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You hand an AI agent a task, watch it work for thirty turns, and end up with something that is close. Close, but not it. The flow works but ignores the edge case you cared about. The migration ran but quietly dropped the records that didn't fit the mold. You got most of what you…
The pitch for AI at a winery almost always arrives as a time number. Buy the licenses and your DTC coordinator gets four hours a week back. Your tasting room manager stops losing Friday afternoons to visit recaps. The webinar slide says it, the vendor says it, and it is not a lie — controlled…
Most AI rollouts in wineries fail on the calendar before they fail on anything else. The day a leader writes "kick-off Monday" on her notepad determines whether the rollout finishes or stalls, and most leaders pick that Monday on the basis of when budget cleared rather than when the team will be able to take…
Six months into running a working shadow team, every CEO I have set up hits the same problem. The CLAUDE.md is now 1,000 lines. The morning briefing has grown to five pages. The Researcher's digest started arriving with seven stories instead of three because three felt restrictive in week four and nobody trimmed it back…
Running a winery is a long game. Building a brand is a long game. Most owners I work with have spent ten or fifteen years inside the business and plan to spend another twenty. The thing that ends careers in that kind of work is rarely the business. It is the body sending a bill…
You said at the start of the quarter that Q4 was about wine club retention. By the middle of November, your time tracking shows 14% of your hours went to wine club work and 61% went to wholesale. The wholesale work is good. The wholesale work is paying. The wholesale work is also not what…
There is a wine club member at every winery who used to order every quarter, and then stopped, and nobody noticed for nine months. They did not unsubscribe. They did not complain. They just stopped. By the time the DTC manager runs a CRM report and sees the lapsed segment, the member is six months…
If you have ever started a Monday wondering what is on your plate, where the week stands, and what is going to bite you by Thursday, you know the cost of a missing chief of staff. The role has a quiet job. It is the person who walks into your office at 7 AM with…
Most winery leaders run their inbox the way a tasting bar runs on a busy Saturday — they triage by volume instead of importance. The wholesale buyer's email that needed a 3-line reply sits at the bottom because it is not urgent. The compliance notice gets a 20-minute response that could have been delegated. The…
Every owner I know has had the same end-of-month conversation with their bookkeeper. The phone buzzes on a Friday afternoon. "What was the May 12 dinner at Healdsburg Bar & Grill?" You try to remember whether it was a wholesale buyer, a vendor lunch, or a team thing. You scroll your calendar, find the entry,…
