3 Questions with Gregor Watson of Roofstock

Gregor Watson

FintekNews is pleased to offer our weekly feature column “3 Questions With”. Each week, we feature a thought leader within a unique sector of fintech and ask them to answer just 3 questions for our audience in their vernacular. This week, we’d like to introduce you to Gregor Watson, Chairman & Co-founder of Roofsock, the first online marketplace created exclusively for investing in leased Single-Family Rental homes that generate cash flow day one. Created by investors for investors, Roofstock provides research, analytics, and insights to evaluate and purchase independently certified properties.

Gregor Watson
Chairman & Co-founder
WEB ADDRESS: https://www.roofstock.com/

What does your firm do/offer within the fintech sector?

Roofstock offers the only transparent end-to-end marketplace for investors looking to invest in rented single-family homes in the US. Creating income from the first day of purchase, Roofstock brings value to the fintech sector by offering a platform for a most efficient transaction. By certifying each home through a third party physical inspection of the home, tenant certification, and ongoing oversight, we take the headache out of being a landlord and offer an opportunity to invest in rising markets across the country.

What is your role within your firm and what do you do there on any given day?

As co-founder and Chairman, I wear many hats at Roofstock. Each day I dedicate time to our “idea lab”, which is where we brainstorm new products and change existing pieces of our platform. It’s great maintaining an active role within the company, watching it grow and thrive.

One of the most exciting parts of this venture: playing a lead role in expanding our business to foreign markets. Roofstock is always seeking new international partnerships and is looking forward to offering our services globally in the future.

What has been the biggest failure in your firm and how did you adapt?

Perhaps our biggest “failure” as a startup was during our first product launch. After spending months working through product features and setting up the website, the excitement for the end result got the best of us. (Looking back, it felt like we were preparing for a Mars landing.) As with any successful venture, we took one step back and two steps forward.

A few days before our launch, our team at Roofstock met with an accomplished entrepreneur not afraid to offer his honest opinion. Always valuing that second opinion, our team immediately came together to improve our product through simplicity. What could have become a Frankenstein design instead became what Roofstock is today – a real estate investment marketplace with an approachable and intuitive platform. We believe our success today stems from this “setback” that ultimately drove us towards creating a seamless user experience on all sides of the transaction.

Gregor is a serial entrepreneur who most recently founded two companies in the Single-Family Rental space, 643 Capital and Dwell Finance. Gregor is considered one of the early pioneers of the Single-Family Rental space, raising some of the first institutional capital in the sector.