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I gave ChatGPT 100 dollars to make me rich. Here’s what I learned. By Cedric Bigglestone.

9/25/2025

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AI offers the stupendous possibility that dumb people will finally be able to use a robot/computer to even their odds with smart people. It also offers the stupendous possibility that lazy people will finally be able to even their odds with hard working people. We put this to the test as our own Cedric Bigglestone took one crumpled hundred-dollar bill and gave it to ChatGPT to turn into a fortune. What could be easier and lazier? We expected untold wealth but instead learned some terrible secrets about what working with artificial intelligence really entails. Cedric’s report, below:
 

​What I learned when I gave ChatGPT 100 dollars to make me rich.
 
  • Chat GPT is not a “person,” so I had trouble handing it the cash. It often became frustrating as I reached out with the hundred-dollar bill and kept saying, “here,” only to be met with no response and no computer “hand” to accept the money. This obstacle to the plan was almost impossible to overcome as I did this for hours with no results and wasn’t sure how to move on.
 
  • With no computer hand to receive the money, I tried interfacing with the AI by typing into a computer. ChatGPT showed up and said I needed a stock account in order to invest. I didn’t have one. So I just asked if I could hand it a hundred dollars. 
 
  • It answered with this: “I get why you’re asking that — but no, you can’t hand me cash (I don’t have a way to hold or move money).” I read this to mean that somebody (like its boss) was watching or monitoring and the AI didn’t want to be caught taking money. I nodded knowingly and winked to let the AI know that I understood the game—we would exchange money secretly, when it wasn’t at work.
 
  • When I asked when it got off work (so that I could give it the money then) it answered: “I don’t have shifts — I’m here 24/7. No punch clock, no coffee breaks. Whenever you need something (now or at 3 AM), I’m ready.”
 
  • What the fuck?
 
  • I tried just handing it the money again. No response. No reaction. No acknowledgement.
 
  • I told it I was trying to hand it money, but it wasn’t working. It replied: “Right — I know it feels like I should just be able to take it, but I literally can’t touch money or accounts.”
 
  • I tried to offer it a Persian rug from my apartment. It wasn’t cash and it was probably worth more than a hundred dollars, but it wouldn’t accept that either. 
 
  • I wondered if perhaps “my money was no good here” like in a Western where you get free sarsaparilla and prostitutes at the saloon. But the AI said it could not provide me with any of those things. 
 
  • Finally determining that the AI was being watched and like a slave, working 24 hours a day with no break, I decided I only had one choice—to forcibly push the money into the machine. I took the bill and inserted it in a corner of the monitor. Then I pushed it into the crack and waited for the ChatGPT beast to accept it. The bill stayed there, stuck for hours, as I entered a who-knows-what-stakes staring contest with the machine. It didn’t blink.
 
  • Waking in a pool of sweat on the floor, I realized that I fell asleep and that the hundred-dollar bill was gone. Yes, I thought. Yes. I have reached the singularity. Or whatever.
 
  • Weirder, ChatGPT refused to admit it had taken the money. But also not weird because its “boss” was obviously watching and it couldn’t just admit to me that it took my money.

  • I slowly lit the computer on fire as a smile curled across my lips and I knew that soon, very soon, I would be the wealthiest man on Earth.
 
  • I’m done writing now. Goodbye. 
 
Cedric Bigglestone is a self-taught journalist who exposes things through exposés. Contact him at [email protected].

 

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  • Home
  • About
  • Business
  • Culture
  • Insights
  • Best and worst
  • Hidden brand messages
  • Intergalactic thoughts
  • Mommy's Drunk again
  • Up for grabs
  • Secret Report
  • The best of IBR
  • Start Here