AI playbook

The AI Side Hustle Starter Playbook

A step-by-step system to go from idea to your first paying customer, using ChatGPT, Claude, Gemini, Grok or DeepSeek as your planning partner.

The AI Side Hustle Starter Playbook is a $24 PDF playbook with 80 prompts across 10 chapters that helps you choose, test and launch a small side business with AI, from idea to first customer. It makes no income promises.

Cover illustration: a person working on a laptop at a desk late at night, with a lamp and a city window

$24 one-time, instant download

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80 prompts in 10 chapters
10 fill-in worksheets
Catalogue of 21 side hustle ideas
PDF to read or print, plus a CSV for Notion, Google Sheets or Excel
Works with ChatGPT, Claude, Gemini, Grok and DeepSeek

No income claims. Results depend on your idea, your effort and your market.

Why do most side hustles never get started?

Most side hustle advice is either vague (“find your passion”) or a pitch for someone’s course. Meanwhile you have a few free evenings, a small budget and no idea which idea is worth testing.

So the notes app fills up with ideas and nothing launches.

What does the AI Side Hustle Starter Playbook do?

It uses AI as a practical planning partner, step by step: pick an idea that fits your skills, time and budget, check that people will pay before you spend money, set your offer and prices, put up a simple one-page presence, find your first customers, and set up basic bookkeeping and tax savings so you know whether you are actually making a profit. It also includes a catalogue of 21 side hustle ideas with what AI helps with, rough startup cost and skills needed.

No income claims here. Most side hustles earn little at first, and results depend on your idea, your effort and your market. The point of the playbook is to test cheaply so you find out fast.

What is inside the AI Side Hustle Starter Playbook?

80 prompts across 10 chapters. Every prompt includes when to use it, the prompt, a follow-up and a tip. You also get a 15-minute quick start, a catalogue of 21 side hustle ideas and a CSV of every prompt for Notion, Google Sheets or Excel.

Chapter 01Pick the Right Hustle for You WorksheetChoose one side hustle that fits your skills, available time, starting budget and real interests, using a simple scoring matrix instead of gut feel.8 prompts
Chapter 02Validate Before You Build WorksheetProve that real people will pay for your idea, at a price that works, before you spend money on a logo, website or supplies.8 prompts
Chapter 03Your Offer and Pricing WorksheetPackage your service into clear options and set prices that cover your time, costs and taxes while staying in line with your market.8 prompts
Chapter 04Name, Brand and a Simple One-Page Presence WorksheetChoose a clear, available name and put up one simple, trustworthy page where customers can see what you offer and contact you.8 prompts
Chapter 05Find Your First 10 Customers WorksheetLand your first paying customers through personal outreach, local and online channels, marketplaces and referrals, using honest, specific messages.8 prompts
Chapter 06Content That Brings Buyers WorksheetCreate a realistic 30-day posting plan that builds trust and brings inquiries, without spending hours a day on social media.8 prompts
Chapter 07Deliver Great Work and Get Reviews WorksheetGive every customer a smooth, professional experience from booking to follow-up, and turn happy customers into honest reviews and referrals.8 prompts
Chapter 08Money, Taxes and Simple Bookkeeping WorksheetSet up a simple money system so you know whether you are actually making a profit, have money set aside for taxes, and have clean records if a tax professional or the IRS ever…8 prompts
Chapter 09Systems and Time Management for a Side Hustle WorksheetRun your side hustle in about 10 focused hours a week with a fixed schedule, reusable templates and a few simple automations, without burning out or shortchanging your day job…8 prompts
Chapter 10Grow, Pivot or Quit WorksheetUse real numbers from your first months to decide, on a set schedule, whether to raise prices, add offers, change direction or stop.8 prompts

Try 3 prompts free

These are real prompts from the AI Side Hustle Starter Playbook, shown in full. Copy one, replace the [BRACKETS] with your own details and paste it into any AI assistant.

Pick the Right Hustle for You · SH-01

Generate 10 ideas that fit your real life

Use it when: You have no idea yet, or too many vague ones.

The prompt

Role: You are a practical small-business coach who helps everyday people start side income without hype.
Goal: Suggest 10 side hustle ideas that fit me.
Context: My skills and experience: [SKILLS_AND_EXPERIENCE]. Things people already ask me for help with: [THINGS_PEOPLE_ASK_ME]. Hours per week available: [HOURS_PER_WEEK], mostly on [DAYS_AND_TIMES]. Startup budget: [STARTUP_BUDGET]. I live in [CITY_OR_REGION] and I [CAN_OR_CANNOT] work in person.
Constraints: No MLMs, no pay-to-join programs, no ideas that need a professional license I do not have, nothing that relies on posting AI content as my own expertise. Be realistic about startup costs.
Output format: A numbered list. For each idea: name, who pays for it, what I would actually do each week, rough startup cost, and one sentence on why it fits me.

Follow-up: Now remove any idea that would take more than [MAX_WEEKS_TO_FIRST_SALE] weeks to earn a first dollar, and replace it with a faster option.

Tip: List more "people ask me about" items than feels necessary. Those are proven demand signals from people who already trust you.

Find Your First 10 Customers · SH-33

Write your warm-list announcement

Use it when: You are ready to tell people you know about your new side hustle.

The prompt

Role: You are a friendly communication coach who helps people share news without sounding salesy.
Goal: Write a short message announcing my side hustle to people I know.
Context: Service: [SERVICE]. Who I help: [IDEAL_CUSTOMER]. Main offer and price: [MAIN_OFFER]. Area or online: [AREA]. Channel: [TEXT_EMAIL_OR_DIRECT_MESSAGE]. Relationship to recipients: [RELATIONSHIP].
Constraints: Under 70 words. Casual and warm. Ask for referrals, not a purchase. Include one specific detail about the offer. No pressure, no exclamation-point overload, no hype.
Output format: Three versions (close friends, acquaintances, former coworkers), each with a blank at the start for a personal line.

Follow-up: Write a gentle follow-up for people who did not reply after a week.

Tip: The personal first line matters most. Mention something real: their kid's team, their new job, the last time you talked.

Grow, Pivot or Quit · SH-73

Run your checkpoint review

Use it when: You have reached a 90-day or 6-month checkpoint.

The prompt

Role: You are an experienced small business advisor who gives direct, numbers-based guidance without hype.
Goal: Help me decide whether to grow, adjust, pivot or quit my side hustle.
Context: Months running: [MONTHS]. Customers total and repeat: [CUSTOMER_NUMBERS]. Revenue, expenses and profit: [MONEY_NUMBERS]. Real hourly rate: [REAL_HOURLY_RATE]. Target hourly rate: [TARGET_RATE]. Average hours per week: [HOURS_PER_WEEK]. Customer sources: [CUSTOMER_SOURCES]. Enjoyment score 1 to 10: [ENJOYMENT]. Life constraints: [CONSTRAINTS].
Constraints: Base the analysis on my numbers. Say clearly what the data does not show. Consider my wellbeing and day job, not just money. No income predictions.
Output format: A short summary of where I stand, a recommendation (grow, adjust, pivot or quit) with reasons, and the 3 most important actions for the next 90 days.

Follow-up: Argue the opposite of your recommendation as strongly as you can, so I can see both sides.

Tip: Bring real numbers. A checkpoint run on guesses is just another mood-based decision.

Who is the AI Side Hustle Starter Playbook for?

It is a good fit if

You want extra income on the side but do not know which idea to start with.
You have limited time and money and want to test before you invest.
You have a skill or hobby and wonder whether people would pay for it.

It is not for you if

Anyone looking for passive income or get-rich-quick schemes.
Established businesses that need a full marketing plan.
People who are not willing to talk to potential customers. No prompt can do that part for you.

Get the AI Side Hustle Starter Playbook

Pick an idea that fits your life, test it cheaply and find your first customer with AI.

$24 one-time, instant download

Secure checkout by Stripe · PDF + CSV · All sales final

Questions about the AI Side Hustle Starter Playbook

Do I need to be good with technology or AI to use this?

No. If you can copy and paste text into a chat window, you can use every prompt in this playbook. Each prompt shows exactly what to fill in, and the free versions of ChatGPT, Claude, Gemini, Grok and DeepSeek are enough for all of it.

Will this tell me how much money I will make?

No, and be wary of anything that does. The playbook shows you how to price your work, estimate your real hourly rate after costs and taxes, and decide whether a hustle is worth continuing. Results vary widely based on your skills, time, market and effort.

How much time and money do I need to get started?

The system is built around 5 to 10 hours a week. Many of the 21 ideas in the catalogue cost under $100 to start; others, like handyman work or meal prep, can need several hundred dollars for tools, insurance or permits. Chapter 1 helps you pick an idea that fits the time and money you actually have.

Is this just a list of prompts?

No. It is a 10-chapter system that takes you from choosing an idea to validating demand, pricing, finding your first customers, delivering the work, handling basic bookkeeping and deciding when to grow. Each chapter has teaching, numbered steps, 8 ready-to-use prompts and a worksheet, plus a worked example that follows one person from idea to first client.

Does it cover taxes and legal basics?

It covers the basics that keep beginners out of trouble: checking local license rules, separating your money, tracking income and expenses, setting money aside for taxes, and knowing when quarterly estimated taxes may apply in the US. It is not tax or legal advice, and it tells you when to bring in a professional.

Does it work with ChatGPT, Claude, Gemini, Grok and DeepSeek?

Yes. The prompts are plain text, so they work in ChatGPT, Claude, Gemini, Grok and DeepSeek and any other chat assistant. Copy a prompt, fill in the [BRACKETS] with your details and paste it in. Free versions work; paid versions tend to give stronger answers on longer tasks.

What format is it, and what files do I get?

You get 1 PDF to read on any device or print and 1 CSV file of every prompt that imports into Notion, Google Sheets or Excel.

How do I get my files after paying?

Checkout is handled by Stripe. As soon as payment goes through you land on your download page, and we email you a link to it. Bookmark it: you can come back any time for fresh download links.

Is this a subscription?

No. It is a one-time payment with lifetime access to your download page. There is nothing to cancel.

Can I get a refund?

No. These are digital files you can download the moment you pay, so all sales are final. That is why every page shows the full table of contents and free sample prompts: you can see exactly what you are getting first. If a file will not open or download, email gary@dgresolutions.com and we will fix it.

Instant download, all sales final. Preview the contents and free sample prompts before you buy. Download trouble? Email gary@dgresolutions.com and we will fix it.

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The The Complete Everyday AI Vault includes the AI Side Hustle Starter Playbook, the other three playbooks and a bonus prompt cheat sheet for $47 instead of $72. You save $25.

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