The Reasoning Show
The Reasoning Show - Reasoning through the AI Revolution
The industry's leading AI podcast, explores how leaders think through AI, technology, and transformation. Each week founders, investors, and operators unpack the decisions behind the systems shaping modern business.
Hosts: Aaron Delp and Brian Gracely
The Reasoning Show
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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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