Gregor Watson

Member Since 2020

Gregor Watson

Chairman & Co-Founder


Greater Oakland CA Area

An entrepreneur at heart, Gregor is constantly examining the ways to enhance and improve Roofstock’s platform and expansion across domestic and international markets as Chairman and Co-Founder. A founder of multiple enterprises, Gregor brings over 15 years of experience in real estate to Roofstock. “We founded Roofstock because we wanted to change the way that things were done - identifying the inefficiencies and delivering a focused digital answer for the real estate industry wasn’t a ‘nice to have,’ but a ‘need to have,’ and I’m proud of the solution that we’ve built.” In addition to Roofstock, Gregor is co-founder at 1Sharpe Capital, an investment firm focused on US and global credit and equity markets with $1 billion in AUM. Gregor is also the founder of 643 Capital Management, which has invested $1 billion in SFR homes nationally and sold his company Dwell Finance, one of the first lenders for the SFR market, to Blackstone in 2015. Gregor is a member of the 2018 San Francisco Business Times’ 40 Under 40 ranking and was also selected as a HousingWire Rising Star in 2019. He received his BA from Regis University in Denver, Colorado.


September 15th, 2020

Got A Business Idea? Start By Finding Your Why

Your competitive advantage lies more in the why of your business than the look of it.

May 21st, 2020

The Four Biggest Mistakes Entrepreneurs Make During A Crisis

It is possible to emerge stronger out of a crisis by acting quickly and strategically.



Roofstock is the leading marketplace for investing in single-family rental homes, offering investment properties in top U.S. markets. The company provides all of the resources for investors to buy, own and sell real estate online, including data analytics, property management oversight and other tools. Roofstock’s transparent, innovative marketplace empowers investors to own cash-flowing rental properties, diversify their investment portfolios and build long-term wealth through real estate. Founded in 2015, the company has facilitated more than $2 billion in transaction volume through its marketplace to date.


Real Estate