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I Let ChatGPT Manage My Portfolio for 90 Days — Here's Every Trade, Every Loss, and What I'd Do Differently
Featured
AI Experiment

I Let ChatGPT Manage My Portfolio for 90 Days — Here's Every Trade, Every Loss, and What I'd Do Differently

What happens when you hand an AI the keys to your investments? Not the sanitised version — the real one, with the 3am panic and the call from my financial advisor.

March 20, 20267 min read
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The $500/Week AI Side Hustle Nobody Talks About (Because It's Boring)

It's not sexy. It's not viral. But it's been paying my rent for 8 months straight.

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Dollar-Cost Averaging Is Overrated. Here's What the Data Actually Says.
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Dollar-Cost Averaging Is Overrated. Here's What the Data Actually Says.

We ran 10,000 simulations over 40 years of market data. The 'boring' strategy isn't always the winner.

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The 'No-Budget Budget' That Saved My Marriage and $18,000 in a Year
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The 'No-Budget Budget' That Saved My Marriage and $18,000 in a Year

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I Used AI to Negotiate My Salary. I Got $12,000 More Than I Expected.
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I Used AI to Negotiate My Salary. I Got $12,000 More Than I Expected.

The exact prompts, the preparation, and the moment the hiring manager paused.

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Every tool, every mistake, and the exact moment it clicked. No gatekeeping.

Mar 202
We Asked 5 AI Chatbots to Build a Retirement Plan. Only One Was Safe to Follow.
AI Experiment6 min read

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I Tracked Every Single Penny for a Year. The Results Were Uncomfortable.
Budgeting4 min read

I Tracked Every Single Penny for a Year. The Results Were Uncomfortable.

The app said I spent $4,200 on things I can't even remember. Here's how I rebuilt my entire money system.

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7 AI Tools That Do Your Taxes Better Than Your Accountant
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7 AI Tools That Do Your Taxes Better Than Your Accountant

We tested all seven with real tax returns. Three found deductions our CPA missed entirely.

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The 50/30/20 Rule Was Built for a World That No Longer Exists
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The 50/30/20 Rule Was Built for a World That No Longer Exists

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How AI Is Revolutionizing Personal Budgeting in 2026

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