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

Why New Yorkers hate AI Friends, Producer Claude gets an update, and the value of human writers in the Age of Slop | E2185

Sep 29, 2025 • 60 mins

Today’s show: Friend’s new AI pendant just wants to be your new pal. So why do New Yorkers hate them? On a brand-new TWiST, Jason and Alex consider the Friend AI pendant, which listens to everything you say all day and then sends you snarky texts about it. WIRED says it’s unhelpful and will make your friends hate you. New Yorkers are so sick of their aggressive subway ads, they’re tagging them with graffiti. But what do Jason and Alex think of the wearable companion? PLUS the value of bringing your last team with you to your new project… why partnerships often lead to purchases… Producer Claude got an upgrade… two fresh TWiST 500 companies… the rise and fall and further fall of Tai Lopez… AND Jason explains the rules of private jets.

Key Points

  • Experienced founders with past venture capital raises, even if they failed, are more fundable due to their knowledge and lessons learned from previous ventures.
  • Persistent recording devices like AI pendants raise significant privacy concerns, as they can capture sensitive and potentially damaging conversations, making them a controversial technology.
  • The growth of AI-generated content services is seen as problematic, with potential long-term impacts on content quality and authenticity, leading to a need for strict guidelines and distinctions between human-created and AI-generated content.
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