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Graphic asking whether margin call risk threatens tax-efficient products built on long/short and box spreads Tax-Aware Long-Short

Margin call me maybe

Sep 28, 2025
Cambria GEW launching with $155 million as a test of mainstream in-kind ETF seeding Section 351 Exchanges

Cambria's GEW launched today with $155mm

Sep 25, 2025
Cartoon questioning whether box-spread borrowing is truly free of credit risk when the borrower is the weak link Box Spreads

Box spreads are "effectively free of credit risk"...I guess?

Sep 23, 2025
Podcast cartoon walking through de-risking concentrated stock via harvesting, exchange funds, CRUTs, and Section 351 Podcasts & Media

De-Risking Chonky Stock Positions with Tax-Loss Harvesting, Exchange Funds, CRUTs, and Section 351 Conversion

Sep 21, 2025
Cartoon laying out five intuitive ways to understand the box spread as a low-cost borrowing tool Box Spreads

Better borrowing via box spread? Why it's worth grokking the box

Sep 21, 2025
Cartoon visualizing that two-thirds of concentrated stocks underperformed the Russell 3000 from 1980 to 2020 Concentrated Stock

2/3 of the time a concentrated stock would have underperformed the Russell 3000

Sep 18, 2025
Graphic on the agony and ecstasy of concentrated stock positions and how rare the extreme winners are Concentrated Stock

The agony/ecstasy of concentrated stocks

Sep 16, 2025
TIPS inflation adjustments generating taxable phantom income without any cash flow ETF Taxation

TIPS taxation: the other phantom menace

Sep 14, 2025
Cartoon of the tax-free endowment model breaking down once taxes hit a private taxable portfolio Podcasts & Media

Taxes mess up the endowment model

Sep 12, 2025
Cartoon comparing the gen AI WealthTech hype to the earlier blockchain wave, WealthTech entering stache-mode Tax-Aware Long-Short

Future Proof: Gen AI is the biggest thing since blockchain

Sep 10, 2025
Cartoon showing the difficulty of managing short positions that sank many 130/30 strategies during the crisis Tax-Aware Long-Short

Managing short positions is "not a trivial exercise"

Sep 7, 2025
Cartoon on a multi-billion-dollar ARKK trade and the debate over whether it was a tax heartbeat trade ETF Taxation

"ploughing several billion dollars into [ARKK] even for a few days is pretty ballsy"

Sep 4, 2025
Infographic explaining why short-side downside keeps tax-aware long/short from locking up like long-only Tax-Aware Long-Short

Tax-aware long/short doesn't lockup easily. Why?

Sep 2, 2025
Eight product trends reshaping taxable wealth strategy, led by long/short and no-distribution ETFs Tax-Aware Long-Short

The (taxable wealth) times they are a-changin'

Aug 31, 2025
Cartoon urging donors to give now as OBBB charitable deduction limitations take effect in 2026 Concentrated Stock

Give it away, give it away, give it away now (literally)

Aug 29, 2025
Cartoon presenting a tax-aware long/short reading list tracing back to the 1973 Black-Scholes paper Tax-Aware Long-Short

Tax-aware long/short reference papers going all the way back to Black-Scholes 1973

Aug 26, 2025
Cartoon of a control panel simulating tax-aware long/short outcomes, balancing pretax alpha against costs and risks Tax-Aware Long-Short

I built a tax-aware long/short simulator/dashboard

Aug 24, 2025
Podcast cover for the Not Advice episode with Nick Maggiulli on The Wealth Ladder's six wealth stages Podcasts & Media

Climbing The Wealth Ladder With Nick Maggiulli

Aug 21, 2025
Graphic on surgeons using tax-aware long/short losses to offset patent royalty income under IRC 1235 Tax-Aware Long-Short

Surgeons use tax-aware long/short to offset royalty income

Aug 21, 2025
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
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