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.
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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.
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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.
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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).
