20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor

Keith Rabois is a General Partner @ Founders Fund, one of the most successful venture firms of the last decade with home runs in the likes of SpaceX, Palantir, Stripe, Anduril, Facebook, Airbnb, Nubank, and many more. As for Keith, he led the first institutional investments in DoorDash, Affirm and has also led investments in Ramp, Trade Republic, Faire, and Stripe. Prior to venture, Keith had the most stellar operating career, joining PayPal when their monthly burn-rate was $6 million; Keith joined LinkedIn, Slide, and Square when they had no revenue. Fun fact, five companies Keith helped build are now publicly traded with market caps >$1 Billion. Three others have been acquired for greater than $1 Billion or are publicly traded IPOs. If that was not enough, Keith is also the Co-Founder and CEO @ OpenStore, acquiring small DTC businesses.

In Today’s Episode with Keith Rabois You Will Learn:

1.) How Keith first came up with the idea for Opendoor? How a conversation with Peter Thiel led to the founding of the first iteration of the company? Why did it take Keith close to a decade to pursue the idea fully, post having the idea in 2003?

2.) The Market: What made Keith so excited to pursue Opendoor from a top-down market analysis perspective? What does Keith look for in markets he likes to invest in? How did Keith expect the market to change and evolve? What did the market do differently to how Keith thought it would behave?

3.) The Business Model: With debt being the oxygen for Opendoor, how many homes did they need to acquire before they could prove they could price homes accurately? What were Keith’s lessons from the first homes they bought? What did not go to plan? Why does Keith disagree, if macro hits real estate, Opendoor’s model is challenged? Why does Keith believe it is stronger then?

4.) The Team: What does Keith look for in the founding teams he backs? How does Keith detect diamonds in the rough? How can teams systematically de-risk an opportunity with their experience? With the benefit of hindsight, what would Keith have done differently with the team?

5.) The Funding: Was fundraising for Opendoor always easy? How did the seed round go down? How does Keith feel today about pre-emptive rounds where little company development has taken place? Why did Opendoor decide to SPAC? Why not direct list? Was this the right choice? What makes for the best SPAC partner?