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

Deel’s growth overshadows SpyGate, Claude learned new skills & the “momentum is moat” debate | E2194

E2194 • Oct 17, 2025 • 78 mins

In this episode, we dive into market chaos and business strategies. Jason discusses the ski season and Open Snow app, and a shift to short, direct calls amid market changes. The team explores AI's expanding opportunities and the potential for trillion-dollar AI companies. They analyze Deel's $300M raise and its industry impact. Roloff Botha joins to discuss venture capital dynamics. We cover startup valuation, growth prospects for Rippling and Deel, and capital strategies. Anthropic's AI skills and applications are highlighted, along with collaboration in LLMs. Jason shares his health journey, and the episode wraps up with a focus on startups, AI, and data balance.

Key Points

  • The venture capital industry is facing intense competition, making it increasingly challenging to achieve high returns, and this is resulting in market dynamics that favor founders more than VCs or LPs.
  • Anthropic's introduction of "skills" for its AI models represents a significant innovation, potentially making enterprise AI applications more efficient and customizable, which could drive higher retention rates and business adoption.
  • In the evolving AI landscape, startups might find greater opportunities and stability in focusing on enterprise solutions rather than consumer applications, as evidenced by improving retention rates and more robust growth trajectories in enterprise AI products.
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