Solopreneurs

AI mentorship for one-person businesses.

Pocket Square mentors one-person businesses on using AI where it saves real time. You are the whole team. AI can take real work off your week, if it is set up around how you actually work.

We built ours that way, running our own companies. Now we help you do the same.

Book a Starter Session
A weekly desk calendar with a coffee cup and a short list of next steps

Start here

Starter Session, $1,500.

A 90-minute AI audit of your business, plus a written plan within 48 hours. We look at where your week goes and what tools you already pay for. Then we tell you the three things to try first.

The full $1,500 counts toward any bigger project within 60 days.

The written plan covers

  • The top 3 things to try first, each scored on time saved, money saved and effort.
  • Your current tools: what to keep, what to cut, and what to add.
  • What AI should not touch in your business.
  • The next step, with a rough price.

What usually comes next

After the session, there are two common next steps.
  1. 1

    Starter Session

    $1,500. A 90-minute audit and a written plan within 48 hours.
  2. 2

    AI Mentorship

    From $2,000 a month, three-month minimum. Two 60-minute calls a month, async access between calls, small builds, and a one-page recap each month. Month one is learning your business. Month two is trying things. Month three is when habits stick.
  3. 3

    Or Build-alongside

    From $5,000 per project, if you would rather set one big thing up together and run it yourself. See every format and price.

How we work

AI drafts. You hit send.
Nothing goes out without a human yes.
Your tools, not a new platform.
We work on the tools you already have.
A document, not a transcript.
Every engagement ends with something written you can keep.
Paid recommendations are disclosed.
If a tool we recommend pays us, we tell you in one line.

More questions? Read the FAQ, or see who you would be working with.

Systems we use every day

Built for a business where one person makes every call.

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 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.

One session. A plan you keep.

If AI is not worth it for your business yet, the plan will say that too.
Book a Starter Session

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