Long before dining out became part of everyday American life, Maxwell Lessing secured his family’s future for generations to come when he opened New York City’s first lunch counter in 1910 to serve Wall Street’s burgeoning workforce.
“He was the first to serve sandwiches and Coca-Cola at a time when people lived in boarding houses, which included their three meals a day,” says Michael Lessing, the fifth-generation CEO of Lessing’s Hospitality Group. Lessing oversees a growing portfolio across the Northeast and Florida, including 23 wedding and catering venues, 16 full-service restaurants, more than 75 corporate and academic dining centers, a historic inn, and even a presidential yacht. “He’d be blown away by what we’ve accomplished and by how we continue to expand and innovate while holding true to his core values.”
PBI visited with Lessing to learn more about this legacy company.
PBI: Why was your great-great-grandfather’s concept so unique?
Lessing: In 1910, lunch as we know it didn’t exist because people lived in boarding houses where they ate their three meals a day. Maxwell saw the future and acted on it—which continues to drive us. We’re always thinking about where we want to be tomorrow.
What is the most valuable lesson your father and uncles instilled in you about leadership and business?
Having the Lessing name isn’t a golden ticket. This is a meritocracy where everyone proves their worth by working hard from the ground up.
What prompted your expansion to South Florida in 2018 with the Pelican Club in Jupiter, followed by catering operations for multiple area businesses?
We were introduced to the area by our family friend from Long Island, Charlie Modica [of Charlie & Joe’s at Love Street] and saw the need for catering venues like we have in New York.
What has adversity taught you?
We’re stronger today because of the toughest crises we’ve faced, including World Wars I and II, the Spanish influenza pandemic, the Great Depression, the Great Recession, the September 11 attacks, and COVID-19. We’re experiencing another one now with AI.
How do you celebrate Father’s Day?
We work! Days, nights, weekends, holidays.
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