Tax Matters Archives

Tax Matters

Out of the Frying Pan and Into the Fire: Selling A Highly Appreciated Stock Without Paying Taxes?

January 30, 2025 — By Victor Haghani and James White[note] This is not an offer or solicitation to invest, nor are we tax experts and nothing herein should be construed as tax advice. Past returns are not indicative of future performance. Thanks to Dave Blob, Larry Hilibrand, Chi-fu Huang and Jeffrey Rosenbluth for their input, and special thanks to Vlad Ragulin for his contributions, and to our colleagues Jerry Bell and Steven Schneider for their help.[/note] ESTIMATED READING TIME:

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.