AI Mentorship and Implementation for Owner‑Run Businesses and Teams

We learn how your business works, then help you use AI where it actually helps.

Pick your path
Nicholas Rhodes, founder of Pocket Square

Nicholas Rhodes, founder of Pocket Square

The practitioner's perspective

We didn't learn this in a classroom.

We built it running two companies. OutSnapped is an event photo booth company that has been running since 2008. Pictor is photo booth software for booth operators. Both run on AI systems we built ourselves and use every day.

AI drafts the work. A person reads it and hits send. That rule runs everything we build, for us and for you.

Pocket Square teaches owner-run businesses and teams to do the same, on the tools they already have. More about Nicholas

How it works

We learn the business first. Then we teach, or build alongside you.

  1. 1

    Learn the business

    Where your time goes. What tools you already pay for. What needs a human.

  2. 2

    Recommend

    What to use, what to skip, and what to try first. Sometimes the answer is "you already own the right tool."

  3. 3

    Teach or build

    Mentoring, a workshop, or setting it up together.

  4. 4

    Hand it off

    You own it. We check back in.

Every engagement ends with a document you keep. No 14-week assessment before anything happens.

One hand passing a red thread to another
A line of people walking uphill toward an open door
A small dark AI character holding out a sealed letter

What we run ourselves

AI drafts. You hit send.

The systems behind our own companies, running every day. Nothing goes out without a person saying yes.

A daily newsletter that checks its own sources

Every morning at 4am, a system drafts the Artificially Intimidating AI brief. It traces every story back to its source. It drafts the issue, the art, and a podcast episode.

It never publishes on its own. A person reads it and hits publish. Each mistake it has made now has a check that blocks it.

An inbox that sorts itself and learns

Every hour, AI sorts the inbox. When I move something, it learns from the correction.

It never changes a sorting rule without asking first.

A company handbook AI can read

We rebuilt the company handbook so AI can read it. Along the way, it found the places where the company contradicted itself.

Start where you are

Pick the path that sounds like you.

I take on two or three new clients a month, so I can actually do the work myself.

Pick your path

Not sure? Send a note and we'll point you to the right one.

Read along

Artificially Intimidating, our AI newsletter

Drafted every morning by the system above. A person approves every issue before it goes out.

Read the newsletter →