“Hire the Right People” with Gregor Watson

I had the pleasure of interviewing Gregor Watson. He is the chairman and co-founder of Roofstock, the №1 marketplace for buying and selling single-family rental (SFR) homes. In his capacity at Roofstock, Watson oversees the development of the proptech company’s platform. He also spearheads Roofstock’s expansion efforts in both domestic and international real estate markets. Watson is a serial real estate and technology entrepreneur who has founded or co-founded multiple enterprises, including 1 Sharpe Capital, a billion-dollar hedge fund; 643 Capital Management, a leading SFR private equity platform; and Dwell Finance, the first institutional bridge lender sold to Blackstone.

Jean: Thank you so much for joining us! Can you share your story about how you became a startup founder?

I’ve always been an entrepreneur. I became the co-founder and chairman of Roofstock by finding a pain point in the market. I was attempting to sell 500 homes that were part of a 1,500-home portfolio in Dallas using the traditional brokerage model, which allows you to only sell one property at a time to a local buyer. The entire portfolio of SFR homes was only exposed to investors in the Dallas/Fort Worth area. At that time in the cycle, the world was starved for yield and the best buyer wasn’t exactly someone down the street. More likely, that buyer was located in…