Post Creator: Rosie Bartley

Reshaping Rental: Using economic pressure to create real estate prosperity with Gary Beasley, Co-founder & CEO, Roofstock

By ICR | Podcast

Sometimes the most innovative business concepts are born from immense industry stress. Today’s guest created a ground-breaking platform in response to the economic pressure cooker of the 2000s’.

On this episode, we’re sitting down with Gary Beasley, who is a co-founder and CEO of Roofstock, an award-winning real estate investment as a service platform for the 4 trillion dollar single family rental sector. The company is backed by Blue Chip roster investors, including Cosla Ventures, Light Speed Venture Partners, Bain Capital Ventures, and SoftBank. Roofstock has completed over $6 billion worth of transactions since its founding in 2015.

Previously, Gary was the co-CEO of publicly traded Starwood Waypoint Residential Trust, now part of Invitation Homes, and is known as a pioneer in the development of the single-family rental sector as an institutional and asset class. Gary also served as CEO of boutique hotel company Joie De Vivre Hospitality, and award-winning solar technology startup GreenVolts.

Between 2001 and 2007, Gary was the CFO of Zip Realty where he led the internet-based residential brokerage through its IPO before eventually being named its President. Gary also spent six years with KSL resorts where he was instrumental in acquiring and integrating over 800 million worth of resort properties.

Gary earned a BA in economics from Northwestern University and an MBA from Stanford University Graduate School of Business where he serves as a regular guest lecturer.


  • What inspired Gary to follow his educational path into business (3:06)
  • Gary’s first role in the business sector, and how it influenced his outlook (4:23)
  • Gary describes what interested him in Stanford University, and his journey to getting there (5:47)
  • Gary’s first job after business school (6:55)
  • Starting with Waypoint Homes and how Gary was introduced to the real estate sector (9:11)
  • How the industry has become an asset class (11:16)
  • Where Gary and his partner saw value in the market, and their approach to starting the business (13:35)
  • Roofstock’s business model, and how it has changed over time (14:58)
  • How Roofstock works together with brokers and agents (18:03)
  • Gary explains their proprietary asset management software (19:56)
  • How COVID impacted Roofstock’s business and business model (21:27)
  • How the current economy is influencing their approach to business at Roofstock (23:13)
  • Gary explains what drew their impressive group of backers to Roofstock (24:59)
  • Gary’s thoughts on the company’s future market opportunities and the possibilities of going public (26:47)
  • Incorporating AI and staying attuned to new tech in real estate (29:05)


ICR Twitter

ICR LinkedIn

ICR Website

Gary Beasley on LinkedIn

Roofstock on LinkedIn

Roofstock Website



If you have questions about the show, or have a topic in mind you’d like discussed in future episodes, email our producer,