Upper School students recently had the opportunity to hear from GVS parent speaker Harold Valestin, father of Liam ’25 and Connor (7th Grade), a real estate broker, investor, consultant, and coach whose career has taken him from Wall Street trading floors to some of New York City’s largest real estate developments.
Valestin began his professional career on Wall Street as a proprietary trader, where he traded firm capital and shared in the profits he generated. But his path changed dramatically following the events of September 11, 2001. At the time, his office was located on the 83rd floor of the first World Trade Center tower. Although he was not in the building when the attacks occurred, the tragedy ultimately led him to reconsider his career.
Encouraged by his father, Valestin decided to explore real estate. “My father told me, ‘You like fast-paced work and making deals—you should try real estate,’” he recalled. With little experience but plenty of determination, he entered the industry and began learning the business from the ground up.
Today, Valestin works primarily with real estate developers, consulting on projects from the earliest stages—when a site is still just a vacant lot—to the completion of major residential or commercial buildings. His work focuses on new development, helping guide projects that transform empty land into homes, offices, and community spaces.
“What I love most is seeing something that starts as dirt become something meaningful,” he explained. “Real estate can take something that doesn’t exist and turn it into a place where people live, work, and build their lives.”
Over the years, his expertise has expanded beyond brokerage and development consulting. Valestin now also teaches and coaches new investors, helping them understand how to buy property, renovate homes, and build long-term wealth through real estate. His experience has also led to speaking engagements where he shares insights on investing and entrepreneurship. At one event, he even addressed an audience of 4,000 people at the Javits Center in New York City.
During his talk with students, Valestin emphasized several lessons that have shaped his career.
One of the most important skills, he said, is learning to listen.
“Listen more and talk less,” he advised. “You have to understand what people actually need before you can help them.”
He also spoke about the importance of building relationships and networking.
“Your relationships are your network for life,” he explained. “If people don’t know you, they won’t know what you do. Even in today’s digital world, face-to-face conversations are still how real business gets done.”
Above all, Valestin stressed the importance of reputation and integrity.
“In this business, reputation is everything,” he told students. “It can take years to build and one second to destroy.”
Through his journey—from aspiring doctor to Wall Street trader to successful real estate professional—Valestin reminded students that careers rarely follow a straight path. With curiosity, persistence, and strong relationships, opportunities can emerge in unexpected ways.