opendoor
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Justine Palefsky and the value of an empty home
Before Kindred, Justine Palefsky learned hospitality in a San Francisco house with a revolving cast of guests. Now she is building a home-swapping network around a question she has carried into her career: what makes people comfortable enough to open the door?
Jeff Kolovson and the Business of Making Risk Disappear
Before Faire could connect shopkeepers and brands across borders, its co-founder learned operations the blunt way: sixty futons, thirty-six hours, and no room for excuses.
Charles Chacko Made the Closing Table a Technology Problem
He built OS National in the unglamorous machinery of title and escrow - then helped turn that machinery into part of a national digital home-buying platform.
Jay Chen
Jay Chen is the interim CEO of Contextual AI, the Silicon Valley enterprise company building a 'context layer' for grounded AI agents. He stepped into the top job in 2026 after co-founder Douwe Kiela and a group of researchers moved to Google DeepMind under a licensing deal. A Wharton MBA who started as a chip engineer at NVIDIA, Chen built his career across product marketing and growth roles at Confluent, Starburst, Opendoor and Twingate before joining Contextual AI as VP of Marketing, where he helped launch its enterprise RAG platform.
Judd Schoenholtz
Judd Schoenholtz is the co-founder and CEO of Deferred.com, a technology-driven qualified intermediary that pioneered the No Fee 1031 Exchange. A repeat real estate founder, he previously built Open Listings (YC W15, acquired by Opendoor in 2018) and Balance Homes (acquired 2023), drawing on a decade of design leadership at the global digital agency Huge.
Luke Groesbeck
Luke Groesbeck is the co-founder and CEO of Foundation, the buyer experience platform that drags homebuilding - one of the last big offline industries - online. After two decades building and scaling Silicon Valley startups including the now-public Opendoor and Eventbrite, he teamed up with two Opendoor colleagues to build what they call 'Shopify for homebuilders': white-labeled apps that carry a buyer from first tour through closing and into the warranty years. Backed by Y Combinator's Summer 2023 batch, Foundation grew 5x in 2025 and now powers the homeowner apps of more than 40% of the top-200 U.S. builders.
Peter Fishman
Peter Fishman is the co-founder and CEO of Mozart Data, a Y Combinator-backed startup that lets anyone spin up a modern data stack in under an hour without hiring a data engineer. An economics PhD who once crunched numbers for the Philadelphia Eagles and ran a bacon hot sauce company, Fishman spent fifteen years building the same data pipelines over and over at Yammer, Zenefits, Opendoor, and Eaze before deciding to package that work into a product everyone could use.
Dan Ashton
Dan Ashton is the CEO and Co-Founder of Brain Co., a San Francisco-based AI company that builds applied intelligence platforms for the world's most complex institutions - from government permit offices to hospital systems. He brought his AI startup Serene AI into Brain Co.'s orbit and now leads a company backed by $30M in Series A funding from Elad Gil, Affinity Partners, Patrick Collison, Reid Hoffman, and Andrej Karpathy. Before Brain Co., he was an early operator at three unicorns - Opendoor, Faire, and Clubhouse - and a McKinsey consultant before that. Brain Co. has already deployed AI that unlocks $375M annually in permitting value and mitigated $100M+ in supply chain losses.
Brett Browman
Brett Browman is a Growth Operating Partner at Khosla Ventures, bringing a hands-on, ER-doctor approach to diagnosing and scaling portfolio companies. A veteran of Silicon Valley's most storied growth stories - first growth hire at both Square and Opendoor - he spent seven years as Operating Partner at Andreessen Horowitz advising companies like ElevenLabs, Character.ai, and Luma.ai before joining Khosla in 2024. Known for getting in the trenches as a fractional growth leader, Browman has helped shape the go-to-market playbooks of some of the fastest-growing startups in tech history.
Jon Chu
Jon Chu is a Partner at Khosla Ventures where he invests at the intersection of machine learning and enterprise infrastructure. A Carnegie Mellon computer science graduate, he has lived on both sides of the table - as a founder (sold his company to Docker), a principal engineer at Palantir during its hyper-growth phase, a product and engineering leader at Opendoor and Facebook/Meta, and now as one of Silicon Valley's most active early-stage AI/ML investors. In 2024, Business Insider named him one of 45 rising stars of the VC industry.
Shaun Maguire
Shaun Maguire is a partner at Sequoia Capital who bridges the worlds of theoretical physics and venture capital. With a PhD in quantum gravity from Caltech under John Preskill, he co-founded the cybersecurity company Expanse (acquired by Palo Alto Networks for over $1 billion) while completing his doctorate. At Sequoia, he leads investments in deep tech, aerospace, defense, and AI, backing companies like SpaceX, xAI, The Boring Company, and Neuralink. Before Sequoia, he was a partner at Google Ventures, where he led investments in Stripe, IonQ, and Opendoor. His unique background combines rigorous theoretical physics research on multiboundary wormholes with a track record of building and backing billion-dollar companies at the frontier of technology.
Keith Rabois
Keith Rabois is a PayPal Mafia veteran, co-founder of Opendoor, and Managing Director at Khosla Ventures whose career spans law clerk, corporate attorney, political adviser, and now one of Silicon Valley's most prolific — and outspoken — investors. He is the first institutional backer of DoorDash, Affirm, and Faire, made early bets on Stripe, YouTube, and Airbnb, and brought the iBuyer model to residential real estate before moving to Miami and catalyzing one of the biggest tech migration waves in recent memory.