Ariel Sassoon // The Leahy Sassoon Team

The Leahy Sassoon Team

ogether with his partner Devin Hugh Leahy, Ariel Sassoon has closed over $400 million in residential deals over the past several years, and in one recent week, Ariel sold $10 million dollars worth of real estate. That puts him and Devin in the top 2% of real estate brokers in the entire United States.
He is a natural conversationalist, which certainly helps him and his team. Ariel also has a unique advantage: he’s a real estate content creator genius. Ariel and his team create custom videos for many of their listings that help tell a story rather than simply highlight the amenities of the property, and they do so in an entertaining and informative style, using high-resolution, studio quality video. He has also made several videos in which he shares his tips on how to film listings.
Ariel and Devin have been featured in Forbes, The Real Deal and many other media outlets. (They even got former President Donald Trump to notice one of their articles.) While our conversation will certainly help people in real estate, his advice, especially on how to “influence” others, can help anyone in the business world.
~ Nesanel

My parents lived in Japan for a few years after they got married, but then they moved to Great Neck, which was an up-and-coming Jewish community at the time. That’s where I grew up.
“When my grandparents were kicked out of Cairo, my grandfather saw an opportunity in Japan, so he took it and ended up opening an export business. My father was born there and lived there until he was of college age and came to America.
“My mother is a baalas teshuvah who helped instill a lot of spirituality in our home. My parents divorced when I was five years old, but they were able to remain cordial. I alternated weeks between my parents, and I even had my own guitar in each home.
“I went to North Shore Hebrew Academy for elementary school, but my mother wanted a higher level of Yiddishkeit, so I transferred to Yeshiva Har Torah in Queens. I spent some of my best years there and made many friends with whom I am still in touch. After attending HAFTR for high school, I went to learn at Reishit in Israel.
“I had some really great rebbeim there. Till today, I listen to Rav Eli Marcus’ weekly mussar shiur on Thursdays. I sort of regret that I didn’t take more advantage of my yeshivah years. I was recently discussing this with Rav Shlomo Farhi, who told me that ‘youth is wasted on the young.’
“I always wanted to do something on my own. I have a creative personality and I get bored easily, so I wanted to do something that would constantly pique my interest.
“As a kid, I did the usual selling lemonade and candy stands. But I was more interested in other hobbies. Although I don’t play much today, I immersed myself in guitar for 12 years, even playing several small gigs. I like to develop skills. When I was learning how to shoot and edit videos for the real estate space, I immersed myself in that for a while.
“I got my first taste of the corporate business world at my sister’s wedding. My father had a friend who was the CEO of a Japanese investment bank, Mizuho Securities. The CEO asked to meet me, saying that he liked the way I ‘worked the room.’ I was 17, and he offered me an internship. I interned there for three summers.
“I speak Spanish, French and Hebrew, but I never attempted Japanese. My father speaks it fluently.
“Next, I attended Baruch College, where I studied economics, thinking that I would pursue a career in finance. At first I was interested in options, but in today’s market, you really don’t have to do much other than look at screens all day long. At a certain point, I realized that I found finance boring, so I tried my hand at real estate. It seemed more exciting and I liked working with people.
“My first job was working for a luxury property group called KSR, which had a small division in residential real estate in New York City. I was lucky to make a deal on a rental property during my first week; $5,000 at a time was a lot for me. I never ended up graduating from college. I only have 14 credits left, but I’ve never found the time or the need to finish. By the way, I’ve never shared that with anyone before!
“I started to really love what I was doing and envisioned my future in residential real estate. I brought in some new sales listings, but I wasn’t getting to where I wanted to be. I knew I needed to go elsewhere, and I thought that Douglas Elliman, one of the largest real estate firms in New York, would be a good fit.
“My plan was to have a meeting with Howard Lorber, the chairman of the board of Douglas Elliman. I knew which restaurant he liked to eat in, so I gave the mâitre d’ my business card and asked him if he could give it to Mr. Lorber. He said, ‘No problem!’ but I knew he’d forget, so I visited several times to remind him. One time, the mâitre d’ told me, ‘Mr. Lorber is actually here right now. Give me another card and I’ll hand it to him.’ A minute later Mr. Lorber came over to say hello, and I told him that I wanted to sit with him for a few minutes for career advice. ‘Sure,’ he replied, and he said that I should email his office to set up a time. I ended up sending 12 emails before I got the meeting. But when we finally met, he offered me a job at Douglas Elliman.
“I worked under two different teams before starting my own team with my partner. It was while working under Luis Ortiz that I learned how important it is to create a visual presentation with a listing, although we do things very differently today.
“One day, a young man named Devin Hugh Leahy joined as a new agent, but there weren’t any extra desks for him. So I offered him mine, and we sat across from each other at the same desk. I could see that he was a hard worker and really understood the numbers game in the industry.
“That year, I had a 650K listing, but I was going to be away for Pesach. I told Devin that my phone would be off for a few days, but if he was willing to show the apartment and would end up selling it, we would split the commission. He might have been a newbie, but he was a natural, and over Pesach he got an accepted offer.
“At that point we started to work together on every listing. We sat down in a pizza shop and decided we needed a website that would lend legitimacy to our new venture. Devin knew someone who said he could build a professional-looking website for $10,000, but for that amount I told him I’d try to see what I could do on my own. Through trial and error, I came up with a solid-looking site.
“One day I came across the videos of Gary Vaynerchuk and Casey Neistat. Vaynerchuk is a successful entrepreneur, and Neistat became famous for his travel vlogs on YouTube. One thing I noticed was that their videos were entertaining as well as high-quality, and I wondered if I could translate them to the world of real estate.
“I decided to create a weekly vlog. We didn’t have too much business yet, so I had some time on my hands. I decided to document the life of a real estate agent. I shot the first seven videos on my phone, posted them online and got over 1,000 views. My friends liked them, so I bought a camera and taught myself how to edit them so they would look like those of a modern YouTube influencer.
“A few months later I was in London and someone stopped me on the street and said, ‘Are you Ariel Sassoon? I’m from Sweden, and I love your vlog!’ It was then that I recognized the full power of what we were doing. When I took my newfound love of marketing and video production and applied them to our listings, it really changed things for us.
“Devin and I now have several agents working for us. We help them grow their careers and offer hands-on advice on every aspect of the business. I oversee the creative side of our work while Devin is the salesman. He knows how much every property has sold for in Manhattan and sets the prices on our listings. Although we can both do what the other does, we focus on our own areas of expertise.
“We generally work with sellers to try to create a narrative. We always look to do things in a creative way. I’ve flown drones out of high-story apartments and create stories based on our listings. We even once made Donald Trump angry when he was president thanks to one of our marketing ideas.
“I have two rules when it comes to our business. The first 10% we earn goes to maaser. I try not to hold onto it, and hand it over directly to someone who needs it. Our second rule is that the next 10% goes into LS Media, which is the part of our company that focuses on marketing. We don’t charge our clients more for our marketing and video production. They pay our percentage for selling their home, and we do all the work that goes into selling it.
“Thank G-d, we have done quite well with our approach. While I don’t want to brag, there really isn’t anyone else out there who does what we do when it comes to creating a visual story of a listing. By the way, that can mean video and/or photography.
“We help breathe new life into old listings. There was a $15-million apartment on Central Park West that was on the market for several years. The owner’s daughter convinced her parents to give us a try, and we went into contract in 36 days.
“Over the years, we have continued to try to improve what we do every day. I am driven because I really love what I do.”

People starting out in real estate find themselves in a Catch-22. They need to show what they’ve done, but they have nothing to show. What’s your suggestion?
I think it’s important to document your journey. Do anything that will create awareness of your career. It can be a LinkedIn post or a WhatsApp status. Then be patient, because it’s inevitable that you will fail. I failed so many times. The vast majority of the deals you work on won’t close. But you learn from every experience, and you do get better.
You have to know before even starting that things won’t always be easy. You need to have patience. There were times when I had zero dollars in my bank account and made investments that crumbled. All you can do is make failure your friend. The hardest thing to do is not be discouraged. It may sound counterintuitive, but you have to put in the work without expecting anything in return. But the results will come.

You do all the shooting and editing yourself? Wouldn’t it be smart to delegate?
Sometimes I have someone else shoot the video or I hire freelancers, but I never delegate the creative direction of anything we do.
I’m not saying that there will never come a time when I hire others. We recently hired a creative assistant to tackle some of the smaller tasks.
Sorry, you can’t just say that you made Donald Trump angry without sharing the full story.
Ha! Okay, it got us in trouble, but here we go.
We had a small one-bedroom listing at Trump Tower on Fifth Avenue. We got the listing around September 2016, when Trump was running for office. Traffic was slow and there really wasn’t much interest; we showed it about once a week.
Then November rolled around and Trump was elected and everything changed. Seven Twenty-One Fifth Avenue became one of the most secure buildings in the country. With the Secret Service guarding the building, suddenly our small listing had potential.
We often send out email blasts about specific listings, as many brokers do, so I came up with what I thought would be an eye-catching subject line: “For Fifth Avenue Buyers Interested in Secret Service Protection” and sent it out. It did its job and led to a few showings, after which I didn’t think about it anymore.
A few weeks later I got a call. “Hi, is this Ariel Sassoon? I’m a reporter from Politico, and I was wondering if you had any comment on your email touting the Secret Service as an amenity of Trump Tower? We’re running it within the hour.” I was blindsided, and of course had no comment.
I called my partner Devin and I was worried that we were about to be ripped in the press. He said, “That sounds great; we might actually get some publicity.”
Politico released the article, and then almost every mainstream publication including The New York Times ran the story. As the media don’t like Trump, we were blasted. Don’t forget that we were still members of a team back then and relatively low on the totem pole. It was probably the most famous press release at Douglas Elliman at the time, and it wasn’t a good one. Howard [Lorber] wasn’t happy, and we were under tremendous scrutiny, although we didn’t know it yet.
To make matters worse, before we heard that Douglas Elliman was upset, we made a video of us touring the apartment at Trump Tower and thanked all the publications that had written about us. Within an hour we got a call that we were being terminated, because Howard was rightfully upset. We went to our manager and asked for a meeting with him so we could apologize. We realized that it looked bad for Douglas Elliman, even though we had no malicious intent.
When we met with Howard he said, “I’m not happy. I don’t know if you guys are stupid or just don’t care, but let me tell you what I have on my hands right now. Donald Trump just called me in the middle of a Cabinet meeting asking me why I have these two idiots going around making a stink and generating all this negative press.” It turned out that Howard and Trump were friends, and we knew we had to beg for our jobs.
When Devin pointed out that this was our first infraction, Howard replied, “You only have to murder someone once.” At the end of the meeting, Howard said that he had to think about what to do with us. We weren’t fired, but we were effectively put on probation.
This was shortly before I began vlogging in 2016. That year we did over $100 million in sales volume. After we’d done $70 million in sales, I asked for another meeting with Howard and asked if I could bring my camera along; he agreed. When we walked in, he took one look at us and said, “Probation is over, guys.” We laugh about it now, but back then it was crazy.

Did you sell the apartment?
After all the publicity, the sellers became way too ambitious in their price, and it didn’t sell until many years later.

How would you define and then reach out to one’s network?
That’s a solid question. I would say that a network has three components. The first involves creating general awareness to target potential clients. The second consists of colleagues. One of the most critical parts of our journey is the other agents we get to know along the way. Other real estate agents are a great source for deals and leads. Finally, there’s what I call the “fame” category. That’s when you try to create something cool and informative and put it out with no direct target audience and hope that it reaches people.
The key is targeting your network with things that interest them and keeping them in your loop. You also don’t want to be sending out email blasts too often so that people won’t view them as spam.
Another great resource is creating your own space where others come and view your influence. That can be LinkedIn, YouTube, Twitter, a blog or even a dedicated WhatsApp status.
In our case, we created something called LS Analytics, where we produce weekly reports on the real estate industry in Manhattan. We’ve even seen other agents use our presentations in their listings. Just try to create useful content and people will pay attention.
I saw your most recent video called “A Childhood Dream, Battery Park Penthouse.” I found it fascinating. It was only 90 seconds long, had no narration and featured a child running up the steps into the apartment and enjoying the view. Really well done!
Thank you. We just went to contract with that property. We often utilize different techniques when telling a story. Here, we wanted to show a place that was perfect for someone to raise children.

Wow! It wasn’t even seen by that many people.
Exactly. But one of the people who did see it ended up buying it. Targeting your content is much more important than “going viral.”

Do you believe that every listing needs a video?
No, but you should make them visually intriguing. A video, when applicable, is great for getting someone excited, but it’s not always the correct move.
We had a listing of a townhouse in Brooklyn, and the current homeowners were very messy and there was clutter everywhere. A video would have been very detrimental. Instead, I virtually staged the apartment by removing the clutter while still maintaining the original design of the floor and walls. I often tell my clients that I don’t need them to clean the place, because I can digitally remove most issues. For example, I can change the bedding, the pillows or add more light. I have a team that helps me implement my vision.
The bottom line is to get the client in through the front door. If it isn’t feasible to create a compelling video, we try to create an environment so someone will think, “I really need to see this.”

Have you ever considered starting your own firm, not under the Douglas Elliman brand?
I don’t really see how it would help me. In fact, I see being connected to Douglas Elliman as a win/win. The 30% we pay them takes care of so many things. We work in a gorgeous office on Fifth and Madison, and we don’t have to worry about lots of the back end that would be our responsibility if we had our own firm. The top successful brokerage teams work the same way for a reason.

What can you do to prevent agents from leaving your team?
You can’t. When they do leave, you have to view it as having had a great agent who helped build your team while he was with you. And if you’re a broker, you have to remember that helping your agents helps you as well. We always use all the tools at our disposal to help our agents, but when they leave, all you can do is make the best of the situation.

I once interviewed a successful broker who was a master at digital staging. Is that the new norm for high-end listings?
I’ve seen a lot of agents get in trouble because they aren’t virtually staging a listing; they’re virtually renovating their listing. There’s a big difference. I won’t change the actual core layout of a space; I’ll simply make it look more visually appealing. Digitally staging when done right can be helpful, but it must be done on a very high level. If you digitally stage a property and someone can tell that you Photoshopped it, it would be better to have never done it in the first place.

How do you deal with stress?
I’m a pretty calm individual and I have a great support system, with the main support coming from my wife. I like to cook, which is a good stress reliever. I will also share that lately I’ve been working on delving more deeply into my Judaism. I daven Minchah every day and try to connect with Hashem. ●

Thank you to my colleague, Ami’s Editorial Coordinator Dalia Maidi, for the introduction. ~Nesanel

To read more, subscribe to Ami