Gary Beasley
CEO and Co-Founder @ Roofstock
Oakland, United States
Gary Beasley is a seed investor at Roofstock in Oakland focused on Travel and Hospitality. Gary has spent most of his career building businesses in the real estate, hospitality and tech sectors. After earning his BA in economics from Northwestern, Gary ventured west to earn his MBA from Stanford, where he caught the entrepreneurial bug and still serves as a regular guest lecturer. Previously Gary was instrumental in acquiring andintegrating more than $800 million of resort properties for KSL Resorts, and spent five years as CFO of online brokerage pioneer ZipRealty, which he led through its successful IPO in 2004. Gary also served as CEO of Joie de Vivre Hospitality, then the second largest boutique hotel management company in the country. Immediately before starting Roofstock, Gary led one of the largest single-family rental platforms in the U.S. through its IPO as co-CEO of Starwood Waypoint Residential Trust, now part of Colony Starwood Homes.
- Total investments:
- 5
- Last investment:
- Lead investor:
- 0%
Last updated:
For AI agents: llms.txt
Industries Gary Beasley invests in
Stages Gary Beasley invests in
Countries Gary Beasley invests in
Round sizes
Round size
- Seed
- $950k–$25M
Investment Focus
Industry
- Travel 2 (40%)
- Hospitality 2 (40%)
- Real Estate 2 (40%)
- Rental 1 (20%)
- Finance 1 (20%)
Stage
- Seed 3 (60%)
- Pre-Seed 1 (20%)
- Series C 1 (20%)
Country
- United States 4 (80%)
- Germany 1 (20%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
NavigateAI
|
NavigateAI is an AI copilot for the physical world specifically designed for construction and field service teams to help them complete projects faster, with higher quality, and at lower costs. | $25M / Seed / May 26, 2026 | |
Urbyo
|
Urbyo is a make possible for more people to buy real estate. And to do so quickly, transparently, and conveniently. | $5M / Seed / Oct 26, 2021 | |
Ribbon Home
|
Ribbon provides alternative home financing to make home ownership achievable by giving homeowners the freedom to buy before they sell, obtain a same-as-cash home loan, or buy even if they don't quite qualify for a conventional loan. Our financing programs are designed to give buyers greater certainty and enable real estate professionals toclose more deals. Today, as a division of Hurst Lending, we’re expanding that mission across the country — combining Ribbon’s buyer-empowerment platform with Hurst’s proven alternative home finance offers. Together, we help buyers, sellers, mortgage brokers, and agents succeed in today’s housing market with solutions designed for real people. | $150M / Series C / Sep 14, 2021 | |
Pinktada
|
Pinktada is a primary and secondary market for hotel rooms, architected on tokenization. Pinktada transforms hotel booking by enabling tokenization in the travel market. The company was founded in 2020 and is based in Houston, Texas. | $415K / Pre-Seed / Jan 05, 2021 | |
Postcard Cabins
|
Getaway is a wellness hospitality company that offers cabin rentals in natural landscapes.The company's experiences are more than the beautiful tiny house nestled in the woods—it’s about disconnecting and living in the present moment. It’s about learning to live without your cell phone (pack it away in our phone lockboxes) and rediscoveringthe art of a good conversation. It’s about tuning out the endless noise of society today and listening to the great outdoors. Getaway's mission is to offer an experience worth coming straight back to: deep and simple enough to help you find yourself, revel in nature, and rekindle the connections most important to you. We’ll provide the basics; the rest is up to you.Outposts are located within about a two-hour drive of major metro cities—far enough to disconnect but close enough for a spontaneous escape. Getaway currently operates three outposts outside New York, Boston and Washington, DC. | $950K / Seed / Mar 01, 2015 |
Co-Investors
New York Angels
2 deals together
75 & Sunny
1 deal together
Affinity Partners
1 deal together
Bain Capital Ventures
1 deal together
Entrée Capital
1 deal together
Fifth Wall
1 deal together
About Roofstock
Roofstock is an online marketplace for investing in leased single-family rental homes in a transparent and low-friction way. The company provides its clients with research, analytics, and insights to evaluate and purchase independently certified properties at set prices. It enables its investors to treat their real estate investments more likestock portfolios, focusing on asset allocation, rather than researching, and buying vacant homes that need to be repaired and leased.Founded in 2015, Roofstock gets its funding from Bain Capital, Ron Conway, Khosla Ventures, Marc Benioff, and other investment companies. It is headquartered in Oakland, California.
Roofstock Contacts
| Name | Phone | Socials | |
|---|---|---|---|
|
Gary Beasley
CEO and Co-Founder
|
|||
Gregor Watson
Co-Founder & Chairman
|
|||
Jake Seid
Advisor
|
|||
Amit Akhouri
VP, Engineering
|
|||
Emil Shour
Growth Marketing
|
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FAQ
What does Gary Beasley invest in?
Gary Beasley invests primarily in Travel, Hospitality and Real Estate startups, most often at Seed and Pre-Seed stage. Most of the 5 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What is Gary Beasley's check size?
Gary Beasley typically joins rounds of $950k–$25M at Seed. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds Gary Beasley participates in.
When did Gary Beasley last invest?
The most recent investment recorded for Gary Beasley closed in May 2026. Shizune tracks 5 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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