Winning in Real Estate with Kelly Killoren Bensimon
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You know, there was this one time before I did my own money rehab when I checked my credit score and I realized I had no idea what it actually meant for my financial future. That's when it hit me. It was time to get serious about my money. We've all had that moment, right? Whether it's saving for something big or finally paying off debt, we all get to a point where we need to make some real money moves.

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Feels like progress. I love hosting on Airbnb. It's a great way to bring in some extra cash.

But I totally get it that it might sound overwhelming to start or even too complicated if, say, you want to put your summer home in Maine on Airbnb, but you live full time in San Francisco and you can't go to Maine every time you need to change sheets for your guests or something like that. If thoughts like these have been holding you back, I have great news for you. Airbnb has launched a co-host network, which is a network of high quality local co-hosts with Airbnb experience that can take care of your home and your guests.

Co-hosts can do what you don't have time for, like managing your reservations, messaging your guests, giving support at the property, or even create your listing for you. I always want to line up a reservation for my house when I'm traveling for work, but sometimes I just don't get around to it because getting ready to travel always feels like a scramble, so I don't end up making time to make my house look...

guest-friendly, I guess that's the best way to put it. But I'm matching with a co-host so I can still make that extra cash while also making it easy on myself. Find a co-host at Airbnb.com slash host. Happy New Year's Eve, money rehabbers. It's Morgan, the EP of the show. As we look back on the year, one of the biggest questions that came up again and again was all about how to make the most of the cuckoo crazy housing market. And I think that's

So today we wanted to re-air an episode with one of our favorite real estate experts, Kelly Ben-Simon, who also was a Real Housewives of New York cast member. Today she shares all about the do's and don'ts of navigating the real estate market, whether you're looking at an investment property or trying to beat out competitors with a great application.

You're also going to hear a bonus story in the middle of the episode from me about how I make a little extra income through real estate. So don't miss that part. Again, it's around the middle of the episode. Here's Nicole and Kelly. I'm financial expert, Nicole Lapin. It's time for some money rehab. ♪ Money rehab ♪

Today, I'm chatting with Kelly Ben-Simon. To Roni fans, Kelly is an icon from the two seasons she spent on the show over a decade ago. Now, she's a successful real estate agent who closed nine figures of sales in 2021 alone. Of course, with real estate being such a hot topic, I wanted to get all of her inside expertise. But there's another money trail I also wanted to follow, the money trail of the real housewives.

Full disclosure, I've never actually seen an episode of The Housewives. I know I'm probably the only person on the planet, but somehow I am still hooked. Despite not watching the show, I see all of these headlines about cast members who have gone bankrupt or are embroiled in some kind of financial scandal. And my question is, why? Why are there so many Housewife stars with financial skeletons in their closet? Seems to be a story there, and I wanted to find out.

Kelly Ben Simone, welcome to Money Rehab. Thank you. I love that, Money Rehab. It's such a great title. Thank you. I think we're going to keep it. How did you start in real estate? So I actually stumbled upon real estate. Unfortunately, my mom fell ill and wanted me to help sell our family properties. And my father's older, so I oversaw that, quickly got my license. And then I

And I wasn't really thinking that, you know, this is like just one million dollar listing had gone on and I was, you know, just finished. I just retired from Housewives, getting my MBA. And I was just like, and I just kind of stumbled into this because I had to do it. And so out of something that's so traumatic came something like so incredible. Who would have known that, you know.

She's asking me to do something to preserve our family, and all of a sudden, I'm pulling in $110 million on my own. I was just about to ask that. I was waiting to throw down that number because you were like, I just stumbled into this little thing. Casual $110 million in sales later. Last year. Yeah, just last year. In one year. One year. Started with the number one deal of 2021. So we're in COVID. Yeah.

No one's in New York City. And I sold 150 Charles, front house of 150 Charles for 42 million, all cash. Nicely done. Yeah, that was really nicely done, actually. A friend of mine happened to be looking for a $30 million apartment for his son. Does that guy want to adopt another child? The one who wants to buy a $30 million apartment? Who else?

who is that kind of person? I mean, they're just New York investors. I mean, I think a lot of these New York, a lot of New York guys knew what was going to happen. They, they forecasted that there was going to be something happening. They were just, they were just bought everything up. Because it was on the down. So,

So buy low, sell high. And so when... Buy low, sell high. That's your business. That's right. But it works in real estate too. You just, it's really hard to time the market. It's hard to figure out the trends of real estate. It's so city specific. What do you think is going on with the real estate market now? If you could give us a pulse check.

Well, so, you know, stock market's your business. Real estate market's my business. But, you know, we had, you know, 14 contracts, over $4 million last week. And four of those were over $20 million.

And it was Thanksgiving. So that's really interesting. I mean, there's a lot of big cash buyers out there. So when people ask me about my business, they're like, well, people aren't selling anything. I don't want to sell. I'm like, well, you can sell. It's like any market. If the person wants what you have, they're going to pay the price for it. So it doesn't matter what the state of the stock market is. It's like people want what they can't have. And the good news about my business is I have a lot of great properties that people

most people can't have. Well, it sounds like it's really a relationship business. Completely. Completely. But this isn't something that I just fell into. People are like, oh, she got her license and all of a sudden she's doing $42 million. This is not how that works. I mean, I went to Columbia. I have my MBA. You know, I had great mentors along the way. I started Elle Accessories. I started Gotham Magazine. Like, I'm used to working with, you know, investors. I'm used to working with advertisers. I'm used to, like, you know, I think...

One reason that real estate really resonates with my clients is because I know everything about lifestyle. I started a magazine based on lifestyle.

So it's like I already put the work in. And so I can kind of sit back and say, okay, this is the strategic opportunity for this apartment. This apartment needs staging. This apartment needs press. This apartment needs a party. Whatever it is, everything needs a little love in some kind of way. And you just can't like, they always say like put lipstick on a pig. Like we don't do that.

I like make it movie magic. I did bid on a place in L.A. and I lost it. So I need help. We've seen these crazy bidding wars. Right. It was like, you know, when interest rates were nothing, lines around the block for open houses, like they were giving something away. I mean, that's for rentals and for sales. Yes. And that's kind of changed as interest rates have gone up. But what would your advice be for winning a bidding war? Well,

To have your financials in order, just be ready to go. Because, you know, for example, my, you know, my daughter is looking at an apartment and they were like, okay, it's not, hasn't even finished yet. It's like they literally, the apartment is in construction and they're like, okay, you need to sell the money, you know, first month's rent, earnest deposit, all this money, like sell it. No checks. Sell like right away.

So you have to be really ready to go. You can't be like, oh, wait, hold on. Let me just get myself together because there is that person that has their money ready to go.

And that's when you lose something. I mean, I don't hate renting. I talk about this a lot too, because if you are taking out a jumbo mortgage and you're paying money every month, most of that's going to interest in the beginning, right? And that's money you're not getting back. So when people say you're throwing money away by renting, you don't get that interest back. You don't get a bunch of other stuff back. You don't get closing costs back. And so...

Do you think we should bring sexy back to renting? I mean, there are so many. I mean, the rental market in New York is just insane right now. And, you know, I think there's a lot of fear associated with buying properties because there's fear with the unknown. And it's not like, you know, because of the volatility of the stock market, people are like, okay, that's a forecasting of what's going to happen in the real estate market. But again, like, you know,

I live in this beautiful building. I just sold, it's approximately, because it's a co-op, so it's approximately 1,800 square feet, one apartment for $2.9 million. And then I sold another one a couple of months later for $4.1 million.

So I basically raised the price of the building. Obviously, the other apartment was a different apartment with a different narrative. But do you see what I'm saying? Like, you can really make really good money or you can, you know, if you're living in a great home, like, for example, like, I represent this insane home on the Upper West Side, 26 West 87th Street, where Billie Holiday, she lived. And it's this phenomenal townhouse. It's been completely renovated for 13.7%.

And, you know, that's a place like if you bought that home, I mean, you could really later on do whatever you want and really make a lot of money. So it just depends. You're not paying a lot of mortgage because you can if you take that big lump sum, like if somebody saved up $200,000 to buy a million dollar place, but they only have 200 grand and they put all that money into their home.

house. They're kind of house poor, and then they can't use that money to put in the market and make more money potentially. So that opportunity cost of the big lump sum sometimes doesn't make sense for people. Well, we have like different buckets. So we've got the Midwestern bucket where they're putting money under their mattresses. And then we have the real estate bucket, and then we have the stock market bucket. So we have like different people trying to figure out their finances in different kinds of ways. And it's just really like

What works for you? Some people are just like, I'm just going to put that cash under my mattress. Which we don't recommend. No, we don't. For the record. But some people are just like, I'm just going to save it for a rainy day because cash is king. Queen. Queen. King and queen. So you may not recommend it, but at the end of the day, sometimes it's good because you

You know, if during COVID, when you had a lot of cash, you could really buy anything you wanted. So just it's there's just three different kinds of buckets. And it's just really what you want to do and how you want to do it. At the end of the day, whether it's real estate, stock market or your mattress, you know, the most important, the number one priority for me in anything that I do with anyone is I tell them like your family, they're your legacy. So you need to give them shelter. I like it. Like that's crucial.

And, you know, food, water and shelter. Those are the things that people need. Everybody needs shelter from the storm. Can we talk about a type of storm? The storm that is the housewives. I think there are a lot of people listening who will know you from Housewives. Do you think there's anything that you learned doing that show that helps you with real estate? I mean, I am so grateful for Housewives and for Bravo because they gave me this massive opportunity.

They basically took my name that was like a small name in New York City and like blew me out of the water. So looking back, this is not something you regret doing. You're happy about being on the show. No. It paid dividends. Yeah. Many, many. I mean, I think that like when everyone ever asked me about the regrets, like the only regret that I ever had was not showing like my real life because it wasn't fair to the single women to.

to not show them like how I was making money on my own. Like they just thought that I was running around, you know, cartwheels, like, you know, like chewing gum, having fun, which is something that I do all the time. But I also know how to make money and provide for my family. And they didn't show enough of that, you don't think? Well, it was, yeah, they didn't want to because they were like, she's a supermodel. And you have to remember too, like back when I was on television in the ice age, it was like 2009, you know,

Being a single parent was definitely not sexy. That was like almost taboo. Being able to provide for your family was like an anomaly. And, you know, just talking about being single was something that's like, oh, you're not with a man. It's like you don't have, you're not a unit. Right. You're not complete. You're not like a traditional family.

So there were all of these interesting layers of things that people didn't want to necessarily hear about. And now people are like, how did you do it? How did you do it? I'm like, I don't know. You ask my kids.

They did it. I didn't do it. I just like pushed them. So we heard rumors that Bravo wants you to come back for a Housewives of New York Legends show. Are you going to do that? I mean, you know, I'm definitely thinking about it. You know, it's like I love the brand and I love the women. So I'm just I'm definitely thinking about it. But leaning more toward yes.

We'll see. Sounds like it. We'll see what happens. I never, you know, you never say never, but you know, everything has to, everything has to align. Hold onto your wallets. Money Rehab will be right back. Hey guys, it's Morgan, the EP of the show. And as you're loving all of these great real estate stories with Kelly Ben Simone, I have another tip for you. Hosting on Airbnb is an amazing way to make your real estate work even harder for you.

I love hosting on Airbnb. Because I work remotely, I'm lucky enough to get to spend summers back where I'm from in Maine. So when I'm away for the summer, I host my apartment on Airbnb, and it's been such a great side hustle. So yes, I am a proud Airbnb host. But what I'm even prouder of is the fact that I got my best friend's mom, Lori, to be an Airbnb host too.

Lori lives in New England and is retired, and she and her husband go off on all these really cool backpacking trips for weeks at a time. And when they're gone, their house just sits empty.

I told Lori that hosting on Airbnb is just a no-brainer for her. Her house could be collecting checks for her instead of just collecting dust. But also, because she's retired, she's just not making the big bucks anymore. And through hosting on Airbnb, she could have some income coming in. That income can help her feel even better about her retirement nest egg, but also can contribute to a slush fund for those phenomenal trips she takes with her husband.

But the idea of having to make the house spotless and coordinate with guests while she's also getting ready for a big trip felt like just too much for Lori. But Airbnb's co-hosting feature changed the game. Airbnb's co-host network is a network of high quality local co-hosts with Airbnb experience that can take care of your home and guests for you.

Co-hosts can do what you don't have time for or just don't want to do, like managing reservations, messaging guests, giving support at the property, or can even create your listing for you. When I told Lori about this, she finally signed up and she has her first guest lined up for the summer thanks to her co-host. Find a co-host for you or for your friend's mom at Airbnb.com slash host. That's Airbnb.com slash host.

And now for some more money rehab. It sounds like it. I mean, Bethany has said that there's always a number to go back to the housewives. Right. Do you have a number? Well, it's work at the end of the day. So there's always a number for everything. It's not a charity. Okay. So what was your, like a ballpark? I don't know, really. Okay. So I'm going to give you $50 million. Would you go back to the housewives? $50 million, I'd probably go back to the housewives. $10 million. $10 million.

We're doing an auction. Why is it 50 to 10? That's terrible. It's usually like 50 to like 47 or like... We're not buying a house here, sister. I'm just trying to buy...

to find the ballpark. That's how I feel. I'm trying to find the range. Everyone's always asking me that. What neighborhood are we in? No, but everyone's like, when they ask me, I'm like, oh, no, no, I don't really like that number. They're like, why? I'm like, which means like 4975. They're like, what? But it sounds like the salary isn't really where you're making the money. But you get paid by episode? It depends on your deal. So there's not a standard thing. Everybody gets. Yeah. I mean, yeah, I don't. I mean, I don't really know what other people are getting. I don't really like a lot of a lot of housewives. They like try to commiserate. I'm like, no, no, I'm like,

I'm good. You don't like talking about it? I like financial transparency. I do too, but I think that you have to be careful, especially on a show like that. It's different when you're working together, but when you're on a show that's being filmed under a microscope on HGTV, I think it's different when you're talking because there's that constant level of competition just gets really, really high.

because of like how much the person's getting paid versus like what's at stake emotionally. Do you know what I mean? Got it. I'm sure Bravo doesn't want everybody talking about it because they'll probably be like some collective bargaining agreement where everybody goes up and tries to get money. But again, like you don't want to be like, you don't want to have, I mean, you wouldn't want to be on a show. You wouldn't want to produce a show where you have like four people already arguing about knowing how much the other person is making. I mean, there's a

balance, right? Because I think, especially for women negotiating in order, this will be a real estate analogy for you, in order to price your house, you need to know the comp of the area. Obviously. Okay. So the same thing works for like salaries, right? If you don't know the comp, like how are you pricing yourself? You're shooting in the dark. Right. That's a good point. But I think that when you're seeing people that are getting like a million versus like other people that are getting like

10,000. I think that that such a, like it doesn't level playing field. And so then people get like at the onset, like ferocious and they don't want that. They want people to be genuine and they want people, they want to like, it's HTTV. You want to see like authentic moments. Yeah.

Although I would argue with housewives, there's been so much financial turmoil for so many of these women that maybe talking about it would be helpful because the number of bankruptcies, the number of financial scandals. Well, I mean, if we talked, if you're talking about actual finance, if you're saying to like so-and-so, like if you went on and were like, hi, this is what you need to do. Or if someone was in a situation with bankruptcy, it,

If you were there to be like, well, I can help you navigate that. I think that's different than like trying to get people to on the onset to be like, you're making 10,000. I'm making a million. Like I'm better than you are, you know, kind of thing. Should I bust into the house? Cause you don't know what's going to, you don't know like who's going to be the breakout star. Like you don't know just because you're making X amount of dollars doesn't mean that you're not going to be that, that you're going to be the breakout star versus the other one. You don't know that.

It depends on like the narrative. It depends on like what they're doing, you know? So I'll be honest. I haven't watched any Housewives franchise at all. You should be on it. Which one should I be on? There's a Potomac. That's not a joke. Okay.

There's Dubai. There's Potomac. They're all over. There's Miami. I'm coming on. I'm going to help these women. There's Beverly Hills. They can tell me. We don't have to put it on. They can tell me how much they're making. I can look at the books because it seems like there's always a headline about a financial scandal on the housewives. There's Jen Shah. There's Erika Jayne. Teresa, I don't know how to say her last name. Chudais. Chudais. Why do you think so many housewives get into financial trouble?

Because I think they lived above their means. I think they get excited. And I think that they forget why the fans want to hear from them. They want to hear their story. And then all of a sudden, they're like, I'm wearing Louis Vuitton. I'm in a G-Wagon. You know, like, I'm killing it. Look at me. I'm

I'm famous. And then all of a sudden, you know, cameras stop rolling. It's like in any business, it's like an entertainment business, like music, modeling, acting. You see all these people like doing so well. And then all of a sudden they stopped doing well and money stops going, you know, coming in. And all of a sudden it's like, you know, then life gets real. So I think you'd be great. I think they would be, you know, I think it'd be great to just have you just like

In general, just like telling women like, you know, how to take care of themselves. I'm in. Sign me up. Because it's not even living within your means. It's living below your means, which is not fun and sexy, but it builds long-term wealth. Just saying. With Erika Jean, she's been having all this trouble with her husband, ex-husband. It came out that she didn't have a prenup or something like that. What do you think about prenups?

It depends on the situation. You know, I think that some situations you should have a prenup. I mean, I didn't have a prenup with my ex-husband. Was that a mistake? No.

No, because I mean, I had money coming in, he had money coming in. And, you know, I just genuinely wanted to, you know, move forward. And, you know, money wasn't the impetus. Like I didn't marry him for money. And I wasn't divorcing him for money. I was divorcing him for freedom and to raise my kids and to give them the greatest life ever. And I just didn't feel like, you know, being with him was doing that.

So I don't necessarily, I don't think of it like that. Like some women are like, oh my God, money, which is great. Or you could flip the script, right? And say like, this is an empowering thing. I'm a woman. I make my own money. Like I need to protect my own stuff. Right. By the way.

Well, there's two sides of it. I mean, I definitely raised my kids with good values and a sense of self, and they've always worked. And, you know, my daughters worked through college, and they've, you know, done everything from, like, babysat to do what, you know, like...

bartending, waitressing, like they've done it all. Personally, I don't know. I mean, it's like, I don't judge people, but I don't marry for the ring. Like I, you know, marry because he's, you know, I married my ex-husband because I thought he was amazing for human. I would, if I thought that was marrying for the ring, like I would have gotten a bigger ring. I think some people think of it that, but,

You know, if you get divorced or if something happens, it's like having insurance. You don't want the state to decide. You just want to be in control of what happens. You can throw it in the fire or whatever. So would you get married again? Definitely. Yeah. I mean, if we're talking about like your inheritance, like your family's inheritance or something like that, like I don't think that that's fair for, you know, for an ex to get that. That's not fair.

But when you bring something to a relationship and you are in the relationship and you're going under contract, you know, it's a transaction at the end of the day. It's a legal contract. I'm going to marry you and this is what we're going to do. And here's the terms of the contract. I mean, that's what it is. So if you don't like the terms of the contract, you probably shouldn't have gotten involved in the first place.

So you're out dating. Yes. How's that going? It's going well. Are you on the apps? Yes. I have a boyfriend. I have a really serious boyfriend. Congratulations. Thank you. When you were dating, did men feel intimidated by you, do you think? No. By your network? No. They're always trying to like take care of me. Men are always like, oh, let me take care of you.

Like it made me feel very insecure. Very insecure. Because you want to take care of yourself. Right. Because it's like, you know, here I have these two girls and what am I going to do? Just be like, oh, okay. Like, let me just, you know, hop into your arms with two. Ready, set, here we go. You know, I felt a big responsibility and people, you know, guys that I were dating were very, very assertive about,

you know, taking care of me made me very insecure. Not to say that I don't appreciate it, but I felt like kind of like it was like, okay, this is the amount of money you're going to get every month. And I was like, what? Wow. Or you didn't want to show that kind of paradigm to your kids too? Right. I mean, the whole thing just really, I didn't agree with me. So with your

With your man. But some people really like that. Like, some people are like, great. Like, at least I know what I'm getting. Like, you know? I mean, again, like, we're talking, you know, honestly. Like, some women just really like that. I just...

That was just never, like, I wasn't raised like that. If I told my father, by the way, I'm marrying this guy and he's going to give me X amount of dollars per month, my father would be like, I spent all this money on this great education for you to think like that? You went to Columbia? He would not be happy. No, he passed and he would not be happy. He would want me to, like, have a partner and to build relationships.

Together. Yeah, he would want me to build. I think that there has to, like, you know, women have to be able to be doing something that really, like, ignites them and makes them feel whole. So that the relationship where it started off is, you know, it ignited for a reason. And then all of a sudden, you know, you go into this transaction, you sign this piece of paper, this, you know, stone goes on your finger, and all of a sudden the dynamics change, right?

And I think that people get lost. And I think it's not about the money. I think it's about they just get personally and emotionally lost. I mean, I know we were talking about money for you, but I think of it more in an emotional way where I have a lot of empathy for both women and men who get lost in relationships. And I don't want someone to be in a relationship with me that feels like that. For someone like me,

I just, you know, I've waited so long to be with the right person. And, you know, I've met a lot of really great guys, but they're definitely not the right person for me. And

And, you know, I just want to have respect for my partner. And I want him to, you know, do everything that he wants to do. And I want to do the same. And do you believe in, like, a co-creation, talking about work or having him help you with things or connections or stuff like that? Yeah, of course. And I think that's really important, too. It's like you, you know, you have to be a supportive spouse. I mean, you can't just be like, oh, just come over here and let me just...

You know, like Shel Silverstein, where like all of a sudden the giving tree is like this little stump. Like that's not fair. Yeah, it's give and take. Listen, I mean, we're talking about finances, but I think that like there's nothing wrong with being in love. There's nothing wrong with that. You don't have to get married for money. I agree. You don't have to get married because you need to like move into an apartment. It's like...

It's so nice to have someone like you as a role model who can talk to women about finances because it's something that's daunting. And I've had to deal with it all my life. I don't talk about it. I know a lot of the housewives are like, I made all this money and they're throwing it around. And all these women are watching and they're just kind of like, what? What about me? I can't even pay bills. So it's hard. It's hard to see all of that. So-

I just want women to be excited about what they have and who they are and, you know, to like recognize that there are checks and balances and the money that goes in, the money that goes out, and just to try to be mindful of what they're doing. Yeah, I think how people are in different parts of their relationship, if they're avoidant or whatever, it just transfers over to how you approach money too. Right. But it sounds like you're saying to viewers or watchers of The Housewives, maybe don't

emulate what you see. Don't be as frivolous as what you're watching on the show. Right, right. But I mean, at the same time, you shouldn't be like, you know, I need to be rich in order to be, you know, to feel good because, you know, there's so many more things, you know, to be happy. And, you know, I've had so many iterations of my life and I've been through so much, you know, so many like peaks and valleys and I don't feel, I still to this day believe in love and believe in like taking care of myself and taking care of other people.

Yeah. What's one financial piece of advice you would give your former self? It's just what I tell myself today. It's just like, you know, there's a little for me, a little for Uncle Sam, and then a little to put away. Yeah. And I'm always like thinking of my girls, like what we're going to do for them and just like just to be balanced about it.

Because like, I mean, what you were saying before about like, you know, to live under your means, some people just can't do that. Some people just, you know, it's like, you know, my father came from absolutely nothing and he gave us so much education, integrity, you know, a healthy mindset. And he lived way above his means, way above his means. But he created, like, we were his legacy. So whatever he spent was, well, we were his stocks.

It's just kind of like a different kind of way of investing. Way of investing.

Money Rehab is a production of Money News Network. I'm your host, Nicole Lappin. Our executive producer is Morgan Levoy. Do you need some money rehab? And let's be honest, we all do. So email us your money questions at moneyrehabatmoneynewsnetwork.com to have your question answered on the show or even have a one-on-one intervention with me. And follow us on Instagram at Money News and TikTok at Money News Network for exclusive video content. And lastly, thank you.

Seriously, thank you for listening and investing in yourself, which is the most important investment you can make. This episode is brought to you by Progressive Insurance. You chose to hit play on this podcast today. Smart choice. Make another smart choice with AutoQuote Explorer to compare rates from multiple car insurance companies all at once. Try it at Progressive.com. Progressive Casualty Insurance Company and affiliates. Not available in all states or situations. Prices vary based on how you buy.