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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