The $100 to $1,000 AI Money-Making Challenge!
Can artificial intelligence turn a mere $100 into a thriving $1,000 business in just 30 days? Follow my journey as I put AI to the ultimate test!
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The 30-Day AI-Powered Business Experiment
For 30 days, I’m taking on a wild challenge: to multiply $100 into $1,000 or more, guided entirely by the strategic genius of artificial intelligence. This isn’t about quick wins or shady tactics – it’s about proving whether AI can lay the foundation for a real, sustainable online business with minimal starting capital and maximum ingenuity.
Each day, I’ll be documenting the process right here and on my YouTube channel. You’ll see the AI strategies I’m implementing, the hurdles I face, and the progress (or lack thereof!) in real-time. Get ready for a rollercoaster of innovation, experimentation, and hopefully, some serious financial growth!
The Official Rules of the Challenge
- Starting Capital: Exactly $100 USD — no additional funds, credit, assets, or bartering allowed.
- Duration: 30 consecutive calendar days, documented daily via video.
- AI Guidance: All strategies must be initiated and guided by AI tools (e.g., ChatGPT, Claude, Perplexity, etc.).
- Human Oversight: Human retains executive control — AI acts as CEO/Coach/Strategist; human may veto, pivot, or question AI, but may not substitute original strategy with human-devised one.
- No Employment: No employment-based income (e.g., Uber, TaskRabbit, Fiverr, Upwork, manual gigs, or paid labor).
- Digital Focus: Must use online, digital, or arbitrage-based income methods only.
- No Existing Audience Leverage: No monetization or traffic from my pre-existing audiences, platforms, or brands.
- Budgeted Tools: All paid tools, services, ads, domains, and subscriptions must be purchased strictly from the $100 budget.
- Total Transparency: Must screen record or screenshot all major AI prompts, responses, strategic decisions, income, and expenses.
- Ethical Conduct: Must comply with platform terms of service, copyright law, and ethical business practices.
- No Hidden Work: All planning, execution, and outcomes must be visible and traceable.
Day 1 of 30
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
Today we asked several AIs what’s the best way to turn $100 to $1000 in 30 days–what’s your best guess on the winning plan?
Day 2 of 30
AI’s TERRIBLE Advice Almost Ended My $1000 Challenge
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
Today we pitted o3 against Gemini Pro 2.5 and had then duke it out until we discovered the sweet spot between low CPA/high conversion for trending keywords on TikTok. Now we have our product idea and ready to create assets!
Day 3 of 30
AI Is Forcing Me to Use Notion and I Almost Quit
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
Notion is my new nightmare. The most unintutive, goofy thing in the universe. But people successfully sell these templates so I gotta learn it and create my first product. How far did I get on the first day, as a complete Notion newbie under AI’s tutelage? You’ll be surprised..
Day 4 of 30
My AI CEO Built a Digital Product in 4 Days (Here’s How)
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
Bro, we created the micro-product for the first part of the funnel. Can’t believe it. Right now, its hard for me to believe anyone will shell out $7 for what is basically a overcomplicated word doc–but apparently people like stuff like this. Tomorrow: WE START MARKETING OMG. I have never run TikTok ads so I expect another steep learning curve.
Day 5 of 30
I Was Ready to Launch, Then My AI CEO Said NO
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
The plan has changed, and we’re back to building. This is a crucial lesson in listening to data over impatience. Subscribe to see how we build the premium product and finally get this business launched.
Day 6 of 30
This Is the Most Important Day of the Challenge (and the most boring)
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
Today: the grind as I try to finish the premium product to complete the line-up.
Day 7 of 30
The AI Kept Failing, So I Had to Teach It
Revenue: $0.00 Expenses: $0.00 Account Balance: $100.00
Today I made a breakthrough in working with AI–you have to train it with the correct data just like a human employee. Garbage in, garbage out. You can’t rely on what its already been trained on, because that data might be outdated and that causes friction and confusion when you try to follow an AI’s instructions.
Day 8 of 30
The Product is FINISHED. Now, We Spend Money
Revenue: $0.00 Expenses: $0.03 Account Balance: $99.97
Bruh–tired is an understatement. The fact that I am building in public holds me accountable. Whereas in the past I might have taken a day off just to catch my breath–this project doesn’t allow for that (except maybe July 4th). Anyway, happy to say the product is DONE–now we enter marketing. Tomorrow we start on the plan and then creating assets for Tiktok. Expenses today were 3 pennies on Replicate for an image using Seedream-3 for the sticker pack which I didnt end up using at all cuz it sucked lol. I also ran one on Flux Kontext Pro which I didnt use but it was free somehow.
Day 9 of 30
The AI’s New Plan to Make $1000 With $0
Revenue: $0.00 Expenses: $0.03 Account Balance: $99.97
Taking most of the day off for family time. Will likely just do one prompt among the big 4 LLMs to see which landing page and delivery mechanism will be best and start setting that up. **Update: they want me to try something new on the marketing front!
Day 10 of 30
My AI CEO Literally Scolded Me for Being Impatient
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
I have never had this happen before–Gemini literally put me in my place and told me in no uncertain terms I was being impatient and my logic was flawed! Dang–that felt good to have an AI stand up for itself and not just bow down to my stupid whims. Read the prompts for the full exchange–its awesome. Spent 38 cents today on Replicate and OpenCreator.io to make images and videos.
Day 11 of 30
The AI’s Plan Was Wrong… And It Made My Product Better
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
All this time, Gemini has been betting on (and hallucinating) some crazy magical one-shot upsell feature in Lemon Squeezy which doesn’t exist. Oops, there goes our original sales funnel. Maybe I should have fact-checked that earlier, lol. We pivoted though and I think this new approach is even better.
Day 12 of 30
No AI, No Strategy, Just Fun
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
Taking the day off to catch some fireworks at a beachside bar. See ya tomorrow!
No prompts today. Happy Independence Day!
Day 13 of 30
My AI CEO’s Weirdest Marketing Idea Yet
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
Finished the 10 vids (well actually i think i made 11-12) that Gemini asked me to create. No idea what I’m doing tomorrow, since Lemon Squeezy hasn’t approved me yet!
Day 14 of 30
I Refused to Follow the AI’s “Inauthentic” Marketing Plan
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
Today was super-annoying. AI wanted me to do some dumb marketing by pretending I was an interested member in online Notion communities to spam my product, and I gave it some alternatives to work on instead, Fortunately it agreed lol. But now I have to learn yet ANOTHER platform before I can launch (Zapier). Man this is getting extremely complicated and I am halway through the challenge with nothing to show for it.
Day 15 of 30
FIST FIGHT AT THE MALL & My AI Project is a Dumpster Fire
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
I went to an upscale mall and some tatooed proto-simians that masquerade as sentient beings decided to cause a ruckus and bloodshed. Many stereotypes were checked off here. Anyway, made lots of progress today despite Gemini suggesting useless delvery mechanisms. It also suggested the right one, so gotta give it credit.
Day 16 of 30
LAUNCH DAY! After 16 Days, We Are Officially LIVE!
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
Finished the landing page and product pages in Easy Digital Downloads and LAUNCHED the first marketing video. No paid ads yet, the plan is to release 11 vids total and pick the winner to run ads against.
Day 17 of 30
The AI Called My Plan a “Panic Boost” & Scolded Me AGAIN
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
Bro I hate waiting, so I wanted to launch 3 organic videos per day. But the AI told me to chill the hell out–again. So what’s the new plan, being as there are only 13 days left to the challenge?
Day 18 of 30
The AI’s Plan FAILED. So I Created an AI Influencer to Save It
Revenue: $0.00 Expenses: $0.41 Account Balance: $99.59
My AI CEO says I’m impatient–but their video plan sucks big time as evidenced by the dismal views on the reels/tiktoks/shorts. So, I made a proposal and Gemini accepted. What do you think of the new plan?
Day 19 of 30
HUGE Win, 3 Strategy Changes, and a TikTok Roadblock
Revenue: $0.00 Expenses: $40.41 Account Balance: $59.59
So we had some great improvement on views thanks to my pivot to the AI influencer yesterday. After a bit of back and forth and several pivots between Gemini, Grok and ChatGPT we settled on the actual plan to run ads! Paid $40, only to be stuck in Under Review on TikTok–which can take 24 hours. This stuff isnt easy : (
Day 20-21 of 30
My AI-advised TikTok Ad Campaign Was a COMPLETE Failure… Then This Happened
Revenue: $0.00 Expenses: $40.41 Account Balance: $59.59
Well well well, if we didn’t just waste like two days waiting for TikTok to approve my account and ads, only for them to finally get approved yet not generate ANY impressions or clicks whatsoever lol. Watch what I did to fix it.
Day 22 of 30
My Ad Campaign Was a DISASTER (Then I Found the Fatal Flaw)
Revenue: $0.00 Expenses: $40.41 Account Balance: $59.59
Okay, time for another conference among the AIs to try to fix our campaign. We ARE getting clicks–just no conversions. So, what do you think the AIs recommended?
Day 23 of 30
IT’S OVER.
Revenue: $0.00 Expenses: $40.41 Account Balance: $59.59
I pulled the plug on the Notion template project. 176 clicks and zero conversions equals a dud which I am not willing to put any more ad money behind. But of course, I hatched another hare-brained scheme along with my AI sidekicks. We keep going til day 30. Mwahahahahahaha!
Day 24 of 30
I QUIT. TikTok is Garbage for Morons.
Revenue: $0.00 Expenses: $42.04 Account Balance: $57.96
TikTok is hot garbage. I hated that platform from day one, just like I hated SnapChat and Vine. Useless. Zero organic reach, content made for idiots. Just the worst. So I uninstalled it and wont be going back until I decide to make vulgar and vile content for sub-humans. Which will hopefully be never. In other news–I continue testing Meta Ads and organic vids on Insta and Youtube.
Day 25 of 30
My Ads Are Getting Clicks, But Still No Sales…
Revenue: $0.00 Expenses: $48.36 Account Balance: $51.64
While I wait for this 3 day ad test to run its course (mandated by Gemini), I educate my self on n8n and actually set up a workflow that scrapes a Reddit subreddit looking for pain points among entrepreneurs and uses AI to figure out potential products to solve them. Interesting…….
Day 26 of 30
ChatGPT vs. Gemini: The AI Debate That Killed My Ad Campaign
Revenue: $0.00 Expenses: $65.33 Account Balance: $34.67
Winding down ads–they just aren’t profitable. ChatGPT puts Gemini in its place. What’s next?
Day 27 of 30
8 Hours of HELL for 1 Line of Code (But I Built an AI Startup Studio)
Revenue: $0.00 Expenses: $66.48 Account Balance: $33.52
Yo building stuff is hard bro.
Day 28 of 30
8 Hours of Studio)
Revenue: $0.00 Expenses: $66.48 Account Balance: $33.52
Today was a day of forensics. What went right? What went wrong? What’s next for me?
Today’s full prompts.
Catch the Notebook LM AI Podcast here: https://youtu.be/UyWId8ibr6M
Day 29-30 WRAP-UP!!
The 30-Day Challenge is OVER. Here’s What I Built Instead.
Revenue: $0.00 Expenses: $66.48 Account Balance: $33.52
Man, what a trip! I’m too tired to type–just watch the vid lol.
No prompts left….I’m all prompted out.
What Should I Ask The AI?
Got a burning question or a strategic idea for the AI? Submit it here! I’ll feature the most compelling audience questions in an upcoming video.