I wrote a post a few weeks ago about how I owe Uncle Sam $10000 and I normally file my taxes the first week of April to leave time for rejections/corrections and payment processing. I opened up TurboTax again and something just didn’t feel right about the whole tax situation. What bothered me the most…
Category: Tax Strategy
I Owe Uncle Sam $10k For 2025
I am relieved that I only owe Uncle Sam $10k for 2025. I had a well thought out strategy to minimize my taxes that all went berserk when I got laid off but things turned out fine. Ironically, I got about $10k in unemployment benefits which I kept in interest bearing accounts knowing that most…
VOO vs SCHD, What About Taxes and Income?
The endless debate on Reddit investing forums seems to be the VOO vs SCHD or Growth vs Income/Dividends. I came across the YouTube video below which does a good job of discussing the pros and cons of each. In the video, investing equal amounts in both VOO and SCHD over 30 years produces $5.6 million…
My Taxable Brokerage Portfolio For 2026
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…
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…