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…
Category: Tax Strategy
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…
Sent Uncle Sam $5000
As a follow up to my earlier post on my taxes, it turns out that $5k was the correct amount to send off to Uncle Sam. It’s always painful to see so much money leave my account but the only thing I can do is build tax strategies to reduce the amount. The $5000 is…
Retirement Planning: Lower Taxes & Return on Capital
As I continue to optimize my investment portfolio for retirement as well looking at tax optimization, I came across this great video on ETFs that focus on return on capital and lowering tax liability. I like the video because it covers that tax advantages and some potential pitfalls of the strategy. I’ve written about return…