AI as a Force Multiplier for Side Hustlers: How to Use ChatGPT as a Thinking Partner (Not a Magic Answer Machine)

If you’re building a side hustle (or trying to get traction in an existing business), the real bottleneck usually isn’t “ideas” or “motivation.” It’s overwhelm: too many moving parts, too little clarity, and zero system for deciding what not to do. In my conversation with Will Denker, the big takeaway was simple: treat AI like a thinking partner that helps you dump the chaos out of your head, sort it into priorities, and turn that into small, consistent actions you’ll actually follow through on.

 (Watch the full Prairie Founders Club AI class by Will Denker here)

What follows is a practical playbook you can run this week, especially if you’re balancing a full-time job and only have a few hours to build.

The real problem: you’re not lazy... you’re overloaded

When I asked Will what he sees most often with leaders and business owners, he didn’t say “they don’t work hard.” He said they feel overwhelmed, they’re doing a million things, and they’re not getting traction on the things that actually move the needle.

That’s the modern curse: the internet hands you unlimited options, so your brain tries to juggle them all. The result is predictable:

• you spin

• you start and stop

• you “research” (which is often procrastination wearing a nice outfit)

• and you end the week feeling behind

Will’s approach is basically an operating system for getting unstuck: use AI to clear the clutter, identify the highest-leverage moves, and build a plan you can execute in real life (with real constraints).

Step 1: Do “the dump” (get the chaos out of your head)

Will calls it “the dump”.... and it’s exactly what it sounds like: you unload the whole messy situation into ChatGPT without trying to organize it first.

This matters because most people wait until they feel “ready” or “clear” before they plan. That’s backwards. Clarity often comes after you externalize the mess.

Use this prompt (copy/paste)

Prompt:
“Here’s my situation. I’m overwhelmed and I need help getting clarity. I have [job/family/constraints]. I’m trying to build [business goal]. My challenges are: [list everything]. My habits/distractions are: [list them]. I feel stuck because [say it plainly]. Ask me the questions you need, then give me the 1–2 highest priority actions for the next 7 days.”

Why it works: you don’t need to “clean it up.” Just talk to AI like you’d talk to a coach.

And here’s the key twist…

Step 2: Ask for brutal honesty (because excuses hate daylight)

Will recommends dumping everything in... including the stuff you don’t want to admit, then asking: be brutally honest with me.

He gave a painfully relatable example: people complain they have no time… but they’re time wasters (hours of TV, distractions, etc.). The point isn’t shame. It’s power. Once the truth is visible, you can act.

Try this follow-up prompt

Prompt:
“Be brutally honest with me. Based on what I shared, what am I doing that’s keeping me stuck? What’s the one change that would create the biggest improvement immediately?”

Will’s framing is basically: let ChatGPT tell you what you’re pretending not to know... so you can stop negotiating with yourself.

Step 3: Turn your life into a “budget” (because math ends arguments)

One of my favorite moments in the conversation: Will compared clarity to doing a budget.

Nobody wants to do a budget… until they see the numbers in front of them. Then the excuses collapse because “math’s math.”

Same thing with time, energy, priorities, and commitments. When it’s vague, you can rationalize anything. When it’s visible, you make better decisions.

A simple “clarity budget” exercise (10 minutes)

Ask ChatGPT to create a quick inventory like:

• Where does my time actually go each week?

• What are my top strengths and weaknesses right now?

• What should I not do?

• What should I do more of?

The important point: focus requires subtraction.

Step 4: Build momentum with embarrassingly small wins

This is where most side hustles die: people set “hero goals” that require motivation they don’t yet have.

Will’s advice: don’t shoot for the moon... make it so easy you can’t talk yourself out of it. He jokes about the classic plan: “I’m going to do 100 pushups a day.” You’re not.

Instead, commit to something almost stupidly small, like one pushup a day, because consistency is the real objective. From there, the win stacks. One becomes three. Three becomes momentum.

He ties it to skill-building too: greatness comes from repeating the boring fundamentals over and over.

My opinion (and what I’d do if I were you)

Small wins aren’t “lowering the bar.” They’re building the identity of someone who follows through. Once that identity is real, you can scale effort.

Use this prompt to design your “minimum habit”

Prompt:
“I need a plan that prioritizes consistency over intensity. Design a daily habit that takes 5–10 minutes and moves me toward [goal]. Make it so easy I can do it on my worst day. Then create a 7-day checklist.”

Step 5: Use AI to prevent MVP overbuild (and validate demand faster)

When we shifted into business-building, we talked about MVPs: minimum viable product, enough for people to buy, use, and create momentum.

The approach is clean:

1. solve a real problem (remove pain or speed something up)

2. market the MVP

3. fulfill

4. improve gradually

And yes, AI can help with market research, identifying who would buy, and what problem you’re solving.

MVP prompt sequence (steal this)

1. Define the problem

   • “Here’s my idea: [idea]. What problem does it solve, and for who?”

2. Define the buyer

   • “Who is the most likely buyer? Describe the avatar in detail and what triggers them to purchase.”

3. Brutal validation

   • “Be brutally honest: is this a real problem worth paying for? What would make it stronger?”

4. Demand reality-check

   • “Would people buy this right now? What proof should I gather in 7 days to confirm demand?”

That last one matters. Because an AI saying “yes” is not the same as the market saying “yes.”

Step 6: Turn marketing from “blank page” into outputs

Once you have a product and a target customer, AI becomes incredibly tactical: ad angles, messaging, examples, variations, hooks.

You can ask for multiple ad concepts aimed at a CEO-type buyer and request multiple examples. You can also do something fun and powerful: ask the AI to think like a specific world-class marketer or business leader (or even “talk to me like Steve Jobs”).

Practical marketing prompts

• “Give me 10 ad hooks for [avatar] who struggles with [problem]. Make them emotionally compelling.”

• “If you were [well-known marketer], what would you put in this Facebook ad?”

• “Write three versions: direct, story-driven, and funny-but-serious.”

Step 7: Pick ONE AI tool and commit for six months

This is underrated: tool-hopping is the new procrastination.

Will’s recommendation: stop chasing every new platform & pick one (he suggests ChatGPT), and stay with it for six months so you actually build the skill.

He uses a driving analogy: don’t obsess over Ferrari vs Lamborghini if you’ve never even driven on a track, just get in a car and learn to drive.

My opinion

Most people don’t need “better AI.” They need better inputs:

• clearer goals

• more honest constraints

• better questions

• a consistent practice

The tool is less important than the reps.

A simple 7-day implementation plan

If you do nothing else, do this:

Day 1 (20 min): The dump + “be brutally honest” prompt
Day 2 (15 min): Strengths/weaknesses + “what should I not do?” inventory
Day 3 (15 min): Choose 1 priority for 7 days (everything else becomes “not now”)
Day 4 (10 min): Define your minimum habit (5–10 minutes)
Day 5 (30 min): MVP clarity: problem → avatar → brutal validation
Day 6 (30 min): Generate 10 hooks + 3 ads + 3 outreach messages
Day 7 (15 min): Review: “What worked? What didn’t? What do I adjust for next week?”

Closing: AI won’t replace your thinking... unless you let it

The best frame from this episode is that AI isn’t just a Q&A machine, it’s a thinking partner that helps you organize the chaos, reduce overwhelm, and act with clarity.

If you’re a side hustler, that’s the whole game:

• get clarity

• pick one priority

• stack small wins

• iterate weekly

And if you want the most unfair advantage? Use “the dump” any time you feel stuck. The moment you stop trying to carry everything in your head is the moment you start moving again.

(Watch the full Prairie Founders Club AI class by Will Denker here)