Today’s show: Jason, Alex, and Lon break down OpenAI’s latest power move: hiring Instacart CEO Fidji Simo to lead its consumer apps. They also dive into the ethical storm brewing around an AI-generated victim statement used in court — is this the future of legal testimony? Plus, they explore how late-stage funding rounds like a “Series G” don’t automatically spell trouble anymore, and what The Checklist Manifesto can teach startup founders. Stick around for another Office Hours, where WhereToWheel gets a shot at the spotlight.
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Timestamps:
(0:00) We kick off the show!
(2:28) Intro: It's all about having a system...
(8:52) Wait, OpenAI STOLE Instacart's CEO?
(10:00) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/banking-solutions
(18:03) Why Adam Curry is the Podfather
(20:08) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(22:53) Would you want to be represented in court by an AI Avatar?
(30:44) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
(35:38) What the heck is "Minor M&A"?
(48:10) When are we all getting humanoid robots?
(53:30) Where2Wheel wants to help you off-road
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Links from episode:
Check out Wheel2Wheel: https://dev.where2wheel.com/
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Follow Where2Wheel:
X: https://x.com/Where2Wheel
Linkedin: https://www.linkedin.com/company/where2wheel-llc/
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Follow Lon:
X: https://x.com/lons
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Follow Alex:
X: https://x.com/alex
LinkedIn: https://www.linkedin.com/in/alexwilhelm
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Follow Jason:
X: https://twitter.com/Jason
LinkedIn: https://www.linkedin.com/in/jasoncalacanis
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Thank you to our partners:
(10:00) Brex. Get the business account trusted by 1 in 3 US startups at https://www.brex.com/banking-solutions
(20:08) LinkedIn Jobs - Post your first job for free at https://www.linkedin.com/twist
(30:44) Vanta - Get $1000 off your SOC 2 at https://www.vanta.com/twist
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Great TWIST interviews: Will Guidara, Eoghan McCabe, Steve Huffman, Brian Chesky, Bob Moesta, Aaron Levie, Sophia Amoruso, Reid Hoffman, Frank Slootman, Billy McFarland
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