Driven in part by AI helping me optimize my investment portfolio, I am updating the ETFs in my taxable brokerage account for 2026. As a high income earner, taxation is a significant issue and driver for me in how I invest my money. Below is a table I created with AI to explain some of…
Category: Tax Strategy
From AI Financial Advisor To Portfolio Action
This week I have started some year end tax planning and thanks to AI, I have also updated my investment portfolio based on some of their recommendations. Regular readers of this blog know that I believe in the three bucket portfolio: taxable, tax deferred and tax exempt. The link in the prior sentence has some…
2025 Tax Planning and 2026 Tax Pre-Planning
There’s only a couple of weeks left in December of 2025 so I decided to ask AI what I should consider from a tax planning perspective for 2025 and 2026. Gemini AI Recommendations Since the current date is December 2025, you are in the critical “final stretch” for the 2025 tax year. The following checklist…
Warning High Earners! New 2026 401k Rules
If you were a “high” earner in 2025 then you definitely need to read this post! As I recently wrote, I got my new 401k setup and had everything planned out but I came across an article that said there are new 401k rules for 2026 and it said some troubling things. I asked AI…
AI 3×3 ETF Porfolio for Roth, IRA, and Taxable Accounts
On the heels of my previous post on having AI create an AI generated ETF portfolio, I decided to have AI analyze 60 covered call ETFs and create a 3 ETF tax optimized portfolio for each type of account: Roth (tax free), IRA (tax deferred), and Taxable account. I am actually impressed with the speed…
September Tax Free Cash: $767.42 & Fear
September and March are my favorite months because those are the months most of my municipal bonds pay me tax free interest. For the month of September, I racked in $623.84 in tax free income. I also have a leveraged municipal bond ETF that paid me $81.56 tax free interest and a non-leveraged one that…
Expat Dangers Of Inadequate Due Diligence (Cry For Me Argentina!)
I am finishing up an exploratory/holiday trip in South America. I checked out a few countries and plan on returning to check out more but I had a death in the family and now have to return back to the U.S. for a funeral. One of the lessons learned however is to be vigilant of…
Greetings From South America!
I’ve been in South America now for almost two weeks and having a great time. This is part vacation and part exploration for retiring overseas that I’ve talked about here, here and here. My wife and I are spending a month down here exploring two countries primarily. It is interesting to see how life happens…
My Genius Tax Plan Has Snared Me
Do you remember the old Wild E Coyote vs Road Runner cartoons? The series of cartoons featured a coyote intent on capturing the road runner with endlessly elaborate traps, tricks and tactics and sadly, he was never successful, the road runner always got the best of the coyote. I feel like that coyote. A few…
Short Term vs Long Term Capital Gains
One costly mistake you don’t ever want to make with an investment move is ending up with short term capital gains tax instead of long term capital gains. The difference of 1 day can cost you a great deal of money. Short Term Capital Gains Generally speaking, short term capital gains occur when you have…