a good synthesizer of information. Like, if you needed something from me or you wanted me to do something, I could do it quickly.
Erica
And then you're like, and then I'm.
Kelly Calorin Bensimon
Gonna do what I want, and then I'm gonna go do exactly what I want.
Erica
Okay, so.
Kelly Calorin Bensimon
Exactly. So I don't know if that's loving to work. I'm just saying.
Erica
Maybe it's that you're just good at it. You seem very entrepreneurial.
Kelly Calorin Bensimon
I am very entrepreneurial, but that's, like, part of the curiosity aspect.
Erica
Okay, so describe the universe. Like, you're a model, you're an influencer, You're a real estate agent. Like, you're a spokesperson. Like, you're a housewife. Like, not really. Like who? Like, give us the world.
Kelly Calorin Bensimon
Well, I built a house, but I'm not a wife anymore. Let's see the world.
Erica
The world.
Kelly Calorin Bensimon
The world. I mean, that sounds great, what you just said. I love that I. The world of Kelly. You know, first and foremost, I'm, you know, a daughter, a mother. Those are the two most important things. I'm a sister. You have a dog. I have a dog. So I'm a dog mom.
Erica
Yeah, that counts.
Kelly Calorin Bensimon
I'm a pet parent.
Erica
Do you have a cat?
Kelly Calorin Bensimon
I don't have no cat. I have no cats. I don't have any cats. I just am a very. I've always been like that ever since I was little. I don't know what it is. I'm just a very curious person. And my dad is a. Was a lawyer, and he used to say, if you don't know the answer, you know where to go find it. Okay, so that's how I was raised. I wasn't raised with. I don't know. I can't do that. It was like, oh, just one second. Let me just look that up.
Erica
Yep.
Kelly Calorin Bensimon
Yep. And so. And there was just a lot of people would make these, like, gross generalizations, and I'd be like, are you sure? I was always questioning people on what they were saying. Not in a mean way, but just, like, for my own self. And so that's where everything just kind of came from. I mean, you know, there's been many, I guess, iterations of me as starting off as a model. And I think that the pattern of my life is that I've always done two things at the same time. So maybe that's where that comes. You're talking about, like, you think that you're a multitasker. I'm a multitasker. So I was in high school and I was modeling. I was in college, and I was modeling. Then I was in college, and I was modeling, and I was writing, and then I was editing, having children, modeling, writing, being on tv. So I was always kind of doing all these different things that were in the same kind of vein. People are like, well, editing a magazine has nothing to do with modeling. I'm like, hello, I'm sorry, what? Or they're like, writing has nothing to do with editing a magazine. I'm like, have you met Anna Wintour? She's a writer. That's her job is. She's an actual. She edits words. That's her job. She's a synthesizer of a narrative. The way you dress. Visual. Visual. That's editing. Those are words describing people. The original storyteller. So just all those kind of things. Just like, I was constantly doing different things, and I think for a lot of People, it's very daunting. They're like, how do you do that?
Erica
How do you do that at once? But for you, it's like second nature. You'd be bored if you were only doing one thing.
Kelly Calorin Bensimon
It feels like, well, I think if I. If I could just write novels all day long, I would be a absolute pig in shit. Am I allowed to say that?
Erica
Yes, you are. We say, we swear liberally.
Kelly Calorin Bensimon
Is that smart to say a pig and shit? Yes, sure.
Erica
That's.
Kelly Calorin Bensimon
Is that very smart?
Erica
Very, very.
Kelly Calorin Bensimon
And so I just, I love to write. I've always loved. I've always loved to write. I've always liked to package things easily for people.
Erica
How do you think about, like the Housewives of it all in this, like the Bravo, the show? Like, do you think about it as a business? Do you think about it as a platform? Do you think about it as a community? Like, what is it?
Kelly Calorin Bensimon
So that's a really good question. It's a loaded question. To answer the first part of it, I went on Housewives because I just gotten divorced and I was like, okay, I'm in my early 30s and I need to make money for my children. I made money all my life, but now I need to really make money for my children. And my parents were like, you, you need to like, amp up your career.
Erica
My dad was like, get back into it.
Kelly Calorin Bensimon
Right? And he was like, you know, this was a time too. This is, you know, this is like 15 years ago when people weren't like, making money. Women weren't like, let me just make money.
Erica
Yeah.
Kelly Calorin Bensimon
Yep, they had jobs, but then they would like, raise their children and they didn't have jobs anymore. And all of a sudden I was working with these children, with my children. And then I got divorced. And then that fear of being able to be a provider really set it 100%. So I went on Housewives to like broaden my scope, okay. Instead of just being like New York based editor, writer, magazines, books, all of these things. I wanted to widen my scope. And I want people to see me like I was a model.
Erica
I could get that life. I get it.
Kelly Calorin Bensimon
That. Right. I could under. I can like meet people and exchange, you know, and exchange with them and feel comfortable like that. And so I had another show that was where I was interviewing the masters of the universe. And then I was doing these like wild things and people are like, you're so sporty. I'm like, I like sports, but I'm not sporty. Like, I am. I have athletic tendencies, but I wouldn't say that I'm a mountain climber or I'm not gonna, like, you know, go skydiving or those. Those things are not like me. You know, I'm not good at that. But if you're like, let's try to run a mini triathlon, I'm like, I'll try it. I don't know how long it's gonna take me, but I'll try it anyway. So I was like, let me just try Housewives and see what's going on. I was on this show where I was swimming with sharks and interviewing the masters of the universe. I was like, how bad could it be?
Erica
Yeah, 100%. You're like, I can do this.
Kelly Calorin Bensimon
Except for I am a very organized. I know who people are. I know what their story is. I'm always like, I know more about the person. You're prepped, Always. And I was just like, I'm just gonna go in this and just be real. And that backfired.
Erica
And was it hard, like, to describe?
Kelly Calorin Bensimon
Like, you had to give, like, the.
Erica
Words of, like, immersing into that experience. Like, what would the three words be?
Kelly Calorin Bensimon
Dangerous, unexpected. And. I'm trying to think of something that's, like, more fun. Dangerous, unexpected.
Erica
And, like, was there an exhilaration to it or, like, a rush or.
Kelly Calorin Bensimon
No, it was like, I always felt like I was in a challenging situation.
Erica
Okay, so, like, alive, like, it was happening.
Kelly Calorin Bensimon
Yeah. Yeah.
Erica
Okay.
Kelly Calorin Bensimon
I know those sound negative, but they're actually kind of fun. Like, dangerous is like. Is like.
Erica
I don't think that's negative at all. It's like, you're in the thick of.
Kelly Calorin Bensimon
It 100%, and you're just, like, not sure what's going on. Yeah, it's, like, unexpected and, like, who's gonna do what? And what are they gonna say?
Erica
And how did you get comfortable in that as a podcast? People think about work. It's how to get better at work. And part of it is finding yourself in over your head and then being able to navigate your way through it. Like, how did you. Because you've really successfully navigated your way through that.
Kelly Calorin Bensimon
That's really nice of you. I had swam with sharks before on that television show, so I literally had swam with sharks. And so I was like, why not? I can figure this out. And there's just. Just women in New York. But I didn't realize. I didn't realize that there was this gross, like, dichotomy between different people, different. The way people saw people's careers and the way, you know, like, this idea of the socialite and all these different words and the way people were being defined. I didn't really. It never really affected me, or I never really, like. I never really thought about it. And when I was on Housewives, it was like, there's a pecking order. There's, you know, you're a socialite. I'm like, a socialite. You don't even know what a socialite is.
Erica
Yeah, yeah. What is that?
Kelly Calorin Bensimon
Like, Nan Kempner is a socialite. We don't have socialites anymore. Everyone's working, and so they didn't even. They were. Their perception of it and mine were totally different. So it was difficult. Sometimes it was difficult. And also, I think that they thought that I was something that I wasn't.
Erica
You're packaged to be something different, right?
Kelly Calorin Bensimon
I mean, okay, I modeled, but that doesn't mean I'm at home modeling. Oh, hold on, girls. I'm just gonna model here while I'm making you breakfast. You know, you don't just. You don't model 24 7. You go, you wear clothes, and then you take those clothes off and then you leave. So it just was interesting the way that I was perceived, and it was actually a really good lesson for me because, you know, raising my kids on my own and just working in all these different arenas, I learned to just be much more cautious about who people are and where their energy lies and what they're thinking versus what I was thinking.
Erica
Yeah. 100%. What they want from you and what.
Kelly Calorin Bensimon
They'Re gonna do with you.
Erica
100%. I think that's great advice. And what's your advice? Do you regret the experience? How do you think about it?
Kelly Calorin Bensimon
I mean, I couldn't regret it. Cause I wouldn't be sitting here with you today. We wouldn't be talking about. But we wouldn't be talking about those kind of things. And I think that people aren't expecting someone. What I hear all the time is that I can't believe someone like you would be in that position. I'm like. Someone like me. Who am I? I'm from Brockford, Illinois. What are you saying to me? Just because I've done some interesting things that I really pushed for and made happen. That's because I wanted that. But that's not. No one gave that to me. And I'm just. I'm very proud of who I am and how I've navigated the world. But, I mean, mostly, like, just providing for my kids.
Erica
Like, facts.
Kelly Calorin Bensimon
That's all I care about. And you Know, if it's like, you know, I got slammed around a couple times, and, you know, but, I mean, that's called endurance.
Erica
Yeah. Yeah. It's resilient.
Kelly Calorin Bensimon
Yeah, it is.
Erica
Resilience. I like that. I think that's super interesting.
Kelly Calorin Bensimon
You know, it's really like, at the end of the day, they're not gonna be like, you know, she was a housewife. They're gonna be like, she was a great mother. She was a great provider. Like, the things that are. Are inherently core values that are super.
Erica
Important that do describe you.
Kelly Calorin Bensimon
And listen, your day to day. Like, I mean, you know this better than anyone that, like, what you're doing is always. You're always reinventing yourself. You're always like, you know, whether it's through social or AI Your job or the people you hang out with, your job you hang out with. Like, whether you're a barstool, Whether you're a Food52, you're always trying to, like, figure out, like, where, you know. You know, it's always uncharted territory, and you're trying to, like, navigate and make things great.
Erica
Yep.
Kelly Calorin Bensimon
So I love that.
Erica
What's your advice to people, like, in the thick of it or who find themselves in a place where you like. I think what's so cool about you is that you were packaged and marketed as a thing. The thing is Kelly, but Kelly is different than Kelly, and you navigated that gracefully. And you are. You seem very optimistic and creative and warm. And what's your advice to people who are going through something similar, probably in a different scale or in a different environment? Like, having seen that journey, having lived that journey and now seeing the other side of it. What's your advice to people in their version of that?
Kelly Calorin Bensimon
I just think to always let your guard down. I think we're living in a world where people are like, I'm just so cool. It's like. Like, okay, if you were cool, you wouldn't say that. You would be talking about what makes you cool or the things that you like that are cool. You wouldn't be defining yourself as cool. So just letting your guard down, being open to things that are super uncomfortable. I mean, I think that's what that's like. The genesis of emotional growth is really just being like, you hit me with your best shot. Let's see what it is. Cause, you know, I'm gonna use this tool in my tool belt. I'm gonna use that tool in my tool belt. I'm gonna come out with all these. Whatever it is that that I know that I've used in the past. That is good. I'm gonna use that. I'm gonna pivot a little bit and use it for other good. And I think that's the best advice is just to be like. And I know that that seems so cliche. Just be really open and available. I don't mean to be, like, spreading your legs. I mean being really emotionally and mindfully open to other people, because we're constantly learning and we're constantly changing, and it's like, if you're just like, that's not how. You're never gonna be, like, on the.
Erica
Train, leaving the station, 100%. You're in the back. And then talk about, like, you're so smart.
Kelly Calorin Bensimon
You're like, yeah, you're in the back. Like, you're like, I got this, Kelly. I got this. No, you are like, I could talk to you all day long.
Erica
And then what about, like, failure? How do you. How do you. Like, you've succeeded, and I'm sure you failed a thousand times. I think everybody fails all the time. I think that's, like, the greatest secret. It's like, everybody's failing all the time. How do you get back up after you've fallen down and you've scraped your knee? And what's your advice to people about that?
Kelly Calorin Bensimon
It's interesting that you're talking about failure, because we're hearing more about it. And I always. When people ask me, oh, what is so great? I'm like, let's just talk about what's so bad about me. Let's talk about all the things that are terrible about me. And then later on, we can talk about. About what's great, but, like, the bad things are the things that I want to work on.
Erica
Yeah, it's more interesting. Totally.
Kelly Calorin Bensimon
Like, I want to, like, I'm always like, what are your thoughts? You know, criticize me. And people are like, no, no, you're so great. I'm like, I don't want you to tell me how great I am. I want you to tell me, like, what I did poorly so we can move forward on that. I think that. I mean, failure drives me. And when people tell me no, I'm like, oh, really?
Erica
Yeah.
Kelly Calorin Bensimon
I'm like, that's so nice for you. I'm just gonna do that better and even more better and better and better. So anytime that anyone says no, I'm always like, oh, that's just so great for you. Nice.
Erica
Thank you.
Kelly Calorin Bensimon
Just gonna be super condescending, and I'm just gonna go and do something that you're never even gonna imagine I could do and do it well.
Erica
Do you like conflict?
Kelly Calorin Bensimon
No. I like possibility. I like resolution. I'm not a conflict person. I don't. Like if somebody says, I have a problem, I'm like, don't worry about it. We'll figure it out. I'm like, no, no, no, no, no. We'll figure it out. I always say, like, stay out of the weeds. I always say, like, hi. Everyone has to say hi. Super, super high. No weeds. No weeds. Just because the weeds just drag you down.
Erica
Yeah. 100%. It's all mindset.
Kelly Calorin Bensimon
You gotta reach out and where you've had so many failures, like I've had. You do not wanna be in the weeds. Like, you're just like, no, no, no, no. There has to be. Be something bigger and better and brighter and shinier. Let's go for it.
Erica
Awesome.
Kelly Calorin Bensimon
But I am very positive, even though I've had so many failures.
Erica
But you should. But that's what makes you positive.
Kelly Calorin Bensimon
Oh, Erica, really?
Erica
It's true.
Kelly Calorin Bensimon
I appreciate that. Okay. Don't you think? I mean, you're so interesting.
Erica
Imagine if you'd been so boring. You'd be so bored with yourself.
Kelly Calorin Bensimon
True. I guess so. Yes, I would be bored.
Erica
I'd be so bored.
Kelly Calorin Bensimon
I'd be so bored. I would be.
Erica
You'd be, like, picking at stuff. You'd be, like, making trouble.
Kelly Calorin Bensimon
I think I would be. I would totally be making trouble.
Erica
You'd be making trouble. How lucky for you.
Kelly Calorin Bensimon
Yeah. You know, you just made other trouble for other people.
Erica
Okay, so what else are you working on that you want the world to know about?
Kelly Calorin Bensimon
You know, I mean, they know about, like, what I'm working on. I mean, they're just, you know, I just want you to follow me on social media and I want you to live with me. I want you. I don't want you to live vicariously. I don't want you to be a voyeur. I want you to live with me and see what I'm doing every single day. Because. Cause I put a lot of time and effort into social being very real. Like, okay, guys, this is where I am right now. Oh, I picked up some dog shit. Hold on one second. On my way to do something else. And it's just like. I just want you to see the real world through my eyes. And it's really important that you do that because a lot of people, they want to give you this image, and I don't have an image. I just wanna highlight all my friends Highlight all their successes, celebrate everyone that's doing well, and, you know, make a lot of mistakes along the way and.
Erica
Make people laugh and do you think in terms of social posts?
Kelly Calorin Bensimon
Make myself laugh, yeah.
Erica
You wanna entertain yourself?
Kelly Calorin Bensimon
I do wanna entertain myself. Yes.
Erica
I like that. Yes. I think it's good for women to want to entertain themselves.
Kelly Calorin Bensimon
Yeah.
Erica
I think it's good to be self entertained. I love to entertain myself 100%.
Kelly Calorin Bensimon
I mean, I'm always like the. I'll, like, talk to anyone anywhere. People are always like, why are you talking to them in the elevator? I'm like, just saying hi.
Erica
I don't know.
Kelly Calorin Bensimon
I don't know. I'm just like, who are you? I like your suit. What's going on? I'm just a very, like, open person.
Erica
Yes. That's amazing.
Kelly Calorin Bensimon
Not open legs. Not open legs.
Erica
Not open legs. Open person. I think that that will be the title of today's episode.
Kelly Calorin Bensimon
I don't like to talk about work.
Erica
Really?
Kelly Calorin Bensimon
Well, no. What, you want me to talk about real estate? You want me to tell you my strategy in real estate, Monica? No, I actually am super interested in that. Okay, you don't want to hear that because people are very.
Erica
Well, you don't want to give other people your strategy.
Kelly Calorin Bensimon
Well, they couldn't do it anyway.
Erica
Well, tell me your strategy then.
Kelly Calorin Bensimon
Okay.
Erica
This is a nerd podcast.
Kelly Calorin Bensimon
Okay. Nerd pod. Oh, yeah. Okay. This is my thing. Hit me. Your strategy. I feel like we're gonna be very good friends. I feel like you and I are gonna be on text chat.
Erica
I would be very happy.
Kelly Calorin Bensimon
What do you think about that?
Erica
I'm excellent at text.
Kelly Calorin Bensimon
Yeah. You're gonna be like, no, Kelly.
Erica
No. I love that.
Kelly Calorin Bensimon
So, like, we could be. It could be like, no. Or it could be, like, on. You could be like, you're on it. Or it's a no. Oh, no.
Erica
I'm a constant. I'm like a. Okay, but what's the real estate strategy? Do you like real estate?
Kelly Calorin Bensimon
You know what? I like lifestyle.
Erica
Okay, great.
Kelly Calorin Bensimon
So. And I know that sounds, like, super cliche. People are like, I'm a lifestyle expert. I'm like, oh, you are. Okay. What does that mean? Like, what are these titles?
Erica
I like lifestyle.
Kelly Calorin Bensimon
I know, me too. But I mean, I once got a title, so. But I guess under. I guess just for, like, the sake of just categorizing it, like, so a lifestyle umbrella. And because I worked in fashion for so long and I edited so many magazines, I mean, you have to rem. I was at Elle Accessories, Gotham, and Hamptons. All three at the same time. So it was 50 issues a year.
Erica
Okay.
Kelly Calorin Bensimon
That's a lot of issues.
Erica
So you're like, I know how to churn through what things should look like.
Kelly Calorin Bensimon
I know how to churn through. I know how to cut. I know how to churn. I know how to edit. I know how to stage. I know what looks good. I know what doesn't look good. I can tell who's gonna do well.
Erica
Okay. Yep.
Kelly Calorin Bensimon
Very quickly.
Erica
You have an eye for talent.
Kelly Calorin Bensimon
I do. I have a strong eye for talent and a really keen ear for narrative. Like, I can tell immediately if someone's fake. And so with the real estate, what I've done is that I have taken. I took my social umbrella because when I first started in real estate, I started because my mother fell ill and she got pancreatic cancer. And she was. She passed with a very short period of time.
Erica
Thank you.
Kelly Calorin Bensimon
Thank you. It was really devastating for our family. And so before she passed, she was a very strong woman. And she told me, she was like, I need you to maintain. Make sure that we sell our family properties. So I did that for. I got my license immediately to do that. To do that in a way that's very unconventional. Do not do what I did. And I'm not gonna tell you how I did it, but I. It just. Let's use the word unconventional. I did it in a very short period of time, and I was not playing around. Okay. Got my license and started selling. And everyone was like, you're just a model. You're like a nobody. You're just a pretty girl. You're an idiot, and no one's gonna buy anything from you. I was like, well, I kind of have bought and sold and built my own homes before on my own, by myself. I know that.
Erica
Without supervision.
Kelly Calorin Bensimon
I know. With no supervision and no one to parent me through it. So I kind of done that. So I think I can help other people. And since I am more of an expert than you are, I think I can do that too. So I've always been, like, battling that. You're pretty, so you're stupid. And so I decided to take social media, and I went to every single new development. This is. New development was like a buzzword, and people are like, what's new development? I'm like, oh, my God. There's like, roller skating rinks. There is like, yeah, there's all types of activities. Basketball courts, bocce ball, pickleball, and everything. So I became this, like, expert in new development because people would Ask me like, oh, what do you like? And I'd be like, this place has this. I know. And they're like, what? What? How do you know that? I'm like, oh, I went to this place. I went to that place. This one's in Brooklyn. This one's over here. And we were like, what are you talking about? I'm like, oh, I. I went there, and then I videotaped them.
Erica
Yeah. And I looked at it, and I went.
Kelly Calorin Bensimon
And I put it on my social. And so I had all these people from all over the world looking at all these new developments. So that's really kind of how it started. And then I just kept shifting and. Because all the. Because I was showing these people the best of the best from new developments, like, exactly what I was doing in fashion at Elle.
Erica
Yeah, 100%.
Kelly Calorin Bensimon
Then I did that on my social. I used my social as kind of a method magazine format for that. And then I switched gears and just started sending emails to my clients. Yeah, Smart. I'd be like, hey, guys, I have something. And one of my clients, during COVID I was like, my client's looking for 30 million bucks. What do you guys have? One guy's like, oh, I have something. I'm like, oh, okay. So he's like, come and see it. I went to go see it. I took a picture. One picture. Sent it to the client, and he's like, okay. He's like, how much? And I was like, I don't know. He goes, well, Kelly, how much? I said, well, you tell me. And he goes, what do you mean? I said. He goes, isn't there a price? I was like, sure. What is it? He's like, what are you talking about? I'm like, what are you talking about? I'm like, yeah, like, what do you. This is the photo. What do you think it's worth? And he goes, 41. I go, I think 42. And he goes, okay. Ten days later, we sold it for $42 million. The number one deal downtown. No way. That's amazing. From no price.
Erica
Amazing.
Kelly Calorin Bensimon
Donna will tell you, like, we were both like. I was like, should I give a price? And I was like, no, don't give a price.
Erica
Good for you. That's ballsy.
Kelly Calorin Bensimon
But that's, like, not real estate. That's not like real real estate. Most real estate is like, 14.95. It's like, I'm not a car salesman.
Erica
I think it is real estate, though. It's. Well, it's not the establishment, and it's not the established Practice. And it's not how it's done.
Kelly Calorin Bensimon
I don't have supervision. Erica, you're not, this is the common thread. There's no supervision. I'm out there in the wild.
Erica
You're like, I'm hustling. And then you're like, can I do it again and again and again and again and again.
Kelly Calorin Bensimon
So smart. And then I'll figure out. Then I started thinking to myself, like, just been hearing all, you know, these guys talk all the time and everyone's talking about generational wealth. And I'm like, what is generational wealth? I'm like, oh, generational wealth is putting money in people's pockets. I'm like, that's what generational wealth is. I mean, there's the big bucket of generational wealth, but then there's the everyday generational wealth of making sure that money is coming through. So when things, you know, recently, now we're in a very volatile situation. So I work in a very high end building and I'm just like, the prices aren't, I don't like these prices. These prices are really annoying me. They're just not what they're. It's not what it's worth. So I just amped up the rent by 45% and sold it and rented six apartments. Seven apartments, seven apartment in 53 days and there's only 50%.
Erica
I think what's interesting about you, I think you don't give yourself credit is one is you are the gig economy, where work is going is no one's going to have one full time job in one place. Everybody's going to do like 10 jobs and you are that, you're like organically that. And then the second thing is like, if you look at Nil, which I used to work a lot in when I was at Barstool, which is like name, image, likeness, which is essentially what's going to happen. The most valuable athletes are not going to be the best athletes on the field. They need to have talent, but it's all about their social 1000% and that's also you. And you're using the assets you have and your editorial eye and your experience to curate, edit and kind of, you have good feel. And I think that's what's so interesting. I think you're like an embodiment of a lot of where things are going.
Kelly Calorin Bensimon
Thank you. Thank you. I think also I don't have a lot of fear that you don't care.
Erica
You seem to, you don't have, you're not inhibited.
Kelly Calorin Bensimon
No because if I don't try, I'll never know.
Erica
Yeah, 100%. And I actually think that's a good thing from being a model, which is you're used to being exposed and just.
Kelly Calorin Bensimon
Being told you're never Good enough.
Erica
Yeah, 100%. See, the rejection doesn't.
Kelly Calorin Bensimon
I don't even think about rejection.
Erica
Yeah.
Kelly Calorin Bensimon
People are like, oh, you know, it's like, something will happen. Don't feel bad. I'm like, no, no, no. It'll be fine. Don't worry about it. We'll just keep going. We'll keep pushing stuff. I mean, another good example. Now I'm gonna brag because now you're making me feel guilty. Here we are.
Erica
Okay.
Kelly Calorin Bensimon
So another good example is one of these amazing developer in the Hamptons. He really develops some of the most beautiful properties in the Hamptons. And he's like, okay, I'm gonna give you my personal home to sell.
Erica
Okay.
Kelly Calorin Bensimon
And I was just like, oh, my God, this is gonna be the worst. Like, he's in real estate. He's a developer. He does this all day long. Like, he's just such an icon. And he's giving me his. His property. So he was like, okay, just put it on the market for this. I'm like, that just doesn't seem right. It doesn't seem right. Doesn't seem right. And I was like, I signed on. I was like, the number doesn't work for me. It just is not working for me. And she's like, why? I'm like, I just can't wrap my head around that number for that area. So I told him, I was like, I'm taking it off the market. He's like, what do you mean? I'm like, I'm just gonna take it off. And then I would send it out to my clients. And I was like, I would be showing it. And then I'm like, I'm gonna it back on. And he goes, okay, for what? I was like, a million dollars more. And he's like, what?
Erica
You're like, yeah, that's not.
Kelly Calorin Bensimon
I'm like, that's what's not going to happen. Three days later, we got an offer and we're closing it next week.
Erica
It's amazing. It's got. I think real estate has got. It's human nature, but it's.
Kelly Calorin Bensimon
It's everything.
Erica
Marketing.
Kelly Calorin Bensimon
It's like, why would that person want a hot pink flamingo boot?
Erica
Yeah.
Kelly Calorin Bensimon
Like, why would a person want, you know, like an interesting. Like, why would people want to, like, be out there on social like, why would people want to do these things that are interesting and gay? Why? It's like I'm just. I don't know, I just. I just. I guess I'm kind of mildly fearless.
Erica
Yeah, I love that. Mildly fearless would be a great T shirt.
Kelly Calorin Bensimon
That would be. Right?
Erica
We should make that as a T shirt.
Kelly Calorin Bensimon
Oh, my God.
Erica
Okay, I'll make you that T shirt.
Kelly Calorin Bensimon
Okay, you make.
Erica
I have a business proposition for you offline too.
Kelly Calorin Bensimon
Okay, good. Well, we could be offline and online.
Erica
Online.
Kelly Calorin Bensimon
We can be both.
Erica
Okay, great.
Kelly Calorin Bensimon
I like business propositions.
Erica
Okay, great. I got one for you.
Kelly Calorin Bensimon
And I like Nil.
Erica
Nil's great. You name, image, likeness.
Kelly Calorin Bensimon
Yeah, I just never thought of myself like that.
Erica
Cuz I'm like that.
Kelly Calorin Bensimon
I'm like always like, just doing my stuff.
Erica
You're just making stuff, right? Okay, I love that.
Kelly Calorin Bensimon
It's like even like veggies made great. Like, I was just eating it because I was just eating well, and now.
Erica
You'Re like, oh, I'll help you. I'll help you find more people to eat that.
Kelly Calorin Bensimon
Right? Just don't ask me to cook it for you.
Erica
No, please. That's nice.
Kelly Calorin Bensimon
I mean, I tried. Yeah. I'm just not good at it.
Erica
Like too much. Yeah.
Kelly Calorin Bensimon
Wait, wait. Yeah, I'm just like, I know my. I know my language. I was like, what is this? I'm like, oh, it's an air fryer. I'm like, oh, okay, hold on. There's fire.
Erica
Thank you for coming to do this. I'm so grateful.
Kelly Calorin Bensimon
You're the best. You're the best. Thank you.
Erica
So big. Thank you to Kelly for joining us. I hope you liked this episode. I enjoyed her very much. We had an event here this morning which was pretty awesome. Eat your veggies, everybody. Veggies made great. I also think it's an interesting trying time at work. And I think work is imperfect, just like people are imperfect. And it is a journey. And thinking. I kind of meant what I said at the beginning of the episode is being able to think about compromise, being able to do an after review about yourself and what you're doing and how you're doing it is really, really important. And. And then going to the nth degree to do things the right way, not cutting corners is super important. I think the not cutting corners thing I'm thinking about a lot. In the weekends I've been like, gardening sounds like a funny word. I'm like, basically doing lawn care and landscaping. And one of the things that I've really been realizing about it like, I'm in the fight with this big wisteria bush right now. I have a big wisteria bush in my yard. And all I can think about is that show on Wisteria Lane. Do you know that? The show, the murderous show with the housewives ladies. What was that show called? Desperate Housewives. Okay, we're having a Housewives episode. So Desperate Housewives. So I have this big wisteria bush, which I will send a picture. I'll give you a picture of. And it was built over a metal trellis. And clearly nobody has trimmed this Trellis in probably 25 years. And I'm being generous on the 25 years. And the wisteria tree or plant or whatever it is has broken the trellis. And there's metal coming out everywhere. And the thing's just like. It's like having a large plant muppet in your yard. The thing is just enormous. So I started to trim it last weekend, and my arms are hurting. Cause my shoulders are, like, all messed up. And then I don't have the arm strength that I'm like, clipping, clipping, clipping, clipping, clipping. And then it's like. Then I got to the. The next thing, and then I was like, all right, now I gotta cut them.
Kelly Calorin Bensimon
I gotta figure out a way to.
Erica
Cut metal and cut the trellis out. And what I was thinking about as I was doing it is you can't cut corners in yard work. Because if you don't pluck the weed or you don't prune the plant all the way, or you don't have the trellis be strong enough to hold the plant as it grows, it's all going to break. Like, there's no hiding it. There's no, like, shoving it under the carpet. There's no ignoring it. It is. It's just happening. And I think it's been a good lesson for me because it is tedious work. It's work you have to do every day. You got to get the job all the way done. And, you know, like, you do an activity or you do a job, and then you're like, I'm tired. I want to go do something else. Or, ooh, there's something better happening. Or, ooh, look over here. Or somebody texts you or something. But really seeing things through all the way, I think is becoming also kind of a rare skill. And not cutting shortcuts when you can and also not taking the shortcut when you want to is going to be a bigger and bigger driver and differentiator at work. So that's it. Thank you for listening.
Episode: Kelly Bensimon on Real Housewives, Real Estate & Reinvention
Date: September 29, 2025
Host: Erika Ayers Badan
Guest: Kelly Killoren Bensimon
In this episode, Erika Ayers Badan sits down with Kelly Killoren Bensimon—former Real Housewife, author, top-tier real estate broker, and serial reinventer. The conversation explores Kelly’s multifaceted career, navigating public perception, her approach to resilience, lessons in leadership, and the parallels between reality television, real estate, and personal growth. Throughout, the tone is candid, lively, and sharply observant, with both women sharing unfiltered insights on work, life, and the art of pivoting.
“Running a project and managing a team… is really about compromise. And being able to get to compromise is really important.” —Erika [03:15]
“I think it indicates a bigger challenge, which is people aren't saving, there is a lot of debt, and… there's some struggle, which is natural because you're in your 20s.” —Erika [07:25]
“I loved this… how great to have done something and then rethought the way you should do it.” —Erika [13:20]
“I just was, you know, raised to work smart. And then enjoy your life.” —Kelly [16:56]
“I went on Housewives because… I need to really make money for my children… and I wanted to widen my scope.” —Kelly [21:02]
“It was actually a really good lesson… I learned to just be much more cautious about who people are and where their energy lies and what they're thinking versus what I was thinking.” —Kelly [25:34]
“Always let your guard down… be open to things that are super uncomfortable. That's the genesis of emotional growth.” —Kelly [28:50]
“Failure drives me. And when people tell me no, I'm like, oh, really? That's so nice for you. I'm just gonna do that better and even more better and better and better.” —Kelly [31:17]
“I had all these people from all over the world looking at all these new developments. That’s really kind of how it started.” —Kelly [38:17] “Ten days later, we sold it for $42 million. The number one deal downtown. No way. That’s amazing. From no price.” —Kelly [39:37]
“I just can’t wrap my head around that number for that area… I’m gonna take it off. And… a million dollars more… Three days later, we got an offer and we’re closing it next week.” —Kelly [43:29]
“If I don't try, I'll never know… I don't even think about rejection.” —Kelly [42:03]
“It’s actually only going well if everybody’s unhappy… ultimately running a project… is really about compromise.” —Erika [02:24]
“Tapping into their 15 grand to pay for stuff… that's just the reality. That's like working in your 20s.” —Erika [07:02]
“You're always reinventing yourself… always uncharted territory, and you're trying to, like, navigate and make things great.” —Kelly [27:38]
“If it's like, you know, I got slammed around a couple times, and you know, but I mean, that's called endurance.” —Kelly [27:11]
“Failure drives me… I'm always like, what are your thoughts? Criticize me… I want to move forward on that.” —Kelly [30:55]
“If I don't try, I'll never know… I don't even think about rejection.” —Kelly [42:03]
“Let your guard down… that's the genesis of emotional growth… emotionally and mindfully open to other people.” —Kelly [28:50]
“I just was… raised to work smart. And then enjoy your life.” —Kelly [16:56]
“I guess I'm kind of mildly fearless.” —Kelly [44:03] “Mildly fearless would be a great T shirt.” —Erika [44:07]
| Segment Topic | Timestamp Start | Notes | |----------------------------------------------|----------------|---------------------------------------------------------------| | Leadership & Compromise | 00:26 | Opening thoughts on compromise at work | | Gen Z & Retirement Savings | 05:32 | Financial pressure and literacy for young workers | | On ‘Staying in Your Lane’ | 09:00 | Jamie Dimon advice, challenging status quo | | Lessons from David Ogilvy & Mickey Drexler | 12:00 | Shortcomings & business rules | | Kelly on Work Ethic & Multitasking | 16:35 | Curiosity, compartmentalization, always doing multiple things | | Entry into Real Housewives | 21:02 | Motivation and impact of show | | Navigating TV & Public Perception | 23:30 | Preconceptions, pecking order, learning lessons | | Resilience and Reinvention | 27:09 | Endurance, core values, advice for others | | Failure & Growth Mindset | 30:34 | Kelly: “Failure drives me…” | | Real Estate Strategy & Social Media | 34:33 | Kelly’s unconventional tactics, leveraging her network | | Bold Real Estate Moves | 39:37 | $42M deal, raising prices, taking listings off market | | Embracing the Gig Economy | 41:06 | Multiplicity, branding, NIL (name, image, likeness) | | Fearlessness & Trying New Things | 42:03 | “I don’t even think about rejection.” |
Kelly’s life is defined by adaptability—moving fluidly between careers, finding lessons in failure, and transforming public misperception into opportunity. She openly discusses her time on Housewives as both a practical move and a learning experience, emphasizing the value of being open, the ability to compartmentalize, and the drive to provide.
Kelly explains how editorial and fashion skills translate directly to curating real estate, especially in a social media-driven age. Her methods are unconventional—leveraging visibility, narrative, and bold pricing strategies as unique differentiators.
The conversation ties back to current work culture: necessity of side hustles, using personal branding as leverage, and challenging norms. Both host and guest agree: having a point of view and flexibility are rare and valuable career qualities.
Erika and Kelly’s mutual admiration is evident, with talk of T-shirts (“mildly fearless”) and possibilities for further collaboration, both online and off. Kelly’s mantra for success—“Let your guard down, be open, be mildly fearless”—serves as both a summary and a call to action for listeners seeking their own reinvention.
For more unfiltered career and leadership insights, follow the Work podcast or visit Erika's Substack.