If you’re not working 9-9-6, are you working hard enough? | E2198
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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
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If you’re not working 9-9-6, are you working hard enough? | E2198

E2198 • Oct 24, 2025 • 61 mins

This episode explores the intersection of sports, betting, and technology, beginning with insider information on LeBron James' injury and its implications for betting and fantasy sports. The discussion shifts to a poker cheating scandal involving NBA figures, examining the legality and monitoring of high-stakes celebrity games. The episode also touches on China's demanding 996 work culture and features insights from Presh on storyboarding methods. Anthropic's deal with Google highlights AI infrastructure investments, while cloud infrastructure's evolution is analyzed through Dropbox's history and David Heinemeier Hansson's views on AWS spending. The episode concludes with a cost-benefit analysis of cloud providers.

Key Points

  • Using AI and technology can significantly streamline and democratize the creative process, making high-quality content production more accessible.
  • The intersection of sports, technology, and betting has created new opportunities and challenges, including the potential for insider information and fraud.
  • Partnerships and strategic use of cloud infrastructure can provide significant advantages to AI and tech companies, allowing them to scale more efficiently and effectively.
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