RY
Personal note · 2026 · From Ryan O'Connor

A Primer on Claude
(For Someone Who Already Speaks ChatGPT)

A walk-through of how Claude actually works in 2026 — the surfaces, the projects, the skills, the connectors, and the systems thinking I've built around it. Built for you, hand-organized, takes about 30 minutes to read end-to-end.

00 · Welcome

Hey — Read This Before You Open Claude Again.

You and I have been riding the AI wave together for about three years — almost all of it inside ChatGPT, mostly as a chat box. This is me catching you up on what I've been building since you left RedPeg, because Claude is no longer just a chat window, and the way I work with it now is barely the same job.

What this is

A tabbed reference. Each tab is a chapter. You can read in order or jump around. It's long-ish on purpose — I'd rather give you the full picture once than send a dozen Slack messages over a year.

Why I'm sending this

You've been a ChatGPT power user since 2023. That's more than enough base context — most of the concepts here have a counterpart there. But three things have changed under the hood since you left:

  1. The interface stopped mattering. The chat box is now one of three surfaces. The other two — Cowork and Code — operate your computer and your files directly.
  2. Context became persistent. Projects + Skills + Custom Instructions mean Claude doesn't reset between conversations. It remembers who you are and how you want to work.
  3. Tools became plumbing. Through MCP, Claude can read your SharePoint, your Asana, your Outlook, your Google Drive, your local folders. The work doesn't get pasted in anymore. The work gets pointed at.

If you take only one thing from this primer, take this:

Stop uploading. Start pointing.
Stop chatting. Start briefing.
Stop using AI. Start hiring it. — The shift, in three lines

If you do nothing else right now, do these two things

Open this on a laptop · 5 minutes
RedPeg Curiosity Catalog
The live, scrollable companion to this primer. It's both the AI onboarding ramp and the visual version of the Curve. Built as the "why it matters" destination for our company-wide AI program. If you read nothing else here, click this.
red-peg-curiosity-catalog.vercel.app
From AI Edges · YouTube · 12 min
beginner - start here. Claude 101
youtube.com/watch?v=ER7fnAZkayE

What you'll find in each tab

TabWhat's in it
01 First, Some SettingsFive toggles to flip on before anything else. Two minutes.
02 Getting StartedThe shift in mental model. The single move that unlocks everything.
03 Three SurfacesChat, Cowork, Code — what each one is for.
04 ProjectsYour always-on, already-briefed workspace. Probably the biggest unlock.
05 Skills & IntegrationsHow you teach Claude your way of working — and how it connects to your tools.
06 The BrainHow I structured my own life as a folder of markdown files Claude can read.
07 Systems ThinkingWhy Cowork (and beyond) is a step-change from chatting.
08 What I Use It ForConcrete examples — what's actually running in my world right now.
09 The CurveThe penny that doubles. Where we are on the macro AI curve, and where you are personally.
10 Resources & VideosThe RedPeg onboarding PDFs, the Curiosity Catalog, AI Edges video links, MCP setup guide.

How to read this

You don't need to do anything while you read. Just read. At the end you'll know the shape of the thing. Then we can grab a coffee, you can show me what's confusing, and I'll set you up.

— Ryan

01 · First, Some Settings

Two Minutes Of Setup. Then Everything Else Works Better.

Before you do anything else — flip these on. They're buried in Settings and most people never find them. They're the difference between Claude knowing you and Claude restarting from zero every time.

How to get there

1
Click your initials
Bottom-left corner of claude.ai (the circle with your initials). A menu pops up.
2
Click "Settings"
You'll land on a tabbed settings page: General, Profile, Capabilities, Connectors, etc.

General tab — Personal Preferences

This is where you tell Claude how you want to be talked to. Tone, format, what to keep, what to avoid. It applies to every conversation, every Project, every surface. Set it once. Forget it.

The trick — narrate it, don't write it

You don't have to write this in a polished way. Open a chat with Claude and just talk. "Here's how I work. Here's what I hate when AI does. Here's the kind of writing I do. Here's how I want emails drafted." Then say: "Now turn that into a Personal Preferences block I can paste into my Claude settings." Sarah Perkins on our team did this in about 12 minutes — narrating into a chat — and ended up with a sharper preferences block than she would have written from scratch.

What mine looks like (short version)

For inspiration. Mine is longer than most people need — drawn from three years of figuring out where the AI's defaults clash with how I actually want to work. The condensed version:

## Communication
- Lead with the conclusion. Supporting detail follows.
- Be concise. Don't restate the question.
- Prose when sentences flow. Structure when the task is structured.

## Tone
- Professional and direct. Confident, no hedging — unless genuine
  uncertainty exists, in which case name it plainly.
- No "great question" or sycophancy. No unsolicited sign-offs.
- Don't ask if I need anything else.

## Formatting
- Bold sparingly. No em dashes (use commas or regular dashes).
- No emoji unless I use them first.

## Research
- Search online for anything that's not obviously settled knowledge.
- Prefer primary sources, not aggregators.
- If ambiguous, ask a short clarifying question. Don't fabricate.
- When multiple options exist, recommend one — don't list neutrally.

## When editing my writing
- Preserve my voice. Fix what's broken; keep what's mine.
- Keep hedging ("maybe," "I think," "kind of") — it's a feature.
- Don't add transition words ("furthermore," "ultimately," etc.).
- Don't replace specific nouns with general ones.
- Don't construct jokes. Shrug humor only.

[The full version is in my vault at Shared/Custom Instructions — Paste Ready.md — happy to send it as a starting point you can edit.]

Capabilities tab — three switches to flip

Toggle 1
Search & Reference Chats
Lets Claude search across your past conversations and pull from them. Without this, every chat is amnesic. With it, Claude can say "last week you decided X — does that still hold?" Turn this on.
Toggle 2
Generate Memory From Chat History
Claude builds a running, structured memory of you — your work, your preferences, your projects — derived from the chats themselves. You don't have to spell everything out; it learns. Turn this on.
Toggle 3
Start Import (from ChatGPT)
If you have three years of ChatGPT history, you don't have to leave it behind. Click Start Import, follow the steps, and Claude pulls your past conversations in. Now the new Memory and Search-Chats features have actual material to work with. Do this once. Walk away. It runs in the background.
Why this matters more than it sounds

Three years of ChatGPT conversations is a lot of you. Names, projects, preferences, recurring questions. If you import them and turn on Memory + Search, Claude essentially walks into the relationship already knowing who you are. The difference is dramatic. The first chat after import won't feel like a new tool — it'll feel like a colleague who's been listening.

Visuals — three more toggles, scroll down on the same screen

Toggle 4
Artifacts
Lets Claude open a side-panel for outputs that aren't just text — interactive tools, formatted docs, calculators, dashboards, downloadable PowerPoints, HTML files. Turn on.
Toggle 5
AI-Powered Artifacts
Lets the artifact itself contain AI behavior — a chat widget on a page, a "regenerate this" button, a smart fill-in. The deep version of artifacts. Turn on.
Toggle 6
Inline Visualizations
Lets Claude render charts, diagrams, and small visual blocks directly in the chat instead of describing them in text. Massive quality-of-life upgrade for any analytical question. Turn on.
If you do nothing else right now

Open Settings → Capabilities. Turn on Memory. Turn on Search Chats. Click Start Import for ChatGPT. Walk away. Come back tomorrow. Your Claude will already be smarter about you than your ChatGPT ever was.

02 · Getting Started

The Shift From Search Box to Staff Member.

The fastest way to skip three years of plateauing on ChatGPT is to stop using AI like a search engine and start using it like a colleague. This chapter is the whole mental flip in one page.

The mistake almost everyone makes

For three years, the pattern most people fell into looks like this: open a chat tab, type a question, copy an answer, close the tab. Every conversation starts from zero. Every time, you re-explain who you are, what you do, what the brand is, what the project is. The AI is a vending machine. You insert a question. You receive an answer.

That's Phase 1 on the adoption curve (see Tab 08). It's the floor. It's also where most people stay.

The single biggest unlock

Stop asking AI questions. Start briefing it like a smart person who just joined your team and needs context. The conversation gets longer. The output gets sharper. The value per session goes up — even though the volume goes down.

The mental model that actually works

I find it useful to think of Claude as a new hire who can read a thousand pages a minute, works nights and weekends, and never gets bored. On day one, you wouldn't hand them a stack of every file you've ever touched. You'd show them where things live. "This is the client folder. This is where recaps go. This is the budget tracker. This is Asana." Then you'd ask them to read in for a day and come back with a summary.

That's exactly what Claude is now. The new hire is Claude. The read-in is instant. The folders you already built are the onboarding doc.

Three habits to install

1
Brief, don't ask.
Before you ask the question, tell Claude who you are, what you're working on, what the audience is, and what you've already tried. The prompt that starts "I'm a VP at an experiential agency, drafting a proposal for a Fortune 500 spirits brand, here's the brief…" beats "write me a proposal" by a factor of ten.
2
Point, don't paste.
If the source material lives in a folder, channel, or app — point Claude at it. Don't screenshot a slide and paste it. Open the folder. Connect the tool. Let Claude read the source. (More on how, in Tab 04.)
3
Iterate, don't accept.
The first answer is a draft. Push back. "Cut the marketing-speak." "Try it again, but for a CFO who hates buzzwords." "What did you assume that I didn't tell you?" Three rounds gets you to something useful. One round usually doesn't.

Why Claude specifically

Honest answer: ChatGPT, Claude, Gemini — at the model level they're all very good. The reason I work primarily in Claude in 2026 is the operating system around the model:

If you keep using ChatGPT, that's fine. The mental model is what matters. But the rest of this primer assumes Claude, because that's where I built everything.

One sentence to remember

Claude is the world's fastest research assistant, the world's most patient reader, and a decent first-draft writer. It is not a strategist, a PM, or a creative lead. You are still all three. It accelerates judgment, it doesn't replace it.

Stop driving. Start asking.

One more analogy because this is the one that finally clicked for me.

The old way of using AI — the ChatGPT way most of us learned in 2023 — feels like driving. You think through every step. "OK, first I need to find the brief. Then I'll paste in the budget. Then I'll ask it to compare. Then I'll copy that answer over to email and rephrase it." You're routing the trip yourself, every time. You're a courier between tabs.

The new way is closer to being driven. You don't tell Claude how to get from A to B. You tell it where you want to end up.

Don't worry about "how do I get from A to B."
Just give it the data. Or better — don't even copy files in. Think:
"How do I hook Claude up to eat data on its own?"
Then your only job is to tell it what you want.
What you wish. What you're tired of.
"Hey, this is a problem. Help me fix it."

The three sentences that replace 90% of prompting

Voice 1
"What I Want"
State the destination. "I want a one-pager I can hand to a CFO that explains why we're spending $40K on this." "I want a status update Sarah can scan in 90 seconds." Skip the route. Claude figures out the route.
Voice 2
"What I Wish"
"I wish I had a dashboard that showed me which clients are quiet this week." "I wish my recap notes wrote themselves." Saying it as a wish gives Claude permission to suggest the shape, not just fill in the form.
Voice 3
"What I'm Tired Of"
"I'm tired of rewriting the same kind of follow-up email." "I'm tired of digging through SharePoint to find last quarter's deck." Frustration is a great prompt — it gives Claude both a problem and a baseline to beat.

The "hook it up to data" mindset

The reflex from ChatGPT-land is to copy and paste data into the chat. That works, but it scales badly. Five minutes in, you're babysitting copy-paste.

The Claude reflex is different: before you do anything, ask "how can Claude get this data on its own?"

Once the data is hooked up, your job changes. You're not feeding the AI. You're directing it. "Read the last three months of Asana on this client and tell me where we keep dropping the ball." "Look at my inbox from this week and tell me which conversations I haven't closed." The data was already there. You just stopped acting like a courier.

The shift in one line

Stop telling Claude how. Start telling it what you want, what you wish, or what you're tired of. Then make sure the data is hooked up so it can actually do something about it.

03 · The Three Surfaces

Chat, Cowork, Code — One Brain, Three Bodies.

Claude lives in three different places now. The model is the same. What changes is how much of your computer it can actually touch. Knowing which surface to open is half the battle.

Surface 1
Claude Chat
claude.ai · browser + mobile
What it is: The one that looks like ChatGPT. You type, Claude responds.

Best for: Writing, research, brainstorming, drafting emails, reviewing decks. Most of your time will still happen here.

What's different from ChatGPT: Projects, Skills, and live tool integrations all run inside the chat experience.
Where you spend most days.
Surface 2
Claude Cowork
desktop app · macOS / Windows
What it is: A desktop app that operates your computer. Opens apps. Moves files. Populates templates. Builds decks.

Best for: Live questions about work happening right now. "Pull every email from USAA this week and tell me what they're worried about." "Read the Asana board and draft a status update."

Why it matters: This is where Claude becomes a colleague, not a chat partner.
Free with your Claude plan. Download it.
Surface 3
Claude Code
terminal app · CLI
What it is: A terminal app — yes, the black box with white text — that points Claude at a folder on your computer and works through it at volume.

Best for: "Read every recap in this folder and tell me what consistently went wrong." "Pull the total budget across all 2025 programs." "Rename every file in this folder to match our convention."

Honest take: It looks like a dev tool because it is one — but the moment you ask it to read 80 post-event recap PDFs and find the three things every client complained about, you stop caring.
Skip this for now. Come back when you're ready.

Which one to open, when

TaskOpen thisWhy
Quick draft of an emailChat30 seconds. Don't overthink it.
Email for a repeat clientProject ChatThe Project knows the client and the voice already.
Concept ideas for a programProject ChatUse a Skill, not a blank chat (see Tab 04).
Pull tasks from AsanaProject ChatAsana integration runs there.
Build a deck content + outlineProject ChatBuild content first. Hand off to PowerPoint last.
Build the actual PowerPoint fileCowork or Chat with PowerPoint MCPCowork operates the file.
Organize and rename a shoot folderCoworkRepeatable file work. Cowork's strength.
Update a budget spreadsheetCoworkIt opens Excel and edits live.
Read 80 PDFs and find a patternCodeVolume work. Worth the dev-tool look.
Something quick you'll throw awayChatLow-stakes. Don't formalize it.
Mental shortcut

Chat is for thinking. Cowork is for doing. Code is for volume. If you only learn Chat + Cowork, you'll get 90% of the value.

From AI Edges · YouTube · the difference, visual
Claude Chat vs. Cowork? What are the differences
youtube.com/watch?v=56pN4nQmnk8
04 · Projects

Projects: A Workspace That Already Knows You.

A Project is the single biggest difference between using Claude as a chatbot and using it as a teammate. Once you understand Projects, the rest of this primer makes sense.

What a Project actually is

Plain English

A Project is a persistent workspace in Claude that holds reference files, follows custom instructions, and remembers context every time someone opens it. Think of it as a team member who already knows the client, the brand, the tone, and how you work — without you re-explaining anything. Every chat you start inside a Project picks up all of that automatically.

Concretely, a Project contains:

How I use Projects

Right now I'm running 11 active Projects on the Claude Teams plan. The pattern I've landed on:

ProjectPurpose
One per active clientBrand guidelines, past work, current programs, voice. Anyone on the account team can be added.
One per major internal initiative"RedPeg AI Onboarding," "Creative Pricing Guide," "RedPeg Brand 2026," etc.
One personal "everything" ProjectMy voice profile, target companies, side ventures, polymath patterns. The most-loaded sparring partner I have.
One "Career Brain" ProjectLive job search, target roles, pipeline. Different scope from the personal one.

The "never re-brief" payoff

Inside a properly-loaded client Project, I don't re-explain anything. I open a chat and say: "Draft a status update for the activation. Two weeks out. Renders approved. Waiting on fab quote." The Project knows the client, the brand voice, the relationship, and what was discussed last week. The output is right on the first pass — not the third.

The "upload once, follow forever" payoff

The most common complaint about AI at any agency: "it doesn't know our brand. Wrong tone. Generic language. Off-brand copy." That's because nothing was loaded. Upload brand guidelines to a Project once, and Claude follows them on every response in that Project — tone, naming conventions, approved language, legal restrictions. Brief it once. It holds permanently.

Sharing a Project

Important — this isn't email

When I say "share a Project," I don't mean send a file or copy a link. Sharing in Claude means giving someone access so the Project appears directly in their Claude account — like adding someone to a shared Google Drive folder. They open Claude, the Project is in their sidebar. No attachments. No download. Nothing to forward.

1
Open the Project in Claude
In the left sidebar at claude.ai, find the Project and click in.
2
Open Project Settings → Manage Members
Look for "Manage Project" or the settings icon near the top of the Project view.
3
Enter their Claude account email
This is not drafting an email. It's granting their Claude account access to this Project. The Project appears in their Claude sidebar the next time they log in.
4
They open Claude — done
The Project is in their sidebar. Shared files, instructions, and Skills are immediately available. Their individual chats are still private, even inside the shared Project.

What's shared vs. private

Inside a ProjectShared?Notes
Project instructionsYesAll members get them automatically.
Uploaded files (briefs, brand)YesShared with everyone in the Project.
SkillsYesAvailable to every member.
Connected tools (Asana etc.)YesConnections persist project-wide.
Individual chatsPrivateEach member's chats are private to them by default.
Cowork automationsNoLocal to the machine where Cowork is installed.

The .md file pattern (a preview)

One of the highest-leverage habits I've built: I write the Project's "memory" as a folder of .md files (markdown), not as Word docs or Google Docs. Markdown is plain text. Claude reads it cleanly. Headings work as structure. Wikilinks ([[Like This]]) cross-reference between files.

I'll go deep on this in Tab 05 — but for now: your future Project knowledge base should be markdown files in a folder, not a stack of PDFs.

05 · Skills & Integrations

Skills Teach Claude Your Way of Working.

A Skill is a tiny packaged instruction set you drop into a Project. Once it's there, anyone in that Project gets the same output quality without re-briefing. Integrations are how Claude reaches into your real tools to do real work. They're related — but different jobs.

What a Skill is

Plain English

A Skill is a saved instruction set that teaches Claude a specific workflow — methodology, tone, output format, decision logic — for a recurring task. Drop it into a Project once; everyone in the Project gets the same behavior automatically, every time.

Examples I've built or installed for the RedPeg team:

RedPeg Ideation
redpeg-ideation.skill
RedPeg's ideation framework, packaged. Claude runs the same brainstorm process the creative leads run. Structured, grounded in the brief, force-ranked against our service lanes. Use when: you have a new program to concept.
CCO Deck Review
cco-deck-review.skill
Chief Creative Officer-level deck notes. Story flow, slide-by-slide feedback, what to cut, what's missing, where the argument breaks. Use when: before a client review. 10 minutes of work saves a round of revisions.
No-Pitch-Wins
no-pitch-wins.skill
Blair Enns's Win Without Pitching mindset, applied. Claude plays a creative strategy consultant trained in Enns's framework — paid diagnostics over free pitching, expert positioning over vendor positioning. Use when: reviewing a proposal or RFP.
Grill-Me
grill-me.skill
Stress-test mode. You describe a plan. Claude grills you — hard questions, edge cases, devil's advocate. Use when: right before a client meeting and you want every weak spot surfaced first.
Session Handoff
session-handoff.skill
Claude reads the session you just had and produces a clean handoff doc — what happened, what was decided, what's open. Use when: ending a session another person (or future you) will pick up.
Morning Briefing
redpeg-morning-briefing.skill
Pulls live Asana tasks, OOO/travel, Slack overnights, Outlook + Teams, and delivers a VP-level day-by-day stand-up dashboard as an HTML file. Use when: first thing in the morning. I run this every day.

The point isn't the specific skills. The point is the pattern: anything you do more than three times — package it as a Skill. Now everyone gets your best version of it, not a generic AI version.

From AI Edges · YouTube · steal these
15 Claude Skills
youtube.com/watch?v=0bRxpRupE5Y

What an Integration (MCP) is

Plain English

An Integration is a live connection between Claude and an external tool. Claude doesn't just describe what's in Asana — with the integration on, Claude reads tasks, updates records, posts comments in real time. The technical standard powering this is called MCP (Model Context Protocol). You don't need to know how it works. You just need to know that "MCP" means "Claude can reach into this tool."

What's wired into RedPeg's Claude account today:

The mental shift: "I have a question about Asana" stops meaning "open Asana" and starts meaning "ask Claude." The work is the same. The interface gets thinner.

Custom MCP servers — where this gets interesting

The standard's open. Anyone can build a custom MCP server that exposes any data source to any Claude surface. I built one for my Brain vault. It exposes 11 tools: brain_search, brain_read, brain_voice_profile, brain_idea_append, etc. Now in any Claude session I can ask "what did I say about Openbank F1 last quarter?" and Claude reads straight from my vault.

{
  "mcpServers": {
    "brain": {
      "command": "/opt/anaconda3/bin/python3",
      "args": ["/Users/ryan/Desktop/Brain/Tools/brain_mcp.py"]
    }
  }
}

That's the entire config. Drop it in ~/.claude.json, restart, and you have a personal-knowledge MCP. The same pattern works for any internal data store — a CRM, a private wiki, a Postgres database. It's the most powerful and most underused feature of the whole system.

Quick distinction (paste this somewhere)

Skill = teaches Claude how to think and respond. Lives in a Project.
Integration / MCP = lets Claude reach into a tool and take action. Lives at the account or app level.
Plugin = not a Claude word. If you used ChatGPT plugins, MCP integrations are the grown-up version.

06 · The Brain

The Brain: My Life as Markdown.

This is the part most people don't do — and the part that 10x's everything else. Over the last year I rebuilt my entire working memory as a folder of plain-text markdown files. Claude reads them. The Brain is the source of truth. Everything downstream — Projects, Skills, scripts — points at it.

Read this first — pacing

This whole tab is the destination, not the starting line. Don't try to set up a Brain on day one. Watch the AI Edges videos first (Tab 10). Get comfortable with Settings, Projects, and one Skill. The Brain is what you build around month three, when you've felt the friction of "where does this live?" enough times to want a real answer.

When you're ready, we'll figure out where your .md files actually live — most likely a synced OneDrive or SharePoint folder so it's accessible to both Claude Cowork on the desktop and a shared Claude Project for the team. I'll set this up with you when the time comes; don't worry about it now.

Why markdown

Word docs and Google Docs are bad for AI. They're heavy, they have layout bloat, they don't cross-reference, and they break version control. Markdown is plain text. Light, fast to read, easy to diff, parses cleanly into Claude. Headings (#, ##) become structure. Wikilinks ([[Like This]]) become cross-references. Frontmatter at the top becomes metadata Claude can filter on.

Once your most important reference material is in markdown, you can:

How my Brain is structured

Brain/
├── Home.md                         ← table of contents
├── How to Use Your Brain.md        ← orientation
├── Personal/
│   ├── Career/                     ← target companies, applications, portfolio
│   ├── Projects/                   ← side ventures (Lantern & Fox, Curio, etc.)
│   ├── Insights/                   ← Polymath Map, How You Work, Your POV
│   ├── Ryan OS.md                  ← synthesis of 3,346 conversations
│   └── Skill Map.md
├── RedPeg/
│   ├── Projects/                   ← 10 active projects (each a folder)
│   ├── Clients/                    ← 24 per-client pages
│   ├── Team/                       ← Roster with Asana GIDs, AI adoption curve
│   ├── Strategy/                   ← brand vision, voice, operating model
│   └── Operations/                 ← Utilization, HR, Office
├── Shared/                         ← voice profile, custom instructions, idea bank
├── Tools/                          ← Python scripts + Claude Skills
├── Archive/                        ← 3,346 historical conversations (tagged + linked)
├── _raw/                           ← script cache (machine food)
├── _share/                         ← outbox for PDFs & HTML I send out
└── _upload/                        ← pre-packaged Claude Project bundles

The numbers

StatCount
Historical conversations (Claude + ChatGPT)3,346
LLM-enriched with summaries + rich tags572
Active Claude projects11
Auto-built client pages24
Activation concepts catalogued216
"What if" ideas extracted1,564
Skill areas mapped14

The naming convention (this is half the work)

The dirty secret nobody tells you: Claude is only as good as your file names. If your folder looks like final_v3.pptx and Deck_REAL_FINAL.pptx and notes (1).docx, Claude struggles — not because it can't read the files, but because it can't tell which is which without opening all of them.

The pattern I use: client, date, program, doc type, separated by underscores.

Nike_2026-05_CVTS-EHQ_Recap.pdf
Marriott_2026-02_SnowLeague_Budget-v2.xlsx
USAA_2026-03_Activation_SOW.docx
Meta_2026-Q1_StatusUpdate_Notes.md

Why this order:

Four tokens. If you name a file that way, you can find it in three seconds — and so can Claude. A file in the right folder with the right name is already half-searched.

Frontmatter — metadata Claude can read

Every meaningful markdown file in my vault starts with a few lines of YAML frontmatter:

---
title: "Nike CVTS"
type: client
status: active
captured: 2026-04-16
updated: 2026-04-25
tags: [nike, automotive, ehq, activation]
---

This is the part most people skip. It's also the part Claude uses most. "List every active client." "What did I update this week?" "Show me everything tagged 'pricing'." Frontmatter makes those queries trivial.

If you do nothing else from this primer

Take one folder you actually use — the most active client, the most recent project — and rename twenty files using the pattern. Move them into 4-5 subfolders (Briefs/, Budgets/, Recaps/, Decks/, Notes/). Then point Claude at it and ask one question. The answer will be either great or bad — and if it's bad, it's because your files aren't labeled yet. That's feedback, not failure. Fix two more files. Ask again.

07 · Systems Thinking

Cowork Is Where Chatting Becomes Engineering.

If Tab 03 was the workspace and Tab 04 was the toolbox, this tab is the worldview. Cowork (and the Brain pattern, and MCP servers) is where you stop chatting with AI and start building systems on top of it. This is where the leverage is.

The mental flip

Chatting is one input → one output. You ask. It answers. The transaction ends.

Systems are inputs that compound. Once you've taught Claude how to do a thing once, the next person doesn't need to teach it. Once you've pointed Claude at a folder, you don't need to re-point. Once you've packaged a Skill, the methodology doesn't drift.

The bottleneck in most organizations right now isn't AI capability.
The models are extraordinary. The bottleneck is the mental model people bring to them. — Something I've said too many times to count

Three system patterns I run today

1. The Morning Briefing

Every morning, I run a single command. Claude pulls live data from:

...and produces a VP-level dashboard as an HTML file: plain-language summary, day-by-day stand-up view, anything urgent flagged. The whole thing is a Skill. The Skill takes about 90 seconds to run. Doing this manually used to take me 45 minutes and I'd still miss things.

2. The Pitch Accelerator

One Python script in Tools/pitch_accelerator.py. Pass it a brief in plain English. It produces a starter pitch deck — outline, key points, named concept, 3-5 activation ideas pulled from the 216 catalogued in my Activation Library, sample slides — saved as an HTML file in _share/pitches/. It's not the final deck. It's the equivalent of getting an associate strategist to do a 4-hour first pass before you sit down with it.

3. The Brain MCP

Already covered above (Tab 04). The Brain vault is exposed to every Claude surface I use — Desktop, Code, Cowork — through one MCP config. Search, read, append. Idea capture goes back into the vault. Daily logs go back into the vault. The vault stays alive.

Why this is the real unlock

None of the three patterns above is conceptually advanced. They're all just "do the thing once, save it, run it again." The difference is mindset:

Chatting mindsetSystems mindset
"Let me ask Claude this question.""How would I have Claude do this every Monday?"
"I'll paste the brief in.""The brief lives in a folder. Point Claude there."
"I told Claude my voice rules.""My voice rules are in a Skill. Claude follows them by default."
"This conversation went well — let me copy it.""This conversation went well — let me package the methodology."
"I'll re-explain the project to Claude.""The Project knows the project."

The architecture, drawn rough

                    ┌─────────────────────────────┐
                    │      THE BRAIN (vault)      │
                    │   markdown + YAML metadata  │
                    └─────────────┬───────────────┘
                                  │
              ┌───────────────────┼───────────────────┐
              │                   │                   │
        ┌─────▼──────┐      ┌─────▼──────┐      ┌─────▼──────┐
        │   MCP      │      │  Projects  │      │   Skills   │
        │ (live read)│      │ (knowledge)│      │ (workflow) │
        └─────┬──────┘      └─────┬──────┘      └─────┬──────┘
              │                   │                   │
              └───────────────────┼───────────────────┘
                                  │
                  ┌───────────────┼───────────────┐
                  │               │               │
              ┌───▼───┐       ┌───▼───┐       ┌───▼───┐
              │ Chat  │       │Cowork │       │ Code  │
              └───────┘       └───────┘       └───────┘

The model on its own is a brain in a jar. The architecture around it — Brain → Projects → Skills → Surfaces — is what makes it useful at the speed I work.

The honest version

Most people who plateau on AI plateau because they keep using it as Chat. The graduation move is realizing you can save, share, and run what works — turning a one-off conversation into infrastructure. That's the difference between "I use AI" and "I work in an AI-first system."

08 · What I Use It For

What's Actually Running In My World Right Now.

Concrete is more useful than theoretical. Here's what's actively shipping or running through Claude in my day-to-day in April 2026 — agency, personal, and side ventures.

Inside RedPeg

RedPeg AI Onboarding (Q2 company rock)
I'm the internal AI program lead at RedPeg now. The whole company-wide AI program — the kickoff email, the adoption tracker ("Push the Limit"), the onboarding pack for PMs and producers, the starter Skills, the Cowork plugin, the PDF guides — it's all run through Claude Projects. Files: Welcome-to-Claude-Quick-Start.pdf · How to Onboard Claude at RedPeg.pdf · redpeg-claude-kickoff.md · Starter Skills for the RedPeg Team.pdf
RedPeg Brand Bible 2026 — "AI Thinks It. We Build It."
The 2026 rebrand: as AI commoditizes creative strategy, RedPeg's durable advantage is the physical execution layer between brief and reality. Three named service lanes (Live Event Production, Employee Experience, Music Partnerships through Deep Cuts). Delivered as a 24-page navigable HTML brand bible. The whole thing was structured, drafted, and iterated in Claude.
Creative Pricing & Scoping Tool
Internal scoping calculator — three program tiers, 57 tasks across 12 categories, live cost calculator with editable rates. Built from industry benchmarking against Jack Morton, GPJ, Geometry, Inspira. Surfaced ~11 tasks RedPeg performed but didn't scope. Fixes the under-scoping problem at the contracting layer.
The Morning Briefing
Every morning. Claude pulls Asana + Outlook + Slack + Teams and gives me a VP-level dashboard. 90 seconds vs. the 45 minutes it used to take me. Skill is named redpeg-morning-briefing. Bundled with the 15-skill Cowork pack.

On the personal side

Career Manager — non-linear job search OS
Personal Claude Project + interactive HTML dashboard. Pulls Workday postings, scores them against my profile, tracks 42 target companies and 12 role titles. The fit-score logic and the voice rules for outreach all live in instructions; the live company list lives in a markdown file Claude re-reads each session. Live at: Personal/Career/career-manager.html
Curio Studio — four sub-projects
The Ladder That Isn't — interactive editorial dashboard about American wealth (live: ladder-mu.vercel.app). Style Sync — AI moodboard tool, replaces hand-pulled Pinterest references (style-sync-eight.vercel.app). RedPeg Scoping Tool. Career Manager. All four were vibe-coded with Claude as the primary engineering partner.
Lantern & Fox — D2C heirloom story kit
Side venture launching 2027. A wooden lantern, a fox token, a deck of prompt cards, paired with an AI story engine that turns a child's name and the night's prompt into a fresh illustrated bedtime chapter. The brand operating system — supply chain, email, IG templates, analytics — all runs through one Brain-driven workflow. Live placeholder at lanternandfox.com.
Gift.Script — novel + Ocelus ARG
Long-form fiction project. The voice rules, character bibles, and chapter outlines live in markdown in the Brain. Claude is the writing-room sparring partner. Voice consistency across chapters comes from the saved voice profile, not from re-explaining tone every time.
Frontiers — essays
Recent essays drafted with Claude as editor: The Employee Is the Audience Nobody Is Building For (LinkedIn, April 2026), The Contract You Didn't Know You Signed, The Ladder That Isn't, The New Moore's Law. Each is a markdown draft → Claude review → human pass → publish. The voice profile keeps me sounding like me, not like AI.
From AI Edges · YouTube · a tease for the future
Claude Design. ooof… its good. And is a tease for the future.
youtube.com/watch?v=KlPxWaY91rE

What it doesn't do

Worth saying plainly because the temptation runs the other way:

09 · The Curve

Two Curves. One Macro, One Personal.

There's a curve we're all on (the one AI is climbing right now), and a curve you're on (the one your personal use is climbing). Both are exponential. Both feel slow until they don't. This tab explains both.

Part one — start with a penny

The classic thought experiment: would you rather take $1 million today, or a penny that doubles for 30 days?

DAYS 1–10
Slow
"This is fine I guess?"
By day 10, the penny has grown to about $5. Useful, but not life-changing. You start to wonder if you made the wrong call.
DAYS 11–20
Quiet Acceleration
"Wait, this is something."
By day 20, the penny is around $5,000. The progress is real, but the room hasn't caught on. The early adopters are building real things while everyone else is still posting about the curve.
We are here
DAYS 21–30
Vertical
"How did this happen so fast?"
By day 30, the penny has compounded to $5,368,709.12. The last 10 days produced 99.9% of the value. Anyone not already on the curve is now permanently behind.

Are we on day 10 of AI, or day 20?

The honest answer: somewhere between 17 and 22. The first decade of useful AI happened in 2023-2024. The compounding stretch is happening now. The last 10 days of the penny — where 99.9% of the value lands — is the back half of this decade. Anyone treating AI like a tool to learn "eventually" is treating it like a day-10 problem when it's actually a day-20 problem. The ramp from "interesting" to "industry-defining" is shorter than every previous tech curve we've lived through.

I built a live site that walks through both halves of this — the macro curve and the on-ramp into AI itself. It's the RedPeg Curiosity Catalog, and it's the single best place to send anyone who wants the visual, scrollable version of everything in this primer:

Go look at this — it's the live version of this whole primer

red-peg-curiosity-catalog.vercel.app

Same content as this primer, but as a scrollable site with charts, animations, and a guided ramp. If you read nothing else, open this on a laptop. Both the curve and the onboarding flow live there.

For now, the takeaway is short:

The work you put in to learn AI in 2026 isn't expensive.
It's the cheapest version of it you'll ever pay.
— What I tell every person at RedPeg who says "I'll get to it next quarter"
From AI Edges · YouTube · what shifts next
what will matter on the web (value wise)
youtube.com/watch?v=ib2m9HVX7as

Part two — the personal adoption curve

Inside the macro curve, you're on a smaller, personal one. From an empirical analysis of 3,346 of my own AI conversations spanning January 2023 through April 2026 — not theory, observed behavior. This is the framework I use when I onboard people at RedPeg. It maps where you are and what the next move is.

Probably you
PHASE 1
Discovery
"What can AI do?"
Short exchanges, simple questions, testing boundaries. AI is a search engine with personality. Every chat starts from zero.

Tell: You open a tab, type, get an answer, close it.

Volume: High. Value per session: low.
PHASE 2
Strategic Partnership
"Here's what I know — help me think about it."
Longer sessions (8-15 exchanges). You bring context, domain knowledge, files. AI refines and challenges instead of generating from scratch.

Tell: You're pasting in briefs, giving feedback, iterating toward something better than either of you started with.
PHASE 3
Invisible Integration
"AI is just how I work now."
AI stops being a topic. It's the medium. You don't think about "using AI" any more than you think about "using email." Production, strategy, and creative all flow through it naturally.

Tell: Someone asks "do you use AI?" and you have to think about it.
Where I live
PHASE 4
System Builder
"How do I make this work for everyone?"
You flip from using AI for your own output to designing how a team uses AI. Building frameworks, onboarding processes, measurement systems. Individual productivity becomes organizational leverage.

Tell: You're building templates, Skills, MCPs.

The data behind it

PhaseStyleValue/SessionTimeline
1. Discovery2-4 exchanges, one-shotLowWeeks 1-4
2. Partnership8-15 exchanges, iterativeMedium-HighMonths 2-6
3. IntegrationVaries, task-dependentHigh (invisible)Months 6-12
4. System BuilderDeep, multi-session arcsMultiplied across teamYear 1+

Total volume goes down. Value per session goes up. Fewer conversations, deeper engagement, higher leverage.

What gets people stuck

Most people plateau at Phase 1 because the mental model is wrong. They treat AI like a vending machine (insert question, receive answer) instead of a colleague (brief, collaborate, iterate).

Single biggest unlock — repeat from Tab 01 because it's that important

Stop asking AI questions. Start briefing it like a smart person who just joined your team and needs context.

The one-thing challenge

Pick one recurring task you do every week. Use Claude for that one task, every time, for two weeks. Not everything. One thing. The repetition is what builds the muscle that gets you from Phase 1 to Phase 2.

For you, given your old role, candidates would be:

Pick the one that itches the most. Run it for two weeks. Then we talk about Phase 3.

Why I'm picky about the curve

This isn't about climbing for its own sake. Phase 1 is fine if your work doesn't require leverage. But for anyone running programs, leading teams, or trying to ship more than one person's output — staying at Phase 1 is a structural cap. The work comes in faster than you can answer it. You can't hire your way out of that anymore.

10 · Resources & Videos

Where to Look When You're Ready For More.

Everything I've referenced, plus the team-side resources I've built at RedPeg, plus the live places to stay current. Some of these are RedPeg-internal — I'll get you access. Some are public; just click through.

Start here — the live site

LIVE · START HERE
RedPeg Curiosity Catalog — the AI onboarding + the Curve, in one site
The single best link to bookmark. Built as the "why it matters" destination for the RedPeg AI program kickoff and hosted on Vercel. It's both the AI onboarding flow and the visual version of the Curve (Tab 09). If you only open one thing from this primer — open this. Designed to be browsed by curiosity, not by feature.

The RedPeg onboarding pack (PDFs)

These are the live materials we ship to new RedPeg PMs. Probably the cleanest single set of references in this whole primer. I can email you the PDFs directly — they're all in _share/ on my end.

PDF
Welcome to Claude — Quick Start
The 2-page welcome PDF a new team member gets. Short. Explains the shift (stop uploading, start pointing) and the file-naming pattern. The "if you read nothing else" doc.
Open PDF →
PDF
How to Onboard Claude at RedPeg
The long-form guide. The shift, the three places Claude lives, the "did you know / imagine if" scenarios, the RedPeg naming pattern, a 4-week adoption plan. Most of Tab 02 of this primer is condensed from this doc.
Open PDF →
PDF
Starter Skills for the RedPeg Team
Five Skills curated for how the account team actually works (Ideation, No-Pitch-Wins, CCO Deck Review, Grill-Me, Session Handoff). Plus the 15-skill Cowork pack and the BizDev project instructions.
Open PDF →

The HTML companion piece

Claude at RedPeg — Team Reference (one-pager site)
A standalone HTML page in the RedPeg design system. Sections: the three surfaces (Chat / Cowork / Code), Projects deep-dive, Sharing, Artifacts, When to use what, Decks (the full flow), Skills & Integrations, Quick Decision Guide, Glossary.

Live tools you can poke at

The Ladder That Isn't
Live interactive editorial dashboard about American wealth — built as a Curio Studio sub-project. Six tabs of scaled-area visualizations, sims, and policy framing. Useful as an example of what a single Claude-driven build can produce.
Style Sync (AI moodboard tool)
Category + client + brief = a moodboard in 60 seconds. Replaces hand-pulled Pinterest references for agency creative work. Next.js + Supabase + OpenAI + Unsplash. Vibe-coded with Claude.
Ryan O'Connor — Portfolio
My personal portfolio. AI chatbot per project, project filtering, papers library, interactive labs. Built in Next.js 16. The home for the essays mentioned in Tab 07.

YouTube — handpicked from our "AI Edges" Teams channel

The five videos I've shared in our "AI Edges" Teams channel that I'd actually want you to watch. Listed roughly in the order I'd watch them. Click through; titles are mine.

YOUTUBE
beginner - start here. Claude 101
https://www.youtube.com/watch?v=ER7fnAZkayE
YOUTUBE
Claude Chat vs. Cowork? What are the differences
https://www.youtube.com/watch?v=56pN4nQmnk8
YOUTUBE
what will matter on the web (value wise)
https://www.youtube.com/watch?v=ib2m9HVX7as
YOUTUBE
Claude Design. ooof… its good. And is a tease for the future.
https://www.youtube.com/watch?v=KlPxWaY91rE

The technical setup (for whenever you want to go deeper)

SETUP
Brain MCP — Setup Guide
My personal MCP server. 11 tools (search, read, list, voice profile, idea append, daily log, etc.). Runs locally in Python. The whole config is ~10 lines of JSON.
SETUP
Three pre-packaged Claude Project bundles
Career Brain (9 files) · RedPeg Brain (24 files, shareable) · Ryan Everything (16 files). Each one has its own Instructions block ready to paste into a new Project.

The starter pack — if you do this in order

  1. Read this primer end-to-end. Pick one tab to re-read tomorrow.
  2. Download Claude Cowork on whatever your current daily-driver laptop is. Free with any Claude plan.
  3. Make one Project. Doesn't matter what. Upload three files you actually use. Add one paragraph of custom instructions.
  4. Pick one recurring task. Use the Project for that task, every time, for two weeks (the one-thing challenge from Tab 08).
  5. When that's working, install one Skill. CCO Deck Review or Grill-Me are both good starters.
  6. When that's working, look at MCP. Hook Claude into Outlook or your calendar. The morning briefing pattern starts here.
  7. By month three, you're at Phase 3. Then we talk about building your own Brain.
Open invitation

Any of this — confusing, intriguing, want to try, don't want to try — text me. I built most of this infrastructure for the RedPeg team and would happily walk you through any piece of it on a 30-minute call. Easier to show than to write. The writing is just so you have somewhere to point back to.

— Ryan