Real estate agents across the nation share stories of the lessons they’ve learned during their time in the industry. This week: Find out how NYC agents Jessica Chestler and Ben Jacobs learned that every deal has the potential to turn into an extraordinary opportunity.

Looking for more advice? Check out Inman’s New Agent Essentials.

In this weekly column, real estate agents across the nation share stories of the lessons they’ve learned during their time in the industry.

As the Chestler Jacobs Team at Douglas Elliman, Jess Chestler and Ben Jacobs work with clients from their NYC backyard all the way to sunny South Florida. They formed their partnership based on friendship — with each other as well as with each of their clients — and it has paid dividends in the form of hundreds of millions in sales.

Along the way, they’ve learned time and again that it doesn’t matter how big or small the individual transaction may be; every deal has the potential to grow into something truly extraordinary.

How long have you been in the business?

JESS: I went to school for something very different, I went for sports broadcasting. When I got my first job offer, I freaked out about it. I realized it was not for me.

At the time, I was helping my parents find a place in the Hamptons, and the listing broker said something along the lines of “How long have you been in real estate?” and it got my mind going. I decided to take the test, I was 21, and that was it.

As a kid, I always was interested in real estate. My parents took me to open houses. I always loved real estate, I just didn’t think of it as a full-time career.

BEN: I come from a real estate background; my family has been buying real estate in Vermont for almost 45 years. My brother runs that business now.

It’s totally different from our current business. It’s not brokerage; it’s operating as a landlord for commercial and residential leases. But real estate was always a topic at the kitchen table so naturally, it’s always been a topic of interest for me.

After I graduated from Skidmore College in Saratoga Springs, New York, I decided to go to New York City. I didn’t know what I wanted to do, but I knew that I wanted to try to live in the city because it sounded exciting, and all my friends from college were going there.

A cousin of mine was working at Corcoran as a broker, and she encouraged me to get my license. So, I decided to go to New York City, get my real estate license, and I interviewed at Corcoran. I started out as a sub-agent for a broker who had been in the business for almost 20 years. We left Corcoran to work at Core, and from there, I went out on my own.

Where do you see yourself in 5 years?

BEN: We are pushing to increase our NYC business while simultaneously expanding in the South Florida market as well as the Hamptons.

In five years, we would like to be operating at the same high level in all three markets to really show our network that we are not just an NYC-focused team but have connections and knowledge in multiple markets. We believe having a footprint in more than just one market will create more opportunity.

What’s one big lesson you’ve learned in real estate? 

JESS: Always remember that there are opportunities that can come from every deal. No price should determine how hard we work on a deal. We look at every deal as equal and an opportunity to do more business.

How did you learn it?

JESS: There have been clients I have worked with for a long time that never transacted. I never made anything of it as I knew that there could always be something bigger to come.

One client that we worked with went another direction and ended up purchasing for a high multiple of what we had once looked for. I think the fact that we treated each deal the same and never made it about forcing a deal gave them the comfort that got us not only the larger deal, ultimately, but a lot of referrals that amassed to a good piece of business in time.

I think our patience and understanding that regardless of price, everyone is buying a home, makes our clients very comfortable.

BEN: I’ve sold 14 apartments in a building that many top agents would have ignored. It’s a wonderful little building comprised of studio and one-bedroom apartments. The price of the units range from $400,000-$600,000.

The first listing I worked on in the building was a small one-bedroom that I ended up selling for a record price in the building.

It took me months to sell, but the reward years later turned out to be me becoming the building expert and selling several more units. So, you never know what can come from one listing, big or small.

What advice would you give to new agents?

JESS: We would tell agents to be patient. The people you may think will be your clients may not be, and the people you least expect to work with you may be your biggest source.

This is a tricky business, but making sure you are respectful makes you respected. There are a lot of opportunities to do what’s best for your clients. Being patient and honest is what gets you there in the most successful way, in our experience.

BEN: If you’re a new agent, I would recommend being patient. Don’t be too consumed on getting a big deal done. Focus on yourself and become an expert in the business. The deals will follow.

Christy Murdock is a Realtor, freelance writer, coach and consultant and the owner of Writing Real Estate. She is also the creator of the online course Crafting the Property Description: The Step-by-Step Formula for Reluctant Real Estate Writers. Follow Writing Real Estate on TwitterInstagram and YouTube.

Do you want to be featured in an upcoming “Lesson Learned” column? Reach out to us here!

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