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!

Where to find Randy:

• Kleiner and Perkins

Timestamps:

(00:00) The Neil Young interview disaster—and how Randy saved it

(02:00) Throwing away the script and learning to “follow the spark”

(03:15) Reading people: Randy’s people-sense and street upbringing

(04:00) Growing up with a salesman and professional gambler father

(05:20) Lessons from watching gamblers: losing stories, tells, and ego

(07:00) How his father’s instincts shaped Randy’s BS-detector in VC

(12:35) Self-awareness, delusion, and Buddhism’s core teaching

(13:40) Coaching as holding up a mirror

(14:20) Randy’s winding path: from upstate NY to Brown University

(15:55) Finding paradise at Brown: curiosity and lifelong learning

(21:30) How meaningful small acts of encouragement can be

(23:00) Enter Bill Campbell: how they met at Apple

(34:00) The inner conflict: purpose vs. title

(37:00) Managing through influence, not authority

(39:30) Bringing the virtual-CEO model into venture capital

(40:50) Success, skepticism, and earning trust at Kleiner

(43:10) Why this? Why you? Why now?

(44:30) “Is this worth failing at?”—the most important founder question

(46:00) The gambler’s wisdom: inviting luck

(48:30) How to make yourself luckier (excellence, flexibility, humility)

(50:10) Most great companies succeed with Plan B, not Plan A

(51:30) A painful miss: the Juicero story

(53:00) PR mismatch, press backlash, and the fatal Bloomberg article

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