How A Real Estate Broker Turned His Bar Prohibition Into A Community Fixture


To Upper West Siders, it can seem like every week brings with it news of a restaurant putting down roots in one of the neighborhood’s slew of vacant retail spaces while another local establishment hangs the proverbial going out of business sign on their front door. Locals have become accustomed to the consistent turnover. Longstanding bars and eateries are few and far between. But Prohibition, located at 503 Columbus Avenue (between W. 85th and W. 84th Streets) is one such rare gem. Richard Herschenfeld, a Compass Real Estate broker and the owner of Prohibition, has made himself a fixture within the Upper West Side community for almost 24 years.

Thoughtful and easygoing, Herschenfeld is a welcoming presence at Prohibition. His is a classic New York story of timing, fate, and reinvention. In the mid-nineties, Herschenfeld was working as an aspiring actor-slash-bartender on the Upper West Side. When he was offered the chance to become a co-owner of the bar, he and his business partners rebranded the venue and created Prohibition which opened in April 1996. The bar quickly became a neighborhood fixture known for its live music, warm environment, and good food. The bar’s weekly performance lineup runs the gamut. On Fridays, it’s rhythm and blues. Saturday night patrons are treated to 80’s and 90’s classic rock hits, while Mondays are dedicated to open mic nights, and mid-week tunes tend toward the singer-songwriter variety.

In recent years, Herschenfeld has once again reinvented himself – joining his friend and colleague John Carapella to create the Carapella-Herschenfeld Team at Compass Real Estate. Herschenfeld credits his decision to move into real estate to his family. “The decision revolved mostly around my daughter,” he said. “I was working many late nights back then and my daughter had begun kindergarten. I enjoyed walking her to school and I really wanted to be part of her growing up, and working late at night wasn’t conducive to that.” As it turned out, his dual roles as owner of Prohibition and as a real estate broker dovetailed seamlessly. In fact, Herschenfeld noted that some of his first real estate sales came from Prohibition regulars who had gotten to know him over the years.

Asked for his insights about how prospective buyers can be successful in the competitive Upper West Side real estate market, Herschenfeld emphasized the importance of organization, developing a realistic financial plan, and determining priorities. “The key is to know ahead of time what you can afford and to get all your financials in order so that when you do go out looking…if there’s something you like, you’re ready to make a move.”

The biggest real estate mistake Herschenfeld often sees? “[People] think they can afford more than they can. You have to be willing to make sacrifices and prioritize. Is a doorman important? ‘Could I consider a walk-up?’ Be open-minded and have your finances in order. Do research on your neighborhood – walk around, do some legwork, see what appeals to you.”

As a long-time businessman and tenant himself, Herschenfeld understands the delicate balance involved in running a successful establishment and remaining on good terms with community members. Based on his own experiences, Herschenfeld provided a few pieces of advice to new businesses attempting to build good will in the neighborhood. “We really try to be a good neighbor. If the police come and tell you to turn the music down, you’ve got to comply. You show up to the nightlife gatherings at the police station. It’s important to establish relationships and try to do the right thing.”

Herschenfeld is proud of his ties to the Upper West Side community and he noted how much he has enjoyed getting to know his neighbors through his work, especially when that work involves a new home. “You really get tremendous satisfaction when you talk to them after they’ve moved in and they’re so happy with their family in this apartment,” he said. “You want them to be happy. It’s a big chunk of money and they put a lot of trust in you. It’s really rewarding.”

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