The Agency’s Tyler Whitman: How to get lucky in real estate

Some people seem like they were born lucky. On paper, at least, Tyler Whitman does too. He was picked to star in Bravo’s Million Dollar Listing, got in on the ground floor of brokerage startup Triplemint and had the boyish good looks necessary to become the media darling he is today.

But Tyler Whitman wasn’t born lucky. Not even close. When he first landed in New York City from Alabama, he could only find work as a waiter and handing out flyers in Times Square. A job he kept during his first year in real estate. He was also clinically obese in one of the most image-conscious industries and cities on the planet. He had a drinking problem. He was unlucky by anyone’s standards.

Like so many ultra-successful people, Tyler Whitman decided to make his own luck. He started working his Manhattan real estate niche relentlessly, joined Triplemint, quit drinking, lost 200 pounds and became a star on Million Dollar Listing. To learn how he did it, we sat down with Tyler to get his take on making your own luck in real estate, his advice for brand new agents and even his best script for drumming up business at parties.

Niche down as an agent, scale up with your team

If you want to succeed in real estate, the first step is to niche down. Find a gap in the market—preferably one you have a passion for—and work it until the wheels fall off. Whitman started out working rentals in Manhattan but didn’t start making enough money to give up his flyer gig until he stumbled onto a lucrative niche other agents were ignoring: fresh Ivy League college graduates.

Starter apartments for Ivy League kids

It all started with a phone call from a new Princeton grad looking for an apartment. Lucky? Maybe. But what Whitman did next turned a lucky break into a highly lucrative niche that finally allowed him to stop handing out flyers. He knew Princeton was a tight-knit community, so he gave his new client white-glove service even though he was only looking for a humble apartment. He did 80 rental deals with Princeton graduates that summer.

From Million Dollar Listing to a team that sells anything it can get its hands on

Whitman parlayed his Ivy League clients into buyers and built his business in luxury real estate — eventually rubbing shoulders with Ryan Serhant on Million Dollar Listing.

After starting his team, Whitman decided he didn’t want to pigeonhole his agents into luxury listings. The market was too small, even in New York City and the Hamptons. This turned out to be a savvy business decision. His team is thriving, working everything from starter homes to eight-figure penthouses. Listings are listings, and listings grow successful businesses.

Here’s Tyler:

“Last year, my team had seven sales north of $10 million, and everything else was almost exclusively first-time buyers. We had a ton of volume under $1 million. That business was huge for us last year. It’s funny; I think our smallest sale was a $400,000 studio, and I had the listing for the 15 Central Park West penthouse that was $48 million. Most people think I just do luxury, but my team does it all now. It all adds up.”

Join the right brokerage, but leave the minute you find something better

If you want to get lucky in real estate, the brokerage or team you join matters more than you might think. Sure, you are an independent contractor, a small business of one, I get it, but opportunities are unevenly distributed in our industry. Some brokerages innovate. Others haven’t changed since the Reagan administration. If you want to get lucky, look for the innovators and be ready to leave as soon as you find something better. Trust me, your broker won’t take it personally.

Whitman worked his Ivy League clients at a small local brokerage, but another lucky phone call transformed his career. It was from a Yale grad he worked with, and they wanted to know if he would join their new brokerage startup, Triplemint.

His career took off as a broker at Triplement, and he managed to parlay social media buzz about his weight loss into a role on Million Dollar Listing. He had lost 200 pounds and knew he had built the skills and knowledge to become the rockstar broker he always wanted to be. He was right.

This year, Whitman left Triplemint for greener pastures at The Agency. A shrewd career move that gave him access to a nationwide network of luxury agents to feed his team more agent-to-agent referrals than they could handle.

The lesson from Whitman’s journey is crystal clear. If you want to get lucky in real estate, jump ship onto a better lifeboat.

Find something that drives you to say yes 

Luck doesn’t favor the prepared; it favors seekers. If you want to get luckier, you need to find something, anything, that drives you to seek out new opportunities to say yes to. It could be a sky-high mortgage, a desire to build a legacy for your kids or to create generational wealth in a community you care about. It doesn’t matter what you choose. What matters is that you have it.

For Whitman, it was the pressure of keeping his spot on Million Dollar Listing. Think that’s a problem you’d love to have? Think again:

“Everyone used to tell me: Of course you became super successful, you’re on a really popular TV show! Being on Million Dollar Listing definitely gave me a confidence boost, but the truth is, clients couldn’t care less that I was on the show. As a matter of fact, I would say the majority of them didn’t watch it, and then the ones that did watch didn’t want to be on it!

This put me under immense pressure as an agent. I needed to have listings that would look good on television. I needed to convince the owners to let the crew film them, and they needed to be really, really nice. So I started showing up for opportunities that I never would have had the guts for strictly because I knew the cameras were following me.“

As a newly minted reality TV star hungry for camera-friendly listing opportunities, Whitman perfected his scripts for anywhere they might arise, including cocktail parties.

Tyler Whitman’s best cocktail party script

Here’s a quick script from Tyler Whitman that will help you get lucky faster and more often. This script solves new agents’ deceptively tricky problem: answering the “So, what do you do?” question at parties without sounding salesy and desperate.

“Whenever I go to a party, I ask everyone I meet what they do for a living before they have a chance to ask me. Who doesn’t love to talk about themselves, right? If they’re not rude, they will ask you what you do for a living. Here’s how I answer them:

I am a real estate agent and I have been out here selling luxury homes for over a decade now.

Inevitably, someone will then say they’re either looking for a home or trying to sell the one they have. Most agents struggle with their responses. They end up sounding desperate and giving an “Oh, hire me, please!!” energy that is a turnoff to most people.

Instead, I defuse the tension with a joke and ask them, “Oh, where do I apply for that job?” or “Is there, like, an online application I should be filling out?”

Sometimes, they reply with something like, “Oh, you’re so cute. You’re so sweet, but we already have a real estate agent,” or “We already know an agent.”

Then I answer with:

Well, this is awkward because now you know two. It’s a very difficult decision to make. I don’t want to step on anybody’s toes, but I hope you’re getting multiple opinions on how you should handle this.

I used this script to get my foot through the door in a playful way that wasn’t salesy or desperate. If I can get through the door, I’ve got a 97% close ratio on getting the deal.”

Your turn

Know an agent who is thriving despite the odds and has actionable insights to share? We’d love to hear from you. Reach out to us here: [email protected].

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