AI Side Hustle

AI SIDE HUSTLE · PRIVATE WORKING SESSION

One useful offer.
One practical next step.

Bring a skill, an idea or a draft. Work with Ashley Kays to shape a small offer and a repeatable AI workflow, then plan how to test it with real customers.

$350 USD · 90 minutes · One-to-one

Request a session time →Find your fit for free

Continues to AI Teachers, our shared session booking page. In the goal field, mention “Side Hustle Working Session” and the offer you want to explore. No payment or reservation is created by a request.

What we work toward

  • A focused offer draft: one customer, their problem, a small deliverable and proposed scope.
  • One editable AI workflow: inputs, prompts, review steps and a quality checklist.
  • A 14-day test plan: a sample to share, conversations to seek and a decision rule.

We agree on one achievable main task before booking. Start with an existing skill or draft so the session can focus on useful work. A full website, production automation, ongoing outreach and customer acquisition are separate projects.

ILLUSTRATIVE EXAMPLE · NOT A CLIENT RESULT

From “I could help with content” to a testable offer

Buyer
An independent consultant who already records useful videos.
First offer
Three edited LinkedIn posts from one approved video, with one revision round.
AI workflow
Review the transcript → draft posts from supported points → check accuracy and voice → get approval.
14-day experiment
Create one permissioned sample, discuss the offer with five relevant buyers, and invite a scoped paid pilot. Record objections and delivery time; revise the offer if there is no meaningful interest.

Pricing and demand remain hypotheses until tested. The session does not guarantee sales or income.

How booking works

  1. Request: share your goal, time zone and two preferred times on AI Teachers.
  2. Agree: Ashley confirms fit, the main task, availability and cancellation/rescheduling terms.
  3. Pay: use the shared Waymaker checkout after agreement. Your appointment is confirmed after payment verification and meeting details.

You keep the reviewed draft, workflow and checklist, with one follow-up question within seven days. Software subscriptions and usage charges are separate and discussed before booking.

Experienced help, beside you

Ashley brings experience across product, design, marketing and teaching, including CodeTeachers, Thinkful and Flatiron School. The session combines practical work with explanations you can use again.

Explore Ashley’s work →

Three focused ways to start

Choose a small deliverable you can review well. These are starting hypotheses; customer conversations establish demand.

Before you book

What if I have no idea yet?

Take the free assessment first. Bring one or two possibilities to discuss; agree with Ashley whether selection or offer development is the best use of the session.

Do I need a paid AI subscription?

Start with your current approved tools. Agree on any tool requirements before booking; software costs are separate.

Is this the free Two Mondays workshop?

No. This is private, paid support on your own task. The founding group workshop is independently free and requires a separate request. See current workshop details.

Will you find customers for me?

We help you define and prepare a test. You conduct the customer conversations and decide what to do with the evidence. No earnings or sales outcome is promised.

Bring the idea you want to move forward.

$350 USD · 90 minutes with Ashley · One agreed task

Request a session time →

Need help choosing? Book a free 15-minute fit call.