White Coat Investor Podcast WCI #450: When You Win the Game, Stop Playing with Bill Bernstein
15 snips
Dec 18, 2025 
Bill Bernstein, a neurologist-turned-financial author, shares insights on reaching financial 'enough' and the emotional shift that follows. He emphasizes the importance of matching liabilities with stable assets like TIPS and SPIAs to secure living expenses. Bernstein discusses the risks of the current market, particularly the potential AI bubble, and his cautious approach to withdrawing from investments. He encourages aligning finances with personal values, advocating for deliberate spending and long-term planning to ensure a fulfilling life after achieving financial success.
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Stop Playing When You Have Enough
- Define "won the game" as having safe assets to cover basic living expenses for many years and then slowly reduce risk.
- Replace portions of risky assets with TIPS or SPIAs to defease necessary spending before touching discretionary funds.
Move Slowly From Risk To Safety
- Unload risky assets gradually as you reach your liability target; do not sell all stocks at once.
- Use a ladder of inflation-protected securities and possibly an immediate annuity for basic expenses.
Make TIPS Practical And Tax-Aware
- Use a TIPS fund if a TIPS ladder is too complex or your heirs can't manage TreasuryDirect accounts.
- Prefer holding TIPS inside tax-deferred accounts and keep stocks in taxable accounts.