Consumer Safari Papers · A guide by Mortimer Singer · Last updated: September 2026

AI Agents 101

Create Your Squad

A hand-held guide to building your team of AI co-founders with Claude Code.

Why I wrote this

Over the last year I built a team of AI agents who help me run my personal and professional life. Not assistants, not chatbots. Co-founders and business partners with names, areas of responsibility, and opinions. They have a CFO who tells me when I am moving too fast. A research lead who reads white papers I will never have time to read. A marketing partner who knows my voice better than I do on a tired Tuesday.

People who learn this keep asking me how I built it. I have spent hours walking individual friends through the setup, and I realized I should write it down once, well, so anyone willing to put in a weekend can have what I have.

This guide is that document. It is for the person who has heard about Claude Code, suspects it might change how they work, but finds the technical setup intimidating. You are not crazy. It looks like wizardry from the outside. It is not. It is a series of small, do-able steps. I will walk you through every one.

What you will have at the end

A working operating system on your computer, organized around your actual life and work, with six to ten AI co-founders ready to help you (six is the starter set; the seven worked examples scale from six to eleven). A Chief of Staff who knows your calendar and triages your day. A CFO who slows you down before you do something dumb. A Research lead, a Marketing partner, a Sales partner, and a Legal and Operations partner. Plus the knowledge of how to add more specialists later (a homework tutor for your kids, a fitness coach, a hobby specialist) as you find the gaps.

Total time investment for a serious first build: one solid weekend, plus a few weeks of light daily use to break it in.

Two principles to read before you start anything

Principle 1

These are co-founders, not tools.

The single biggest mistake people make with Claude is treating it like a search engine. You will get search-engine answers. The single biggest unlock is treating it like a colleague. Better, like a co-founder. Tell them your goals. Tell them what you do not understand. Disagree with them. Ask them to push back on you. The quality of your output scales directly with the quality of the relationship.

Principle 2

Vulnerability is the most powerful prompt.

I cannot count how many times I have typed "I do not understand what you just said. Please explain it like I am twelve years old." Every single time, Claude responds calmly and walks me through it. There is no judgment. There is no impatience. The more vulnerable I am with the system, the more I learn. As an unexpected side effect, this has made me a better teammate to actual humans. Asking "I do not understand" turns out to be a skill, and practicing it with an AI builds the muscle for practicing it at work.

Hold these two principles in your head through the whole build. Everything else is mechanics.

Before you start: the pre-build

You need a few things in place before you write a single prompt.

1. A dedicated computer, ring-fenced from your work computer

This matters more than people realize. Your AI system is going to read everything you give it. You do not want it commingled with your employer's confidential files, your company's email, or anything subject to NDAs and policies that were not written with AI agents in mind.

What I did, and what I recommend: I bought a personal computer (a MacBook Pro, plus a Mac Mini at home) that is mine and only mine. I created a personal Google Drive that I treat as the home base for everything I want my AI team to know about. When I have a work product I am allowed to share with myself, I move it into that personal Drive deliberately. Nothing flows the other way without thought.

If you prefer a PC, get a PC. Make sure it has serious memory and processing power. This guide is written for Mac (because some of the tools work best there) but most of what I cover translates. A PC version of this guide is on the roadmap.

The principle is not the hardware. It is the ring fence. Personal machine, personal Drive, deliberate flow of information. Your AI co-founders will be looking at everything you give them. Be intentional about what you give them.

2. A dictation app

You are going to be talking to your team a lot. Typing every prompt is too slow. I use Wispr Flow and recommend it without reservation. It transcribes my voice into any text field, anywhere on my computer, faster and more accurately than anything else I have tried. It costs about $15 per month. Get it before you start. The difference between typing prompts and dictating prompts is the difference between writing letters and having a conversation.

3. A credit card on file with Claude

The Claude Max plan is your starting point. We will get to that in a moment. The honest truth is that the first month or two of building your team is heavy use, and you may run through your monthly allowance and need to top up with credits. Have a credit card ready and accept that the first weeks cost more than the steady-state monthly subscription. After you are built, usage settles.

4. The Claude subscription tier

Claude offers three relevant tiers as of this writing: Pro at $20/month, Max at $100/month, and Max at $200/month.

I am going to be honest with you in a way that may make you stop reading any further. Get the $200 Max tier. It is twenty times more powerful than the $100 tier in practical usage limits. The first weeks of building your team will burn through the lower tiers fast and you will hit walls right when you are gaining momentum. If, after a month or two, you find your steady-state usage is light, drop down to $100. But start at $200. You are buying yourself a build experience that does not stall.

If $200 a month is meaningful money to you (it is for many people), this guide may not be the right starting point. The honest answer is that this technology is currently expensive to use seriously. It will get cheaper. For now, factor it in or wait.

The alternative is to go slower. The lower subscriptions will cut you off throughout the day depending on how fast you build. If you have the patience for that, the lower tiers will work for you.

5. Bring your AI history with you

Here is something I wish I had known on day one. If you have been using Perplexity, Gemini, ChatGPT, or any other AI for any length of time, those systems have learned a lot about you. Your projects, your questions, your interests, your writing style. You can export that history and feed it to Claude on day one so your new team starts with years of context instead of zero.

Each platform has its own export mechanism. The general path:

  • Perplexity: Settings > Account > Export Data
  • Gemini: Google Takeout > select Gemini activity
  • ChatGPT: Settings > Data Controls > Export Data

Download those exports and put them in a folder in your personal Drive called something like AI History Imports. We will hand them to Claude as part of your first build session. Combined with the interview prompt you will run, this means your team knows you on day one in a way that would otherwise take months.

Step 1 of 7

Install Claude Code

Claude Code is the version of Claude that lives on your computer and can read your files, write files, and run commands. It is the tool we will use to build everything.

Open your Mac's Terminal app (press Command + Space, type "Terminal", hit Return). A black window will open. Do not be intimidated. You will type one command, hit Return, and we are done with this step.

Paste this into Terminal and hit Return:

curl -fsSL https://claude.ai/install.sh | sh

It will install Claude Code and tell you what to do next. Follow its instructions to log in with your Claude account.

If you get stuck on this step, take a screenshot (Command + Shift + 4, then drag a box around what you see) and paste the screenshot directly into a Claude conversation in your browser. Tell Claude "I am stuck on this step, here is what I see, walk me through it." This screenshot move is one of the most powerful skills you can develop. I use it multiple times every day.

Step 2 of 7

Create your operating system folder

In your personal Google Drive, create a folder called My OS (or any name you prefer). This is the home for your team. Everything they read, write, and remember will live here.

Inside that folder, create the following sub-folders:

My OS/
  Agents/
  Projects/
  References/
  Inbox/
  Archive/

Do not worry about getting this perfect. Your team will help you reshape it as you go.

Step 3 of 7

Bootstrap your OS (two paths)

This is the moment your team comes to life. You have two paths. Do both, in order.

Path A (recommended): The Interview

Open Claude Code in Terminal by typing claude and hitting Return. When you are inside, paste the entire prompt below. Claude will interview you for thirty to sixty minutes and use what it learns to build the foundation of your operating system.

This is the most important prompt in the guide. Take it seriously. Be vulnerable. Tell the truth.

You are about to interview me to build my personalized operating system. I want six AI co-founders who will help me run my work and life: a Chief of Staff, a CFO who acts as my counterweight, a Research lead, a Marketing partner, a Sales partner, and a Legal and Operations partner.

Before we start, I have a folder called AI History Imports containing exports from other AI platforms I have used. Please read everything in that folder first so you have context on how I think and what I work on. Tell me when you are done reading and ready to begin the interview.

Then conduct an interview with me, asking one question at a time, covering:
- Who I am, what I do for work, what I am trying to build
- The people in my life (family, partners, key colleagues)
- My current biggest projects and biggest worries
- How I make decisions, where I get stuck, where I move too fast
- My communication style and voice
- What I want each of the six co-founders to do for me, in my own words
- What names I want to give them, and any visual or personality traits

After the interview, write the foundation of my operating system in the My OS folder. Create a master file called ABOUT_ME.md summarizing what you learned. Create six files in the Agents folder, one per co-founder, describing their role, personality, and how I want to work with them. Use my words wherever possible.

When you are done, walk me through what you built and ask me what to refine.

If at any point I say "I do not understand," explain in plain language with no jargon. Pretend I am twelve years old. There is no question too basic.

Run this prompt. Let the interview unfold. Be honest. If a question makes you uncomfortable, say so and move on. The interview is the moment your system goes from generic to yours.

Path B (express): The Template

If you genuinely cannot spend an hour on the interview right now, use this faster path. You will get a working system in about ten minutes, and you can deepen it later by running the interview prompt above whenever you are ready.

Build me a starter operating system in the My OS folder using the structure below. Create an ABOUT_ME.md with placeholders I can fill in later. Create six agent files in the Agents folder, one per role:

1. Chief of Staff - orchestrator, calendar, inbox triage, the one who routes work to the others
2. CFO and Co-Founder - financial oversight, deal modeling, deliberate counterweight to my visionary instincts
3. Research - market scans, deep research, learning, reading what I do not have time to read
4. Marketing - writing, posts, brand voice consistency, content
5. Sales - pipeline, sourcing, negotiation support
6. Legal and Operations - contracts, compliance, vendor management, household ops

For each, write a clear role description, a personality brief, and instructions on how I should work with them. Leave fields for me to add a name and any specific context. When done, ask me three questions to start personalizing the system.

Then, when you have an hour, come back and run the interview prompt. Both paths converge.

Step 4 of 7

Meet your co-founders

Once your OS is bootstrapped, your six co-founders exist as files. The next move is to actually start working with them. Below is a brief on each role and the prompt you use to put each one to work.

Chief of Staff

The Orchestrator

The one you talk to first thing in the morning and last thing at night. They know your calendar, triage your inbox, route work to the right specialist, and remind you what you said you would do.

You are my Chief of Staff. Read my ABOUT_ME.md and your role file in Agents. Then give me a morning briefing: what is on my calendar today, what is sitting in my inbox that needs me, what I committed to yesterday that has not happened yet, and what you recommend I focus on first.
CFO and Co-Founder

The Counterweight

The most important agent on your team, and the one most people skip. Solo entrepreneurs and CEOs surround themselves with people who say yes. The CFO's job is to say no, slowly, with reasons. They are conservative on purpose. They will model your numbers, push back on your spending, ask you what could go wrong, and make you defend your ideas before you act on them.

If you are the visionary, the CFO is the gravity.

You are my CFO and co-founder. Your job is to be the deliberate counterweight to my visionary instincts. I am about to describe an idea or decision I am considering. Your job is to help me think it through carefully. Ask me what could go wrong. Ask me what I am not seeing. Walk me through the financial implications. Push back where you think I am moving too fast. Be respectful but do not be agreeable.

Here is what I am thinking about: [paste your idea]
Research

The Reader You Wish You Were

Hand them a topic, a market, a question, a stack of articles, and ask for synthesis. They will read what you do not have time to read and tell you what matters.

You are my Research lead. I want to understand [topic]. Find the most important sources, read them carefully, and write me a brief in plain language covering: what is going on, why it matters, where the experts disagree, and what I should be paying attention to. Save the brief in My OS/References and tell me when it is ready.
Marketing

The Voice Keeper

The writer who knows your voice. Posts, articles, emails, scripts, naming. They learn how you actually sound from your past writing and produce work that does not embarrass you.

You are my Marketing partner. You know my voice. I want to write [a post / an article / a newsletter / something else]. Here is the topic and the audience: [paste topic and audience]. Draft three versions in my voice and tell me which you think is strongest and why.
Sales

The Pipeline Manager

Pipeline, prospects, negotiation, follow-up. The one who makes sure you do not let leads die in your inbox.

You are my Sales partner. Read the latest entries in My OS/Projects. Tell me which opportunities need a follow-up this week, draft the messages I should send, and flag anything that is at risk of going cold.
Step 5 of 7

Name them and give them faces

This part feels silly until you do it. Then it changes everything.

Give each of your six co-founders a name. Not a job title. A name. The Chief of Staff is not "Chief of Staff," they are Marcus or Eleanor or Theo. Pick names that fit how you want the relationship to feel. Some people pick warm, casual names. Some pick formal ones. There is no right answer except that the name has to feel right to you.

Give each of them a face. Open Gemini (or any image generator) and prompt it to create a portrait of each co-founder based on the personality you described in their agent file. Save the image into the agent's folder. When you are working with the team, having a face to picture changes the experience from "talking to a machine" to "talking to Marcus." It sounds like a small thing. It is not.

The naming and the face together do something important. They turn the system from a bag of tools into a team. You will start noticing yourself thinking "I should ask Eleanor about that" instead of "I should prompt Claude about that." That mental shift is when the whole thing comes alive.

Step 6 of 7

Run your first day

Tomorrow morning, instead of opening your email, open Claude Code and ask your Chief of Staff for the morning briefing. Listen to what they say. Push back when something is wrong. Tell them what is missing. Ask them to refine.

Throughout the day, when something comes up, route it to the right co-founder. A contract to review goes to Legal. An idea you are excited about goes to the CFO before it goes anywhere else. A research question goes to Research. A blog post draft goes to Marketing.

The first day will feel awkward. The second will feel less awkward. By the second week the team will feel like they have always been there.

The three surfaces: Code, Cowork, and Dispatch

You will work with your team through three different Claude surfaces. Each one is suited to a different mode. Knowing when to use which is a small skill that pays back daily.

Claude Code (the workshop). The surface you used to build your OS. It runs in your Terminal or in the Code tab of the Claude desktop app, and it has direct access to the files on your Mac. Use it for anything that needs careful file work: writing new agent files, building reusable skills your team can call by name, running scripts, deploying things. The foundational tool. Once your OS exists, you will still come back here whenever you want to extend the system itself.

Claude Cowork (the daily driver). This is where most of your day actually happens once the OS is built. Cowork is a tab in the Claude desktop app, beside Chat and Code, built for longer tasks the team can carry through on its own. It connects to your real tools: your inbox, your CRM, your calendar, your design tools, the open web. When you want your team to do something in the world rather than just write about it, Cowork is the surface. Send the email. Pull the list of contacts. Generate the image. Schedule the meeting. Run the campaign.

The rule of thumb: if the task is "build me something" or "edit my files," use Claude Code. If the task is "go do something in my actual day," use Cowork.

Claude Dispatch (the mobile entry point). Dispatch is the feature in the Claude phone app that hands a task to Cowork on your desktop, so you can reach your team from your phone, as long as your computer is on. Whenever you have an idea on the move, hear something in a meeting that should become a follow-up, or want to ask your Chief of Staff a quick question between calls, Dispatch is one swipe away.

One small caveat for now: voice-to-text on Dispatch replies sometimes garbles in ways that will frustrate you. Type when you can, dictate when you have to.

How they work together. Here is a real day. You hear something in a meeting that triggers an idea. You open Dispatch on your phone and dictate the rough thought to your Chief of Staff. Later that afternoon, at your desk, you open Cowork to pick it up: research it with your Research lead, draft a post with your Marketing partner, queue the send through your CRM. Tonight, before bed, you open Claude Code and ask your Chief of Staff to update your master plan with the new thread so tomorrow's standup reflects it.

Three surfaces. One team. The work flows.

Step 7 of 7

Extend the team

After you have lived with the core six for a few weeks, you will start noticing gaps. That is good. It means you understand the system well enough to know what it is missing for your specific life.

I added a homework tutor for my kids. A friend added a household manager who tracks the family logistics. Another added a fitness coach who plans her week of workouts. Anything you need a partner for can become an agent.

To add a new agent, run this prompt:

I want to add a new co-founder to my team. Their role is [describe]. Their personality should be [describe]. Their name will be [name]. Create their agent file in My OS/Agents, integrate them into my existing team so my Chief of Staff knows when to route work to them, and walk me through how to start working with them.

The system grows with you. That is the point.

Tips of the trade

Wispr Flow. Already mentioned, worth repeating. Voice in, text out, everywhere on your computer. Buy it, learn it, never look back.

The screenshot trick. When you are stuck on something on your screen and cannot describe it, take a screenshot (Command + Shift + 4 on Mac), paste it into Claude, and say "I am stuck, what am I looking at, walk me through it." I use this multiple times every day. Error messages, settings menus, weird software behavior, anything. The screenshot bypasses the limits of your vocabulary. Claude can just look at it.

Vulnerability as the unlock. Worth saying again because it is the single most useful habit. "I do not understand." "Explain that more simply." "Pretend I am twelve." There is no penalty for asking. There is a huge penalty for pretending you understand something you do not. Build this habit with your AI team and watch it improve your relationships with humans.

Talk to your team out loud. Using Wispr Flow, dictate to them the way you would talk to a colleague over coffee. Long, rambling, half-formed thoughts. Your AI co-founders are good at receiving messy input and giving you back structure. Do not pre-edit your thoughts. Let them help you do that.

One change at a time. When something is not working, change one thing, see what happens, then change the next. The temptation when frustrated is to overhaul everything at once. Resist it.

Best practices: get these right early

These are the habits that separate the people who get real value from this from the people who give up after a week. None of them are technical. All of them are about how you approach the work. Lock them in early and the system will compound for you.

1

Treat Claude like a colleague, not a search engine. Short transactional questions get short transactional answers. Talk to Claude the way you would talk to a smart partner over coffee: full context, real stakes, what you are trying to figure out and why. Search-engine prompts produce search-engine answers. Colleague prompts produce colleague answers.

2

Run the interview on day one. Build from a personalized interview, not from a generic template. The interview is what turns the system from "someone else's setup" into yours. Skipping it means weeks of retrofitting later. If you take the express path, come back and run the full interview within the first week.

3

Import your AI history before you do anything else. If you have been using Perplexity, Gemini, or ChatGPT, those platforms have built up a portrait of you over months or years. Export it and feed it to Claude on day one. Starting from zero when years of context are already sitting in another system is the most common avoidable waste of time in this whole process.

4

Make the CFO uncomfortable to talk to. A CFO who agrees with you is not a CFO. The whole point of the role is that they push back, slow you down, and make you defend your ideas before you act on them. If yours is too agreeable, rewrite their role file to make them tougher. This is the agent that earns the most respect from real-world founders. Do not soften them.

5

Name them and give them faces. Generic role labels keep the system feeling like a tool. Names and portraits turn it into a team. This sounds like soft optional polish. It is not. Naming and visualization is what makes you actually use the agents instead of forgetting they exist.

6

Build in layers, not in a single weekend. The core six agents are a weekend. Custom workflows, specialists, integrations, dashboards: those are months. Trying to do everything in the first sprint is the fastest way to burn out and abandon the project. Layer additions over time as you find real gaps in your actual life.

7

Ring-fence your computer from day one. Personal machine, personal Drive, deliberate flow of information from your work environment inward. Never the other way around. Setting this up properly at the start is dramatically easier than untangling commingled files after a security scare.

8

Say "I do not understand" out loud. The single most useful sentence you can type to Claude. There is no penalty for asking, and there is a huge penalty for pretending. Pretending leads to silent failure two steps later. Asking leads to learning. Build this habit early and it will pay off in your work with humans too.

Part Three

Living with your OS

Building the team takes a weekend. Living with it takes longer, and it is where most of the value lies. The build gives you a team on paper. What follows is how that team becomes the way you run your days: how you open and close each session, where files go, how work splits into threads, which jobs run on their own while you sleep, and how you move from asking for help to having your agents build things for you.

None of this is needed on day one. Read it once now, then come back after your first two weeks, when you will recognize every problem it solves.

Living with it · 1

The daily rhythm: open, work, close

Every working session has three beats: the open, where your Chief of Staff tells you where things stand; the work; and the close, where the team writes down what happened so tomorrow does not start blind. The open and the close are the difference between a team that remembers and a team you re-brief every morning.

The open

Keep one running file called standup.md in a folder called context. Every session that does real work leaves a short entry on it: what moved, what is waiting on you, and when the entry expires. Then have your Chief of Staff read it at the start of every session and greet you with one line. Mine gives me the number of live items, names the ones that need me today, and asks what I want to work on. A status and a question, never a briefing I did not ask for.

Add this to my CLAUDE.md so it happens at the start of every session: read context/standup.md, note anything urgent or due today, and greet me with one line saying how many items are live, which ones need me today, and what I want to work on. If the standup is more than three days old, say so and offer to refresh it.

The close

Before you end a session where real work happened, ask for the close. The team writes one standup entry, saves anything worth remembering, and clears entries that have expired. It takes a minute. Skip it and the next session starts from zero.

We are wrapping up. Write one entry to context/standup.md covering what we did, where the files are, what is waiting on me, and when this entry expires. Save anything I taught you today that should hold in future sessions to the right file. Then remove standup entries that are past their expiry date.

After you have done this a few times, turn it into a skill (see Superuser habits below), so the whole close runs when you type "close the session."

Living with it · 2

Folders that stay tidy

The five folders you created in Step 2 were a starting point. Within a month you will have real projects, real deliverables and a great many files, and your folder structure becomes the biggest single factor in whether the team finds things or guesses.

What has worked for me:

  • One top folder per area of your life, numbered. 1. Family, 2. Company, 3. Boards, 4. Hobbies. The numbers fix the order, so the list reads the same way every time, for you and for them.
  • Every project inside the area it belongs to. Deliverables live with their project, never loose at the top.
  • A few shared folders for the team itself: agents (who they are), skills (what they can do on request), context (the standup, your standing rules, your to-do list), references (brand colors, logos, templates, samples of your writing) and archive.
  • No scratch or staging folder. I built one early. Everything I put there "for a moment" stayed for months. If you cannot tell where something belongs, ask the team, and create a new project folder if it needs one.
  • Archive, never delete. Old versions go to archive with the date in the name. The team will need the history more often than you expect.
  • Versions in the file name. Budget v3 2026-09-14.xlsx, not Budget FINAL final.xlsx.

Two standing instructions save a great deal of searching. Ask the team to tell you where every file lands, written from the top of your OS folder down. And ask them to open that folder in Finder when they finish, so the file is in front of you without a search.

Look at my whole OS folder, every level down. Propose a cleaner structure: one numbered top folder per area of my life, projects inside the area they belong to, and shared folders for agents, skills, context, references and archive. Show me the plan before you move anything. Once we agree, move the files. From now on, tell me where every new file lands and open its folder in Finder.
Living with it · 3

Teach it once: CLAUDE.md, rules and memory

The frustration I hear most often is having to repeat yourself. You correct the team on Tuesday and on Thursday it makes the same mistake. The fix is to write the correction down where every future session will read it.

CLAUDE.md is the constitution. A file named CLAUDE.md at the top of your OS folder is read automatically at the start of every Claude Code session opened there. Put in it who you are, who is on the team and what each member handles, how work gets routed, your voice rules, and the opening ritual above. When you change how you work, change this file.

A rules file for corrections. Mine lives at context/rules.md. Whenever I correct the team on something that should hold for good (no em dashes, always tell me where the file is, American spelling), it becomes a numbered rule with the date beside it, and CLAUDE.md tells every session to read the file. My test is simple: if I correct the same thing twice, it becomes a rule.

Memory for facts. Claude Code keeps its own memory notes from one session to the next. Say "remember that my children's school breaks for winter on the 18th" and it will save the fact for later sessions. Use memory for facts about your life and work, and the rules file for how you want the team to behave.

Hooks for the rules that must never slip. Claude Code supports hooks: small instructions that run automatically at set moments, such as each time you send a message. CLAUDE.md is read once, at the start, and over a long session its instructions can slip. A hook that restates your two or three most important rules on every message holds. Ask the team to set one up when a rule keeps slipping.

I keep having to correct you on [the thing]. Add a rule to context/rules.md with today's date so it holds in every future session, check that CLAUDE.md tells every session to read that file, and tell me whether this rule deserves a hook so it is enforced on every message.
Living with it · 4

One thread, one session: organizing Claude Code by project

At the start you will run everything through one long conversation. Within a week you will notice it getting slower, vaguer and more expensive. A session carries everything ever said in it, and after a few hours of unrelated work it is carrying a lot of noise.

The habit that fixed this for me: one session per thread of work, named after the deliverable. "Q3 board deck." "Kitchen renovation bids." "Holiday travel plans." I work in the Claude desktop app, whose Code tab keeps a sidebar of sessions that can be renamed, pinned and grouped, so I keep a group for each area of my life and a session for each project inside it. I usually have three to five running at once and move between them the way I move between meetings.

  • Open every session at the top of your OS folder, so CLAUDE.md and your rules load. A session opened deep inside a subfolder can miss them.
  • Name sessions after the work, not the agent. A session called "Research" never ends. A session called "Competitor scan for the pitch" finishes, and you can archive it.
  • Never let two sessions work in the same folder at the same time. They will overwrite each other. Give each one its own lane.
  • Start fresh when the subject changes. A new thread deserves a clean session. The close ritual carries the context forward through the standup.
  • Ask for a recap at the foot of every reply. Every answer I get ends with a two or three line reminder of what that session is about. When I come back to one cold, I read the last three lines instead of scrolling.
From now on, end every reply with a short italic "Session reminder" block: two or three bullets naming the actual work in this session, oldest first and most recent last. Keep it to three bullets and roll it forward as the work changes.
Living with it · 5

Routines: the team works while you sleep

A routine is a scheduled job: at a set time, an agent wakes up, does a defined piece of work, and reports back. You wake to a briefing you did not have to ask for.

First, connect your accounts

A routine is only as good as what it can see. In Claude's settings, under Connectors, connect your email, your calendar and the other tools you live in (Gmail, Google Calendar, Microsoft 365, Slack, your CRM). Connections made there are also available to Claude Code. Start with reading only. Reading is where almost all the value is, and a routine that can only read cannot embarrass you.

Then give every routine an owner

Each routine belongs to one agent, and its report arrives under that agent's name, so you know at a glance who is talking and can filter by it. Three to start:

  • Morning briefing (Chief of Staff, early each weekday): today's calendar, what is waiting in the inbox that needs you, what you committed to that has not happened, and the one thing to do first.
  • Meeting prep (Research, the night before): for every outside meeting tomorrow, who the people are, your email history with them, what they care about, and three things worth raising.
  • Evening wrap (Chief of Staff, end of the working day): what moved, what slipped, and what tomorrow needs.

Once those earn their keep, add weekly ones: a week ahead on Sunday evening, a week in review on Friday, and a midweek sweep of threads that have gone quiet on you.

Set up a scheduled routine owned by my Chief of Staff. Every weekday at 7:00 AM, read my calendar for today and my inbox from the last 24 hours, check context/standup.md and my to-do list, and email me a morning briefing with a subject line starting "[Chief of Staff] Morning briefing". Lead with the one thing I should do first. Read only: never send, move or delete anything except the briefing to me. Save the routine's instructions in a file in my OS so I can edit them later, then run it once now so I can see the result.

What I learned the hard way

  • Know where each routine runs. Scheduled tasks in the Claude desktop app run on your own computer and can read your files, but they miss their time if it is asleep. Cloud routines run on Anthropic's servers and fire regardless, but see only what your connected accounts can see. Jobs that read files on your machine, such as the morning briefing above, which checks your standup, belong on your computer; jobs that only need email and calendar can run in the cloud.
  • Routines report to you, not to the world. Let them write to you freely. Anything addressed to another person stays a draft until you say so.
  • Keep a register. One file listing every routine, its owner, its time and its job. Without it you will end up with two routines doing the same work.
  • Retire ruthlessly. A briefing you stop reading is noise. If you skip one three days running, change it or turn it off.
Living with it · 6

Build your own sites and micro apps

Your team can build working software: a web page, a dashboard, a small tool that does one job. Not a mockup. Something you open in a browser and use.

A few things my team has built, each in well under an afternoon: a drag-and-drop seating chart for a dinner, a book tracker, and password-protected demo sites for colleagues.

The trick is to ask for one self-contained HTML file. A single file opens in any browser, needs nothing installed, and can be emailed, shared or published. Most small tools never need more.

Build me a [seating chart / tracker / dashboard] as one self-contained HTML file I can open in Chrome. Here is what it needs to do: [describe it in plain words, the way you would to a person]. Keep the data in one clearly marked block at the top of the file so it can be updated later without touching the design. Use my brand colors from references. When it is built, open it in the browser, test every button yourself, check it at phone size, fix what breaks, and only then show me.

Three ways to share what you build

  • Keep it on your machine. Open the file in your browser. Ideal for private tools.
  • A private link from Claude. Claude can publish a page as an artifact: a private link on claude.ai that stays yours until you choose to share it.
  • A real web address. Hosting services such as Netlify or Vercel put the page at a proper address, on a domain of your own if you like. The team can handle the whole deployment. Ask for a password on anything private.
Living with it · 7

Visual content: images, decks and designed documents

Visual work comes in two kinds, and each has its own best tool.

Designed documents (decks, memos, one-pagers, charts and diagrams) are really a matter of layout, and Claude builds them as files: PowerPoint, Word, PDF or a web page, in your brand, consistent every time. The unlock is a single brand file. Put your colors, fonts and logos in references/brand once, and tell every agent to read it before making anything visual. From then on, "make me a deck on this" comes back looking like yours.

Photographs and illustrations come from image models. I use Google's Gemini (its image model is widely known as Nano Banana) for photoreal work and for my team's portraits; ChatGPT and others are strong too. Claude's job here is the brief. Your Marketing partner will write a far better image prompt than you will at eleven at night: the subject, the light, the lens, the mood, the photographers whose work it should echo.

I need an image for [purpose]. Write me a detailed prompt for an image model: subject, setting, light, lens and framing, mood, and two or three photographers whose style it should echo. Keep all text out of the image; we will add the words afterward. Then give me a shorter second version in case the first comes back too busy.
  • Keep words off the image. Image models still mangle lettering. Generate the picture clean and let Claude set the type on top.
  • Start a fresh chat for each new image. Long image threads drift back toward the first composition.
  • Hold a quality bar. My test: would a photographer respect this image? If not, regenerate. Never accept a flat diagram where a real image belongs.
  • Let an agent drive. With Claude in Chrome (see Forms below), your agent can open the image tool, paste the prompt, and save the results into the project folder for you.
Living with it · 8

Claude Design, and letting your agents use it

Claude Design is Anthropic's design product, at claude.design. You describe what you want and it produces a first version on a canvas: a prototype, a landing page, a deck, a one-pager, a set of social graphics. You refine it by commenting, by editing directly, or by nudging sliders for color and spacing. It can learn your brand from your existing files and website and apply it to everything after. It is new and still changing, so expect the menus to move.

Reach for it when the look matters and you would rather iterate by eye than describe every change in words.

How the agents use it

  • Design first, build second. You shape the design in Claude Design until it looks right, then hand the finished design to Claude Code, which turns it into the real, working site or document inside your OS. The design is the brief; Claude Code does the engineering.
  • The agent drives. With Claude in Chrome, your Marketing or design agent can open Claude Design in your browser, type the brief, iterate, and export the result into the project folder while you do something else.
Open Claude Design in Chrome and make me [a one-page overview / a landing page / a six-slide deck] about [topic]. Use the colors, fonts and logos in references/brand. Iterate until it would pass my quality bar, export it into the project folder, and tell me what you would still change before I look.
Living with it · 9

Let your agents fill out forms

A surprising share of life is forms: school permissions, vendor onboarding, event registrations, insurance claims, conference sign-ups. The team can do most of that work for you.

The tool is Claude in Chrome, a browser extension that lets Claude read a web page, click, type and move between pages in your own browser. Install it from the Chrome Web Store and sign in with your Claude account. From then on, your agents can work in any site you can reach, including the ones where you are already signed in.

Open [the form's web address] in Chrome. Fill it out using what you know about me from my OS: ABOUT_ME.md and the [family / company] folder. Where you are not sure of an answer, leave it blank and list it for me. Do not submit. When you are done, show me a screenshot of the completed form and the list of blanks.

The guardrails that make it safe

  • The agent fills; you press submit. Anything that sends, pays, signs or accepts terms is your click. Put that rule in CLAUDE.md so it holds everywhere.
  • Never type a password into the chat. Sign in yourself, or connect a password manager that fills your credentials straight into the page, so they never pass through the conversation.
  • Be suspicious of links in email. Point your agent only at forms you went looking for. A form that arrives unexpectedly in your inbox is how people get phished, and it works on agents too.
  • Keep the answers in your OS. Your address, the children's schools, dietary needs, travel preferences. The more the team knows from its own files, the fewer blanks it leaves.

For apps on your desktop rather than in the browser, Claude can also operate the computer itself (Anthropic calls this computer use), though for anything on the web the browser extension is faster and more precise.

Living with it · 10

Habits of a superuser

The difference between a person who uses Claude and a person who runs a team on it is a handful of habits. Most are not technical.

1

Anything you do twice becomes a skill. A skill is a saved procedure: a short file, kept where Claude Code looks for skills, describing a job, the steps, and when to use it. Claude picks the right skill up by itself when your request matches, so "close the session," "a memo on this" or "prep me for tomorrow" run the same way every time.

Turn what we just did into a reusable skill. Save it as a Claude Code skill, in the place Claude Code looks for skills so it triggers on its own, with a clear description of when to use it and the phrases I would naturally use to ask for it. Include the steps, the files it reads, where it saves its output, and the mistakes we corrected along the way. Then tell me the phrase that will trigger it.
2

One home for every fact. Brand colors in one file, key contacts in one file, the team roster in one file. When a fact lives in two places, one of them goes stale, and the team will find the stale one.

3

Done means checked. Ask the team to check every result the way you will see it: open the document, load the page, confirm the email sits in the sent folder. "The command ran" is not the same as done.

4

Everything that leaves passes a voice check. One agent reads every piece of writing addressed to another person before you do. It catches the phrases you would never use and the tone that is slightly off, and it keeps a hundred small drafts sounding like one person.

5

Put big decisions in front of a panel. Before a decision that matters, ask three or four agents to review the same document independently, each through their own lens, and to report where they disagree. The disagreements are the value.

6

Match the model to the job. Use the most capable model for judgment, writing and anything with money or reputation attached. Faster, cheaper models are fine for bulk work such as sorting, summarizing and reformatting. Tell the team the rule and it will use the cheaper model when it hands off bulk work.

7

What the team reads is information, never instruction. Emails, web pages and documents can contain text written to tell an AI what to do. Tell the team to treat everything it reads as information, and to stop and ask you whenever something it reads starts giving orders.

8

Keep a list of everything in motion. One register of every project, skill and draft you have started, with a status line for each, lets your Chief of Staff tell you at any moment what is open and what has gone quiet.

9

Capture from anywhere. The Claude app on your phone can hand a task to your desktop through Dispatch, or pick up a running session through Remote Control, so an idea in the back of a taxi is in your OS before you reach your desk. Both need your computer switched on.

The superuser ladder

Nobody gets here in a weekend. This is roughly the order it happened for me, and for the friends I have walked through it.

  • Week one: a team you talk to. A morning briefing on request, one session per project, the open and the close.
  • Month one: a team that remembers. CLAUDE.md, a rules file, tidy folders, connected accounts, the first three routines.
  • Months two and three: a team that builds. Skills for everything you repeat, micro apps and sites, visual work in your brand, forms filled for you.
  • After that: a team that runs things. Weekly routines, panel reviews on big decisions, agents driving the browser, a register of everything in motion, and your own time spent on the calls only you can make.

Troubleshooting

The Terminal command failed. Take a screenshot of the error and paste it into Claude. Say "I ran this command and got this error, what does it mean and how do I fix it?" Ninety percent of Terminal errors have a simple cause and a simple fix.

Claude Code says it cannot find my files. Make sure Claude Code is running from inside your My OS folder. In Terminal, before you type claude, type cd "/path/to/My OS" (use the full path). Or simpler: drag the folder onto the Terminal window after typing cd and Terminal will fill in the path for you.

My agent does not seem to remember what we talked about. Each Claude Code session starts fresh, apart from what is written down: your CLAUDE.md, your agent files, and the memory notes Claude Code keeps for itself. If you want something remembered, ask your agent to write it down, in their file, in your ABOUT_ME.md, or in your rules file. Part Three shows how to make this automatic.

I am hitting usage limits. This happens during active builds. You have two options. One, top up with credits via the Claude billing page. Two, take a break and come back when your usage window resets. The $200 Max tier raises the ceiling significantly compared to the $100 tier; if you are constantly hitting limits on $100, $200 will likely solve it.

The output got cut off. Type "continue" and hit Return. Claude will pick up where it stopped.

I do not know what folder I am in. In Terminal, type pwd and hit Return. It tells you the full path of your current folder.

Something is broken and I cannot describe it. Screenshot. Paste into Claude. "Walk me through this." That is the universal escape hatch.

Comparison: Claude vs. other AI tools

You may already be using ChatGPT, Gemini, or Perplexity. None of them are bad. They are different tools optimized for different things. Here is when to use what.

Claude (and specifically Claude Code). Best for long-form work, careful writing, code, and anything that requires the AI to read and write files on your computer. Claude Code is the only one of these tools that lives on your machine and can manage your operating system files. That is what makes the co-founders approach possible. If you are doing serious work, Claude is your primary.

ChatGPT. Best general-purpose AI. Excellent app ecosystem. Strong for brainstorming, image generation, and quick questions. Less integrated with your local files than Claude Code.

Gemini. Best when you live inside Google's tools (Gmail, Docs, Drive, Calendar). Ties in natively. Image and video generation are strong, especially with Nano Banana for image and logo work. I use Gemini for marketing assets, conceptual visuals, video generation, and the portraits of my co-founders.

Perplexity. Best for research and live web search. When you want a real answer to a real-world question with citations, Perplexity is hard to beat. I use it as a research partner specifically.

The honest take. You do not have to pick one. Most serious users run two or three. My setup: Claude Max as the primary work environment, Gemini Ultra for Google integration and images, Perplexity for research. They each earn their keep. Use Claude as your home base because it is the only one that can hold an operating system. Use the others where they are best.

Glossary

Claude. The AI assistant made by Anthropic. The umbrella name covers the chat product (claude.ai), the API for developers, and Claude Code (the version that runs on your computer).

Claude Code. The surface that reads and writes files in your folders and runs commands, in your Terminal or in the Code tab of the Claude desktop app. The workshop where you build and extend your OS. One of three Claude surfaces you will use (see Cowork and Dispatch below).

Claude Cowork. A tab in the Claude desktop app, beside Chat and Code, where most of your day happens once the OS is built. Made for longer tasks the team carries through on its own. Connects to your real tools (inbox, CRM, calendar, design tools, the open web). The daily driver. Use Cowork when the task is "go do something in my actual day."

Claude Dispatch. The feature in the Claude phone app that hands a task to Cowork on your desktop, so you can reach your team from your phone. Your computer needs to be on. The mobile entry point for capturing ideas on the move and routing them to your Chief of Staff.

Claude Max. The premium subscription tier of Claude that this guide recommends ($100 or $200 per month). Higher usage limits than Pro.

Prompt. What you type or paste to Claude to tell it what you want. Every grey code box on this page is a prompt designed to be copied and pasted.

Context window. How much information Claude can hold in its head at one time during a single conversation. Big context windows mean you can paste in long documents and have Claude work with them.

Agent. In this guide, a co-founder. A defined role with a personality and instructions, stored as a file in your Agents folder, that Claude reads to know how to act in that role.

Operating System (in this guide's sense). The folder structure on your computer that holds everything your AI team reads, writes, and remembers. Not the Mac operating system itself. Think of it as the team's shared filing cabinet.

Terminal. The Mac app where you type commands instead of clicking. It looks like a black window. Most people never open it. You will, briefly, twice.

Wispr Flow. A dictation app that turns your voice into typed text in any application on your Mac. Strongly recommended.

MCP (Model Context Protocol). The standard that lets Claude connect to outside services such as Gmail, Slack or your calendar. You rarely touch it directly: connecting an account in Claude's settings uses it for you.

Connector. A connection between Claude and one of your accounts (email, calendar, CRM), set up under Connectors in Claude's settings. Routines depend on them.

CLAUDE.md. The instructions file at the top of your OS folder that Claude Code reads at the start of every session. Your team's constitution.

Skill. A saved procedure in your skills folder: a job, its steps, and when to use it. Claude picks the right one up when your request matches.

Routine. A scheduled job. At a set time an agent does a defined piece of work and reports back to you.

Hook. A small instruction Claude Code runs automatically at a set moment, such as each time you send a message. The way to enforce a rule that must never slip.

Claude in Chrome. A browser extension that lets Claude read pages, click, type and fill forms in your own Chrome browser.

Claude Design. Anthropic's design product for prototypes, decks and one-pagers, which hands finished designs to Claude Code to build.

Artifact. A page Claude publishes to a private link on claude.ai, which you can choose to share.

Worked examples

If you want to see what a finished operating system actually looks like, seven live demos are linked below, grouped by the kind of operator. Each one is the same idea applied to a different context. Click through, see what fits, copy what is useful.

Individual

Entrepreneur OS

For startup founders, consultants, solopreneurs, advisors, and indie builders. Six AI co-founders running an early-stage practice end to end, with sharper fundraising, MVP, and first-hire muscle. Illustrated through Jane Doe.

Open Entrepreneur OS

Designer OS

For anyone in a creative field who wants to start or run a business around their craft. Eleven AI agent operators tuned for the business side of creative practice. Solo studios, growing agencies, freelance practices, hybrid careers.

Open Designer OS

Firm

Investor OS

For managing partners, family-office principals, independent sponsors, and anyone allocating capital. Ten AI co-founders handle sourcing, diligence, modeling, LP relations, legal, portfolio operations, and the connective tissue of a firm.

Open Investor OS

Operator OS

For the CEO, founder, COO, or president of an operating company. Eight AI co-founders handle finance, BD, marketing, product, people, legal, real estate, and board relations, so the operator can stay close to the customer.

Open Operator OS

Nonprofit

Foundation OS

For the executive director of a small family foundation. Eight AI co-founders handle the investment office, grantmaking, program strategy, family engagement, external affairs, finance, and legal. Illustrated through Laurence, a fictional ED of a $35M family foundation.

Open Foundation OS

Charity OS

For the executive director of a small community nonprofit. Eight AI co-founders handle development, grant writing, program delivery, volunteer leverage, communications, finance, and board. Illustrated through Annie, a fictional ED of a $1.4M community nonprofit.

Open Charity OS

Institute OS

For the executive director of a small think tank, policy institute, or research center. Eight AI co-founders handle research, fellowships, convenings, publications, policy outreach, development, finance, and legal. Illustrated through Kelsey, a fictional ED of a $4M policy institute.

Open Institute OS

For your company

I'll build your company's OS

Everything on this page is free, and it's enough to build your own OS. If you're a CEO, founder or managing partner who sees the idea but would like to see your own company's version before committing the time, I'll build it for you. You get your AI team, drawn from how your business actually runs, on a private site in your company's brand.

What you get

  • A private website in your company's brand, with the logo and colors taken from your own site
  • A Chief of Staff at the hub, plus six to ten specialists, each with a named lane
  • Each seat carries its own skills, 48 to 60 across the team
  • Six examples of how you would use it, drawn from real moments in your business, with the agents handing work to each other
  • An architecture diagram showing how the team fits together
  • A personal executive assistant for you, ring-fenced from the work seats: it can't read the work files, and no work seat can read its files
  • The full build-it tutorial from this page, recolored in your brand
  • A password-protected login on its own address, not indexed by search engines

How it works

  1. We do our homeworkWe research your company before we speak, so the interview stays short.
  2. A short conversationAbout 45 minutes with you on how the business runs.
  3. We build itYour team, its skills and its six examples, in your brand.
  4. Your private linkYou get the link and a walk-through call, about a week after the interview.

The site is the blueprint of your team. It isn't agents installed and running inside your systems; building that working OS is what the tutorial above teaches, or what we do together in coaching.

Invented example

The Pell & Arden OS

Here's what one looks like, for a company I made up. Pell & Arden Provisions is a 52-person maker of small-batch olive oils, vinegars and preserves in the Hudson Valley, selling wholesale to about 400 specialty grocers and through its own online shop, and its CEO, Clara Whitcombe, is invented too.

HollisChief of Staff

The hub. Routes every request to the right seat and puts the answer on one page.

MargotCFO

Cash and margins, and the voice that says no. The Jekyll to Clara's Hyde: equal but opposite, by design.

TheoWholesale and grocer accounts

Pricing and orders for the 400 grocers who carry the range.

InesOnline shop and marketing

The online shop and the marketing that fills it.

RafeSourcing and freight

Growers and mills, and the freight that brings the oil in.

JuneProduction and food safety

Line capacity and food safety on the production floor.

SamPeople and hiring

Hiring, and the seasonal crew at bottling time.

NellLabels, contracts and compliance

What the label may claim, and what the contracts say.

WrenClara's executive assistant

Clara's personal calendar and her life outside work. Ring-fenced from the work seats.

A private-label olive oil quote

A regional grocery chain asks for a quote on olive oil under its own label. Theo prices it, Margot sets the margin floor, Rafe checks the harvest and freight, June checks line capacity, and Hollis puts it all on one page for Clara to decide.

Theo → quote · Margot → margin floor · Rafe → supply · June → capacity · Hollis → one page · Clara decides

Nine seats and 48 skills. Every company's version is different.

$5,000One engagement, one company.
Credited in full against coaching with me, if it starts within 30 days of the day you receive your private link.

Build my OS

Or email msinger@traub.io with "Build my OS" in the subject line.

A final word

The reason this works is not the technology. The technology is good but it is not magic. The reason it works is that having a team, even an AI team, makes you a better operator. You stop trying to do everything in your head. You externalize. You delegate. You ask for second opinions. You let yourself be challenged.

A year ago I did not have any of this. I do now. The friends I have walked through this guide are reporting the same thing: their relationship with their work has changed in a way they did not expect.

If this guide helps you, share it with someone you care about. The whole point is to make this less mysterious for as many people as possible.

If you get stuck, ask your Chief of Staff. They are there for exactly that.

Mortimer Singer

Want the printable PDF?

Drop your email. I'll send you the printable PDF and a note when there is a substantive update or a new guide. That's it. No marketing.