Tax Loss Harvesting is Overrated

A friend of mine who reads this blog emailed me recently for advice about about tax loss harvesting (abbreviated TLH in this article). The allure and promise of TLH, to pay less in taxes, is indeed sexy. Who doesn’t like this promise? TLH is one of the major supposed value-adds of robo-advisors like Wealthfront and … Read more

2020 Tax Software is Live

The 2020 edition of FreeTaxUsa is now live (link). Despite the scammy name, it’s a great piece of software that I’ve used since 2016. They give the federal software away for free and charge a modest fee for state tax filings. Since I’m cheap (understatement of the century), I do my state filings on my … Read more

2020 Tax Calculator

Overview 2020 is almost over (good riddance!), so perhaps now would be an appropriate time to assess your 2020 tax withholdings for taxes due in April 2021. I find it slightly annoying that TurboTax & TaxAct don’t update their tax calculators until mid-late November, so perhaps my spreadsheet can fill the void for someone wanting … Read more

Who Wants to Be a Millionaire?

So you want to be a millionaire?   Introduction I know quite a few people who are older and broke. Given the extremely favorable market returns over the past many decades, I find myself having little sympathy for such individuals. The purpose of this blog post is to see whether my lack of sympathy is … Read more