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Published 31st August, 2026.
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 by clicking Here
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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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Timestamps
About us
The High Flyers Podcast features in-depth interviews with the world’s most relatable role models in business, tech, finance, government and sport in the US, Australia, Singapore, India and New Zealand.
Launched over 6.5+ years ago - our 275+ guests come from various industries around the world including:
Investing and Finance (VC, PE, Pension Funds, Family Offices)
Our guests across venture capital, growth investing, institutional capital, banking, pension funds and family offices include: Keith Rabois (MD, Khosla Ventures), Jason Collins (CEO, BlackRock Asia Pacific), Ryan Beiermeister (Partner, Founders Fund), David Haber (General Partner, Andreessen Horowitz), Kevin Hartz (Managing Partner, A*), Mike Vernal (Partner, Conviction; Ex-Sequoia), David Schneider (Growth Fund Co-Lead Partner, Coatue), Venky Ganesan (Managing Partner, Menlo Ventures), Mark Suster (Managing Partner, Upfront Ventures), Kelland Reilly (Partner, Airtree; Ex General Atlantic, D1), Niki Scevak (Managing Partner, Blackbird), Paul Bassat (Managing Partner, Square Peg), David Neal (CEO, IFM Investors), Sam Sicilia (CIO, Hostplus), Michael Kim (Partner, Cendana Capital), Beezer Clarkson (Partner, Sapphire), Gautam Chari (Head of Capital Commitments, Bank of America), David Shein (Managing Partner, OIF), Vivek Bhatia (CEO, MUFG), Rowan Simpson (Founder, Hoku) and more.
Technology, AI and software (Startups, Big Tech, Publicly Listed)
Our technology, AI and software guests include Jodie Auster (Uber’s Global Head of Travel), Sukhinder Singh Cassidy (CEO, Xero), Rob Giglio (CCO, Canva), Mel Silva (MD, Google), Jean-Michel Lemieux (former CTO, Shopify and Atlassian), Anil Sabharwal (Global VP, Google Chrome, Photos and Drive), Shiv Rao (CEO, Abridge), Jesse Zhang (CEO, Decagon), Dylan Babbs (Co-Founder & CTO, Profound), John Willett (Co-Founder & COO, Rogo), David Eckstein (CFO, Legora), John Haddock (CBO, Harvey), Stevie Case (CRO, Vanta), Jeanne DeWitt Grosser (COO, Vercel), Cristina Cordova (COO, Linear), Elena Verna (Head of Growth, Lovable), Jack Zhang (CEO, Airwallex), Tim Doyle (CEO, Eucalyptus), Andrew Fraser (President, Halter), Bowen Pan (creator of Facebook Marketplace) and more.
CEOs, Boards and Major Company Senior Executives
Our guests leading some of the world's largest and most recognisable organisations include Brad Banducci (CEO, Woolworths Group), Aleks Spaseska (CEO, Kmart) Michael Schneider (CEO, Bunnings), Paul Grosmann (CEO, R.M.Williams), Andrew Penn (CEO, Telstra), Vandita Pant (CFO, BHP), Sanjeev Gandhi (CEO, Orica), Craig Tiley (CEO, Tennis USA), Brendan Hargreaves (CFO, Officeworks), Andrew Fraser (Board Chair, Bank of Queensland), Jaddan Cummerford (CEO, Unified Music), Ed McManus (CEO, Deliveroo) and more.
Government and Policy Makers
Our government, diplomatic and public-policy guests include Malcolm Turnbull (Prime Minister of Australia), Amit Singh (Managing Partner, Mandala), Peter Varghese (Secretary of Australia's Foreign Service), Philip Green (Australia’s High Commissioner to India), Brendan Dowling (Deputy Secretary, Australia's Department of Home Affairs), Mukund Narayanamurti (General Manager for South Asia, Austrade) and Ryan Neelam (CEO, Centre for Australia-India Relations, Australian Government).
Professional Athletes
Steve Solomon (400m Olympic Sprinter), Ed Cowan (Former Test Cricketer), Trent Cotchin (3x Premiership Winning Captain, Richmond FC), Lisa Stahelakar (World Cup Winning Captain, Australian Womens Cricket Team).
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