2 | KEITH RABOIS - Former Square COO, Co-Founder of $1B+ startup OpenDoor, and VC at Founders Fund
Play • 32 min

This week, Cory speaks to entrepreneurial executive and investor Keith Rabois, who is best known for his early-stage startup investments in YouTube, Airbnb, Palantir and also his operative roles in building PayPal, LinkedIn, Slide and Square. He is also currently a partner at Khosla Ventures and the co-founder and executive chairman at Open Door. In this weeks episode, Keith talks about how he transitioned from law to tech, what convinced him to leave the safe path into the uncertain times of the dot-com era, the early PayPal days, the hardest role to fill in a company today and how to discover a hidden talent.


Keith Rabois (@Rabois) is a highly respected tech entrepreneur, investor, and business leader. He’s most widely known for his involvement in PayPal, LinkedIn, Square, Yelp, and YouTube. Keith is now a partner and investor at Khosla Ventures.

Keith got his start in tech in February 2000 after friends convinced him that he needed a career change. He dropped off of his career path at the time, which was headed towards becoming a lawyer, to work in tech. A month later, the “Dotcom” crash began, but Keith never gave up. “Building a company from scratch to success is a very rare and very challenging thing. By definition, It’s not intuitive; it’s not easy; it’s not something you can just pick up a book, read, and say ‘I’m going to be a successful founder.’”

Keith primarily focuses on the leadership and composition of a startup. As a former COO, Keith helps companies form strong teams that can overcome early challenges. “One of the things that a good investor can do is help identify gaps between core team and key DNA that’s required for success, and help bridge that gap in networks and help find and identify people that may be the appropriate fit,” says Keith.

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