AI SHERPA · THREDUP AI MAKER WEEK · JUNE 29 2026
WWW.AISHERPA.ME
1, 2, 3
Claude
The three levels of Claude and what to ask of each one.
HOW WE WORK
We put AI to work for people. Not the other way around.
500+
hours of hands-on
AI coaching
We start with you, not the technology. The whole point is to make AI serve the way you already think and work: hands-on, practical, and genuinely fun. You walk out with AI working for you, not one more tool to manage.
Santiago Restrepo
AI SHERPA · YOUR GUIDE FOR THE DAY
The room today
This is who's in the room.
From your own registration answers. Almost everyone here already uses AI every day, so we are not starting from zero. We are going further.
Curious, barely tried it
0%
Build projects, use Co-Work
22%
Build & automate with Code
0%
Live from registrations as of this morning.
The shape of the day
Two halves. First you master the basics, then we build together.
Morning
Master the basics
01Understanding the Claude ecosystem: the models, and the three ways to work (Chat, Cowork, Code)
02Talking to Claude well, and building your master prompt: prompts, brain dumps, Wispr Flow
03Build your first assistant with Projects
04Turn your assistant into a Skill, and build skills from scratch
05A look at what's next: plugins, scheduled tasks, and other advanced features
06Other models worth knowing: Gemini for deep research, ChatGPT for image generation
Afternoon
Build together
›Building in public: bring a real problem you are working on
›We work through it live, screens shared, as a group
›Open Q&A: anything you want to put on the table
›Watching each other build is how the whole room levels up
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Module 01 of 06
Understanding the Claude ecosystem
Haiku
Fast and lightweight, for quick high-volume tasks.
Sonnet
The balanced default for most everyday work.
Opus
The most capable, for the hardest reasoning.
Fable
The newest and most experimental, rarely seen.
To let people actually use these models, Anthropic built three environments to work with them.
The Framework
There are four ways to work with Claude.
Most people don't know the difference.
1 Claude Chat / WEB
2 Claude Cowork / DESKTOP
3 Claude Code / TERMINAL
4 Claude API
4 · API
Claude API
You wire Claude straight into your own software.
An API is how two pieces of software talk to each other, with no person typing in between. Instead of you chatting with Claude, your own tools call Claude directly: to read, write, sort, or generate, at scale and on their own. It is how Claude gets built into a product or a workflow that just runs. We will not go deep today, just know it exists.
Built for: developers and automations
1 · Web
Claude Chat
You rent a cubicle in their building.
You rent a workspace inside Anthropic's offices. Your password is the key to your account, and your files live on their servers, not yours. Space is limited, but you can reach it from anywhere, even your phone.
Instruction layer: Master Prompt
2 · Desktop
Claude Cowork
You bring the mind into your own house.
Instead of going to their offices, you bring Claude home. It works directly in the folders on your computer: no uploads, no size limits. Folder instructions give it a memory that loads every session. Powerful, with guardrails still on.
Instruction layer: Folder instructions
3 · Terminal
Claude Code
You hand over the keys to the whole house.
Full access to your machine. It can build, run, and ship, not just talk. The most powerful and the most technical of the three. Memory, skills, and automations all live here.
Instruction layer: CLAUDE.md, skills, hooks
Across Chat, Cowork & Code
What lives where.
● Available
◐ Partial
○ Not available
| Capability | Chat | Cowork | Code |
|---|
| Standing instructionsa note Claude reads every time | ● | ● | ● |
|---|
| Projects & project filesa saved workspace of context and files | ● | ● | ◐ |
|---|
| Memory across sessionsit remembers between conversations | ● | ◐ | ● |
|---|
| Skillsteaches Claude a task, your way | ● | ● | ● |
|---|
| Pluginsa bundle of skills, connectors and commands | ● | ● | ● |
|---|
| Connectors (MCP)a live link to your other apps | ● | ● | ● |
|---|
| Subagents & agent teamsClaude spins up helper Claudes | ○ | ◐ | ● |
|---|
| Hooksauto-rules that fire at set moments | ○ | ○ | ● |
|---|
| Scheduled tasks (local)recurring jobs on your machine | ○ | ● | ● |
|---|
| Cloud Routinesrecurring jobs that run in the cloud | ○ | ○ | ● |
|---|
| Remote / background agentsstart it, walk away, it finishes | ○ | ○ | ● |
|---|
| Artifactsa live panel for docs and dashboards | ● | ◐ | ◐ |
|---|
| Direct local file accessworks right in your computer's files | ○ | ● | ● |
|---|
| Code execution sandboxactually runs code to test things | ○ | ● | ● |
|---|
| Computer useclicks, types and navigates a screen | ○ | ◐ | ● |
|---|
THE ONE FILE TO REMEMBER
CLAUDE.md: the note Claude reads every time.
Think of CLAUDE.md as a sticky note left inside a folder. Every time Claude opens that folder, it reads the note first: who you are, how you work, what matters. Each surface has its own version of that note.
Chatthe Project instructions
Coworkthe Folder instructions
Codethe CLAUDE.md file itself
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Module 02 of 06
Talking to Claude well, and your master prompt
Demo 1 · Claude Chat
Start at the front door: Claude.ai.
What it is
Claude.ai, in your browser or on your phone. The most accessible way in, and where most people meet Claude.
Where we will take it
Past quick answers. We give Claude a Master Prompt, then build a specialist that does real work.
Like renting a cubicle in Anthropic's building.
Demo 1 · The Master Prompt
Tell Claude who you are. Once.
Most people treat Claude like Google: short questions, generic answers. The unlock is context. Answer eleven questions out loud, and Claude writes your Master Prompt.
The 11 questions
Built once, by voice
1Your name and what you do
2Years in your field, and where you have worked
3The two or three projects that define you
4What you are working on right now
5The biggest problem you are solving today
6Your strongest belief about your work
7The tone you want from Claude, and the one you do not
8The role Claude should play: assistant, partner, or coach
9The habits that work against you, and what to flag
10Who you work with and for
11The language you work in
01Answer 11 questions out loud
02Wispr Flow turns your voice into text
03Ask Claude to write your Master Prompt
04Paste it into your profile
A living document. Refresh it after any big change, or at least every six months.
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Module 03 of 06
Build your first assistant with Projects
Demo 1 · Build a specialist
Build a specialist, then put it to work.
Now that Claude knows you, give it one job. The same idea, getting more specific each step.
Knows you
Master Prompt
General context about who you are and how you work.
general
One job
System Prompt
A specialist built for one task, dropped into a Project.
specific
Delivers
Real task
Finished deliverables, ready to use.
result
Demo 1 · The System Prompt
Give it real expertise.
You don't have to be the expert. Claude researches the field first, then writes the brief that makes it one.
A System Prompt is the brief for one job: the frameworks it follows, the method it uses, and what a good result looks like.
Frameworks
Method
Guardrails
Output format
Voice
Built with Deep Research
01Define the one job
02Deep Research the ideal expert
03Claude writes the System Prompt
04Drop it in a Project, then run the task
Claude does the research, so you don't have to be the domain expert.
Demo 1 · Two kinds of instruction
Master Prompt vs System Prompt.
Everywhere
Master Prompt
About you.
Lives in your profile. Applies to every chat you start.
One project
System Prompt
About one job.
It is the project's instructions. Applies inside that Project only.
Your turn
Okay, now you build it.
Build your own assistant from scratch. You have about 20 minutes, and you can ask questions any time as you go.
01Define the job that needs to be done
02If it needs it, do the deep research first
03Ask Claude to write the system prompt
04Drop it into a Project
05Add any resources it needs
06Test your assistant and iterate
About 20 minutes · ask questions any time
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Module 04 of 06
Turn your assistant into a Skill
Module 04
What is a skill?
A skill is just a folder you can zip up and share (its packaged file ends in .skill). Plain files tell Claude how to do one job well, and it only opens them when it needs them.
The shape
your-skill/
SKILL.mdthe instructions (its system prompt)
scripts/optional code it can run
references/material to consult
templates/reusable templates and assets
An example
dashboard-builder.skill/
SKILL.mdThe recipe Claude follows: ask which numbers matter, read the data file, apply our colors, then build and lay out the charts. Its description, "build me a dashboard," is what makes Claude reach for it.
scripts/build_dashboard.py turns a spreadsheet into finished charts, so Claude runs the code instead of rebuilding the logic each time.
references/brand-guidelines.md holds our palette, fonts and chart styles, so every dashboard comes out on-brand.
templates/past-dashboards/ are two or three we shipped before, for Claude to match the layout.
Same four parts as any skill, filled with real contents. Then you invoke it anywhere: any chat, Cowork, or Code, by slash command or just by asking.
Project vs Skill
Same ingredients. One stays put, one travels.
In a Project
As a Skill
Instructions
Your system prompt
=
SKILL.md
Reference material
Files you add
=
references/
Templates & examples
Files you add
=
templates/
Code it can run
not its job
+
scripts/
Static. A project lives in one place. You bring your work to it.
Portable. A skill goes anywhere. Invoke it by slash command or just by asking.
Built an assistant you rely on? Because the anatomy is almost identical, you can lift it into a skill, use it everywhere, and share it with your team.
Module 04
When and why to make a skill.
Make a skill when a task is repeatable. Build it once and it works for you every time, and you can share it with the whole team so everyone runs your best process.
Two ways to build one
1 Plan it first
01Scope the job and what the output should be
02Write the steps into SKILL.md
03Add what it needs: a template, references, a script
04Test on a real task, then refine
Example: a "weekly report" skill you design up front.
2 Do it, then compound it
01Just do the task with Claude, normally
02Refine until the output is exactly right
03Say: "turn everything we just did into a skill"
04Claude writes the SKILL.md from your process, then save
Example: you nailed one great deck, now make it repeatable.
Your turn
Now make a skill.
Turn the assistant you just built into a skill, or create a brand-new one. About 10 minutes, and ask questions any time.
Easiest path: do the task with Claude, get the output right, then say "turn this into a skill."
About 10 minutes · ask questions any time
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Module 05 of 06
A look at what's next
Demo 2 · Claude Cowork
Now bring Claude to your files.
The wall in Chat
Claude.ai is capped on file size and cannot reach your computer. You upload one file at a time.
What Cowork changes
Claude works directly inside a folder on your machine: every file at once, no uploads, no size limits.
Demo 2 · What we start with
A folder full of spreadsheets.
Demo 2 · The prompt
Anatomy of a good prompt.
The dashboard is only as good as the brief. Here is what we gave Claude, and why each piece matters.
"Hey Claude, I need your help with something."
Context · who it is for
A folder, Harbor & Pine, for a client: an Amazon FBA seller buried in disconnected Excel files.
The problem · why it matters
He has no single place to see the state of his business or make decisions. It is cumbersome and easy to lose track.
The ask · what to do
Research the best dashboard designs and practices, read all of the data, and propose a highly visual, interactive dashboard he can act on.
The bar · what good looks like
A self-contained HTML file, easy to share and understand, following strong UX/UI and front-end practices.
Room to think · trust its judgment
Use HTML, CSS, React, or whatever fits. Think about what would truly be impactful for his business, and why.
Demo 2 · The result
Messy files become a live dashboard.
Click to open the live dashboard
Demo 3 · Claude Code
Now hand Claude the keys.
The edge of Cowork
Cowork builds inside your folder. Putting things live, wiring up tools, and running big multi-part jobs is still on you.
What Code unlocks
Claude gets your whole machine and the internet: sub-agents for bigger builds, and live websites it can deploy and maintain, once set up, with very few manual steps.
You still don't write code. You describe the outcome.
Demo 3 · The prompt
Anatomy of a bigger prompt.
Same idea, bigger reach. This brief asks Claude to research, design, check its own work, and put the site live.
"Okay Claude, on my desktop there's a folder called Harbor & Pine Goods."
Context · where the data lives
A folder on my desktop with the data from an Amazon FBA seller.
The goal · what to build and why
A commercial website that gives them a web presence: tell their story, show their products beautifully, and link back to their Amazon listings.
The ask · the build steps
Find which products they sell, spin up a sub-agent to search the web for high-quality photos, then use your front-end design skill and study great comparable sites.
Quality loops · make it check itself
Before showing me: critique your own design, spin up a graphic-design agent to review it against the design skill and propose fixes, then navigate the site with Playwright to confirm it holds up.
Ship it · deploy live
Host it live on Vercel using my Cloudflare account. You build and deploy; guide me through the one manual step, pointing the CNAME.
Demo 3 · The result
The same data becomes a live website.
Click to open the live website
Beyond the basics
Other advanced features.
Plugins, skill chaining, and routines: how you go from one assistant to a whole system that runs itself.
Advanced features
What is a plugin?
If a skill is one capability, a plugin is the box you pack many of them into, plus the hooks, connectors and commands they need, as one installable, shareable unit.
report-pack · one plugin
Skill: build report
Skill: make charts
Skill: brand check
Hook
Connector: Drive
Command: /report
Plugin-only perks
One install for the whole set
Ship a fix once, everyone's copy updates
Keeps the whole team on one version
Skill or plugin? Make a skill for one job. Make a plugin when you want to ship a whole toolkit to others and keep everyone on the same version, updates included.
Advanced features
Skills can call other skills.
A skill's instructions can tell Claude to run another skill, so one job hands off to the next. You build small pieces and chain them into big ones.
Report skillwrites the draft
→
Chart skillbuilds the visuals
→
Brand skillapplies the styling
We do this in our own system: the call-triage skill hands off to the summary skill automatically. Claude does the calling by following the instructions, there is no hidden skill-to-skill wiring.
Advanced features · Claude Code
Routines: your AI on autopilot.
A routine is a task you save once and let run by itself in the cloud, on a schedule, even with your laptop closed. Like a cron job, but it's a whole AI teammate: it reads your sources, decides what matters, and does the next step. (A Claude Code feature.)
Good for
A morning briefing of what changed overnight
A weekly report, written in plain language
Inbox or backlog triage, summarized to Slack
A docs scan that flags what has gone stale
Skip it for
One-off tasks: just do them now
Anything that needs your sign-off mid-way
Faster than once an hour
High-stakes, real-time decisions
Most run on a schedule. They can also fire from an API call or a GitHub event for connected workflows. A "done" status means it ran, not that it nailed it: spot-check.
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Module 06 of 06
Other models worth knowing
Other models worth knowing
Claude's home base. Call a specialist when it helps.
Gemini
Google
For what's current
Grounded in Google Search + YouTube
Deep Research pulls 50 to 100+ sources
Best when the answer changes weekly
Grok
xAI
For the social pulse
Reads live posts on X directly
Best for breaking news + sentiment
Weaker on academic or technical depth
ChatGPT
OpenAI
For images
gpt-image-2: legible text in images
Strong character consistency
Neck-and-neck with Nano Banana Pro
Claude stays home base for analysis, synthesis, and building. These are specialists you reach for on purpose.
A research move
Two researchers beat one.
Run the same deep research on Claude and Gemini, then let Claude fuse the two.
Your question
↓
Claude writes the deep-research prompt
run the same prompt on both
Claude runs it
Gemini runs it
↓
Claude fuses both
↓
Shared truth
trust it most
Complementary
what only one found
Contradictory
dig in here
Another tool worth knowing
NotebookLM: it only knows what you give it.
Upload your own sources and it answers only from them, citing the exact passage, so it won't invent anything beyond your material. Great for studying a dense pile of documents or pressure-testing a dataset. Free with a Google account.
›Grounded answers with inline citations
›Audio Overview: turns your docs into a podcast
›Auto summaries, study guides, FAQs, timelines
›Works on web and mobile
Careful with proprietary data. On the free tier your feedback can be human-reviewed. Use a Workspace or enterprise account for anything confidential.
Working with data
Trust, then verify.
Models sound most confident exactly when they're wrong. A few habits keep you safe:
›Cross-reference: run the same task on another model and compare.
›Spot-check the data: hand-verify a random sample; on a generated spreadsheet, trace 5 to 10 cells back to the source.
›Ask for sources: "where did you get this?" and make it cite the passage.
›Make it check its own work: have it list each claim, verify them one by one, and flag anything it is unsure of.
›Run it a few times: keep the answer that recurs, since hallucinations rarely repeat.
›Keep a human in the loop on anything high-stakes.
A tip to take with you
Talk to it. Don't type.
Why dictate
About 3 times faster than typing
You give a fuller, richer prompt instead of rationing keystrokes
Wispr Flow: press a key, speak, and clean text lands in any app with the filler stripped out
Why it works
These models are built from language: they learned by predicting the next word across enormous amounts of text
So the closer your input is to natural, complete sentences, the more it looks like their training, and the better they respond
Typed: "competitor analysis Q3 slides." Spoken: "Look at our top three competitors, pull what changed in their positioning this quarter, then draft three slides I can present." Same effort, far more for Claude to work with.
A tip to take with you
Treat it like a smart colleague.
The newer models reward collaboration over commands. Don't bark a task, work with it like a sharp coworker:
›Co-define before you delegate: open with your standards as questions and the relevant files, ask it to shape the task with you, then say "go."
›Stay in the messy middle: collaborate while the task is still fuzzy; a strong model holds the thread when you flip from exploring to executing.
›Brief by meaning, not file names: describe what a thing is and roughly when you made it, and let it find and assemble the context.
›Co-write your prompts: develop a series of prompts together, then have it run them in order.
›Delegate real, long work: with clean context it takes on big documents and multi-step jobs, not just one-liners.
›Re-test every few weeks: what's possible keeps shifting as models update, so don't lock in a workflow.
Adapted from Nate B Jones's AI workflow.
Recap
One Claude. Three ways to work.
1Chat
Rent a cubicle
Claude.ai in your browser or on your phone. Best for everyday thinking: writing, analysis, research, and building a specialist inside a Project.
You give it a Master Prompt
2Cowork
Bring it to your folder
Works directly inside a folder on your computer. Best for turning a pile of files into something useful, like a live dashboard.
You give it Folder instructions
3Code
Keys to the machine
Your whole machine and the internet. Best for big builds Claude can research, refine through its own loops, and ship live.
You give it a CLAUDE.md
Thank you.
Now let's put it to work.
aisherpa.me · cal.com/santiago-restrepo
