The High Flyers Podcast with Vidit Agarwal

Jesse Zhang is the Co-founder & CEO of Decagon, one of the world's fastest-growing AI companies. In just two and a half years, Decagon has grown to around 500 employees, raised approximately US$500 million from investors including Andreessen Horowitz, Accel and Bain Capital Ventures, and today powers AI customer service for many of the world's largest airlines, banks, retailers and technology companies.

In this rare in-depth conversation, Jesse reflects on growing up in Boulder, Colorado, an intensely disciplined childhood shaped by maths competitions and Chinese immigrant parents, graduating from Harvard in just three years, and why his first startup taught him far more than his second.

Vidit and Jesse explore how Decagon found its billion-dollar opportunity by interviewing hundreds of customers, why they reached US$1 million in ARR with just two people, how to hire exceptional talent, why speed has become the ultimate competitive advantage in AI, building one of Silicon Valley's leading AI companies, and what it really takes to scale from founder mode to leading 500 people.

Please enjoy exploring your curiosity.

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00:00:00 Who is Jesse Zhang?

02:10 The Huawei story that shaped Decagon

07:20 Why Maths Olympiads create successful founders

13:05 Leaving Harvard a year early

17:40 The startup that nearly broke him

23:30 Losing two co-founders

29:15 Why he started again

34:20 The question that found Decagon

40:10 Hitting $1M ARR with just 3 employees early on

45:25 Learning enterprise sales from scratch

50:35 Building AI agents before the hype

56:15 Why Decagon is beating bigger rivals

1:02:20 Hiring only "serious people"

1:08:15 Letting go as CEO

1:13:10 Marriage, sleep & startup obsession

1:17:05 What he's really building

________

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Join our stable of commercial partners including the Australian Government, Google, KPMG, Vanta, Allens, Macquarie Capital, City of Sydney and more. 

Show notes and more episodes here

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Get in touch with our Founder and Host, Vidit Agarwal directly here

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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), 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),

David Eckstein is the CFO of Legora, one of the world’s fastest-growing enterprise software companies, which grew from $1 million to $100 million in Annual Recurring Revenue (ARR) in just 18 months.

David reflects on his parents’ divorce, graduating from college in three years, and realising at 22 that he was “living someone else’s life” before leaving investment banking for Silicon Valley.

Vidit and David explore his journey through Box, OpenDNS, Menlo Security and Vanta to Legora; helping sell OpenDNS to Cisco; investing in more than 100 startups; and how 16 years of relationships helped Legora attract $1.5 billion in investor demand and raise a $600 million Series D.

They also discuss the changing role of the CFO, AI economics and token spend, how to diligence a startup before joining, lessons from exceptional founders, Legora’s extraordinary growth, and David’s philosophy of loyalty and giving more than he takes.

Please enjoy exploring your curiosity.

________

00:00:00 Meet David Eckstein

00:05:00 Why Loyalty Drives Everything

00:13:00 The Obsession With Permanence

00:23:00 “I Was Living Someone Else’s Life”

00:28:00 How Relationships Helped Raise $600M

00:38:00 The New Economics of AI

00:45:00 Lessons From Four Hypergrowth Companies

00:55:00 Why He Bet His Career on Legora

01:05:00 What Makes Legora Special

01:12:00 The Hardest 25 Days of His Life

01:15:00 Give More Than You Take

01:21:00 Rapid Fire

________

Get in touch with us via email at contact@curiositycentre.com

Join our stable of commercial partners including the Australian Government, Google, KPMG, Vanta, Allens, Macquarie Capital, City of Sydney 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

________

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), 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), 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), Philip Green (Australia's Ambassador/High Commissioner to India), Vivek Bhatia (CEO, MUFG), Cristina Cordova (COO, Linear) and more.

Episode #263 features Gautam Chari, Managing Director and Head of Capital Commitments (Asia Pacific) at Bank of America.

Growing up in Mumbai, Gautam thought his path was already written. Like many students of his generation, he became a civil engineer, started work on construction sites and expected to spend his career building physical infrastructure. Instead, a series of bold decisions took him to Australia, into investment banking, and eventually to one of the world's largest financial institutions.

In this rare and deeply personal conversation, Gautam reflects on the teachers who changed the trajectory of his life, the culture shock of moving from Mumbai to Adelaide, breaking into investment banking without a finance background, living through 9/11 in New York, and the lessons from building a global career across Sydney, London, New York and Hong Kong. 

Vidit and Gautam explore why the best careers are rarely linear, the difference between confidence and conviction, how great leaders develop judgment, why listening is an underrated superpower, the AI investment cycle, and why the Australia-India relationship will be one of the defining economic stories of the coming decades.

This is Gautam's first-ever podcast interview. 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, Vanta, Allens, Macquarie Capital, City of Sydney and more. 

Show notes and more episodes here

Follow us on LinkedIn, Twitter, Instagram, or YouTube

Get in touch with our Founder and Host, Vidit Agarwal directly here

Contact us via our website

________

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), 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), 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), Philip Green (Australia's Ambassador/High Commissioner to India), Vivek Bhatia (CEO, MUFG), Cristina Cordova (COO, Linear) and more.

Join our stable of commercial partners including the Australian Government, Google, KPMG, Vanta, Allens, Macquarie Capital, City of Sydney and more.

________

Welcome to the eleventh episode in our special series with the Australian Government and their Centre for Australia–India Relations (CAIR), spotlighting the growing Australia–India relationship across technology, business, media, culture and sport. Previous guests include Renowned Music Composer Tushar Apte, Australia's High Commissioner to India Philip Green, MUFG's CEO Vivek Bhatia, Ex Secretary of Foreign Affairs Peter Varghese, NAB's EGM Sweta Mehra, Deputy Secretary of Australia's Home Affairs Brendan Dowling, Orica's CEO Sanjeev Gandhi, Sports Journalist Bharat Sundaresan, Cricket Legend Lisa Sthalekar and CAIR's CEO, Ryan Neelam, reflecting the breadth of Indian-Australian leaders at the most senior levels.

Welcome to this classic episode. Classics are our favorite episodes from our back catalogue, published as frequently as possible. These are N of 1 conversations with N of 1 people. This is a replay of Episode 202, originally released in April 2025— one of our most loved classics. 

Brad Banducci is the recent CEO of Woolworths Group, one of the world's largest retail businesses, generating more than $65 billion in annual revenue, employing over 200,000 people and serving millions of customers every week.

In this rare interview (and his first since he left Woolworths after 8+ years) Brad reflects on growing up in South Africa during apartheid, the lessons learned from his entrepreneurial family, and the experiences that shaped his identity, ambition and worldview long before he stepped into the CEO's office.

Vidit and Brad explore his remarkable journey from engineer and management consultant at Boston Consulting Group to leading one of the Southern Hemisphere's most complex organisations. They discuss intrapreneurship versus entrepreneurship, making high-stakes decisions with imperfect information, leading through transformation at scale, and the leadership philosophy behind one of his most memorable ideas: being directionally correct beats being perfectly right.

They also unpack failure, purpose, family, curiosity, succession, building leaders who outperform you, and why the best executives spend less time chasing certainty and more time moving towards what matters.

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, Vanta, Allens, Macquarie Capital 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

________

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), 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), 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), Philip Green (Australia's Ambassador/High Commissioner to India), Vivek Bhatia (CEO, MUFG), Cristina Cordova (COO, Linear) and more.

Episode #261 features Ameet Bains, CEO of the Western Bulldogs, an AFL club with more than 65,000 members, $100 million in net assets, and a reach spanning elite sport, community programs and one of Australia’s fastest-growing regions.

Ameet reflects on growing up as the son of Indian migrants, embracing both Australian and Punjabi cultures, and the entrepreneurial sacrifice his parents made to fund his education and future.

Vidit and Ameet explore his journey from lawyer at MinterEllison and Toyota to AFL executive, the setbacks and missed opportunities that ultimately shaped his career, and the leadership lessons learned from managing player contracts, building high-performing teams and leading through intense public scrutiny.

They also discuss sustaining success in elite sport, balancing ambition with family, the future of AI in organisations, engaging Australia's rapidly growing Indian community, and why humility, service and long-term thinking matter more than headlines.

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, Vanta, Allens, Macquarie Capital, City of Sydney 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

________

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), 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), 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), Philip Green (Australia's Ambassador/High Commissioner to India), Vivek Bhatia (CEO, MUFG), Cristina Cordova (COO, Linear) and more.