At $5 million to $20 million, investing stops being about picking winners and becomes about not losing what you already won. Broad index funds remain the core for a reason: the S&P 500 has compounded at roughly 10 percent annualized over the long run, and few managers beat it after fees and taxes. The top long-term capital gains rate of 23.8 percent makes every unnecessary trade expensive.
This hub covers portfolio construction at scale: asset allocation and rebalancing, index and factor ETFs, direct indexing and tax-aware investing, alternatives like private credit and real assets, managing concentrated positions after an exit or IPO, and the platforms and tools worth using. It is written for investors whose stakes are too high for generic advice and whose biggest risks are concentration, taxes, and their own behavior in a drawdown.
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Browse all articlesInvesting: common questions
How should I invest after selling my business?
Diversify first, optimize second. A windfall concentrated in cash or a single stock should move into a broad, low-cost allocation on a schedule set in advance, whether immediately or over months. Lump-sum investing has beaten dollar-cost averaging in most historical periods, but the behavioral goal is getting fully invested without a decision you may abandon halfway.
Do alternative investments make sense at the FatFIRE level?
Selectively. Private credit, real assets, and private equity can add diversification and yield, but illiquidity, fees, and the dispersion between good and bad funds are all larger than in public markets. A portfolio that is already diversified, tax-managed, and cheap sets a high bar for added complexity, so most FatFIRE investors cap alternatives at a minority sleeve.
How do I manage a concentrated stock position?
Set a target weight and a schedule to get there. Tools include staged sales planned around the 23.8 percent top long-term rate, exchange funds that swap concentrated stock for a diversified basket, collars to bound downside during the wind-down, and donating appreciated shares. The failure mode is waiting for a better price that never has to arrive.