Topic
Concentrated Stock
De-risking a concentrated low-basis position: staged selling, exchange funds, collars, variable prepaid forwards, and charitable strategies.
58 posts
When a stock donation might be taxed like a sale
When an acquisition turns a stock into cash before the deal actually closes
Variable Prepaid Forward vs. Collar/Margin Loan
Erkko Etula on concentrated stock risk at Basis Northwest 2026
Announcing... 351.tax (database and visuals)
Safe Harbor Ep 2: "More Likely Than Not"
Capital loss as a service
Variable prepaid forward vs. option collar
AQR's Joseph Liberman is presenting at Basis Northwest
Introducing "Safe Harbor: The Quellos Fraud"
Option collar phantom income
Managing Concentrated Public Stock Positions by Seeding an Exchange-Traded Fund
Economic substance really ties the room together
Is Your Alpha Big Enough to Cover its Taxes? (Jurassic Park edition)
With stocks at all-time highs, reasons to diversify are apparently at all-time lows
Concentration risk and volatility drag
Concentrated risk = generational wealth?
Why "walking down" a concentrated position by seeding ETFs could be problematic
Opportunity zone investing is real estate investing
Substance over form shenanigans
A new HOPES for derisking concentrated positions
Donate and deduct: AGI limit heatmap
"Just sell the damn stock"
Concentrated public stock solution Sankey diagram
Donating appreciated stocks is NOT always better than donating cash
An exchange fund will seed an ETF in-kind... again
Comprehensive wealth planning takes the cake
The exchange fund 7-year "lockup" is likely a myth
The big bad list of concentrated stock solutions
Should tax-aware long/short investors care about black swan short sale bans?
De-Risking Chonky Stock Positions with Tax-Loss Harvesting, Exchange Funds, CRUTs, and Section 351 Conversion
2/3 of the time a concentrated stock would have underperformed the Russell 3000
The agony/ecstasy of concentrated stocks
Give it away, give it away, give it away now (literally)
Holding Too Much Company Stock?
Avocado Orchard: RSUs, Vesting, and Too Much Company Stock
Diversification "makes very little sense for anyone that knows what they’re doing" 🤨
Tax-aware long/short: "Not enough focus on the end game"... until now
How Bitcoin could become bone fide collateral
Diversification vs. "lottery ticket"
