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

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

Aug 8, 2025 • 79 mins

Today’s show: Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about. First up, Jason thinks it’s time for Tim Apple to exit the stage in lieu of a product obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair? PLUS we’re talking Ripple’s acquisition of Rail, Donald Trump’s new AI chatbot, Bumble’s new direction, Airbnb’s potential paths forward and MUCH MUCH MORE.

Key Points

  • Apple's innovation has stagnated since the passing of Steve Jobs, with Tim Cook's leadership focusing more on operational efficiency rather than groundbreaking products.
  • The launch of ChatGPT-5 has been underwhelming despite incremental improvements, highlighting the commodification and intense competition among large language models.
  • State-level regulation of AI, as seen with Illinois' prohibition of AI therapy, may become more common, reflecting local governance's approach to rapidly evolving technologies.
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