Every winery owner I know has had the same wish at some point. A real chief of staff. Someone who reads your inbox at 6 AM and tells you what mattered. Someone who pulls the dossier before the wholesale buyer walks in. Someone who tracks the receipts so finance does not call asking what the dinner was for. The pieces of that team are familiar — assistant, researcher, speechwriter, connector, sparring partner. Most wineries cannot afford any of them.
What changed last year is that you can now build a working version of every one of those roles on your own computer. It reads your data and runs on a schedule, writing in your voice. The team is a defined set of agents, each with explicit inputs, scheduled tasks, and one outcome it owns. I ran a webinar that walked through nine of them in 80 minutes and built three of them live. This post is the entry point for the blog series that came out of that session.
This series covers what each agent does, in what order to build them, and why the order matters more than any single agent.
The nine roles every shadow team covers
The webinar opens with a single slide that names the nine. Read them in order:
- Executive Assistant — hourly inbox triage, pre-meeting briefs, draft replies in your voice.
- Chief of Staff — assembles the morning briefing at 7 AM by pulling from the other agents.
- Researcher — reads industry news, customer feedback, and competitive signals on a schedule.
- Personal CFO — categorizes receipts as they come in, ships the weekly expense report on Friday.
- Speechwriter — drafts content in your voice on the schedule your Connector built.
- Connector — flags relationships going quiet, plans 30/60/90 outreach, builds your content calendar.
- Compass — writes you one page a month on where your calendar drifted from your stated priorities.
- Health Team — logs the body. Photo-of-meal calorie estimates, weekly pulse, monthly doctor notes.
- System Tuner — reviews the other eight and recommends what to prune.
There is a tenth role I name in the webinar and then leave intentionally human. A mentor. Someone who has lived what you are living — walked through a bad vintage, made the hire that did not work, sold the brand they built. The shadow team has nine seats because the tenth one is not a job for software, no matter how good the software gets.
The version that fits your operation will not match this list exactly. The list above is the standard nine. Treat it as a template. Your version will diverge.
The five-field anatomy
Every agent in the webinar is described in the same five fields. The fields are deliberately boring. The discipline of using them is what keeps the agents from drifting into generic chat helpers.
- Inputs. The data the agent reads. Calendar. CRM. Bank feed. News sources. Your daily notes. If you cannot list the inputs in one breath, the agent is too vague.
- Skills. What the agent knows how to do with those inputs. Drafting in your voice. Clustering customer feedback into three themes. Comparing your calendar against your quarterly priorities.
- Scheduled tasks. When the agent runs. Hourly, daily, weekly, event-triggered. A schedule is what turns a clever prompt into a system.
- Outputs. What lands on your desk when the agent is done. A 5-line digest, a draft, a flag, a monthly letter. Never a sent email. Never an executed transaction.
- Goal. The one outcome the agent owns. The reason the agent exists. If two agents share a goal, you have one agent split across two files.
Once you internalize the five fields, you can design an agent for almost anything. The skill is closer to the one a good hiring manager uses to write a clean job description than it is to anything technical.
The daily chain — why order matters
A common mistake is to build nine agents that all run on their own islands. That is not what the system does. The shadow team works because the agents read each other's outputs.
The weekday morning chain runs in this order:
- 6:00 AM — Researcher. Reads the wine industry sources, filters for what matters to your operation, writes a five-line digest.
- 6:30 AM — Speechwriter. Reads the Researcher's digest. Checks the Connector's content calendar to see what audience today targets. Drafts the day's content piece against both.
- 7:00 AM — Chief of Staff. Assembles the briefing. The Researcher's digest sits on top. The Speechwriter's draft is in the review queue below. Open commitments, today's calendar, drift flags, all in one doc.
By the time you sit down with coffee at 7:30, the morning has been done for you. You read the briefing. You approve or revise the draft. You walk into the day knowing what mattered and with the next piece of external content already written. Nothing autonomous has been sent. Everything is staged for your eyes.
This is the part of the system the webinar names Compound-the-Colleague. The agents share what they know. The Researcher feeds the Speechwriter. The Connector feeds the Speechwriter. Six months in, the agents have read more of your business than any human assistant ever could. The team gets sharper the longer it runs. That compounding is the moat.
Three named moves you can use this week
Three teaching moves run through the talk and show up in every per-agent post in this series.
Step-Back. Design from the goal, not from the prompt. Most agent failures come from someone writing a clever prompt before deciding what the agent owns. The five-field anatomy is Step-Back applied to design — start with the goal, propose the inputs and skills, push back. The Compass agent is Step-Back applied to your whole calendar; it zooms out and asks what is still earning its place.
Compound-the-Colleague. Wire the agents to read each other. Most of the wins live in one agent reading another agent's output. A clever single agent moves the needle less than a boring chain of two does. The morning chain is the canonical case. The Connector building the content calendar that the Speechwriter writes against, every day, is another.
Interview. Let the agent ask the questions. The Connector interviews your CRM and your stated goals to surface the wine club members who have gone quiet. The Compass interviews your vault and your time tracking to find where you drifted. Most CEOs try to spend more time at the keyboard. The interview pattern flips that; the agent does the asking, you do the answering.
You can apply Step-Back, Compound-the-Colleague, and Interview to almost any AI work, in any tool, even if you never build the full shadow team. That is why I name them.
A 90-day install order
The most expensive way to do this is to try to build all nine at once. The cheapest way is one a week, in a specific order, for nine weeks. Two months and one week.
Here is the order I recommend in the webinar.
- Week one — Researcher. Pays for the stack immediately. The first morning the digest lands, you start the day with the industry already read.
- Week two — Speechwriter. Ships your publishing rhythm. Depends on the Researcher's output, which is why it comes second.
- Week three — Personal CFO. Takes the worst part of your month and makes it disappear.
- Week four — Executive Assistant. Begins to relieve the inbox backlog and the meeting prep gap.
- Week five — Chief of Staff. Now you have enough upstream outputs to make the morning briefing worth assembling.
- Week six — Connector. Relationships and content calendar. Pairs naturally with the Researcher and the Speechwriter you already have.
- Week seven — Compass. The most uncomfortable agent. Saving it for week seven lets the first six produce enough data for the Compass to read.
- Week eight — Health Team. The long game.
- Week nine — System Tuner. Comes last because it reviews the other eight.
If something is not working after two weeks of using it, do not be precious. Kill it and try a different angle. The throwaways are how the system finds the shape that fits your operation. Aim for a working team; the perfect plan is a distraction.
Where to start this week
The full per-agent breakdowns:
- The Researcher — the agent that pays for the stack in week one.
- The Speechwriter — every external word in your voice, on a schedule.
- The Personal CFO — receipt categorization at the point of photo.
- The Executive Assistant — hourly inbox triage and pre-meeting briefs.
- The Chief of Staff — the morning briefing that assembles the rest.
- The Connector — relationships, networking, and the content calendar.
- The Compass — the page a month no one else will write you.
- The Health Team — the agent that catches the body before the body sends the bill.
- The System Tuner — the agent that keeps the other eight earning their place.
The worked examples throughout the series run on Not Really Wines, our fictional demo winery at NunnCurtis Labs. Maren Holloway is Co-Founder and CEO. NRW makes premium non-alcoholic wine, vacuum-distilled from Sonoma fruit, with three SKUs — Chardonnay, Pinot Noir, and Rosé. The team runs a Tasting Bar in downtown Healdsburg, ships DTC to forty-two states, sells through a subscription called The Society, and works with about thirty wholesale accounts in Sonoma and the East Bay. NRW exists for exactly this kind of demonstration, so I can be specific about what an agent does against a real operation without surfacing a real client.
The recording of the webinar, the agent files, the coverage map template, and the calendar to book an audit are at nunncurtislabs.com/webinars. Read the series. Pick the first agent and install it this week.