Real Estate Broker

Lisa Simonsen, the top Luxury Real Estate Broker in the U.S., shares her journey and ambition to be the best at whatever she does. She advises not to hold onto something you never had and to be cautious of sharing your dreams with others who may not handle it well. The episode has a celebrity flair, big city attitude, and big dream swagger.

Follow Lisa on Instagram.

Check out Lisa’s website.

See all things Dia Bondi here.

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Lisa Simonsen, the top Luxury Real Estate Broker in the U.S., shares her journey and ambition to be the best at whatever she does. She advises not to hold onto something you never had and to be cautious of sharing your dreams with others who may not handle it well. The episode has a celebrity flair, big city attitude, and big dream swagger.

Follow Lisa on Instagram.

Check out Lisa’s website.

See all things Dia Bondi here.

Dia Bondi  00:19

Hey everyone, this is Lead With Who You Are and I'm Dia Bondi. On this show, we explore and discover what it superduper means to lead with who you are. And we're doing it with people who embody just that across industries across disciplines across the globe. In this episode, we're talking with Lisa Simonsen about her journey to becoming the nation's top luxury Real Estate Broker. We all have ambitions, some more hidden than others. And today, Lisa shares with us her loud-and-proud ambition to be the best at whatever she does. She shares some gems in this episode, like don't hold on to something you never had, and to be careful with who you share your dreams with, as they just might not be able to handle it. Well. This episode has a little celebrity flair, big city attitude and a dream big swagger. Let's go. Hey, just a quick reminder, you can subscribe to this show on your podcast platform of choice. We're live nearly everywhere and you can always listen to the show at If there's a leader or innovator in your life, who is it their shiniest when they lead with who they truly are, Please share the show with them. And rate subscribe and leave us a review makes a huge difference in the reach that the show has when you let everyone else know what you love about the show. Thanks so much. Lisa Simonson is a luxury Real Estate Broker at Douglas Elliman Real Estate. She began her stellar real estate career over a decade ago and quickly achieved a position within the top half percent of all real estate brokers nationwide. She set sales records for the Plaza Hotel residences all not on the public market and executed entirely through her personal contacts. She has dozens of record breaking townhouse sales throughout Manhattan, both on and off market and many large deals in partnership with Knight Frank with Danish and Caribbean roots. She has a long developed and well curated global Rolodex. Lisa speaks internationally and is a frequent guest on television and radio programming. At home in New York, Lisa provides a complete suite of capabilities and services in real estate. And we're happy to have her here on the show today to talk about her journey and how she leads with who she is. Welcome, Lisa. So hello, Lisa. And thank you so much for being with us today on the show you are a leader in luxury real estate with a significant personal brand along with a role on in reality TV. And I perceive you as someone who is ambitious and driven. And I'm having you on the show today to learn about your career and your goal getting journey, your story and how you've led with who you are along the way. So a little bit, think of like of your how of the work that you do and the career that you've built. So I work with a lot of ambitious women and project as like an auctioneer. And my hope is that your story and your journey can accelerate folks and women who may be listening today to help unstick maybe where they're stuck on lops unlock something and help them put their foot on the gas in a way that is aligned to who they actually are. So they can lead with who they are. So hello, Lisa.


Lisa Simonsen  03:58

Hello. And thank you so much for having me here, Dia. You're an amazing woman. It's you know, I feel very privileged to have some time here today. I think that the you know, if I look back on where I was, and my life trajectory and what has gotten me to here, I had an unusual childhood. I had a wonderful childhood, but I grew up with my Danish mother in a small town in Canada. And she was extremely academic. In fact, when she moved to heaven, she had six degrees. And her message was always you need to be smart. Don't rely on your looks. And she had six degrees. She was a lawyer or a doctor. So she and she also made sure I had a great education. She worked many jobs to make sure that I went to private school. I also grew up with my grandmother who was completely the opposite, who said to me just rely on your looks be beautiful and nothing else matters. So I had to do different messages growing up. And I like to think I took the best of both of them. I don't know if that's what other people would tell me. But so that's a little bit of the how, and growing up, or at least moving to New York in the 90s. And having, always just having aspirations of doing more, and not more necessarily financially, but just more, I'm never satisfied. And I think that's a fine line, of course, because it's stop and smell the roses. However, I want to, I want to smell the roses very quickly and move to the next.


Dia Bondi  05:32

That's beautiful. And I liked his maybe now that we have a little bit of that context, start with the question we start on the show with every time which is, how might you answer this question today? Who are you? Who are you today?


Lisa Simonsen  05:46

Yeah, I am a businesswoman. I am in working, you know, always doing things that challenge me, I just got my Florida license. So I'm not a great student. That was very challenging for me. I work out everyday, that's easy for me. So I always like to challenge myself to things that are very uncomfortable. I don't like sitting in front of a book, or zoom for hours and learning things. So that to me is great to just go right out of my comfort zone. I have three children, I get up at five in the morning, make sure I have breakfast with them. And then I'm on to you know, I'm very career driven, and very passionate about what I do. And always pushing the envelope always looking for things that are different, and not ever been boxed in. I was in fitness before this. And I really like who I am right now is looking forward to the next 10 years. I feel like I'm in the best part of my life, one of my new team members. He's a very famous boxer. And he sent me a great tape and it was with the horses, you know, racehorses can, you know they have the blinders on? You can only go forward, you can get the horses when they're racing, they can look sideways or backward. And that's where I'm at right now. That's who I am. Now, today, I'm not going backward. I'm not going to look sideways, I'm going forward. And in fact, when I was doing a New Year's, you know, post, just came out of my mouth naturally. I said, I'm not doing resolutions this year. I'm doing solutions. And I really, I was very sort of impressed with myself that I said that because it just flowed. And that's true. It's solutions. And I think there is no one walking around that can't be empowered by that. Because resolutions is kind of corny, I'm gonna lose five pounds, and I'm not gonna have selections.


Dia Bondi  07:35

I don't do any resolutions.


Lisa Simonsen  07:37

Forget it. Forget resolutions. They're stupid, or they're not stupid, but it's not. You know, it's cliche. What is the solution? And every single person can use that word. When our children are annoying. That's our husband or boyfriend, our lover, life business team members. What's the solution here? What can I do? We now pull back the control and figure out a solution. Maybe we need to, you know, so that's why I'm now I'm figuring out solutions. And I'm thinking of the racehorse.


Dia Bondi  08:03

Beautiful. So maybe you are, you know, maybe you are the racehorse, I love it. Tell me a little bit so folks can understand sort of what your luxury real estate practice and business look like.


Lisa Simonsen  08:15

There's a few comments or thoughts that I have when I hear this. We are luxury. That's what the Simonsen team brand stands for is luxury. However, and I pride myself on this, and I've I've sometimes been pigeon holed, which we really work against, "oh my god, I never thought you'd be interested in my apartment. It's 500,000 Or a million dollars." I take the same pride in those sales as I do in the Uber sales where I break records, because business is business and I treat every sale exactly the same. So that's just very important for me. So yes, we are luxury. I do luxury. But my team does everything.


Dia Bondi  08:55

Sure. And so can so people can kind of imagine on a revenue scale. What are your, can you say out loud what kind of revenue you're doing in your business right now? Just to give people a sense of scale?


Lisa Simonsen  09:08

Yeah, well, I mean, we do you know, we break records, we sell things for $5,500 a foot that was probably the one of our recent records, we do price ranges, obviously, well over $20 million. And definitely continue to break records all through New York.


Dia Bondi  09:29

I imagine it's a very exclusive place to be in and there's not a lot a lot of players at that level. And as you think about the business that you've built, the reputation that you've built, the ambition that you have, sort of followed to create it. What have been one or two key moments along your path that you feel have been instrumental in bringing you to where you are now?


Lisa Simonsen  09:52

Our business and I just recently had this I worked very hard in a deal for a few years. And it was right there. I mean, it really was right there, fell apart. And even me at my moment, I definitely had a pity party. And I was told that 15 years ago with a very dear friend of mine, who when I had a deal fall apart, "oh, God, I would have dummies.." like Lisa. He's like just telling me it's okay. What do you need? Do you need an hour day week? What do you need to get over this? Because you gotta like, you know, move on. And that's something that is, it's so fundamental in learning about moving forward, and really not getting stuck and having as many balls in the air not in a foolish way of sort of jumping around. But you know, we really, when things fall through, it really is next.


Dia Bondi  10:38

Yes, yes.


Lisa Simonsen  10:40



Dia Bondi  10:41

And what was that circumstance 15 years ago, and the deal fell apart was that ...  It was a board refusal, it was a co op board, which is what we have in New York, and it was a board refusal, and didn't work out. But my more recent deal that fell apart was a really sort of a game changing deal. I was going to be you know, sort of on every page of the newspapers and the Wall Street Journal, etc. And we were there, and then it fell apart. And that did kind of us. You know, and I think that it's just a great thing in life to remember, especially when you're in business, you have to be on to the next and sounds like that's been instrumental in you being able to continue to build even in the face of those evaporating deals, right? Absolutely. And it's never, you know, we have to also and I think, like, I like to remember this, we really can't hold on to things we never had. So the reality is that check ... Say that, again, we can't really ..


Lisa Simonsen  11:33

... hold on to things that we have never had.


Dia Bondi  11:36

Beautiful. Yes.


Lisa Simonsen  11:39

So even though my client wired the millions of dollars to the buyer, excuse me, the seller, I had never got, my commission had not arrived. I had already started maybe spending some of it. However, it actually had not cleared the bank account. So you know, I was having a pity party. But I really didn't. Yeah, I under I get why I was upset two years later, but it hadn't really happened.


Dia Bondi  12:03

I love that that's so beautiful. The idea of not really holding on to something you never really had. It's like there's this gap between where our mind is our ambition is our thoughts are and the reality actually the pragmatic truth. And, you know, we have to live in this balance all the time, of like leaning into our vision for ourselves, you know, imagining what the future will look like when you know, you've got to keep your eyes on the horizon, but also not hold that so tightly, that it holds you hostage, right?


Lisa Simonsen  12:38

That's exactly right. Absolutely.


Dia Bondi  12:41

So as you think about the key decisions that you made along the way that were really critical to building your career, what might those be? Decisions. Not things that happened to you, but decisions you make? Can you imagine? Can you tell us one or two key decisions that have been critical to bringing you to where you are.


Lisa Simonsen  12:59

The decision for me is when I was a trainer, I My decision was, I'm not satisfied, because I'm seeing people that work no more than I do. And they are making more money and has spending less time so it was a decision that I wanted to do what they were doing, and figure out why Why were we both working the same amount of hours, and their paycheck looked different than mine. So it was a decision to move from one career and take a risk that something I was very good at, into another.


Dia Bondi  13:30



Lisa Simonsen  13:31

It was a decision of not this is not I'm not satisfied, I'm happy but I'm not satisfied. That was a decision.


Dia Bondi  13:37

What did it take to make that decision?


Lisa Simonsen  13:40

My decisions are motivated by what I never want to have happen. So when I look at certain people, that helps me make a decision like that is not going to happen to me and I'm going to make a decision and I'm going to leave fitness and go into real estate.


Dia Bondi  13:52

That's so interesting. So while I don't do resolutions because I you know, I find that like goals and things that I want show up and get named and claimed kind of on a rolling basis throughout the year. There's no reason to just you know, peg it to the turn of the year. I was on a run this last weekend and I have in the Northern California coast wrong along the ocean a place that just begs you to think about your life you know, it is so huge and huge and majestic and I was thinking about you know in this year what I wanted to no longer say yes to you know it kind of points to what you're talking to around identifying what is not going to be a reality for me.


Lisa Simonsen  14:39

Yes, that's exactly that's exactly right.


Dia Bondi  14:41

So as you think about the goals so in Project: Ask Like An Auctioneer, we've got a goal to help a million women ask for more and get it in use asking us success strategy and and I've been in front of hundreds and hundreds and hundreds of women's my keynotes and workshops talking about what they want, and what their goals are. And in that, in that work, I've sort of done a little pattern matching and pattern seeking. And it sort of turns out that I can recognize sort of three goal types. And I want to share those with you and ask you which one you imagine is your gold type. All right. So, you know, I've noticed, and I work with a lot of women, you know, in technology and social impact, we have women in product, we have, you know, sales leaders a lot, because I'm here in Silicon Valley, a lot of folks in Silicon Valley, and the types of goals go like this one, are recognition, goals, goals that, you know, say I, you know, I want a gold medal, I hold the trophy, I earned a certain amount of income, I got the bonus, I got the public recognition. And these are these, these come in also the forms of like, title, right? And those are great. They are a particular kind of goal.


Lisa Simonsen  15:49

I'm the Chair. I'm the Chairman, I run the top, right.


Dia Bondi  15:52

Yeah, exactly. Like the and these are legit. The second type goal type I noticed are folks who sort of like, love and pursue mastery of something, it's not about being recognized for it necessarily, but knowing they're excellent that the person that picks up a violin and says I am going to be masterful in this, even if I play for only my cats, you know, people who are like, I want to be masterful in my particular the this the sole data scientist on a team who has deep knowledge and mastery of something. And then the third one is are folks that are like have experiential goals. And that's very interesting. I've talked to a lot of women who think these are not goals, they'll say, I don't really care about titles and money. And you know, I don't care about being the best at something I just want to have, I just want to be done at four o'clock, I just want to travel a month, every year with my family. I just want to you know, they want to have certain kinds of experiences. Experiential goals. So I'm curious of those three recognition, mastery of experiential, which ones might yours be?


Lisa Simonsen  16:54

I'd say one than three, I'd say both.


Dia Bondi  16:57



Lisa Simonsen  16:58

Yeah, I'd say both. I'm a Gemini.


Dia Bondi  17:02

Yeah, you always have to have two sides of a coin. So as you think about your, your recognition goals, what form do they take? And when did you when did you sort of know that these types of recognition goals were important to you?


Lisa Simonsen  17:16

Well, I think I didn't, it again, it sort of just happened. It's like how television has always, you know, presented itself to me, I don't have an agent, it's just been a phone call. We want you, you know, we want you to audition for blank. I think that same with the recognition, I've really had only two careers in my life, Fitness and real estate. And I've excelled at both of them. So it's just my personality type. When I look back to even physically what I did with fitness, you know, I was definitely not the trainer standing telling, I was running, you know, a incredible amount up and down hills. In fact, I ran the Big Sur marathon. So, the recognition has just happened as being you know, a, whatever you want to call it, but I've excelled at anything I do I excel at just because that's my personality, and I don't do anything halfway.


Dia Bondi  18:03

And experiential goals when you talk about what do experiential goals look like for you?


Lisa Simonsen  18:08

Experiential goals, I just think that you know, that's so much part of life. And I think the more mature we get, the more you know, it's like with my kids we have our places they've been to in the Caribbean or here where and I'm like, You know what this is I want them to we want to go here we want to go there. So I think I have if you come to you know our home, I'm very meticulous about our year and book on memories. Because I feel like at the end of the day, that's all we have is our memories so experiences that really is it at the end of the day, no matter where we are financially. We remember like when we're mother was cooking or this or that whatever it is so experiences to me that sort of really the name of the game.


Dia Bondi  18:47

When you you talked in the beginning of our conversation about sort of being that you know the racehorse of the blinders on you know, always forward like an extreme amount of focus. What are your goals look like today?


Lisa Simonsen  19:00

My goals? Well, it goes back to I almost don't don't even use the word goals. Goals to me are almost the resolutions because I you know, years ago have done goals, I want to lose three pounds, I want to not have no more you know, wine on during the week or whatever, whatever it is right? Spend less at Starbucks, but I think now it's not really about that for me it is My word is really and I'm sticking to it solutions.


Dia Bondi  19:25

So talk to me a little bit about you know, about the maybe the asks that you made before we started our recording today you were talking about this notion that like you know, you don't get what you don't ask for and can you look at your career and name asks that you've made that have changed everything?


Lisa Simonsen  19:43

I definitely believe ask not get not and it's not in a greedy way or inappropriate way. But I think as one is continuing to move forward in life that you really need to know your value and step it up. And I think a lot of people get I, you know a lot and it's communication is very difficult for for people. So I always like to communicate and do it with integrity. And also just stepping up the bar on what an you know, there's that very famous book, Thinking Big, it's as easy to think small as it is to think big. So and you can't ask for big, of course, if you're not, you know, you aren't pulling, you have to, it has to be in alignment, right?


Dia Bondi  20:32

Can you can you think of a specific ask that you maybe have made in your career where you did go big? I think of, you know, the very first ask I made early on in my career that sticks out as being a major level up was asking to come on board with somebody who ended up being sort of my early mentor in my career. And it was a I mean, it was like, it was a big break moment for me. And I remember being like, this could go one way or the other, but I'm gonna, I'm going to ask, I'm gonna ask in a way that is outsized, almost, to my, you know, to my resume, or my current skills. And it was, I mean, it was the most thrilling and wonderful experience because it was a way for me to sort of stand tall in my own potential. And I'm just curious, if you have a particular ask that comes to mind that you've made in your life a specific one to a specific person or organization that that stands out as being pivotal?


Lisa Simonsen  21:28

Well, I think when I started fitness, and I met Cindy Levy, she's the Editor In Chief and still a very dear friend of mine, and I was extremely nervous meeting her, she's, you know, sort of the Anna Wintor of the publishing business. And I went in and told her, I had my company, which was called Simonsen Says what I wanted, and I was, again, you know, behind the scenes internally, extremely like, like, Cindy Levy, and I really had not done anything sort of conventionally when it came to training, I didn't work at gyms, I didn't do any of that fit that you'd have to do this or that. And so here, I wasn't, she gave it to me. She put me in all of her magazine, she put me into something that at that point, that was called the self challenge. And where I was training three celebrities to show you know, everyone, there's always time to work out people that have very busy schedules. And that was, I think, that would be a great example, I really had no, I really was sort of like, Oh, my God, you know, but I did it. And it was sort of life altering at that point in my career in fitness.


Dia Bondi  22:28

I think it's an interesting thing you point to, to that you made that ask after not having the conventional trajectory that would be expected for you to have when you make an ask like that. And I think that's something really important. There's sort of like an easy way to get locked in for us to think that, firstly, these five things need to happen before I'm allowed to make a particular ask. And it's not always true.


Lisa Simonsen  22:51

It's not true at all, and everything in my life. Again, growing up in Edmonton, as you know, a biracial child with a Danish mother. Everything in my life, that's happen all my big moments. If you just talk to someone, they tell, that's not gonna happen.


Dia Bondi  23:08

So talk to me about what you dream about for yourself now.


Lisa Simonsen  23:13

Well, I don't even like to think of dreaming. I think I like to think of an action plan because dreaming and hoping, a little bit are dreaming and hoping. And so I have to, one needs a plan. They need to have intention when I wake up in the morning. And it's not that I'm some spiritual guru. But, you know, again, dreaming and hoping I try to, it's wonderful to you know, lay on the beach and dream.


Dia Bondi  23:35

Okay, so what do you plan for yourself?


Lisa Simonsen  23:37

I plan, I feel like I'm only starting. It's only beginning. It's like the book, the television. My team is right now I have incredible people, very interesting, dynamic people joining my team, all the all different backgrounds and stories. And so I feel that I'm just starting the best part of my, you know, career right now, with a lot of interesting history to get me here.


Dia Bondi  24:01

So writing a book is one thing that's slated for yourself.


Lisa Simonsen  24:04

Absolutely. Writing a book, the hit television show, which is, of course, is very important. And I have been asked to do shows I have not chosen to do. So it's not that I'm desperate to see myself on TV, but it's really about branding, and Instagram and social media. So I that's the reason that I did a show that I felt felt it was right on brand. It's about being a mentor, and someone switching their careers. And so that is another definitely something else that you know, is moving forward opportunities with television.


Dia Bondi  24:36

Will your book have an opportunity to serve you say that, you know, it's about being a mentor? Will your book be a way to scale that voice to bring that mentor voice out into the world?


Lisa Simonsen  24:47

 100% That's exactly what I want it to be. And that's what gives me when I think about it, it's so much inspiration, because so many of my friends will say well what would lead to do or their daughters follow me And to think that I could inspire someone that just to me is incredible.


Dia Bondi  25:03

On that same theme, and maybe to wrap our conversation if there were, you know, two pieces of advice to give to young ambitious women who have, you know, idea and a vision for themselves, what is, and maybe are at the beginning of a new chapter, what is your advice to help them get to the next level?


Lisa Simonsen  25:22

It's a great question. I It's a wonderful question. Because it's hard to, there's, that's such a big topic, but there's some definite, you cannot, you have to be very careful about the people you surround yourself with, you are really the sum of you know, and this isn't me coming up with this line, this is anyone that says this, you are the sum of the people you spend time with. So you know, and I think you have to be very careful with who you're sharing your dreams with. Because most people can't handle it. And most people are just surviving, and they're miserable. So if you have a really great idea, and you tell your grandmother or your aunt or your best friend who, you know, is mad at their boyfriend, Oh, yeah, you know. So yeah, I just think one has to be very private on certain thoughts, and keep them only with people that also get it. And that's not a lot of people. So be very careful who you're sharing your information with. And be careful or be aware of who you're spending time with.


Dia Bondi  26:19

I love that you're pointing to this idea of being careful with who you're sharing your dreams with so that they are not getting stepped on or you know, there's it doesn't have


Lisa Simonsen  26:28

Oh, exactly. And listen, tell tell someone with a Gulfstream who has, you know, great art collection and is running a company or dream and they'll probably say that's really interesting. Let's talk about it tell someone who is miserable and working on a job they hate, your dream, they'll probably say, that's never going to happen.


Dia Bondi  26:47

It's interesting. There's a this is something I talk about in my book is like an auctioneer that we have to let our dreams be known. But you're almost layering another nuance on top of that, which is make your dreams be known in a choosy way.


Lisa Simonsen  26:59

In a cheesy way to share your dreams with that person who share if you want to write a book, don't talk to someone who's never written a book, right? So, choose if you want to be you know, the best barber in the city, don't talk to the person who just lost, you know, the job, the only job they had, like, just choose carefully, who we're sharing our information with? Or who are we're sharing our dreams with.


Dia Bondi  27:23

And to finish our conversation. As you think about embodying who you are and using it to lead. What does that mean for you? Does it mean bringing your whole self to all of your challenges? Does that mean, you know, activating your own internal courage to be successful? Like what does it mean for you to lead with who you are?


Lisa Simonsen  27:45

I think it means being authentic. I have to, you know, I have to be authentic he and people under know if you're at when I moved to New York, I studied acting and I was a horrible actor, because I can't fake it. So does that mean if I disagree that I'm you know, rude or anything else? Of course not. But I think authenticity people, they get authentic. They know when they're connecting or they're being sold something. Right? So I think leading with who I am, is starting with being authentic.


Dia Bondi  28:13

Beautiful. Thank you, beautiful answer, and probably the most direct and, and, and I don't know, brief when we've had so far.


Lisa Simonsen  28:24

Well, I think that if you spoke to anyone if you took 15 People that know me, whether it be a best friend to you know, someone at the local barber store, no one would ever say that she's not authentic and that doesn't work for everyone. Authenticity.


Dia Bondi  28:38

Lisa, thank you so much for being with us today. It's great hearing your story. Lead With Who You Are is a production of Dia Bondi Communications, scored, mixed and produced by Arthur Leon Adams, the third and Executive Produced by Mandy Miranda. You can reach out to us at Or leave us a voicemail at 341-333-2997 you can like rate, share and subscribe at Apple podcasts, Google podcasts, Spotify or wherever you get your favorite podcasts. Go to for shownotes and to learn about all it is that we do to help you speak powerfully and lead with who you are.

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