2020 HW Vanguard: Gary Beasley

Roofstock, CEO and Cofounder

Gary Beasley, CEO and Cofounder, Roofstock

Gary Beasley is the driving force behind Roofstock’s mission to power the future of real estate investing.

He has more than 25 years of success in starting, growing and operating real estate businesses—two of which he led to IPO — and was one of the first to apply technology at scale to the real estate industry. 

In the last 12 months, Beasley has continued to expand Roofstock’s service infrastructure, product suite and has led the company to hit major new milestones that have positioned the company  for long-term success. 

Within three years of launching in 2016, the platform had already facilitated more than $2 billion of transactions. 

In December 2019, Beasley led Roofstock’s effort to close on a new round of funding to the tune of $50 million. The over-subscribed funding round attracted existing and new investors alike, including Citi Ventures, the venture arm of Citibank, and Silicon Valley Bank, one of the most prominent banks serving California’s tech sector. 

The timing was critical to helping Roofstock weather the temporary market dislocation created by the COVID-19 pandemic just a few months later. 

The funding round attracted widespread attention and served as an important indicator of investor faith in Beasley’s leadership and Roofstock’s long-term prospects. In the face of the pandemic, Beasley has kept Roofstock focused on continuing to innovate, and investors have responded with growing interest in the company’s products and services. 

Beasley has earned a 96% approval rating on Glassdoor, a testament to his leadership and the vibrant workplace culture he’s built at Roofstock.

What’s the best advice you’ve ever received?
My father told me repeatedly as a kid, “Don’t get frustrated, get more determined.” I think about this whenever I find myself getting frustrated and immediately start thinking about what I can do to impact the situation positively. Then I start to feel better. He was teaching me grit.

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