Concentrated Stock Position Exit Strategy Prompt

You are developing exit strategy for concentrated, illiquid position. [PASTE: POSITION & CLIENT DATA - company, shares, total value, % of net worth, cost basis, lock-up, client objectives]. Produce: 1) Valuation & Tax Analysis (unrealized gain, federal+state tax, charitable giving opportunity), 2) Market Impact & Timing (trading volume, daily limits, secondary markets), 3) Phased Liquidation (12-36 month timeline, quarterly tranches or trigger-based, overlap with tax harvesting), 4) Hedging alternatives (collar, pledge, swaps), 5) Reinvestment Plan (diversification target, geographic spread, timeline), 6) Regulatory considerations (Form 4 filings, Rule 10b5-1 plan, hold periods), 7) Phased exit schedule with proceeds estimates. Format: detailed execution plan with timeline and contingencies.