Issue No. 24Week ending Sunday, June 14, 2026436 episodes · 1837 articles
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WWDC Kicks Off, Jobs Up, Tech Down, VC Horror Stories Go Viral | Diet TBPN

With John Coogan, Jordi Hays, Tyler · Sunday, June 14, 2026

The episode covered Apple's WWDC 2026 announcements, focusing on Siri's AI integration and the implications of its "private cloud" strategy. Discussions also included the surprisingly robust US job market, the ongoing challenge of inflation leading to potential rate hikes, and a viral thread of "VC horror stories" detailing founders' negative experiences with investors, including controversial practices like Sequoia's multi-tranche deals. Finally, a brief but intense debate arose around the potential link between phone usage and declining fertility rates, sparking questions about tech companies' responsibility.

Key takeaways

  • Founders aren't asking for revolutionary AI, just practical implementations of existing best practices, like those seen in ChatGPT, Gemini, and Claude. Read more →
  • Apple's "private cloud" AI for Siri implies off-device processing, directly contradicting typical on-device claims and raising questions about its true nature. Read more →
  • Top VCs are not immune to bad behavior: Jordi Hays recounts a GP falling asleep during a critical $15 million Series A pitch, a stark reminder that even at the highest levels, basic respect can be missing. No one acknowledged it, setting a bizarre tone for the room. Read more →
  • Multi-tranche deals, like those at Sequoia Capital, involve VCs investing at different valuations. While not illegal for the fund, John Coogan notes founders who misrepresent these blended prices to employees or later investors could be committing securities fraud, projecting a valuation "less than 50% of the one projected to the market." Read more →

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