In 2015, Gary Beasley was CEO of Starwood Waypoint Residential Trust – which at one point managed more than 15,000 single-family rental properties – when he found himself frustrated with inefficiencies in the real estate marketplace.
The current system made it difficult to sell Waypoint’s properties with tenants in them, because the traditional MLS only listed vacant properties, and it was 
affecting the company’s bottom line.
Not content to sit back and wait for someone else to fix the problem, Beasley jumped on the opportunity to build a solution. Beasley has an entrepreneurial spirit that motivated him to instigate change, providing an answer to a problem that had been plaguing the marketplace.
Beasley partnered with Gregor Watson and co-founded Roofstock, an online marketplace for buying and selling single-family investment properties not listed in MLS. Using Roofstock’s marketplace, investors can own cash-flowing SFRs, diversify their investment portfolios and build long-term wealth through real estate.
Now, Roofstock has become a major disrupter in the space, surpassing $1 billion on property transactions earlier this year. It also collected $42 million in Series C funding, a 20% increase over its initial round thanks for demand from insiders and new strategic investors.
Since the beginning of 2018, Roofstock has nearly doubled its market presence thanks to the leadership of Beasley and Watson. The company now has SFR homes for sale in 40 markets and 23 states, and it continues to work on expanding its footprint.
What’s the best advice you’ve ever received?
“A college professor advised me to do something I am passionate about with my career, and not to just chase the money. His view was: If you love what you are doing, you will put in the time and effort and find a way to be successful. Plus, you will enjoy your day-to-day more.”
