02
Business
The operator's craft, and the value architecture of a modern business.
30+ years · six companies · OpticWise · Peak Property Performance
Built, lost, and built again, for real. The operator's receipt.
The operator's craft (building, leading, deciding, resilience under fire) and the value architecture of a modern business: data, AI, category. Two clusters.
Operator resilience first. Zero fear of failure: fear of failure changes behaviors; after you've nearly died twice, losing a company doesn't register the same way. Bet on the model you believe in, with skin in the game: I zeroed out OpticWise revenue to rebuild on recurring clients, and fronted a six-figure personal check to land the first anchor. Write the check. Then you'll watch yourself perform. Recurring revenue plus a long engagement cycle is a business worth loving.
Shut a dead business fast. It's self-respect, not failure. My biggest regret: waiting eighteen months to close a company I knew was dead at eight. Cut to the core, run leaner, earn more: in 2008 revenue fell $12M to $2.5M. I cut everything except the customer, went from two dozen people to five, and netted more than the bigger company had. Revenues are vanity, profit is sanity, cash is king.
Then the value architecture, and the core deliverable most men are missing: you'll learn to operate with AI the way I do. AI is non-negotiable: go AI-centric, but never hand it the decision. AI is your thought partner, not your thought leader. I architect, code, deploy, and strategize with it every day, about two years ahead, and I teach the method. Data is gold: own it, control it, don't give it away. Process before technology: nail the process first, then build the tech around it. People first, always.
Frameworks you'll use
- Bill's Five Questions
- Strip It Down
- Keep or Kill
- With Me, Not For Me
- No Unique Problems
- Go Where the Gap Is the Biggest
- Thought Partner, Not Thought Leader