In this Expert Success Story, discover how Ryan Kaplan has used his background as a developer, a down-to-earth yet competent, confident approach, and some good old-fashioned best practices to close Experts deals totaling over $50M in just 18 months. Ryan’s high-profile clients acquired through the program include a pro athlete and one of the wealthiest families in New York City. He says he never would have connected with these clients, and many others, if it weren’t for Experts.

If you want to know what success looks like in the Experts program, look no further than Ryan Kaplan. 

Ryan has been in real estate for 16 years, most recently joining Douglas Elliman as a broker in March 2020. Before entering the brokerage side of things, Ryan spent some time on the investment side as a developer – a background that “gives him a unique and valuable skill set as a buyer’s agent,” according to his StreetEasy Business Advisor, Carlo Romero.

Ryan joined Experts in August 2020, and has quickly become one of the most successful Expert agents in sheer numbers alone. His deals within 18 months in the program have totaled over $50M, with deals ranging in price from $1.05M to $9.65M. That’s an average of over $4M each – one of the highest in the program. Ryan says 40-50% of his total business now comes from Experts.

He’s sold in a number of neighborhoods, including the West Village, NoHo, Tribeca, Cobble Hill, and Carroll Gardens. His deals also span a range of property types, from condos, co-ops, and townhouses to new developments. Ryan started out in Experts as a team member, primarily receiving connections from his team leads, but as a result of his high conversion rate was quickly able to earn status as a top Expert and expand his own eligibility within the program. 

Here’s how he got there.

“Well, it’s sort of like why online date?”

Person using dating app

Ryan had a simple reason for joining the Experts program: to connect with more people. Astutely, he compares it to online dating. “Well, it’s sort of like why online date? You’re hoping to meet people that you wouldn’t have come across before,” he elaborates. “In a professional case, I’m hoping to meet clients I wouldn’t have come across before.” 

Ryan notes that it was an interesting endeavor for him, as he was just starting to expand from development to brokerage. “I had a whole client base that I wanted to build out, and this was another avenue to test,” he says. “And thank God I did. It’s become a huge part of my business and introduced me to amazing clients, really exciting deals, and friends too.”

Finding his edge as an Expert

One of the first things Ryan noticed about the program was how relevant his connections were to his experience. He first started receiving leads on buildings he sold in as a broker at Douglas Elliman – some of which he had also worked on as a developer. 


“They got a better match via me, because of all the background I had in that territory.”


“What was helpful was I had several years of experience combing through this neighborhood from an investment standpoint and a zoning standpoint, which dovetailed into brokering in that area,” Ryan explains. “And then Experts came along and started kicking me clients that were within this territory.”

Due to the relevance of the connections, Ryan found it easier to win over these leads and turn them into clients. Not only were his leads a good match for him, but vice versa. “They got a better match via me, because of all the background I had in that territory.”

Ryan’s Business Advisor, Carlo Romero, thinks Ryan’s developer background gives him a unique edge as a buyer’s agent. It’s given him a penchant for matching his clients with the right property for them, in both the short and long term, and for looking at properties holistically. “He’s able to evaluate a property from the perspective of someone who might be acquiring it himself – appreciating its uniqueness, understanding the long-term potential of its neighborhood and location, and understanding the costs and benefits of potential renovations,” Carlo says.

Acting as an advisor, not just an agent

Two businesspeople in New York City looking at tablet

When asked what the biggest surprise of the program has been for him, Ryan said it’s how many buyers are receptive to working with a buyer’s agent. After spending many years in the real estate business, Ryan had the perception that with all the brokers flooding the market, the pool of buyers seeking a buyer’s agent was probably very small. However, his experience in the Experts program quickly proved him wrong. 

“There were a ton of people at a variety of price points – several at very high price points – that when spoken to in a certain way and guided in a certain way, were very amenable and eager to work with me and get my advice on their process,” Ryan says. “That was definitely a surprise.”


“If you want to get to a certain point in the business, you can’t just be someone who unlocks a door and points out how many bedrooms and bathrooms there are.”


However, Ryan also acknowledges that technology has made it challenging for agents to prove to clients that they still offer value. “Tech is taking away some of the things that were expected of agents to do,” he notes, such as advertising listings. As a result, “agents have to be better and smarter at a more narrow scope of things to prove that they are worthwhile for the clients they’re representing.” 

“If you want to get to a certain point in the business, you can’t just be someone who unlocks a door and points out how many bedrooms and bathrooms there are. It’s not enough,” he adds.

Nowadays, Ryan prefers the term advisor to agent. It’s the true purpose he believes people in his profession should serve. “You have such competent professionals giving you advice in your legal, in your investment management, in the stocks you pick. The person who’s advising you to buy your real estate should be as well educated and as technically sufficient as any of these other professionals in your life,” he says.

A lesson from business school

During the first call, Ryan is all about making clients feel comfortable with him, however long that takes. This creates a relationship in which clients can be open and honest. “You just have to be on the phone with them for a long enough time where they become comfortable with you. Suddenly you go from, ‘Oh, this was like a telemarketer, and now this is someone who I’m kind of gossiping about my real estate process with,'” he says.


“If I’m quantifying it, try and be on the phone for 10 to 20 minutes.”


Speaking of call length, Ryan recalls something he learned in business school: the longer someone walks around in a store carrying an item they’ve picked up, the higher the chance they’ll purchase it when ready to check out. “And I find that that rule is totally applicable to your first phone call when you’re prospecting a client through Experts,” he remarks. “The longer you can stay on the phone with them, the more you can talk about, the more ideas you can kick back and forth, the more you can laugh about.”

“If I’m quantifying it, try and be on the phone for 10 to 20 minutes. 20 minutes is on the longer side. But there should be enough content to talk about at least for 10 minutes.”

Confidence, competence, and humor

StreetEasy Expert real estate agent Ryan Kaplan conducts interview

In addition to keeping the client on the phone for a while, Ryan summarizes his approach during the first call in three words: confidence, competence, and humor. He also believes that competence begets confidence. 

“You have to be talking to someone like you’re on the phone with your best friend. If you are too salesy, people pick up on it,” he says. “You will be more confident if you are more competent. If you know what you’re talking about, it’s going to be easier to speak about it.”

Ryan also believes in the power of humor, because at the end of the day, clients need to see their agent as a human being they’d enjoy working with. “I think one of the most disarming things is humor. If you can be funny, if you can be relaxed, a little bit witty, it humanizes you and it’s going to make people want to work with you,” he says. “Because they’re not only making this decision on who they think is going to be smart, they’re making it on who they want to work with.”


“You will be more confident if you are more competent. If you know what you’re talking about, it’s going to be easier to speak about it.”


Overcoming misconceptions

Ryan concedes that many buyer’s agents face an uphill battle of misconceptions. “I don’t think people trust brokers. I think brokers have a stigma of being the used car salesman of the real estate industry,” he admits. “There are a lot of people assuming that if a broker’s involved in a transaction, then it’s more expensive, they’re being pressured towards doing something, and they’re getting information they don’t trust.”

How can today’s agents overcome these misconceptions? Ryan comes back to competence, and surprising clients with your knowledge and problem-solving skills. 

“I think you overcome people’s misconceptions by showing that you have value to add that’s outside of something they had considered,” he says. “You have to be really competent in what you’re talking about. You have to understand real estate at a higher level than anyone you’re talking to who’s buying a home, because then you bring something up, a concern, or you come up with a solution to a problem that they wouldn’t have on their own. You do that one time and suddenly they’re thinking, ‘Well, what else haven’t I thought of?’ Or, ‘What else do I need this person to help me solve?’ And then they want you to go forward.”


“I think you overcome people’s misconceptions by showing that you have value to add that’s outside of something they had considered.”


Another thing Ryan suggests emphasizing: it’s free! “You’re a free resource, right? In New York City, it’s a wonderful thing,” he says. Ryan notes that many buyers are unfamiliar with how fee structures work in real estate, and that the buyer’s agent is compensated by the seller. Many are also used to being renters and having to pay broker fees. He admits he wasn’t even aware of this when he bought his home.

Meeting clients he wouldn’t have met otherwise

Two businesspeople walking down stairs

Ryan’s comparison of the Experts program to online dating is an apt one, especially in his case. It’s put him in front of people he may never have encountered without Experts, just like online dating can connect people who never would have met otherwise. This is by far his favorite thing about the program, and it’s allowed him to expand his business tremendously. 

“The program has introduced me to clients that unequivocally I would not have met otherwise, had I not been on this platform ready to connect with these people,” Ryan says.

And they’re not just any clients. “I’ve just picked up and signed contracts with my first pro athlete through Experts. He’s a pretty famous guy in New York,” Ryan says. “I definitely would not have met him if it wasn’t through Experts. He’s actually buying right around the corner with me.”

To his pleasant surprise, he also landed one of the wealthiest families in New York City through Experts. “It was very surprising to see somebody that established and well connected who had no buyer representation in their network,” he says.


“The program has introduced me to clients that unequivocally I would not have met otherwise.”


Ryan can’t say enough about this aspect of the program, and how much he attributes it to his success. “It really does introduce you to people that you wouldn’t have access to. The serendipity wouldn’t have been there. The mutual connections wouldn’t have provided it otherwise,” he points out.

“I’m on the top team in the country, I’m one of the top producers on my team, and to say that Experts hasn’t been a part of that would be false because it is such a percentage of my business.”

The time he won over a client in 20 minutes

Ryan can get a lot done in 20 minutes. It seems to be a magic number for him: it’s how long he prefers to stay on the phone with a new lead, and it’s the amount of time it once took him to win over a big client.

“There was one client, very big budget, major wealth manager in the city, like Forbes 40 Under 40 kind of guy. Whenever we spoke on the phone, he was so busy he had to keep hanging up,” Ryan illustrates. 

Ryan wanted to make sure the client understood that he was a buyer’s agent, not the listing agent, but didn’t have a chance to before they had booked an appointment. He called the client on the way to the appointment and left a voicemail to disclose his role. “He called me back and was polite but kurt, and was like, ‘No, I didn’t realize what I was…I don’t want representation. I was confused. This wasn’t clear to me.'”

Rather than giving up right there, Ryan told the client: “Totally fine. You don’t have to use me. Do you mind if I walk with you? I’d be interested to see this lot that you’re looking at.” The client said yes, and Ryan met up with him and his partner. “We had a 20-minute showing and I said, ‘I have 20 minutes to make these people fall in love with me,'” Ryan says. 

And that’s exactly what he did.

“By the end of the showing, he was apologizing to me, saying ‘Meeting you was a complete gift to this process.’ I’m working with him now, we’re friends now and I’m probably going to be selling his apartment that he currently owns. So it’s going to be a double deal, and he’s referred me to clients.”

How did he pull it off? “I had to be very tactful about the comments I made when we were walking. I had to show that I was really knowledgeable. I had to demonstrate my personality. I needed to position myself as an ally to this person in this process so by the time we left the building, he was like, ‘I can’t go forward without you,'” Ryan explains. “And it actually worked. That was a challenging one, but it turned into an awesome opportunity.”

His advice for new Experts

Ryan brings it all back to being personable with clients, and staying confident, competent, and humorous. “When you speak to people, everyone’s a human. Be professional, be knowledgeable, but talk to people in a relatable and human way,” Ryan advises. “Your best chance is to talk to them the way you would someone you’ve known your whole life.”

“If you’re thinking in your head, ‘I’m on the phone with my old friend right now,’ you’re going to be smiling. You’re going to have certain tonal inflections that you can’t even consciously control, that I do think translate over a phone and help the process. So know what you’re doing and play it cool when you’re on the phone.”