Aloha Uncle Sam

Moana Surfrider Hotel, Oahu, Hawaii

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It’s that time of year again, when households across the land are excited to fill out their tax forms. Yeah for Tax Day!

Goal #1 is of course to minimize tax burden using the numerous options available. Be sure to contribute to those deductible IRAs and 401ks!

Some households will have a zero or even negative tax burden, but most will have a tax obligation for the year. This is usually paid at least in part through paycheck withholding or estimated tax payments.

This is also the case for us since we pay Self-Employment tax on blog income. (But… plans are in motion to reduce/eliminate this.)

And I don’t know about you, but if I have to pay some taxes…. I at least better get a ridiculously cheap trip to Hawaii out of the deal.

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Something for Everybody

(I was feeling a little frisky today, so this one is fun….)

Several years ago I wrote a post with a rather obnoxious title, Never Pay Taxes Again, in which I outline our strategy to minimize our tax burden in the years to come. It is still one of the most popular posts on this rather obnoxious blog.

Then I recently outlined how we’ve paid no income tax for 4 years while increasing Roth accounts from $0 to $100k and raising basis in our stock portfolio by $145k. Not only was this all tax free, but will be tax free forever.

As you might expect, quite a few people have taken time out of their busy schedules to express their opinion about the taxes of a guy who writes stuff on a blog. There is something truly magical about the Internet that encourages this kind of sharing.

The strongest opinions seem to come in 3 main forms:

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4 Years of Tax-Free Living

The end of 2016 marks the completion of 4 full years of choosing leisure over labor.

It’s been a fun ride so far… we’ve seen a large swathe of the world, birthed a baby, and experienced 5 or 6 minutes of fame.

But how effective have these 4 years been in terms of implementing our tax minimization strategies? Are Roth IRA Conversions and Capital Gain Harvesting just fantasies we keep while working, or do they actually produce results in the real world?

Let’s do a financial check-up and see how we are doing.

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Retire Early.

Travel the World.

Let's do this.

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