The Class Of: The PayPal Mafia
PayPal had 776 employees when eBay bought it. Thirteen are in the famous photograph. What the SEC filings show about what everybody else actually got.
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Hosting: Dinners, Salons, and the Private-Entertaining Economy
Americans halved their social calendar in twenty years. At the top of the wealth ladder, hosting got more expensive and more valuable — because convening people is the one thing money can’t simply buy.
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Raising Heirs: Teaching Wealthy Kids About Money
Wealthy families spend a fortune teaching heirs to budget. The research says the variable that actually matters is when you tell them what exists — and most families wait until the mid-twenties.
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Insurance for the Wealthy: Umbrella, Art, Kidnap, and Estate
The art and the house are the easy part. Liability has no ceiling and the catastrophe map is closing. How insurance actually works above $5 million in net worth.
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Liquidity: How Much Cash the Wealthy Actually Keep
Two 2026 studies put high-net-worth cash holdings at 24% and 5%. Both are right. What that gap reveals about how wealthy households actually manage liquidity.
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Real Estate as an Investment: How the Wealthy Actually Use Property
Depreciation, leverage, 1031 exchanges, cap rates, syndications and REITs — how wealthy households actually use property as an asset class, and why real estate is a smaller share of their balance sheet than almost anyone assumes.
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Equity Compensation: RSUs, ISOs, and the Tech Wealth Engine
RSUs, ISOs, NSOs, ESPPs, the AMT trap, 83(b), and tender offers — how tech equity compensation actually turns a salary into seven figures, and where it goes wrong.
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Multiple Streams of Income: The Myth, the Math, and What Wealthy Households Actually Do
“The average millionaire has seven streams of income, according to the IRS.” The IRS never said it. Here’s what the actual tax data shows about how wealthy households really earn.
