Tax Matters
FilterTax Matters
Out of the Frying Pan and Into the Fire: Selling A Highly Appreciated Stock Without Paying Taxes?
February 5, 2025 — More than a few investors have made huge returns through concentrated holdings or fabulous venture capital success stories. It's natural that many, if not most, of these happy investors would like to take some chips off the table and diversify their portfolios - and, if possible, they'd like to do it tax-efficiently too.
Tax Matters
Direct Indexed Tax Loss Harvesting: Is the Juice Worth the Squeeze?
August 27, 2024 — Direct indexed tax loss harvesting is incredibly popular nowadays, and has become a huge selling point for some companies - but is it all it's cracked up to be?
Tax Matters
Bitcoin is Nothing Either Good or Bad, but Sizing Makes It So
July 7, 2022 — Bitcoin isn't an inherently good or bad investment - but said investment can turn sour quickly if you're not paying attention to sizing.
Tax Matters
Do Options Belong in the Portfolios of Individual Investors?
March 23, 2022 — In a recently-published article in the Journal of Derivatives, we ask whether or not options make sense for a broad class of investors.
Tax Matters
To Realize, or Not to Realize
October 22, 2020 — With the US presidential election just a few weeks away, now is definitely a good time to think about capital gains taxes and how things may change.
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