Is Cursor having their Docker moment?

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 SHOW VIDEO: https://youtube.com/@TheCloudcastNET CLOUD NEWS OF THE WEEK: http://bit.ly/cloudcast-cnotw NEW TO CLOUD? CHECK OUT OUR OTHER PODCAST: "CLOUDCAST BASICS" SPONSORS: [VASION] Vasion Print eliminates the need for print servers by enabling secure, cloud-based printing from any device, anywhere. Get a custom demo to see the difference for yourself. [DoIT] Visit doit.com (that’s d-o-i-t.com) to unlock intent-aware FinOps at scale with DoiT Cloud Intelligence. [FCTR] Try FCTR.io (that's F-C-T-R dot io) free for 60 days. Modern security demands modern solutions. Check out Fctr's Tako AI, the first AI agent for Okta, on their website 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? FEEDBACK? Email: show at the cloudcast dot net Bluesky: @cloudcastpod.bsky.social Twitter/X: @cloudcastpod Instagram: @cloudcastpod TikTok: < FEEDBACK? Email: show @ the enterprise ai show dot com Bluesky: @TheEntAIShow.bsky.social Twitter/X: @TheEntAIShow Instagram: @TheEntAIShow