20 Items

Featured Insights

When a $10 Million Tax Break Isn't Worth the Wait

What if selling your startup shares could mean paying little to no federal capital gains tax? QSBS is one of the most powerful and overlooked wealth-building opportunities available.

May 20, 2026

Featured Insights

Robbing Peter to Pay Paul: A(nother) Look at Long/short Direct Index Tax-Loss Harvesting

The case for LSDI improves meaningfully in specific circumstances, but for many investors being pitched the strategy, the math doesn't support the hype.

April 13, 2026|9 min

Tax Matters

Demystifying 351 ETF Exchanges

Investors have learned to love the ETF as an investment vehicle, and for good reason - but for investors holding assets with unrealized gains in taxable accounts, making the switch can seem unattractive.

March 6, 2026

Investing 101

Size Matters in the Roth IRA Conversion Decision

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...

June 18, 2025|9 min

Featured Insights

Where Did I Put My Investments?

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

April 9, 2025|7 min

Featured Insights

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

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.

February 5, 2025

Tax Matters

Direct Indexed Tax Loss Harvesting: Is the Juice Worth the Squeeze?

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?

August 27, 2024

Tax Matters

Bitcoin is Nothing Either Good or Bad, but Sizing Makes It So

Bitcoin isn't an inherently good or bad investment - but said investment can turn sour quickly if you're not paying attention to sizing.

July 7, 2022

Tax Matters

Do Options Belong in the Portfolios of Individual Investors?

In a recently-published article in the Journal of Derivatives, we ask whether or not options make sense for a broad class of investors.

March 23, 2022

Tax Matters

To Realize, or Not to Realize

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.

October 22, 2020

Featured Insights

Back to the Future: Reviving a 19th Century Perspective on Financial Well-Being

We tend to assess our net worth by the market value of our assets - but it might be more natural to think of it as a stream over time.

May 13, 2020

Tax Matters

When it Pays to Pay Capital Gains

It may seem counter-intuitive, but for investors with a steady stream of short-term capital gains, their investment approach can be improved.

March 11, 2019