Keith Rabois: Accumulating Advantages

My guest today is Keith Rabois, the Managing Director at Khosla Ventures. At Khosla, Keith focuses on the consumer internet, education, enterprise, financial services, and digital health.    Keith has had a front-seat to Silicon Valley history. He’s had five bosses in his career: Peter Thiel, Max Levchin, Reid Hoffman, Jack Dorsey, and Vinod Khosla.    In this episode, we talk about the lessons of sports from the San Francisco 49ers to the Oakland A’s. Keith shares a story from his first week at PayPal, where he went on a run with Peter Thiel, which sparked his hiring philosophy. Then, we talk about the future of education, how to find undiscovered talent in society, the power of accumulating advantages, and how to raise the level of ambition in society. Keith has built more billion dollar companies than just about anybody on Planet Earth, and all that wisdom shines through in our conversation.    

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LINKS:

Find Keith online:

Twitter

Linkedin

Khosla Ventures page

Wiki page

People mentioned:

Peter Thiel

Max Levchin

Reed Hoffman

Jack Dorsey

Vinod Khosla

Bill Walsh

Blake Masters

Elon Musk

Erik Torenberg

Bill Thompson

William Safire

Pat Riley

Jerry Garcia

Books mentioned:

The Score Takes Care of Itself

Lend Me Your Ears: Great Speeches in History

The Winner Within

Other mentions:

Khosla Ventures

Square

Stripe

Opendoor

Zillow

Stratechery

Aggregation Theory

SHOW TOPICS

1:32 - Outlining the book, The Score Takes Care of Itself and its significance for entrepreneurs. “Rather than focusing on the score, focus on the process and the rest takes care of itself.” Also detailing Bill Walsh, the underlying infrastructure that he built, and the philosophy that successful companies like Square and Apple have used.

4:41 - Leadership lessons that can be learned from sports and the insights that Keith learned from Peter Thiel in the past on evaluating people and on building great companies. Pairing yourself with people that cover your blind spots and weaknesses.  

9:20 - Emulating companies like Apple, Amazon, and Tesla rather than companies like Google or Facebook. The problem with people choosing the easier path in building companies and detailing building things from the ground up rather than inheriting other companies infrastructures.

12:28 - Thoughts on people who are naive about markets doing better than those who have more experience and know the markets. Hiring people who have expertise to jump the learning curve that comes with starting successful companies.

15:43 - Ways to accelerate learning and jump learning curves. Reading (primarily books and printed materials), find experts and constantly inquire, and using experts to find the right path to take. How Keith began venturing into real estate and him detailing his journey with it.

21:28 - Keith on using Twitter and his experience with finding a specific thread on China, then meeting the author of the thread. Examples of writing insightful things online and the potential in doing so. Finding people and breaking through to clutter with original content.

26:07 - Detailing accumulating advantages with companies and the effects of them. A few examples of what accumulating advantages may be within companies. A bit on accumulating advantage at the individual level, as well.

32:08 - What Keith has learned from being a bit of a Silicon Valley historian and why conference room names are predominantly Silicon Valley names. Also, a bit on why you would want to understand the history of Silicon Valley and the history of successful companies. Reading less short-form content and long-form content. Being a voracious reader.

36:35 - A musical example of being aware of things in the past and learning from tradition. Mixing original sparks with tradition. Learning more so you can better interpret information. For example, artists seeing ten-times more in a museum than an average person would.

42:47 - Keith describing the process of speech-writing and comparing it with coding. Also detailing what makes certain speeches stand out from others. William Safire’s book on great speeches, Lend Me Your Ears: Great Speeches in History.

45:30 - Creating ambition and the fluctuation of ambition over time. Discussing ambition more, spending time with the five most ambitious people you know, and believing that things are possible. Keith’s experience with ambition while growing up and his experiences with moving into tech. Specializing in your strengths and surrounding yourself with complimentary people.

52:28 - Becoming the only person in the world that does what you do and detailing this concept. Where he learned the concept and how Keith describes this for himself.

56:22 - What Keith has learned about organization and productivity that scales down to an individual level. Allocation of time and under-valuing your time. Detailing how the number one predictor of success is knowing how to efficiently allocate your time and how to get the most output out of that time.

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