October 10, 2017


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.

Show Notes
  • 1:06

    How Keith started in law and what he was like as a teenager

  • 3:08

    How Keith’s friends convinced him to join the tech world

  • 5:49

    The market crashes and the landscape for investors and startups shifts dramatically. Peter Thiel tells Keith that he should come work for him

  • 8:08

    Keith discusses the most common mistakes young founders make today. “I think one of the biggest mistakes people make is not selecting the DNA of their core team to be appropriate for the market and product they need to build.”

  • 9:47

    Keith answers the question “What’s the hardest role to fill in your opinion?”

  • 13:05

    Keith outlines his daily routine, which is sometimes thrown off be getting stuck on Twitter

  • 13:57

    Where most entrepreneurs are wasting time

  • 16:27

    How to make difficult decisions

  • 17:39

    Keith lists the top thing he’s learned from colleagues including Peter Thiel and Max Levchin

  • 18:55

    How Keith finds undiscovered talent

  • 23:17

    Keith answers “If you were to start a company today, what are some of the areas that interest you most?”

  • 25:00

    Keith talks about one of his favorite self-help books, The Upside of Stress

  • 25:56

    How startups and controversy are linked

  • 27:02

    What’s controversial today that won’t be tomorrow

  • 28:59

    Advice for a student or professional who is lost and doesn’t know what to do next

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