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#47, Randy Komisar, Entrepreneur and Investor — Lessons learned from a professional gambler, the role of luck your career, and the key decisions that drive the quality of your life


Randy Komisar is an entrepreneur and investor at Kleiner Perkins.
Previously, he was a co-founder of Claris Corp., served as CEO for LucasArts Entertainment and Crystal Dynamics, and acted as “virtual CEO” for such companies as WebTV and GlobalGiving. Randy also served as CFO of GO Corp. and as senior counsel for Apple Computer, following a private practice in technology law.

Randy is a founding director of TiVo and serves on the Roadtrip Nation Advisory Board and Orrick’s Women’s Leadership Board. He is the author of the best-selling book,The Monk and the Riddle, as well as several articles on leadership and entrepreneurship. He is also the co-author of Straight Talk for Startups, the insider best practices for entrepreneurial success, Getting to Plan B, on managing innovation, and I F**king Love that Company, on building consumer brands.

This conversation with Randy Komisar is just spectacular! We dive right into how he turned his interview with Neil Young from disaster to success, why growing up with a professional gambler sharpened his communication skills, the way that luck factors into your career, and the way to maximize your chances of serendipity coming your way.

You’ll learn pearl after pearl of wisdom from Randy in our conversation, including a crucial question he asks as an investor to any entrepreneur to assess what they’re made of.

Randy’s such a great storyteller, and this discussion is not to be missed!


Key highlights in the episode

  • How Randy turned his interview with Neil Young from disaster to success (02:39)
  • How Randy’s background, growing up with his dad, who was a sales professional and professional gambler, greatly influenced his career, especially his ability to read people as an investor (06:02) 
  • What are the indicators/signs that suggest someone is lying (11:33)
  • The difference between a liar and a deluded person (13:46)
  • Randy’s journey to becoming a lawyer (17:47)
  • How Randy met Bill Campbell and how it shaped his career (26:05)
  • How did Bill Campbell become a legendary coach in Silicon Valley? (31:48) 
  • Randy’s motivation for joining Kleiner Perkins (39:14)
  • What prompted Randy to become a ‘virtual CEO,’ and what was his role as a ‘virtual CEO’ for the companies he worked with? (41:27)
  • The difference between gambling and venture capital and how luck factors into your career (50:08)
  • How to maximize your chances of serendipity coming your way (53:14)
  • What he looks for in entrepreneurs and the questions he asks to assess what they’re made of (59:00)
  • Should Founders be the CEOs of their companies as they grow? (01:05:08)
  • What Randy wishes he had known earlier on his journey (01:07:07)
  • His advice for founders as they embark on their journey to grow into leaders (01:08:00)


Notable Quotes

  • “A liar is somebody who tells you something they don’t believe. A deluded person is somebody who tells you something they do believe, which is false.” ~Randy Komisar (13:46)
  • “You can set the course, but you can’t set the objective.”  ~Randy Komisar (17:14)


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People Mentioned and Other Resources:

  1. Neil Young
  2. Bill Campbell
  3. Steve Jobs
  4. Bill Gates
  5. Trillion Dollar Coach:
  6. Straight Talk for Startups:
  7. Getting to Plan B:


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