I scaled multiple businesses to 8 figures!! now I'm rebuilding everything in Claude. Help me not screw it up.
EYYYYY I'm an entrepreneur based in Miami. Over the years I've scaled multiple projects to 8 figures and built communities with several million followers combined. I mention this only to give context about the scale I'm operating at day-to-day. Right now I'm migrating my ENTIRE operation to Claude. Not just isolated tasks — I'm designing a global architecture from scratch that includes: - A "mother project" that orchestrates my whole life and businesses - Subprojects for each company/client I collaborate with - A daily personal assistant that reviews my goals, routines, and decisions - Reusable global skills (proposals, meeting notes, content, etc.) - Local skills only when the project context justifies it - Automated workflows for the tasks I do repeatedly The philosophy I'm building on: a minimal root CLAUDE.md (more of a "map" than a container), dense context at lower levels, skills with lazy loading so I'm not burning tokens unnecessarily, and a clear separation between tools (scripts), workflows (procedures), and skills (packaged expertise). My question for the community: What architectural decisions did you make that you later wished you'd done differently? I'm especially interested in hearing from those of you who have already been running Claude Code at real scale for months — not the YouTube tutorials, but the painful lessons that only come from daily use. A few things I'm specifically debating: 1. Global skills by default and local by exception, or the other way around? 2. How do you balance automating everything vs keeping manual control on critical decisions? 3. Which daily workflows gave you the biggest ROI from day one? 4. Any expensive early mistake you can help me avoid? I'm planning to document the entire process and I'm happy to share the learnings with the community as I go. The idea is for this to also serve as a case study for other entrepreneurs who want to do the same. Thanks in advance to anyone who takes the time to reply. Comments are worth gold at this stage 🙏