This episode moves from the origin of “rule of thumb” to why most investing rules of thumb don’t work for real people. Tom and Don explore a Yale professor’s personalized allocation model, walk through tax-smart strategies for funding a child’s car while managing Roth conversions and capital gains, warn about liquidity risks in private credit after restrictions at Blue Owl Capital, explain how to structure IRA withdrawals through disciplined rebalancing, and close by addressing market-timing anxiety for retirees sitting heavily in cash. The through-line: simple rules are comforting, but thoughtful planning beats shortcuts every time. 0:04 What “rule of thumb” really means and why investing is full of them 2:17 60/40, 100-minus-age, and why simple formulas fall short 3:16 Yale professor James Choi’s personalized allocation formula 4:35 Why a 25-year-old probably should be nearly 100% in stocks 6:25 Spreadsheets vs. real-world investors 9:39 Portugal caller: funding a daughter’s car purchase tax-efficiently 13:28 Roth conversions, 12% bracket strategy, and zero capital gains planning 16:46 Rebalancing opportunity: selling VTI vs. Schwab Intelligent Portfolio 19:16 Private credit warning: liquidity restrictions at Blue Owl Capital 23:45 The illusion of “safe” high returns in private lending 26:53 IRA withdrawal strategy: sell winners when rebalancing 29:35 Annual vs. monthly withdrawal discipline 31:34 60/40 vs. 70/30 — how much difference really matters 33:32 Retirement income simplification: fewer funds, easier rebalancing 34:48 Seattle caller: $1.45M in money market and market-timing temptation 36:18 Why market timing fails and when an advisor earns their keep Learn more about your ad choices. Visit megaphone.fm/adchoices