Concentrated Stock: Keep, Sell, or Gift?

Get the field-tested playbook for reducing single-stock risk and managing taxes—without an immediate full sell-off. 

What’s inside:

• How to decide among sell, hold, or gift—and the trade-offs of each

• Smart selling: 10b5-1 plans, coordinating with deferred comp, timing gains

• Equity comp tactics: 83(b) election pitfalls, AMT considerations

• Gifting moves: donor-advised funds, charitable trusts, family trusts & FLPs

• Keep-but-hedge strategies: collars, puts/calls, index proxies, exchange funds, stock-protection funds

• Liquidity without “selling”: margin diversification & prepaid forward contracts

• A simple framework to right-size your position using expected growth vs. odds of success