Keith Rabois' home-buying disruptor Opendoor, politics, innovation; Cyan Banister @AngelSummit E630

15 Mar 2016 · 40 min
39:46

In this interview, Jason Calacanis talks with Keith Rabois about the disruptive home‑buying startup Opendoor, its technology‑driven approach to buying and selling houses, and how it reshapes real‑estate market dynamics, agent incentives, and mortgage processes. The conversation then shifts to Rabois' broader political and philosophical outlook, emphasizing his libertarian beliefs, support for marijuana legalization, and the role of capitalism in creating value. Rabois also shares the story of his long‑standing angel‑investing partnership with his wife Scott, describing how their complementary personalities (introvert vs. extrovert) and skill sets (legal/complex financing vs. networking and pitching) enable them to source and back over 100 companies, including Uber, Postmates, SpaceX, and Topsy. He explains their deal‑flow strategies—leveraging alumni networks, hackathons, and events like the Open Angel Forum— and illustrates the social impact of their portfolio companies through personal anecdotes. Finally, they discuss their evergreen investment philosophy, reinvesting returns into the ecosystem, and directing profits toward philanthropy, especially marijuana‑legalization advocacy, urging aspiring entrepreneurs and investor couples to align purpose with profit.

Chapters

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