Lisa Simonsen
Lisa Simonsen

Lisa Simonsen

One of the world’s most successful luxury real estate agents talks business, brokers, and how to maximize time in and out of the office.

When Lisa Simonsen needs help in an area outside her field of expertise, she does some research, hires the best people, and then trusts them to do their jobs. When it comes to luxury real estate, though, Simonsen is the expert. Clients count on her to produce results, and she does, routinely delivering revenues that place her in the top .05 percent of residential real estate brokers nationwide. Her deals in Manhattan have included a $48 million sale at the Plaza—which she executed through personal contacts without going to market—and, recently, a $22.75 million transaction at Abi Chelsea on West 19th Street. 

After a successful stint running her own fitness company, called Simonsen Says, she began working in 2007 for the Douglas Elliman brokerage, where she oversees a team of seven and is preparing to open offices in Florida and Los Angeles. She lives in New York City with her husband and three children and serves on the boards of Phoenix House, a nonprofit drug rehabilitation organization, and Sanctuary for Families, which helps victims of domestic abuse.

Though Simonsen presents an effortlessly glamorous exterior, a combination of discipline, vision, and hard work defines her. On her social media platforms, she never misses a chance to emphasize the time it takes to be successful. In an age of surface perfection, where the tedium of the daily grind is rarely shown, Simonsen’s transparency about the muscle required to secure clients and properties and close multimillion-dollar sales is refreshing. Also refreshing is her commitment to helping younger women in the industry with well-founded advice and not an ounce of condescension. 

During our hour-long chat, we touched on Simonsen’s current stint as a coach on the television show Kendra Sells Hollywood, where ex-Playboy Playmate Kendra Wilkinson tries her hand at being a real estate agent. The episodes serve up typical reality show fare, and it’s easy to question how much of it is genuine versus manufactured entertainment. But Simonsen’s interest in helping Wilkinson succeed seems real. “This was a great opportunity to be a mentor as well as a coach,” Simonsen said. “We all know the feeling when someone wants to put you in a box. Just because Kendra was one thing at one time doesn’t mean she can’t learn to now be a successful businesswoman. I’m rooting for her.”

Lisa Simonsen boarding private jet
Lisa Simonsen boarding private jet

Do you remember the first time you flew privately?

I was very fortunate when I was a teenager—my best friend's father had a Global Express and we went to Sardinia. It was pretty awesome. Another time, we were in Austria with her grandmother, with whom I had a very special connection. She said, “I want Lisa to see Scotland.” The freedom! I was around 17 years old, and I remember thinking, “Wow—you just call the pilot, and off you go.

How does business aviation help your business?

It’s so much more efficient. We all have these very busy lives, juggling children and all those things. All of a sudden, the three hours you used to spend at the airport are yours again. It allows me time to bond with a client and build a relationship. It's a luxury, of course, but it makes such a difference.

How do you manage your day?

Everyone is busier than they were 20 years ago—always going, going, going. A friend of mine once said he’s not going to ever run out of money, but he's definitely going to run out of time. Time is our most valuable asset. I am very aware of every moment in the day, and I won't even allow my team members to start heading into the wrong conversation. That's a waste of time. Five minutes here, five minutes there—that's time we can be building the business or raising brand awareness. You have to always keep your radar up for when you're wasting time.

You have spoken a lot about setting a positive mindset for the day.

I like to get up very early and get a jumpstart. I get my thoughts together. When you have children, if you have a couple of hours before the craziness starts, it's a great way to get ahead of the day. I’m conscious of words. When I'm doing a deal, I'll say when we close that deal, not if. I teach my kids that in the morning, there is no whining. We start with, “Good morning.” There's gratitude. Words matter. Affirmations matter. It all adds up to the quality of our life. 

How do you handle the emotional complexities of the broker/client relationship?

I originally was a fitness trainer, and I had a company that was very successful, and my skill set has not changed. Before I was selling lifestyle; now it’s real estate. My clients trust that they’re with someone who knows what they're doing and will give them great advice. I like to tell my clients: “I'm not here to sell you anything. I'm here to advise you.” There’s so much involved with finances, and they need to know that you're certain about their investment. We [real estate agents] get into people's lives. Maybe it’s a husband and wife who want separate bedrooms. They need to feel completely comfortable and trust you.

What is your advice for someone hiring a real estate broker—or any professional, for that matter?

I don't care if it's a shrink or an accountant, once I do the research, I commit to someone, I trust them, I take their advice, and I stick in my lane and what I’m good at. But sometimes people don't take the [expert’s] advice. If you don’t trust your broker, maybe you're with the wrong broker. You need to be confident about the person who’s giving you advice.

Lisa Simonsen on private jet
Lisa Simonsen on private jet

Do you ever have to put up boundaries with clients?

Not often, but it happens. There have been deals where the client did not listen to me, and they lost something they really wanted. Sometimes it’s just not the right fit, and maybe I'm not the right person for certain people. And if it's not working, it's not working. Some clients suck your energy. We have to be aware of where we're putting our time. And if we just take out a calculator and think, I'm going to earn X with this client, but if I spend 20 or 30 minutes a day, the time starts adding up quickly.

What do you look for when hiring a member of your team?

How many people are actually willing to do the work? It’s also about smart work because we all have friends who have worked 18 hours a day and not necessarily gotten where they wanted to. Success comes from a combination of smart effort, work, and grind. Also, you're only as good as the weakest part of your team. When there's anything going wrong on my team, I only look at myself. I'm going to start doing a seminar on how to be prepared for a real estate job interview because I often see a certain sense of entitlement where a candidate expects to start with $20 million deals instead of putting in the work.

You spend a lot of time mentoring people. Why is giving back important?

It was in my DNA and how I grew up. My mother had six degrees and she really went to what you could call extreme. She was always for the underdog—we had prisoners living with us when I was a teenager! When I was 10 years old, I was in church reading to kids. It’s just how I grew up. I'm very comfortable helping others, and people organically come to me for advice.

Lisa Simonsen on private jet with child
Lisa Simonsen on private jet with child

Do you ever slow down?

For sure! Half the time I have [casual] hats and no makeup on. I love to be glamorous once in a while, but I also love to chill.

How do you handle setbacks?

Everybody falls down, and I have many times. It's about how quickly you get up. Early on I had a setback, and I went into my manager's office, and he listened to me. And then he just said, “How long do you need for your pity party? Do you need five minutes? An hour? Even if you need the day, it's OK. Figure out a time, and after that, snap out of it.” It has always stuck with me because stuff happens to all of us, no matter how great we look on Instagram. It doesn't matter if it's Bill Gates or the Kardashians, stuff is happening to all of us all the time. People who are successful—they're able to take it all day long. They're able to compartmentalize and keep going.

This interview has been edited and condensed.