Gary Beasley
About Gary Beasley
Gary Beasley is the co-founder and CEO of Roofstock, a real estate marketplace based in Oakland, California. Crunchbase lists him in that role since May 2015. He has a BA in economics from Northwestern and an MBA from Stanford, where he still guest lectures.
Before Roofstock he spent most of his career in real estate, hospitality and technology. He integrated more than $800 million of resort properties for KSL Resorts. He was CFO of online brokerage ZipRealty for five years, including its 2004 IPO. He was also CEO of Joie de Vivre Hospitality. Immediately before Roofstock, he led a large single-family rental platform through its IPO as co-CEO of Starwood Waypoint Residential Trust.
Crunchbase records four personal investments for Gary Beasley before the NavigateAI round: Postcard Cabins (Seed, March 2015), Pinktada (Pre-seed, January 2021), Ribbon Home (Series C, September 2021) and Urbyo (Seed, October 2021). Crunchbase also lists him as an advisor to Pinktada and a board member at Urbyo.
NFX Signal shows the same four deals. It tags him as an angel at Roofstock and ranks him in seed and pre-seed lodging/hospitality, real estate/proptech, IoT and fintech.
The Lounge deals desk lists NavigateAI's $25M Seed round (May 2026) among his AI rounds. Crunchbase's activity feed for his profile also shows NavigateAI raising on May 26, 2026, from Affinity Partners and 19 other investors. We found no public statement from him on his AI investment thesis, and no other AI deals.
His recorded angel deals are at pre-seed and seed, plus one Series C (Ribbon Home). The sectors are proptech, lodging and hospitality, IoT and fintech, and he is based in the San Francisco Bay Area.
NFX Signal lists an investment range of $100K to $5.0M with a $1.5M sweet spot. This is a third-party listing, not a statement from him, so treat it as indicative. We found no public statement from him on what he looks for in founders.
- NavigateAI: AI company that raised a $25M Seed in May 2026; listed on the Lounge deals desk and in Crunchbase activity.
- Urbyo: Seed round of about $5M in October 2021 per NFX Signal; he is listed as a board member.
- Ribbon Home: Series C of $150M in September 2021 per NFX Signal.
- Pinktada: Pre-seed round of $420K in January 2021 per NFX Signal; he is listed as an advisor.
- Postcard Cabins: Seed round of $950K in March 2015 per NFX Signal.
Investing activity
Gary Beasley appears in 1 AI deal tracked by the Lounge deals desk, rounds totalling $25M. The rounds are mostly Seed, with a median round size of $25M. The most recent is NavigateAI (Seed, $25M, May 2026).
Gary Beasley most often invests alongside Elad Gil, Winston Weinberg, Zach Frankel and Lennar, and the companies they back on Lounge are mostly in AI.
Deals
Frequently asked questions about Gary Beasley
Who is Gary Beasley?
Gary Beasley is the co-founder and CEO of Roofstock, a real estate marketplace in Oakland, California. He is also an angel investor. Earlier he was CFO of ZipRealty and CEO of Joie de Vivre Hospitality, and he was co-CEO of Starwood Waypoint Residential Trust.
Has Gary Beasley invested in AI startups?
Yes. The Lounge deals desk lists the NavigateAI $25M Seed round from May 2026, and Crunchbase shows the same round in his activity. His other recorded angel deals are in proptech, hospitality and fintech.
What is Gary Beasley's typical angel check size?
He has not publicly stated one that we found. NFX Signal lists a range of $100K to $5.0M with a $1.5M sweet spot. That is a third-party estimate.
What stage does Gary Beasley invest in?
His recorded deals are mainly pre-seed and seed, from Postcard Cabins in 2015 to Urbyo in 2021. He also invested in Ribbon Home's Series C in 2021.
How should an AI founder approach Gary Beasley?
He has no public pitch guidelines that we found. His public profiles show real estate, hospitality, fintech and marketplace experience, so a pitch that draws on those areas or a warm introduction through his network may be the most relevant route.
Where can founders find Gary Beasley online?
He has a LinkedIn profile, linked on this page. We did not find a verified X account or personal site. His Crunchbase and NFX Signal profiles list his investments.
Is Gary Beasley an angel investor?
Yes. Gary Beasley invests personally as an angel.
What AI companies has Gary Beasley invested in?
Gary Beasley's AI investments include NavigateAI. The 1 round on Lounge are listed on this page with amounts, dates and co-investors.
What stage does Gary Beasley invest at?
In the rounds tracked on Lounge, Gary Beasley has invested at Seed, with a median round of $25M.
Who does Gary Beasley co-invest with?
Gary Beasley's most frequent co-investors on Lounge are Elad Gil (1 deal), Winston Weinberg (1 deal), Zach Frankel (1 deal), Lennar (1 deal) and Affinity Partners (1 deal).