Meeting
2026-06-22 - Andy Milligan - 1:1 (0925)
Gist
Chris and Andy Milligan had their regular 1:1, mostly riffing on the future of web platforms (WordPress vs headless CMS vs Webflow vs Sanity) and Chris's idea for a lightweight block-based CMS. They also discussed Andy's stalled CMO/event goals, a potential Webflow-sponsored event, and Chris's ongoing coaching relationship with Anil Gupta of Multidots, including a planned trip to D.C. Andy mentioned he may drop EO to spend more time meeting with Anil and Chris, and will ask Chris for sales pipeline advice on an upcoming proposal.
Distilled from the transcript by claude-sonnet-5 · Jul 25
What came out of it
Decisions1
- Andy decided to prioritize regular meetups with Anil over continuing Entrepreneurs Organization
Risks and blockers3
- Andy has not yet done outreach for the event/community idea despite saying he would
- Webflow's pricing model and lack of code ownership seen as a long-term risk to its position
- Chris worries the $15k website sales model may not be sustainable long term
Open questions3
- Will WordPress's market dominance hold up against headless/AI-native alternatives in coming years
- Will the web design market bifurcate into cheap commoditized sites versus high-end custom creative work
- Whether Webflow can find a viable path upmarket to enterprise
Next steps4
- ClientAndy will send Chris pictures from the conference
- ClientAndy will ask Chris for advice on sales pipeline and proposal language
- ClientAndy plans to do outreach for the event/community batching idea he liked
- MeChris will travel to D.C. end of July for two days with Anil Gupta
A record of what was agreed, not a task list — nothing here was scheduled.
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