Claude Cowork/Code Copilot — Recurring 1-on-1 Coaching + Hands-On Execution (Hourly, Long-Term)

I'm a 50-year financial services veteran, bestselling author, and podcast host (890+ episodes). I run multiple businesses and produce a constant stream of books, content, and communications. I've adopted Claude Cowork and Claude Code as the backbone of how I work going forward — and I need a copilot. **What this is:** A recurring, paid, hourly 1-on-1 relationship. Think flight instructor plus copilot. Two jobs in one: 1. **Teach me, live.** Screen-share sessions where you show me exactly how to do the specific thing I need — no curriculum, no workshops, no theory. I bring the question, you give me the answer fast. 2. **Take the controls when it's over my head.** Tasks too complex for me get offloaded to you directly. **My setup (non-negotiable — you must be fluent here):** - Mac desktop, Apple ecosystem: Apple Mail, Apple Notes - Dropbox as the local file home base for Cowork - No Google Workspace, no Notion, no Slack. Don't pitch me a migration. **You must have:** - Real, current, hands-on experience with **Claude Cowork specifically** — not just Claude Code, not just ChatGPT, not general "AI consulting" - Claude Code and Claude.ai (Projects, Skills, connectors, MCP) expertise - Proven ability to teach a smart non-engineer — clearly, quickly, without jargon - Availability for a weekly standing call plus async questions between sessions **How I work:** I'm direct. I know exactly what I want. I don't do group learning and I don't waste time. If you can answer a question in two minutes, answer it in two minutes. I pay well for speed and expertise, and this engagement has no end date — books, content, organization-building, and communications work will keep coming indefinitely. **To apply:** Skip the boilerplate. Tell me: (1) one real thing you've built or automated with Claude Cowork, (2) your experience working within an Apple/Dropbox environment, and (3) your hourly rate and weekly availability. I'll do paid one-hour trial sessions with my top candidates and pick one. If you're a doer who can also teach, this is a long-term seat in the cockpit.