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