Keith Rabois: Accumulating Advantages North Star Podcast

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 be