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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Show notes and more episodes here
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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),
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),
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