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Concentrated Stock


Prepaid Forward Contracts: A Tax-Efficient Path to Diversifying Concentrated Stock Positions
For founders, executives, and early employees who have built significant wealth through a single stock, the question of how to diversify is rarely simple. Selling triggers capital gains taxes that can consume 20% to 37 % of the proceeds. Holding can concentrate risk in ways that would make many portfolio managers uncomfortable. And for those subject to SEC reporting requirements or company blackout periods, even the decision to sell isn't entirely theirs to make. Enter the

Mike Germain, CFA
Mar 217 min read


Exchange Funds: A Sophisticated Hedging Strategy for Concentrated Stock Positions
For high-net-worth investors who have built substantial wealth through a single stock — whether from founding a company, years of equity compensation, or an early investment that appreciated dramatically — concentration risk is one of the most significant threats to long-term financial security. While the position may have generated extraordinary returns, holding a disproportionate share of wealth in one security exposes the investor to company-specific risk, sector downturns

Mike Germain, CFA
Mar 195 min read
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