Most people are still typing one-off prompts and wondering why AI gives them generic answers. The problem isn't the tool. It's that you never gave it your context. In this one, Craig and Caitlin open up their actual AI stacks, the tools they pay for, the ones that saved real hours this week, and how each of them built a thinking partner that knows their business well enough to push back.
What We Cover:
- Why a thinking partner is only as good as the context you feed it, and how Craig loads his with team roster, financials, and real business data
- Caitlin's "second brain" setup in Claude Cowork: a markdown brain file, a memory file, and a session-audit skill that holds her accountable when she's procrastinating
- The daily brief that reads your email and Notion for you, and how it surfaced a brand opportunity Caitlin had completely missed
- Craig's tool-by-tool breakdown: Poke as the $10 pocket assistant, Claude as the thinking partner, Perplexity as the researcher, plus Higgsfield for scary-good AI video
- Why orchestrators like Perplexity Computer can replace nine subscriptions, and where the real cost barriers kick in
The One Thing: Start with the thinking partner, and feed it your context. Set it up as a project, give it your real business data, and update it regularly. You do not need code or full automation to get value. Even the "training wheels" version saves hours a day, whether you are the owner, second in command, or an assistant.
Craig Brooks is CEO of Clarity Creative Group. Caitlin Smith is a brand designer and strategist. They love talking about marketing, talking to people that do marketing, and marketing themselves.