OpenAI Scoops Instacart’s CEO, AI in the Courtroom & Off-Road Startups | E2123

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,