Tax Matters Archives

Tax Matters

Size Matters in the Roth IRA Conversion Decision

June 18, 2025 — Converting a Traditional IRA to a Roth IRA – commonly called a “Roth conversion” – is a process that allows you to move retirement savings from a traditional IRA to a tax-free Roth IRA...

Tax Matters

Where Did I Put My Investments?

April 9, 2025 — What's the best way to distribute your stock and bond holdings between your taxable and non-taxable investment accounts?

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.