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. * 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 Subscribe to the TWiST500 newsletter: https://ticker.thisweekinstartups.com Check out the TWIST500: https://www.twist500.com Subscribe to This Week in Startups on Apple: https://rb.gy/v19fcp * Links from episode: Check out Wheel2Wheel: https://dev.where2wheel.com/ * Follow Where2Wheel: X: https://x.com/Where2Wheel Linkedin: https://www.linkedin.com/company/where2wheel-llc/ * Follow Lon: X: https://x.com/lons * Follow Alex: X: https://x.com/alex LinkedIn: ⁠https://www.linkedin.com/in/alexwilhelm * Follow Jason: X: https://twitter.com/Jason LinkedIn: https://www.linkedin.com/in/jasoncalacanis * 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 * Great TWIST interviews: Will Guidara, Eoghan McCabe , Steve Huffman , Brian Chesky , Bob Moesta, Aaron Levie , Sophia Amoruso , Reid Hoffman , Frank Slootman , Billy McFarland * Check out Jason’s suite of newsletters: https://substack.com/@calacanis * Follow TWiST: Twitter: https://twitter.com/TWiStartups YouTube: https://www.youtube.com/thisweekin Instagram: https://www.instagram.com/thisweekinstartups TikTok: https://www.tiktok.com/@thisweekinstartups Substack: https://twistartups.substack.com * Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916