OpenAI Scoops Instacart’s CEO, AI in the Courtroom & Off-Road Startups | E2123
This Week in Startups
Jason Calacanis
4.4 • 1.3K Ratings
🗓️ 10 May 2025
⏱️ 73 minutes
🧾️ Download transcript
Summary
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:
Linkedin: https://www.linkedin.com/company/where2wheel-llc/
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Follow Lon:
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Follow Alex:
LinkedIn: https://www.linkedin.com/in/alexwilhelm
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Follow 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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Substack: https://twistartups.substack.com
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Subscribe to the Founder University Podcast: https://www.youtube.com/@founderuniversity1916
Transcript
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| 0:00.0 | If you did this to me after I died and tried to speak for me using what appears to be a 25 cent AI model makeover, I would come down and haunt you until I couldn't anymore. |
| 0:10.6 | You know, like it's just abusive. |
| 0:12.1 | I feel like we are going to be in a future where everybody's going to have in their will. |
| 0:15.6 | Like, please don't make an AI avatar of me after I'm dead. |
| 0:19.3 | So it's like your organs. |
| 0:20.3 | Right. |
| 0:20.6 | I will give my organs. |
| 0:21.6 | I will not give my soul and my likeness away. |
| 0:24.8 | Yeah. |
| 0:25.1 | It's probably a good time to bring this up. |
| 0:26.6 | In your contract, obviously, you didn't read it thoroughly enough. |
| 0:28.8 | We have the rights in perpetuity to have you do all 10 Q's and quarterly earnings even after you pass. |
| 0:33.8 | I'm fine with that, actually. |
| 0:34.9 | Yeah. I'm fine with that, actually. Yeah, but your kids get like $100 per hour residual. |
| 0:39.7 | Let me ask you that. |
| 0:40.6 | Done. |
| 0:41.8 | This weekend startups is brought to you by Brex, the financial stack founders can bank on. |
| 0:47.0 | Unlike traditional business banking solutions, Brex has no minimums and no transaction fees. |
| 0:51.2 | And you can get 20 times the standard FDIC protection. |
| 0:54.4 | Get the business account trusted by one in three U.S. startups at brex.com slash banking |
| 0:58.5 | dash solutions. |
| 1:00.0 | LinkedIn jobs. |
... |
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