This Week in Startups

GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162

199 snips
Aug 8, 2025
In a critical discussion, the hosts suggest Apple may need a leadership change to revive its innovative edge. The launch of GPT-5 prompts questions about whether we’re entering an AI trough of despair. Ripple’s bold acquisition of Rail raises intriguing regulatory discussions. They also explore Bumble's new direction and Airbnb's potential paths amid changing travel dynamics. The episode wraps up with a look at the intersection of technology, marketing, and ethics in AI, particularly regarding its role in therapy.
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INSIGHT

Apple Resting On Steve Jobs' Legacy

  • Apple has exhausted much of Steve Jobs' product roadmap and now prioritizes margin over bold consumer bets.
  • Jason Calacanis warns the company rests on legacy products instead of pursuing new, risky innovations.
ADVICE

Force A Product‑Obsessed Leadership Change

  • Announce a successor and buy startups to seed competing product teams.
  • Jason Calacanis advises Apple to create internal competition by acquiring founders and forming SWAT teams to spark innovation.
INSIGHT

GPT‑5 Feels Incremental, Not Transformational

  • GPT‑5 felt like an iterative improvement rather than a leap, delivering fewer errors but limited wow.
  • Jason and Lon both described the release as underwhelming despite measurable accuracy gains.
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