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For the past 24 years, Richard Herschenfeld has provided countless New Yorkers with a place to escape from the hustle and bustle of everyday life with good drinks, appetizing dishes, and amazing music at his Upper West Side bar, Prohibition.

Prohibition has become a community mainstay — now-famous musicians Gavin DeGraw and Rachel Platten launched their careers there, countless couples have fallen in love after chance encounters at the bar, and staff members have even gotten married there.

“The one thing from Prohibition that matters the most to me are the relationships that have started at Prohibition,” Herschenfeld said. “I hear all the time that someone met their husband there, met their wife there or had their first date there.”

“I even met my wife there,” he added with a chuckle. “A friend told me I had to meet this girl he was working with, so they came [to Prohibition] after some event they had for a show. As soon as we met each other, we hit it off and we’ve been married for 11 years.”

Herschenfeld at Prohibition.

In his journey to becoming a master bartender and restauranteur, Herschenfeld gained a love for serving people, something that ultimately pushed him to real estate six years ago.

“It seemed like a natural progression,” he explained. “I’d made so many contacts at the bar over the years and it was a good way of putting them to use.”

“Most of all, real estate just gave me the time to be there for my daughter,” he added. “I wanted to be part of my daughter’s growing up, and I enjoyed walking her to school in the morning, and it wasn’t conducive working nights.”

Herschenfeld pulled his hours back at the bar and began putting his all towards real estate, passing his licensing test and starting a career with Compass where his first deals were from Prohibition regulars.

The first months were difficult, Herschenfeld noted, but things began to turn around after a Compass sales manager introduced him to John Carapella, his current teammate.

Herschenfeld and his teammate, John Carapella.

“It’s really great to work with someone else so you can bounce things off each other,” he said while noting that Carapella helped show him the ropes. “It can be a lonely business when you’re on your own, so if you can get in with a team, do it.”

Since then, Herschenfeld has found his footing in real estate, specializing in selling luxury listings in the neighborhood he’s come to love and still finding time to run Prohibition with co-owner Michael Trenk.

He uses the same approach to customer service that he learned as a bar owner — make sure no client leaves unhappy.

“It’s important to treat people well and be sincere because people can see right through you when you’re not being sincere,” he said. “I put my heart into Prohibition because our goal was to do the best we could so no one would leave unhappy, and that’s how I feel about real estate.”

“People are really putting their trust into you with one of the biggest decisions of their lives, which is purchasing or selling their biggest asset,” he added. “I don’t want to let them down, and I do whatever it takes to make them happy.”

“Just really care and the end result will come.”

In honor of Inman’s Agent Appreciation Month, we’re highlighting agents with extraordinary stories through a new series, Agent Plus. Do you know someone who should be highlighted for their work inside and outside of the office? Send your nominations to AgentPlus@inman.com.

Email Marian McPherson

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