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Nick Maggiulli's Wealth Ladder showing tax mistakes growing costlier at each wealth level Podcasts & Media

"The cost of tax mistakes increase tenfold with every new wealth level"

Aug 19, 2025
Cartoon of rotation ETFs keeping capital compounding to sidestep the tax drag of traditional fixed income Podcasts & Media

The end of fixed income with F/m's CEO

Aug 17, 2025
Podcast cartoon on holding too much company stock and weighing selling, hedging, and exchange funds Podcasts & Media

Holding Too Much Company Stock?

Aug 16, 2025
Cartoon showing tax-aware long/short leaders pulling away as AUM grows faster than earlier estimates Tax-Aware Long-Short

Ha... tax-aware long/short is growing faster than I thought

Aug 15, 2025
Podcast cover for the Not Advice episode on RSUs, vesting, and concentrated company stock risk Podcasts & Media

Avocado Orchard: RSUs, Vesting, and Too Much Company Stock

Aug 13, 2025
Poll results graphic on whether tax-aware long/short is transforming taxable wealth, from 181 respondents Tax-Aware Long-Short

Is tax-aware long/short transforming taxable wealth? 181 people opined.

Aug 12, 2025
Six-month holding rule permanently disallowing part of a municipal bond fund tax loss Tax-Loss Harvesting

Worse than the wash sale rule? Betterment's head of investing weighs in.

Aug 10, 2025
Cartoon pushing back on Buffett-style anti-diversification advice that fuels concentrated single-stock risk Concentrated Stock

Diversification "makes very little sense for anyone that knows what they’re doing" 🤨

Aug 8, 2025
Cartoon on pairing tax-aware long/short with an estate planning envelope to focus on the end game Tax-Aware Long-Short

Tax-aware long/short: "Not enough focus on the end game"... until now

Aug 5, 2025
Cartoon imagining self-custodied Bitcoin accepted as bona fide margin collateral to unlock diversification Concentrated Stock

How Bitcoin could become bone fide collateral

Aug 3, 2025
Cartoon on the SEC permitting in-kind creation and redemption for crypto exchange-traded products ETF Taxation

Bitcoin in-kind is "cheese on the beach"

Aug 1, 2025
Graphic on direct indexing ossification and how factor rebalancing sustains tax-loss harvesting over time Tax-Loss Harvesting

Is tax-loss harvesting valuable after the first few years?

Jul 29, 2025
Diversification beating a concentrated lottery-ticket stock in DFA research Concentrated Stock

Diversification vs. "lottery ticket"

Jul 25, 2025
Cartoon pairing tax-aware long/short with bold no-distribution ETFs as disruptive forces in taxable wealth Tax-Aware Long-Short

Tax-aware long/short and some bold ETFs could change everything

Jul 22, 2025
Cartoon flagging the obscure six-month ETF tax-loss harvesting rule as a hidden tax landmine Tax-Loss Harvesting

ETFs have a tax-loss harvesting rule nobody knows about

Jul 20, 2025
Cartoon on brand marketing for tax-aware products, the overlooked investment most asset managers skip Direct Indexing

Marketing tax-aware products

Jul 18, 2025
Cartoon launching Albatross, a sub-newsletter on concentrated wealth, riffing on the Ancient Mariner Concentrated Stock

Introducing Albatross, a sub-newsletter about concentrated wealth

Jul 15, 2025
Graphic explaining variable prepaid forwards for hedging concentrated stock positions Concentrated Stock

Variable prepaid forwards for the rest of us

Jul 13, 2025
Tax-aware long/short solving tax friction to unlock further portfolio diversification Tax-Aware Long-Short

Could tax-aware long/short power additional diversification?

Jul 11, 2025
Cartoon of ChatGPT hallucinating an OBBB change to the $3,000 capital loss limit that never happened Tax-Loss Harvesting

OBBB (allegedly) increases $3,000 capital loss deduction; makes EBL limit permanent

Jul 8, 2025
Cartoon framing tax deferral as an interest-free loan from the Treasury, the time value of paying later Tax-Loss Harvesting

Would you rather pay $1 in tax this year or next?

Jul 6, 2025
Cartoon framing a taxable wealth revolution, tying revolutionary themes to modern tax-aware investing strategies Concentrated Stock

The taxable wealth revolution

Jul 4, 2025
Cartoon on the tracking-error trap of tax-loss harvesting a volatile holding like Nvidia Tax-Loss Harvesting

Should you ever tax-loss harvest Nvidia?

Jul 1, 2025
Timeline graphic charting failed attempts to raise the $3,000 capital loss deduction limit since 1978 Tax-Loss Harvesting

The many failed attempts to update the $3,000 limitation on capital loss deductions

Jun 29, 2025
Investment capital returning to direct indexing with long/short acquisitions on the rise Direct Indexing

Adventure capital returns to direct indexing

Jun 27, 2025
Cartoon testing whether tax-aware long/short losses can offset capital gains from a large concentrated exit Tax-Aware Long-Short

Is tax-aware long/short a capital gains escape hatch following an exit?

Jun 24, 2025
Cartoon on combining a variable prepaid forward with tax-aware long/short to diversify concentrated stock Concentrated Stock

VPF + tax-aware long/short for diversifying concentrated stock

Jun 20, 2025
Cartoon showing a direct indexing portfolio ossifying into an expensive index fund as basis falls from harvesting Direct Indexing

How does direct indexing become an expensive index fund?

Jun 17, 2025
Cartoon on no-income bond ETFs that defer tax by making zero distributions until sale ETF Taxation

The benefit of bonds without the drag

Jun 15, 2025
Spaceballs-themed graphic on the IRS Data Book reporting $5.1 trillion in FY2024 gross revenue Podcasts & Media

Spaceballs and the IRS data book are here

Jun 13, 2025
Tax-aware long/short losses lowering the income that drives higher Medicare premiums Tax-Aware Long-Short

Tax-aware long/short could cut Medicare costs

Jun 10, 2025
Cartoon of AQR rebutting five common critiques of tax-aware long/short with charts and numbers Tax-Aware Long-Short

AQR addresses 5 critiques of tax-aware long/short

Jun 8, 2025
Cartoon urging readers to skip the Trump-Musk feud and read a tax-aware investing roundup instead Podcasts & Media

Trump/Musk cage match is boring. Read about taxes instead

Jun 6, 2025
Cartoon showing tax costs spreading like contagion from one ETF share class to another after a switch ETF Taxation

ETF share class “tax contagion” is, sadly, something we need to care about

Jun 1, 2025
Cartoon on the FTSE Russell direct indexing survey and its overstated AI tax-efficiency claims Direct Indexing

Direct indexing FTSE Russell survey is interesting, but AI claims are 💩

May 30, 2025
Graphic listing 14 adviser use cases for tax-aware long/short strategies beyond offsetting short-term gains Tax-Aware Long-Short

14 use cases for tax-aware long/short strategies

May 28, 2025
An exchange fund unblocking billions by seeding an ETF in-kind under Section 351 Section 351 Exchanges

How an exchange fund unblocks billions by seeding an ETF in-kind

May 25, 2025
Cartoon of dividend chasers buying at the top while a front-runner captures the predictable price reversal ETF Taxation

Dividend chasers... YOU are the yield

May 23, 2025
Cartoon on Betterment acquiring Rowboat Advisors to add direct indexing to its platform Direct Indexing

Betterment acquired Rowboat Advisors for a quicker path to direct indexing and to "do it all"

May 21, 2025
Cartoon revealing the options trick behind buffer ETFs' unusually low distributions and high tax efficiency ETF Taxation

What's behind the preposterous tax efficiency of buffer ETFs?

May 18, 2025
Cartoon on AQR's finding that direct indexing completion portfolios poorly hedge concentrated stock risk Concentrated Stock

AQR's latest: direct indexing "largely ineffective" at culling single-stock risk

May 16, 2025
Graphic summarizing One Big Beautiful Bill changes to SALT, EBL, and Opportunity Zones, but not the loss limit State & Local Tax

The One, Big, Beautiful Bill updates SALT, EBL, RQOF, but not LOL3K

May 14, 2025
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