Developer, Entrepreneur, Author Jerry Rosengarten Shares His Journey

By Hope Walborn | May 31, 2024 | 4 min. read

Gerald “Jerry” Rosengarten, author of “Jump on the Train (to make money)” is a serial entrepreneur with a storied career, from designing the leisure suit—a hit in the 1970s—to building landmark projects like The Bowery Hotel in New York. Here, he shares a bit about how he got into commercial real estate more than 50 years ago, as well as some of the challenges he’s overcome since.

The Leisure Suit

Born in Brooklyn, Rosengarten’s career took off after designing the leisure suit, which he manufactured in an MGM building in New York City. He also ended up subletting the space, which he found to be a very successful way of making money. As the fashion phenomenon died, Rosengarten turned to new ways of repurposing the space and earning income.

A Start in Commercial Real Estate

“New York was falling apart,” he recounted. “Especially the real estate world at the time. Space was vacant all over the place, especially manufacturing buildings, which I had some familiarity with. Eventually, I realized the space was very reliable and I created living lofts in New York.”

As more factories closed, many artists began living in vacant factory lofts that weren’t zoned for residential occupancy. Rosengarten decided to become a real estate developer. He bought a building and began making legal lofts, essentially bringing legal loft living to Manhattan and kicking off his career in real estate.

Real Estate Success (Finding Drizzlers)

After creating the lofts, Rosengarten renovated a 12-story factory into a medical center, which was the cornerstone of his success as a New York City real estate developer. He leased the building for 50 years, dubbing it his “drizzler,” or, in other words, a source of passive, steady income.

“You want to have your drizzler so you’re not under the pressure of day-to-day life where you’re looking for your next dollar,” Rosengarten shared. “You want to be in a position where you can pursue other things. That’s how you create success.”

Since the kickoff of his real estate career, Rosengarten has completed various other successful development projects. In addition to building The Bowery Hotel, a recognized A-list destination, he also built 17 floors of residences above the Theater for the New City. The theater was being foreclosed on when Rosengarten took on the development project and pledged to keep the six stages below operating.

Rosengarten’s book, “Jump on the Train (to make money)”

Facing Challenges and Advocating

Alongside a multitude of real estate successes, Rosengarten has faced numerous challenges over his more-than-50-year career. Despite the roadblocks he’s come across, he’s faced them head-on and learned something from each obstacle.

For example, in Florida, Rosengarten built two floors of housing in a retirement community called Kings Point in the 80s. When he realized no one had taken into account the lack of elevators in a community with aging residents, he tried to put one in, only to be faced with backlash.

“I thought I was doing a great thing,” he said. “People on the lower floor didn’t think I was doing a great thing. They fought it.”

But Rosengarten fought back and advocated for accessibility, aiming to increase ease of movement for retired residents on the second floor and in the community, including his own parents.

“It was two years before a lift was put in,” he recalled. “Today, there are 700 lifts in Kings Point.”

Rosengarten has also come across hurdles while building his 100-acre solar farm. An advocate for green technology and environmental initiatives, he’s had to fight back against neighbors, government entities and local utilities during all stages of the project. The farm now eliminates the release of 36,000-42,000 tons of carbon annually, which is equal to the emissions of 6,000-8,000 cars.

Rosengarten’s Advice

For those in the real estate industry, Rosengarten’s advice is to work hard and think outside the box.

“Money is what you’re looking for in real estate,” he said. “Money is an income stream that you can do whatever you want with. You can buy a piece of land and build something that other people will want. You can build housing. You can buy a building and upgrade it. It’s all a matter of what you see and where you are.”

“The trick is to see something different,” he added. “Everybody does this thing, right? It’s all a matter of day-to-day 9-5 work. For those who see something different, they can change their lives. And then, as the book says, you jump on the train to make money.”

Rosengarten’s book, “Jump on the Train (to make money)”, details more about his career, including his development projects, obstacles, triumphs, personal experiences and more. Learn more at It is available on Amazon.

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