This episode is supported by Xero, helping businesses use AI with
more control through JAX, its in-platform AI finance partner. Get
90% off your plan for your first 6 months at
xero.com/highflyers.
________
Keith Rabois is Managing Director at Khosla Ventures and one of
Silicon Valley’s most influential technology investors and
operators. He held senior roles at PayPal, LinkedIn, Slide and
Square, co-founded Opendoor and OpenStore, and has backed more
than 15 companies that have gone public, including YouTube,
Palantir, Airbnb and DoorDash. A perennial Forbes Midas List
investor, Keith has ranked as high as #4 in the US and #8
globally.
In this unusually personal conversation with Vidit, Keith goes
back to the beginning: growing up in a middle-class Jewish family
in Edison, New Jersey, reading the encyclopedia cover to cover
and becoming what he calls a “high-credentialist kid.” He
explains how that pursuit took him through Stanford, Harvard Law
School, a federal appellate court clerkship and Sullivan &
Cromwell before he abandoned the path “cold turkey” at 29 to join
a startup almost nobody remembers.
Keith reflects on the people who changed the direction of his
life, including Peter Thiel, Reid Hoffman, Vinod Khosla and Sam
Altman. He shares why Peter’s criticism forced him to become more
quantitative, why he waited to join LinkedIn until the company
needed his particular strengths, and what the rarely discussed
Slide chapter taught him about platforms, pivots, organizational
design and failure.
He also reveals how he identifies top 1% talent, why hiring
exceptional people matters more than becoming a better manager,
and why “the team you build is the company you build.” Keith
explains why he still takes every note by hand, refuses laptops
in meetings and measures how he invests every hour of his time.
They also explore venture capital in the AI era: how to separate
real product-market fit from corporate curiosity, why rapid
revenue can conceal a fragile company, and why enduring
advantages matter more than momentum. Keith also explains why his
greatest edge remains becoming the first institutional investor
in exceptional founders, and why launching a competitive venture
fund today may require at least $500 million.
Please enjoy exploring your curiosity.
________
Get in touch with us via email at contact@curiositycentre.com
Join our stable of commercial partners including the Australian
Government, Google, KPMG,, Allens, Macquarie Capital, Xero, JP
Morgan and more.
Show notes and more episodes here
Follow us on LinkedIn, Twitter and Instagram
Get in touch with our Founder and Host, Vidit
Agarwal directly here
Contact us via our website
This episode is supported by Xero, helping businesses use AI with
more control through JAX, its in-platform AI finance partner. Get
90% off your plan for your first 6 months at
xero.com/highflyers.
________
TIMESTAMPS
00:00 – The Real Keith Rabois
02:51 – His Online Persona
03:25 – Childhood and family
05:45 – Spotting Talent Before Everyone Else
06:50 – Xero
07:40 – The Parents Who Shaped Him
11:05 – The Ultimate Credentialist Kid
13:00 – Why Tech Was Never the Plan
16:10 – Becoming a Lawyer at Six
19:00 – Stanford, Harvard and Status
24:00 – Quitting Law at 29
28:05 – Growing Up With Peter Thiel
31:00 – Learning From Tech’s Best
36:00 – Between PayPal and LinkedIn
39:00 – Peter Thiel’s Career-Changing Criticism
42:00 – Talent Beats Management
44:00 – Finding the Top 1%
47:00 – His Executive Assistant Mistake
51:00 – No Laptops, One Pen
53:00 – The Lessons From Slide
57:00 – Vinod Khosla’s Best Advice
59:00 – Is AI Revenue Built to Last?
01:02:00 – Real Demand or Corporate Curiosity?
01:05:00 – Building a VC Fund Today
01:08:00 – Does Focus Still Win?
01:09:00 – Rapid Fire
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The High Flyers Podcast features in-depth interviews with the
world’s most influential figures in business, tech, finance,
government and sport. Launched in 2020, it has ranked in the
global top ten for past three years, with listeners in 27
countries and over 200+ episodes released, and featured in
Forbes, Daily Telegraph, and at SXSW.
Our guests include -- Malcolm Turnbull (Prime Minister of
Australia), Keith Rabois (Managing Director, Khosla Ventures),
Jason Collins (Head of BlackRock, Asia Pacific), Brad Banducci
(CEO, Woolworths), Michael Schneider (CEO, Bunnings), David
Eckstein (CFO, Legora), Kevin Hartz (Partner, A*; Founder,
Eventbrite), Jesse Zhang (CEO, Decagon), Vandita Pant (CFO, BHP),
Elena Verna (Head of Growth, Lovable), David Haber (a16z
Partner), Jodie Auster (Uber's Global Head of Travel), Rob Giglio
(CCO, Canva), Jean-Michel Limieux (CTO, Shopify and Atlassian),
Stevie Case (CRO, Vanta), Cristina Cordova (COO, Linear), Gautam
Chari (Head of Capital Commitments, Bank of America), John
Haddock (CBO, Harvey), Mark Suster (Partner, Upfront Ventures),
Niki Scevak (Partner, Blackbird), Craig Tiley (CEO, USA Tennis),
Jeanne DeWitt Grosser (COO, Vercel), Paul Bassat (Partner, Square
Peg), Bowen Pan (Creator, Facebook Marketplace), Peter Varghese
(Secretary of Foreign Affairs, Australian Government), Sam
Sicilia (CIO, Hostplus), Jack Zhang (CEO, Airwallex), Tim Doyle
(CEO, Eucalyptus), Sukhinder Singh Cassidy (CEO, Xero), Sanjeev
Gandhi (CEO, Orica) and Philip Green (Australia's Ambassador/High
Commissioner to India).
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