By Phin Upham

When the Flatiron building first debuted, it received some mixed reviews. It’s one of New York’s most iconic buildings today, but it opened to complaints about the number of windows. One review at the time suggested that one would have a wonderful office to watch the proceedings below, but a terrible one for actually transacting business.

Still, the building attracted considerable praise and managed to fill its target occupancy rate. Harry Black, who led the syndicate that owned the building, had made several improvements to the building in order to increase its ability to monetize, including the addition of a retail space.

The building was completed in 1902, but sold in 1925. Harry Black needed cash for a company he was starting, so he decided to sell the Flatiron in a $2 million transaction to Lewis Rosenbaum. Rosenbaum held it until 1933, when they failed to make its mortgage and the building went up for auction.

The building changed dramatically after the start of World War I. Equitable Life Assurance owned it and made several improvements to the quality of the structure. They improved the elevator, for instance, and had the building fully rented by the 1940s.

It was sold again in 1946 to a company called Flatiron Associates, which was headed by Harry Helmsly. His firm, Helmsley-Spear, owned the property until 1997. Although, they made only superficial changes to it because of the ownership of the building. Under contract, no changes could be made without tenant consent. When the widow of Harry Helmsley finally sold her share to Newmark Knight-Frank, they replaced the antiquated elevators and made several modern enhancements to try and preserve the building.

About the Author: Phin Upham is an investor at a family office/ hedgefund, where he focuses on special situation illiquid investing. Before this position, Phin Upham was working at Morgan Stanley in the Media and Telecom group. You may contact Phin on his Phin Upham website or LinkedIn page.