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
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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