Listen to This Podcast Episode Here

by Patrick O’Shaughnessy

My guest this week is Keith Rabois. Keith is currently an
investment partner at Khosla Ventures, but has a storied and diverse background
as an investor, entrepreneur, and executive. He has worked in senior positions
at Paypal, LinkedIn, and Square; has led investments in companies like Stripe,
YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to
transform the process of selling a home through technology.

One fun fact about Keith is that he may have the most
impressive list of bosses I’ve ever seen, which we discuss during the episode.

We cover a lot, but one thing we kept returning to was
business strategy. Keith’s frameworks for gaining and building strategic power
helped me clarify my thinking on the topic, and his examples of contrarian
thinking will hopefully make you question some commonly held beliefs.

Please enjoy our conversation.

For more episodes go to

Sign up for the book club, where you’ll get a full investor
curriculum and then 3-4 suggestions every month at

Follow Patrick on Twitter at @patrick_oshag

Show Notes

1:35  (First Question)
– A look at his investing philosophy

3:16  – Favorite
examples of his own investment history

            4:40 – 7
Powers: The Foundations of Business Strategy

5:07 – Understanding what is anomalous in a given investment

7:07 – How much a secret needs to be protected within a

11:51 – Why accumulating advantage with data is of interest
to Keith

15:12 – Digital health companies and ideas that he finds

16:17 – Nuance around financial services that investors
should be mindful of

17:56 – How do they evaluate managers ability to recruit

19:36 – How similar are the roles of entrepreneur, board
member, investor, etc that Keith has had in his career

24:02 – Ways that Keith is a contrarian, including his
feelings on “lean startup.”

27:04 – Is problem identification a specific skill set

28:29 – Objection with experimentation/iteration

30:02 – Bad ideas in venture

31:36 – What he likes about Apple

            31:51 – Creative
Selection: Inside Apple’s Design Process During the Golden Age of Steve Jobs

32:26 – Interview questions for identifying great talent

35:41 – Elements of good design

37:14 – Impact of platforms on opening new opportunities

38:42 – His take on valuation in the early stage environment

40:33 – Advice he would give people early in their careers

43:58 – Do high growth companies get beat by established
larger businesses

45:25 – Popular narratives that he thinks are just wrong

48:22 – His thoughts on how people should learn, balancing
experience vs information gathering

50:00 – Other investors that are taking a unique approach to

51:57 – Reflecting on the entrepreneur as a client model of
private equity

55:04 – Books that he recommends that is least known

            55:18 – The
Upside of Stress: Why Stress Is Good for You, and How to Get Good at It

56:30 – Kindest thing anyone has done for Keith

Learn More

For more episodes go to

Sign up for the book club, where you’ll get a full investor
curriculum and then 3-4 suggestions every month at

Follow Patrick on twitter at @patrick_oshag

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