Brian Gracely (@bgracely) and Brandon Whichard (@bwhichard) discuss the big changes happening around AI developer-assistants, across Cursor, Windsurf, OpenAI and Google.

SHOW: 941

SHOW TRANSCRIPT: The Cloudcast #941 Transcript

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SHOW NOTES:

  • Cursor Series-C Funding ($9.9B valuation)
  • New Cursor Pricing Tiers
  • Updated Cursor Pricing (June 2025)
  • Cursor apologizes for unclear pricing changes (TechCrunch)
  • Promiscuity of Modern Developers (Redmonk)
  • Aaron Levie speculates that coding-assistants are involved with 50% of AI usage today
  • Anysphere, the startup behind coding app Cursor, hired two former Anthropic leaders
  • Measuring the actual impact of AI coding (Changelog)
  • Windsurf’s CEO goes to Google; OpenAI’s acquisition falls apart (TechCrunch)
  • Windsurf 2-3x’d headcount, and then the founding team walked. Pretty wild (X.com)

Topic 1 - What happened (basics of the pricing change)?

Topic 2 - How was this communicated?

Topic 3 - Where was the confusion?

Topic 4 - Wasn’t this inevitable because of huge costs and funding rounds?

Topic 5 - How do we square the “developers don’t pay for anything” and “AI-native vs. AI-augmented” when developers are still in the loop?

Topic 6 - Does this inevitability mean AI coding-assistants can’t be a standalone business, but need to be in a bundle?

Topic 7 - WTF Windsurf?

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