Building a high-ticket course idea with ChatGPT

From vague idea → validated offer → launch-ready in one conversation.

Mar 30, 2025

This morning, I decided to consult a conundrum I’ve been having to ChatGPT:

“You’re a coach who’s really good at teasing out my expertise and guiding me into creating a product or service that could generate passive income. What questions would you ask me?”

I got this idea from this conversation between Dan Shipper and David Perell where instead of asking AI for stuff, you can ask the LLM to ask you questions instead to pull answers out of you.

What’s crazy to me is that this really helped me think divergently. I probably do not have the confidence to even think this far. But within the confines of the chat log with ChatGPT, I felt safe enough to explore what “unconventional” paths I can take.

This is a summary log of that chat.

🧠 Phase 1: Clarifying My Expertise

ChatGPT asked me a bunch of questions:

What do people ask you for help with?
What have you solved for yourself that others struggle with?
What systems or skills feel second-nature to you?
What would you give a TED Talk on tomorrow?

Through this, a few themes surfaced loud and clear:

I’ve consistently built things — writing, YouTube, ghostwriting, digital products — while working full-time
I don’t rely on hustle; I rely on energy management and quiet systems
I’m really good at finding “third doors” — unconventional, high-leverage ways to make progress
I believe deeply in creative self-loyalty: you don’t need permission to build something of your own

That was the seed.

💡 Phase 2: The Offer

We played with a few directions — but one phrase stuck:

Cheat on Your Job
A 6-week guided experience to help ambitious creatives unlock unconventional, sustainable side income — without burning out.

It felt spicy and subversive in all the right ways.

Not about quitting your job in a blaze of glory.
Not about becoming a content machine.
Just about quietly building something that feels like you — without asking for permission.

🎁 The Product Itself

Here’s what ChatGPT suggested. I wanted a high-ticket offer that people would pay upwards of $2,000 for, which Nicolas Cole said is easier to get than 100x customers paying $20:

Cheat on Your Job
→ 6-week live cohort
→ Weekly sessions, templates, and optional 1:1 coaching
→ Focused on building a creative side hustle around a full-time job

What it helps with:

Uncovering your high-leverage “thing”
Designing energy-first systems for consistency
Quietly launching and validating a service, project, or product
Navigating the fear, doubt, and logistics of building while employed

🏷️ Pricing for the pilot:

$997 for core program
$1,500 with 1:1 support

✅ Validation Strategy

Instead of building everything up front, I wanted to validate the idea with the market first so ChatGPT suggested this. I even asked it to refer to Noah Kagan’s Million Dollar Weekend book that I admittedly haven’t read but know that it’s spot on for this kind of thing:

A landing page with a waitlist
Personal outreach to folks who’ve asked me about side hustles
Social media posts across LinkedIn, Substack, and Instagram
A 5-part essay series to build narrative and trust

📝 The Essays

Each essay is designed to reflect the real emotional arc of building something on the side:

Cheat on Your Job – The flagship manifesto
Why You Don’t Need Permission to Start – For the rule-followers
How I Built Things While Working Full-Time – Systems, not hustle
What No One Tells You About Building a Side Hustle – Identity, fear, guilt
5 Side Hustles I’d Start If I Were You – Tactical, practical, testable

The idea is to see if these 5 essays go on Substack for 5 weeks in a row, if there would be enough market validation for it.

It’s insane that this whole conversation happened with me just going back-and-forth with an AI this morning. And now I’m going to be reflecting on it for the next few days to see if I want to build it out.

By the way, if this sort of thing (either the “Cheat on Your Job” thing or this AI log) interests you, drop a comment below.