Concentrated stock advisors

Common planning guidelines flag any single position above 10-20% of investable assets, but the real question is what happens to your life if the stock falls by half. If your employer is also the source of your income, your true exposure is even higher than the position size suggests.

Selling on a schedule, hedging strategies, exchange funds, charitable strategies like donating appreciated shares, and staged diversification plans. The right mix balances tax cost, concentration risk, blackout windows, and any insider-trading constraints like 10b5-1 plans.

Spread sales across tax years, harvest losses elsewhere, donate appreciated shares to charity or a donor-advised fund, and prioritize selling the lots with the highest basis. A staged plan usually beats an all-at-once sale on taxes, even though it takes longer.

It's a pre-arranged trading plan that lets company insiders sell shares on a set schedule without regard to what they later learn. If you're an executive or have access to material non-public information, it's the standard, clean way to diversify - set it up with your company's compliance team.

Sometimes: if you have genuinely asymmetric information about long-term prospects, low basis with estate step-up ahead, or restrictions that make selling costly. But 'it's done well so far' is not a strategy - the decision to hold should be made deliberately, revisited regularly, and sized so a bad outcome doesn't change your life.