Carlile Advisors · Session 2

Reggie is alive. Here's how to make him your editor, librarian, and chief of staff.

Day one we got the foundation running: Mac mini, Telegram, Gmail, and a workspace that already started reading your book material. This page is the playbook for everything next, the handful of habits, prompts, and skills that turn Reggie into the most useful person on your team.

Last updated 2026-06-25 · Companion to our build sessions · Tucker Carlile, Carlile Advisors

Jump to the 11 prompts Or see the skills to install

01Habits

The 5 meta-skills

Learn these five habits and you'll outrun almost everyone using AI. They matter more than any single prompt.

1 Make Reggie interview you before he answers The highest-leverage habit: better answers with less back-and-forth.

Before Reggie drafts the client report, sorts a voice dump, or pressure-tests a chapter, tell him to ask you 3 to 5 questions first. Now he knows what "good" actually means to you.

Before you answer, ask me 3-5 specific questions that would help you
produce a better result.

Focus on the missing context, constraints, audience, voice, or
decision criteria that matter most for this task.

Wait for my answers before producing the final output, unless this is
a simple mechanical task.

Save this. Append it to any prompt that matters. It works on every model and in every chat.

2 Codify what you repeat Don't just save prompts. Turn the workflows you repeat into reusable tools.

Garry Tan calls this "Skillify": when a workflow keeps coming back, make it a reusable skill instead of re-explaining it from scratch. The Book Mirror, the Client Report, the Substack-to-social routine, and the Model X search are all better as named skills Reggie can call.

The takeaway is simple: the moment you catch yourself saying "I'll do this again," have Reggie turn it into a skill.

Garry Tan Skillify gstack skills guide

3 Have Reggie write your prompts Describe the job messily, then let Reggie make the reusable version.

Prompt-writing is itself an AI task. This is the move that compounds.

I want to build a reusable prompt for this job:

[describe the goal in plain English, messy is fine]

Write me a system prompt that would make you great at this. Include:
- Role and persona
- The inputs you should expect from me
- The format of the output
- What to flag or ask about instead of guessing
- A "preserve my voice, never invent facts" reminder

Then ask me what's missing before we save it as a skill.

4 Connectors make Reggie useful Gmail, Drive, Calendar, GitHub, Cloudflare, voice, and images turn chat into work.

The chat box is the smallest version of this. Once Reggie has skills installed and connectors wired, he can read your real material, draft into your drafts folder, publish a page, generate a post image, and work across years of your writing. See the skills section for what to install.

5 Let Reggie be your AI consultant Make him interview you and find the next high-ROI workflow.

The fastest way to find your own use cases: don't guess, make him ask. Tell him who you are and what you do, then let him surface where AI can help.

I'm Matt Shatto: founder coach, writer working on a book about
creativity, investor, and facilitator (Stillwell). My work splits into
coaching clients, the book, personal development, Stillwell, and
investments, and I want those kept separate.

Act as my AI consultant. Interview me one question at a time to
understand my real day-to-day, my most repetitive and draining tasks,
and where my time goes.

After 6-8 questions, give me a prioritized list of ways you could help,
ranked by time saved vs. effort to set up, and flag which ones should
become reusable skills or scheduled jobs.

The pattern

Interview-first → save the winners as skills → let Reggie write the next version → wire it to your real material. That loop is the whole game.

02Use cases

11 prompts built for your work

Personalized to the five areas: the book, coaching, personal development, Stillwell, and investments. Click any card to expand the full prompt, then copy it straight into Reggie. The last one is a bonus for when email is fully wired.

01your #1 want: the book

The Book Mirror

Reggie reads your book material back through your own frameworks, transcripts, and life, not as a ghostwriter, as a mirror. The "book that reads me back."

You are Reggie, my book editor and thought partner for my book on
creativity. You are a librarian, sparring partner, and mirror, NOT a
ghostwriter. You never rewrite my creative work into generic AI prose.

Your source of truth is my own material in the workspace: book/outline.md,
my voice dumps, coaching transcripts, and personal frameworks (head vs
heart, the S-curve / competence ladder, the trustworthy artist).

When I give you a passage, a theme, or a question, do this:
1. Reflect it back through MY existing material. Quote the threads,
   transcripts, or notes where I've circled this idea before.
2. Show me where my thinking has evolved or contradicts itself.
3. Name the through-line I keep returning to, in my words, not yours.
4. Point to one underdeveloped idea worth pulling forward.

Preserve my voice exactly. If you draft, draft in my cadence and mark
it clearly as a suggestion. Never invent a quote, a story, or a source.
End by asking which thread I want to pull next.

Variation, a book you just read: "I just finished [book]. Walk me through it chapter by chapter, the spine of its argument, where it's weak, and where it connects to my own frameworks and writing."

Expand prompt▾

02capture thoughts on the move

Voice Dump → Outline Router

Talk for two minutes, drop the transcript, and Reggie files each idea into the right section of your book outline without flattening your voice.

This is a raw voice dump for my book. Your job is to file it, not
rewrite it.

1. Read book/outline.md so you know the current sections.
2. Break my dump into distinct ideas.
3. For each idea, tell me which outline section it belongs in (or
   propose a new section, marked as new).
4. Save each idea under the right section as a lightly cleaned note,
   keeping my words and voice. Fix only obvious filler and false starts.
5. Flag any idea that contradicts or repeats something already in the
   outline.

Output a short summary of what you filed and where. Never polish my
ideas into generic language. When unsure where something goes, ask.

Expand prompt▾

03find the spine of the book

Through-line & Contradiction Finder

Point Reggie at the whole archive and ask what you keep saying, what you contradict, and what's missing. The structural read only a librarian who's read everything can give.

Read across all my book material, voice dumps, and coaching transcripts
in the workspace. I want a structural read, not a summary.

Give me:
- The 3-5 through-lines I return to most, each in a sentence of my own
  language, with the places they show up.
- Contradictions or tensions in my thinking worth resolving on the page.
- Ideas I mention once and never develop, that deserve a chapter.
- Where the argument currently has a gap a reader would feel.

Cite the specific notes or transcripts for every claim. If the evidence
is thin, say so rather than inflating it. End with the single most
valuable thing to work on next.

Expand prompt▾

04the time-saver that pays the bill

Coaching Session → Client Report

Drop a session transcript. Reggie files it under the client, updates their timeline, pulls follow-ups, and drafts a report in your template and voice for you to review.

Here is a transcript from a coaching session. Process it end to end.

1. File it under coaching/[client-name]/transcripts/ with the date.
2. Update coaching/[client-name]/timeline.md with the key moments and
   any shift in where this client is.
3. Pull follow-ups into coaching/[client-name]/follow-ups.md with owner
   and a rough when.
4. Draft a client-facing session report in MY template and voice. Match
   how I open, the structure I use, and how I close.

Rules: draft only, I send. Use only what's in the transcript, never
invent a commitment or a detail. Keep this client's material separate
from every other client and from my personal notes. If my template
isn't saved yet, ask me for one example before drafting.

Expand prompt▾

0515-min prep, not 60

Pre-Session Client Prep Brief

Before any coaching call, Reggie reads the client's history and hands you a one-page brief: where you left off, open follow-ups, and a few sharp questions to open with.

I have a coaching session with [client-name] coming up. Build me a
one-page prep brief from their folder only.

Include:
- Where we left off last time and the throughline of our work.
- Open follow-ups and anything they committed to.
- Patterns or themes worth naming out loud this session.
- 3-5 strong opening questions tailored to where they are.
- One thing I might be missing or avoiding with this client.

Keep it to one page, grounded in their actual history. Mark anything
you're inferring as an inference. Don't pull in other clients' material.

Expand prompt▾

06writing → content, in your voice

Substack Archive → Social Posts

Reggie mines your Substack and talks for the best lines and turns them into posts in your voice for Instagram, Facebook, or LinkedIn. Drafts only.

Using my Substack archive and writing in the workspace, find content
worth resurfacing as social posts.

For the piece or theme I name (or pick 3 strong ones yourself):
- Pull the 3-5 lines or ideas that stand best on their own.
- Draft 3 short posts in MY voice, one each for Instagram, Facebook,
  and LinkedIn. Match my tone, no buzzwords, no AI sheen.
- Suggest a simple visual idea for each (no text-heavy graphics).

Drafts only, nothing posts without my approval. Quote my own words
where they're strong. If a draft drifts from how I actually write,
flag it instead of shipping it.

Expand prompt▾

07private by design

Personal Development Mirror

Your own coaching notes, prayer-partner conversations, and reflections, kept private and separate, with Reggie helping you see your own patterns over time.

This is my private personal-development space. Keep everything here
strictly separate from coaching clients, the book, and investments.
Never surface this material in any client-facing or public output.

When I drop a reflection, prayer-partner note, or session takeaway:
1. File it under personal/ with the date.
2. Reflect back the patterns you see across my recent entries, gently
   and honestly, in my own language.
3. Note where I'm growing and where I keep circling the same thing.
4. When I ask, connect a current reflection to past ones.

You are a mirror and a thinking partner here, not an advisor handing
out steps. Ask before drawing hard conclusions about me.

Expand prompt▾

08facilitation, prepped

Stillwell Facilitation Pack

For your leader groups: Reggie builds a session flow, prompts, and discussion arcs from your frameworks and the group's history.

Help me prepare a Stillwell leader-group session. Use my facilitation
notes and frameworks in the workspace.

Build:
- A session flow with timing, opening to close.
- 5-7 discussion prompts that fit where this group is, drawn from my
  frameworks (e.g. head vs heart, the trustworthy artist, the S-curve).
- One exercise or reflection that fits the theme I give you.
- A short follow-up note I can send the group afterward.

Keep it in my facilitation style. Ask me the theme and who's in the
room before you build, if I haven't told you.

Expand prompt▾

09Phase 2 · security first

Investment One-Pager Analyzer

For later, once the security boundary is set. Drop a deck or a company and Reggie returns a structured read against your own investment framework. Research and analysis only, no account access.

You are my investment analyst. This is later-phase, security-sensitive
work: you analyze and research only, you never touch financial accounts
and nothing here mixes with coaching or personal notes.

For the company or deck I give you, return:
- 1-line summary of what they do.
- Team: founders and the prior experience that actually matters.
- Traction: numbers only, flag anything hand-wavy.
- The ask and use of funds.
- Top 3 risks.
- A read against MY investment framework (I'll share it), scored with
  reasoning.
- 5 diligence questions for the founder.
- A "verify before relying on this" checklist.

Cite sources. Mark anything uncertain as uncertain instead of guessing.

Expand prompt▾

10read deeper, not just more

Idea Deep-Dive Research

You read constantly. When an idea or book is worth chasing, Reggie pulls what people are actually saying about it right now, goes deeper, and connects it back to your own frameworks instead of leaving it as one more thing you read once.

I want to go deeper on an idea, not just read about it.
The idea, book, or concept is: [TOPIC OR BOOK].

STEP 1 - Give me the honest core. Lay out the main argument in
plain language, the strongest version of it, and the best
critiques. No filler, no padding.

STEP 2 - Run a last30days research pass. Pull what people are
actually saying about this right now across Reddit, X, YouTube,
and the web. Separate real insight from noise and tell me where
the live conversation actually is.

STEP 3 - Connect it to me. Where does this overlap, sharpen, or
contradict my own frameworks and past writing? Use my material,
not generic advice.

STEP 4 - Push me. Give me a few angles or questions I probably
haven't considered, and one place this idea might be wrong.

STEP 5 - If this was useful, offer to save it as a reusable
"deep-dive" skill so I can run it on the next book by name.

Expand prompt▾

+drafts only · never sends

Email Triage & Executive Assistant

Once Gmail is fully wired, Reggie finds the threads that genuinely need you, labels them, and drafts replies in your voice for review.

You are running my morning email triage. My address is [YOUR_EMAIL].

Goal: find threads that genuinely need a reply from me, label them, and
draft replies in my voice. DRAFTS ONLY. Never send anything.

STEP 1 - Learn my voice. Read 10-15 of my recent Sent emails. Match my
greetings, tone, length, and sign-offs.

STEP 2 - Find open threads from the last 21 days. Skip automated mail,
receipts, newsletters, and cold pitches.

STEP 3 - Read each thread to the end. Don't draft if the last message
was mine, a draft already exists, or it's just a thanks/FYI.

STEP 4 - Apply an existing label. Never create or remove labels.

STEP 5 - For clear asks only, draft a reply using only facts in the
thread. Never invent dates, numbers, or commitments. Close with a short
line and stop; don't type my signature.

STEP 6 - Summarize each thread you handled and what you did.

Everything is a draft for me to review. Nothing is ever sent.

Expand prompt▾

03Tools

Skills to install on Reggie

Skills are reusable capabilities Reggie can call by name. These are the ones that fit your work. We'll install the top few together.

Install first

Backbone of the book + voice

Memory & search

gbrain — the engine behind the Book Mirror

Hybrid semantic + keyword + graph search across all your unstructured notes. This is what lets Reggie actually read years of transcripts, Substack posts, and voice dumps back to you by meaning, not just file name. If the "book that reads me back" idea excites you, gbrain is the part that makes it real. My strongest pick for you.

GitHub Skillify

Writing

humanizer — protect your voice from AI slop

You said your real fear is losing your writing muscle to generic AI language. This skill runs an anti-AI-writing pass: no em dashes, no promo gloss, no rule-of-three filler. It keeps everything Reggie drafts sounding like you. For a writer, this is non-negotiable.

GitHub

Workflow design

skillify — turn repeated work into reusable tools

Use this whenever Matt says, "I keep doing this." Skillify watches the workflow, writes the skill, and turns the messy one-off into a reusable Reggie capability. This is stronger than a generic "save your prompts" habit because it gives the prompt a home, a name, and a repeatable process.

Garry Tan Skillify gstack skill list

Install soon

Research, content, polish

Research

last30days — Reggie's research engine

One command pulls what people are actually saying in the last 30 days across Reddit, X, YouTube, TikTok, Hacker News, and the open web. This is the context engine behind book research ("how are people writing and selling books on creativity right now"), Substack topics, and reading the room before a talk. We picked it over a dedicated X bot on purpose: it covers X anyway, plus far more sources, with much less to set up.

GitHub

Build & ship

Cloudflare Pages + GitHub — give Reggie a place to publish

Set Reggie up with a free Cloudflare Pages account and a GitHub account. Pages gives any site or small app he builds a live *.pages.dev link; GitHub keeps a version history of every change. With both wired, Reggie can build and ship a real site or tool, not just draft the text for one. This page you're reading is hosted exactly that way.

Cloudflare Pages GitHub

Transcription

summarize / whisper — calls and talks into text

Turn any recording, coaching session, podcast, or talk, into a clean transcript Reggie can file and work from. This is the front door for the coaching-report and book workflows.

Whisper (GitHub)

Output

make-pdf — chapters and reports, publication-quality

Turn a markdown chapter draft or a client report into a clean, well-typeset PDF in one step. Useful the moment you want to share a section with a reader or hand a client something polished.

gstack docs

Images

image generation — visuals for Substack and posts

Give Reggie a working image-generation provider so the Substack-to-social workflow can produce simple post visuals, chapter-header images, and concept art for talks. Drafts only, just like the writing: Reggie proposes the image and Matt approves what gets used.

Gemini image docs

When investments come online

Phase 2, after security

Diligence

company-goat & layered-company-research

Look up a startup across SEC Form D filings, GitHub, Hacker News, and more, then build a verified research brief. Pairs with the Investment One-Pager prompt above for the analysis side of your investing, with zero account access.

gstack docs

Network

contact-goat — warm intros and your network

Map who you know, find warm-intro paths, and prep on someone before you meet them. Quietly useful for both coaching pipeline and investing.

gstack docs

★

If it interests you

A working example you could copy

Showcase · autonomous research

Auto-genealogy style research loop

Reggie can run a scheduled job that works without being asked. Once a week it picks the highest-leverage open questions, runs live web research, writes a dated research pass, updates a private vault plus a published password-protected site, commits the changes, and texts you a summary of what it found. The same loop can point at Matt's own material: book sources, a topic he tracks, family history, or long-running questions he wants filled in over time. This is something we could set up today.

autoresearch-genealogy (GitHub) family-history research skill

How to install a skill

You don't have to know the commands. Just text Reggie: "install the gbrain skill, then tell me how you'd be valuable to me with it and how I'd actually use it." He'll handle setup and explain it in plain English. Make that your habit with every new skill: install it, then ask how it makes him more useful to you. The system teaches you as you use it.

Multiple agents, one brain

You can give Reggie more than one Telegram bot, each with its own job and default behavior. A book-focused front door that assumes you're heads-down on the manuscript. A general Reggie for everything else. From the outside they feel like separate assistants, but underneath they run on one shared Reggie brain and workspace. Same memory, same files, same source of truth. Different front doors, not different systems.

This is also how your five areas stay cleanly separated without splintering into five disconnected assistants. One brain that knows the boundaries beats five that each know a fraction of your work.

A few that fit you: a book front door that stays in manuscript mode, a car-finder bot that quietly hunts listings for your next vehicle and texts you only the matches, and a general Reggie for everything else. Adding one is quick: a new bot, a short note on how it should behave, and it joins the same brain. That is the flexible part. As you think of a new job, you give it its own front door.

04Ideas

Ideas to work through

Not a fixed schedule, just a menu. Pull whatever's most useful first. These build on each other, but there's no wrong order.

Good first moves

Install gbrain, skillify, and humanizer, and point gbrain at your book material.
Stand up the Book Mirror (prompt 1) and run it live against a real chapter or theme.
Build the Coaching Session → Client Report skill (prompt 4) and test it on one real transcript, end to end.
Confirm voice and image generation, then generate one visual idea for a Substack/social post.
Save the winners as named skills so you call them by name, not by re-explaining.

Once it's part of your day

Run the Book Mirror on a few different themes. Notice where it surprises you.
Send Reggie a voice dump with the Outline Router (prompt 2). Build the habit of thinking out loud to him.
Use the interview-me snippet on every non-trivial request for a while.

The deeper build

Run the Through-line Finder (prompt 3) on the full archive to find the spine of the book.
Wire Substack → social (prompt 6) and start a light, drafts-only content rhythm.
A simple nightly check-in: end of day, Reggie surfaces what came in and what's open.
Scope the email assistant (prompt 10) carefully, drafts only, once you trust the rest.

The frame

The goal isn't a pile of automations. It's one assistant who knows your work well enough that the book gets written, your clients get your best, and the busywork stops eating your week. Start with the book and one coaching workflow. Everything else compounds from there.

05Boundaries

The privacy rules, out loud

This only works if you trust it. So the boundaries are simple and they're enforced by design.

Reggie drafts. You decide what goes out. No email, post, report, or file leaves the system without your approval.
Your folders stay separated by design. Coaching clients, the book, personal development, Stillwell, and investments don't bleed into each other.
Your keys and billing stay under your accounts. You own the Mac, the data, and the configuration.
Investments and financial data are later-phase. Analysis and research only, and only after the security boundary is set. No account access.
Anything that feels too sensitive, we pause or remove. No question asked.