The High Flyers Podcast with Vidit Agarwal

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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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.

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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).

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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Kevin Hartz is the Co-Founder of Eventbrite and Xoom, and Co-Founder and General Partner at A*, the early-stage venture firm whose latest fund is $450M. Xoom was acquired by PayPal for more than $1B, Eventbrite went public, and Kevin has backed some of technology’s most important companies from the earliest stages, including PayPal, Airbnb, Palantir, SpaceX, Anduril, Ramp and Decagon.

In this conversation with Vidit, Kevin goes back to the beginning: growing up in the Bay Area before Silicon Valley became Silicon Valley, studying history at Stanford and Oxford, returning home “fairly lost,” and nearly choosing medicine before the internet pulled him into technology. He shares how friendships with Peter Thiel and the early PayPal team shaped his trajectory, why he chose to build Xoom instead of joining PayPal, and what it felt like to later be “brushed aside” as CEO.

Kevin also reflects on building Eventbrite with his wife Julia while raising a family, the relentless reality of being a scaling CEO, and how identity changes when a company that defined two decades of your life is no longer yours. He explains what the PayPal Mafia taught him about talent, why the best founders create leverage by surrounding themselves with exceptional people, and why some founders are simply an “automatic check.”

They also explore A*, how Kevin finds the next generation of breakout founders, the extraordinary valuations and competition in today’s AI market, why relationships still matter at seed, and what decades of building and investing have taught him about ambition, judgment and the people you choose to spend your life around.

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.

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TIMESTAMPS

00:00 – Meet Kevin Hartz

02:56 – Xero

03:56 – Childhood and family

16:00 – Stanford vs Oxford

21:00 – “I was fairly lost”

24:00 – PayPal, Peter Thiel and Xoom

30:00 – Getting pushed out as Xoom CEO

33:00 – Tech then vs now

35:00 – Why Eventbrite had to exist

43:00 – The reality of being CEO

45:00 – Building with Julia and becoming a dad

48:00 – What the PayPal Mafia taught him

53:00 – Investing in a wild market

56:00 – Who is Kevin Hartz after Eventbrite?

59:00 – Building A* after the SPAC era

1:02:00 – Finding the next great founder

1:04:00 – Why Ashwin was an “automatic check”

1:08:00 – Kevin’s dream dinner table

1:11:00 – The question Kevin asks every founder

1:13:00 – Why “I’d be happy to” is banned at A*

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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), 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).

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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Dylan Babbs is the Co-Founder and CTO of Profound, one of AI’s fastest-growing marketing companies, which reached a $1B valuation within 18 months and has raised $155M+ from Lightspeed, Sequoia, Kleiner Perkins, Khosla Ventures and others. Previously a design engineer at Uber, Dylan is a licensed private pilot and maps obsessive with a distinctive approach to engineering, product and design.

In this conversation with Vidit, Dylan shares how an obsession with maps shaped his approach to product and design, why years of side projects eventually led him to leave his dream job at Uber, and how meeting James Cadwallader at South Park Commons led to Profound. He unpacks the three things every successful startup needs, why founders should stop “swimming upstream”, and how Profound grew far beyond even the founders’ expectations.

They also explore Profound’s bigger bet on how AI is reshaping marketing, what Fortune 500 CMOs are asking today, the rise of the “marketing engineer”, product taste and speed, and why learning to fly taught Dylan to “run towards the anxiety.”

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. 

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TIMESTAMPS

00:00 Meet Dylan Babbs
02:25 Xero
03:25 Growing up in Silicon Valley
04:35 Why maps are fascinating
19:35 Berlin + starting a business
26:35 Puerto Rico + learning to fly
30:35 “Run towards the anxiety”
38:35 Uber + walking away
42:35 Meeting his co-founder
49:05 3 things every startup needs
53:35 Product taste + speed
56:35 Building Profound
59:35 Fast tracked revenue growth
1:03:35 What Fortune 500 CMOs want
1:07:35 The rise of the “marketing engineer”
1:10:35 Can the giants copy Profound?
1:13:35 Profound’s data moat
1:16:35 Flying, surfing + 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), Jason Collins (Head of BlackRock, Asia Pacific), Brad Banducci (CEO, Woolworths), Michael Schneider (CEO, Bunnings), David Eckstein (CFO, Legora), 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).

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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Damien Lewke is the Founder & CEO of Nebulock, an AI-native cybersecurity company building autonomous technology to find threats before they become major attacks. Previously, he worked across CrowdStrike, Palo Alto Networks, Arctic Wolf and Northrop Grumman, four leading names across cybersecurity and defence, and studied AI at MIT. Nebulock has since run 300M+ AI-powered investigations and surfaced 4,000+ security incidents missed by existing tools.

In this conversation with Vidit, Damien traces the unconventional journey that led him there, from pursuing professional football in Germany and selling shoes in Los Angeles to discovering cybersecurity through an internship, working in Asia Pacific, and eventually quitting his job without a perfect plan to start Nebulock as a solo founder.

They unpack why cybersecurity is harder today than 12 years ago, how AI could automate hacking at scale, and why even the world’s best security tools still miss attacks. Damien also shares why he interviewed 90 customers in 90 days before writing a line of code, the 30-page manifesto that helped launch Nebulock, what he learned inside some of cybersecurity’s defining companies, and why he still runs 1,000 miles every year.

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. 

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TIMESTAMPS

00:00 Meet Damien Lewke
03:50 Xero
04:50 Growing up between America and Germany
14:20 Chasing professional football
21:00 Discovering cybersecurity
24:00 Cybersecurity: 2014 vs today
29:00 The DNC hack → CrowdStrike
38:30 Australia, Palo Alto + MIT
47:00 Why he became a solo founder
53:00 Why AI changes cybersecurity
57:00 Building Nebulock
1:00:00 Can the giants copy it?
1:05:00 90 customers before writing code
1:12:00 Hiring exceptional people
1:20:00 AI vs AI: the future of cyber
1:24:00 Running 1,000 miles + 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), Jason Collins (Head of BlackRock, Asia Pacific), Brad Banducci (CEO, Woolworths), Michael Schneider (CEO, Bunnings), David Eckstein (CFO, Legora), 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).

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. Terms apply.

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Luke Anear is the Founder and CEO of Mitti, the global technology company formerly known as SafetyCulture. Founded in 2004, Mitti has grown into a US$1.6 billion company with 850+ employees, helping tens of thousands of organisations improve how work gets done. Today, it is expanding across AI, computer vision and insurance, building on more than 3.5 billion workplace images and an insurance business that has already written US$115 million+ in premiums.

After more than 20 years building the company, Luke stepped away from the CEO role completely exhausted. Eighteen months later, he’s back in the chair, has made more changes in five months than he says he did in the previous decade, and is rebuilding the business for the AI era.

In this candid conversation, Luke shares how dropping out of school and cycling through 18 jobs and businesses shaped him, including living in his car before making $42,000 in a single night, and why he regrets selling 28% of SafetyCulture for just $2 million. Vidit and Luke unpack the chaos of scaling from 25 to 300+ employees, why stepping away became “one of the best things that ever happened” to him, what he’s doing differently in his second stint as CEO, and his ambition to build Mitti into a $10 billion revenue business.

They also explore why AI is pushing software from horizontal to vertical, Mitti’s expansion beyond traditional SaaS, the surprising lesson Luke learned on a job site in Nepal, and the more personal side of a founder who flies helicopters, makes films and once took his children out of school to travel the world making documentaries together.

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

________

TIMESTAMPS

00:00 Why SafetyCulture became Mitti
02:10 Introduction
07:00 Xero
10:15 Living in his car to making $42K overnight
20:30 How SafetyCulture really started
25:30 Selling 28% for $2 million
31:30 Stepping away and returning as CEO
36:00 The mistakes of scaling too fast
44:15 Why AI is making software more vertical
46:30 What Nepal taught Luke about global expansion
54:00 From SaaS to insurance
1:03:00 “I was cooked”: burnout and becoming a different CEO
1:15:00 Documentaries, his kids and flying helicopters
1:23:00 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), Jason Collins (Head of BlackRock, Asia Pacific), Brad Banducci (CEO, Woolworths), Michael Schneider (CEO, Bunnings), David Eckstein (CFO, Legora), 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).