People spend years, sometimes decades, building toward a liquidity event, then have surprisingly little time to prepare for what comes next. Whether the event is a business sale, an IPO, a tender offer, or an inheritance, several important questions often need to be addressed well ahead of time: H...
Equity compensation can feel like a bonus — a reward for good performance, a perk on top of base pay. But “bonuses,” “rewards,” and “perks” imply a short-term, and unexpected, windfall. Strip away that framing, though, and equity comp mirrors the conditions of long-term investing: it...
Each year, open enrollment arrives with a familiar checklist of forms, including plan comparisons and contribution elections. Most employees begin the process by opening the benefits guide and reviewing the available options. While that approach seems logical, it may actually lead to the wrong quest...
A Phoenix couple retires in 2023. (They’re fictitious, but their situation isn’t.) The following year, they sell a rental property they’d owned for two decades — a smart move that freed up capital and simplified their finances. The property had appreciated nicely. The timing made...
“The Happiest Place on Earth” I took my eight-year-old son, Eli, to Disneyland last week. Just the two of us for three days, no agenda beyond being together. I had planned the surprise quietly for weeks. I wanted to do something that belonged only to him during a season of life that has asked ...
Like most parents of school-aged children, I recently went through the time-honored tradition of shopping for the many items on the annual back-to-school supply list. As anyone who has had to complete this search knows, it can be equal parts exciting, exhausting, and expensive. I know the tradition ...
Most retirees enter retirement with money spread across multiple account types: taxable brokerage accounts, traditional IRAs, 401(k) plans, Roth accounts, maybe a pension or annuity. That raises the question: which accounts do you use first? The conventional wisdom is simple: spend taxable account...
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