#31 - How to handle concentrated stock positions

We dig into the real risks of single-stock wealth, why diversification protects your future, and how to navigate taxes, FOMO, and strategy without losing what you’ve earned.

• defining concentration by impact on your life, not a fixed percentage
• where big positions come from, including employer equity
• why FOMO and upper bounds distort judgment
• winners vs diversification and the humility of market history
• thinking in after-tax terms and ditching pre-tax anchoring
• immediate sale vs staged sales and bracket-aware plans
• tax loss offsets as pressure relief, not a driver
• donating appreciated stock and donor-advised funds
• step-up in basis for late-life planning, with limits
• securities-based lending for short-term liquidity
• charitable remainder trusts and pooled vehicles
• double risk of employer stock when your job matches your shares
• survivorship bias in success stories and durable principles