I started by uploading screenshots of my Roth IRA and Solo 401(k) from Monarch. You can also copy/paste tickers and balances — ChatGPT doesn’t need perfect data.

Then I asked:

ChatGPT gave me a full breakdown. It spotted which funds generate income, what kind of income (dividends, interest, capital gains), and how they’re taxed depending on the account type.

I didn’t upload any taxable account information, so most of my investments checked out okay for efficiency concerns.

ChatGPT did note this one for me:

It’s a great gut check — especially if you mostly set it and forget it like me.

Here’s what I learned (or was reminded of):

I’d heard all this before, but having ChatGPT apply it to my actual accounts made the advice feel much more actionable.

Next, I wanted to see how I could improve my asset location — not my asset allocation. That means keeping the same mix of investments, but putting each one in the account where it would be taxed most efficiently.

That means: keeping the same overall mix of investments (stocks, bonds, REITs, etc.) — but placing each one in the account where it would be taxed most efficiently.

To make the exercise more useful, I added a hypothetical taxable brokerage account alongside my real Roth IRA and Solo 401(k).

I asked:

Here’s the setup I gave it:

I assumed the same assets from Step 1.

The dollar amounts here matter — because you can’t just shove everything into the “ideal” account type. You have to work within the limits of the space you’ve got.

ChatGPT broke down each asset class and recommended where it should live for maximum tax efficiency — while keeping my overall portfolio the same.

The result is the same portfolio, less tax drag over time, and a clearer strategy for which account gets what.

Finally, I wanted to prep for tax season.

So I asked:

If the current market price of an investment is lower than what you paid for it, you may be able to sell it at a loss — and use that loss to reduce your taxes.

Here’s how that looks in practice:

In both cases above, you’d be selling for a loss, and you could harvest that loss to offset other capital gains (or up to $3,000 of ordinary income per year).

ChatGPT gave me some TLH-Safe alternatives for avoiding wash sales:

Quick refresher: the wash-sale rule disallows a loss if you buy a “substantially identical” investment within 30 days before or after selling. That’s why knowing good replacement funds is key.

It also warned me about swaps that might be an issue:

⚠️ A Quick Heads-Up

AI is great for spotting potential red flags, but is not a substitute for a human advisor.

Always run big portfolio changes by a professional who understands your full financial picture and tax situation.

Still, ChatGPT gave me a major head start — and a few easy wins I’d been overlooking.

Want to try this yourself? Start here:

🧠 ChatGPT (GPT-4) – For tax Q&A, asset location, and harvesting ideas
📊 Portfolio Visualizer – To backtest allocation shifts or compare tax outcomes
💰 Monarch or YNAB – Track which accounts hold which investments
🧾 Empower / FutureAdvisor – Basic but free portfolio checkups

One quick note: This newsletter is for educational purposes only and does not constitute financial advice. I’m not a financial advisor — just someone sharing ideas and tools I’ve found useful. Use what works for you, skip what doesn’t, and always do your own research before making financial decisions and using the tools shared in this newsletter.