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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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),

#265 Jesse Zhang: Decagon's CEO on Maths Olympiads, No Small Talk & Transforming Airlines, Banks, Large Corporates

The High Flyers Podcast with Vidit Agarwal

#265 Jesse Zhang: Decagon's CEO on Maths Olympiads, No Small Talk & Transforming Airlines, Banks, Large Corporates