This Week in Startups
This Week in Startups
Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.
Jason Calacanis
PodcastAI
PodcastAI

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

E2123 • May 9, 2025 • 74 mins

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.

Key Points

  • Using AI avatars of deceased individuals in court cases raises significant ethical concerns around manipulation and authenticity.
  • The success of secondary funds in the private market is a positive indicator of increased liquidity and confidence in early-stage investments.
  • Expanding "Where to Wheel" to include broader agritourism activities could open significant new markets and opportunities.
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