Testing ChatGPT. 

I uploaded some files from a brokerage account and had them analyzed. After verifying they were analyzed correctly I then went on to see what else it could do for me.

I gave it some thoughts, asked it to come up with an efficient prompt.

"When I started the brokerage account, my focus was on dividends. I ultimately determined to invest $100k and no more, to make it simple for guaging returns. I also make a point of reinvesting dividends on my own. It became fun. as things progressed i saw the dividend mindset wasn't the greatest, and shifted how dividends were reinvested. I can see now some ETFs are better than others. I also determined not to invest more than $5k of my own into any one investment."

this is what it came up with.

Rethinking My Dividend Strategy: 2025 Audit of a $100K Experiment

Original Strategy

When I launched my brokerage account, I had three simple rules:

• Cap the total investment at $100,000 — easy to track and manage.
• Limit any single holding to $5,000 — diversify but stay hands-on.
• Focus on dividend-paying stocks — and manually reinvest the dividends.

It was fun at first. I liked being in control of where each dividend landed. But over time, I saw cracks in the logic. The dividend mindset started to look like a dead end. It was too yield-focused, blind to total return. Some ETFs just worked better overall, regardless of income payout. That forced a shift: I started placing dividends where they made the most sense, not where they came from.

Now I’m challenging the foundation:

• Does the $5K-per-holding cap make sense in 2025?
• Is manually reinvesting dividends still worth it — or am I micromanaging a job that automation could do better?
• Which ETFs actually outperform on total return, not just yield?
• How does this approach stack up against other long-term strategies?

No fluff. No sales pitch. I don’t want investment advice — I want to know if the logic behind my strategy still holds.

So, I posted it to the original thread where I uploaded the documents.

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Sharp Review: Logic & Efficiency in 2025

(ChatGPT Response)

1. $5K-per-holding rule

• Pros (then): Risk mitigation, forced diversification, simplicity.
• Cons (now): It’s arbitrary. Limits your ability to capitalize on conviction plays or outperformers.
• 2025 take: Loosen this. Consider percentage-based caps (e.g., 5–10% per holding). Let winners run — just don’t let them eat the whole portfolio.

2. Manual dividend reinvestment

• Pros (then): Hands-on control, enjoyable, potentially more strategic.
• Cons (now): Time-intensive, inconsistent, subject to personal bias or delay.
• 2025 take: Unless you're clearly outperforming automation, automate core reinvestments and refocus your effort.

3. Dividend focus

• Reality: High yield ≠ high performance. Many high-dividend stocks underperform due to lack of growth.
• 2025 take: Focus on total return ETFs. Dividend growth funds (e.g., SCHD, VIG) have a role but shouldn’t dominate.

4. ETF selection

• Top performers: QQQ, VGT, ITOT, VOO have outpaced most dividend ETFs in total return.
• 2025 take: Use metrics like Sharpe ratio, drawdowns, and compounding. Tools: Portfolio Visualizer, Morningstar.

5. Comparison to modern long-term strategies

• Your style: Hands-on and disciplined — but rigid.
• Modern alternatives: Lazy 3-fund portfolios, smart-beta sector tilts, automated rebalancing, tax-loss harvesting via robo-advisors.

Conclusion

Your system worked well for the dividend era. But 2025 is a different game. Prioritize adaptability. Total return > yield. Strategy > tradition. Keep control where it counts — and automate the rest.