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Gregor Watson

Chairman & Co-FounderRoofstock

Oakland CA Area

Member Since April 2020


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.

Published content


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

expert panel

Congratulations! You’ve just had a great pitch meeting with an investor. But holding an investor’s attention during your pitch is only the beginning of securing a deal. The real challenge lies in staying top-of-mind afterward.  To ensure a lasting good impression, you’ll want to keep the conversation going with investors post-pitch. A panel of Young Entrepreneur Council members shared effective ways to continue the discussion after your meeting.

expert panel

When launching a startup, business owners often receive a lot of advice from everyone around them. As a new entrepreneur, it can be difficult to parse through it all and determine what truly applies to your business.  With all the noise around you, you might be left feeling more overwhelmed and confused than before. To help you identify the right (and wrong) tips, we talked to members of Young Entrepreneur Council about common pieces of startup advice they disagree with. Here’s what they flagged as unhelpful insights you don’t need to follow when launching your company.

expert panel

Within an organization, some skills are far more valuable than others. If your business is looking at hiring new employees, then these skills should be a primary focus for your interviews. Knowing what skills are crucial for an enterprise to grow and thrive helps you figure out if an employee may be worth hiring, even if they don't fit the ideal. Sometimes the company needs more than just the right qualifications for their employees. That's why we asked 16 professionals from Young Entrepreneur Council (YEC) the following question:

15 Ways for Leaders to Encourage Employee Self-Teaching

expert panel

Within any company, the ambitions of individual team members should aid the overall organization. However, it takes a leader to fuel, direct, and inspire this ambition into a way that helps both the team members and the organization as a whole. One way leaders can get their team members to realize their ambitions is by guiding them toward self-teaching and taking initiative, as a way of expanding their knowledge and skills while also seizing new opportunities within the company. To help, we asked 15 members of Young Entrepreneur Council the following:


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

Company details


Company bio

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

Company size

201 - 500

This member is no longer active.

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