Tax Matters Archives

Tax Matters

Size Matters in the Roth IRA Conversion Decision

June 18, 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.This article is based on an email exchange with Yale Professor Barry Nalebuff in which he shared his insightful analysis of the Roth IRA conversion decision. Thanks also to our friend Larry Hilibrand, as well as our colleague

Tax Matters

Where Did I Put My Investments?

April 9, 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. Thank you to Larry Bernstein, Larry Hilibrand, Doug Lucas, Bill Montgomery and Mike Piper for their many insightful comments and suggestions. Of course, all errors are our own.[/note]ESTIMATED READING TIME: 7 min. What's the best way to distribute

Tax 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.