Mechanics of Money archive
Private markets, allocation, tax strategy, business operations, and the psychology of wealth, without the usual optimism tax.
Sep 23, 2026 · 5 min read
Why a winning startup investment can still leave you waiting for cash, plus the spending habits that can outlive the reasons you started saving.
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Sep 21, 2026 · 5 min read
Why the same $250k investment can make perfect sense for one person and be a huge mistake for someone else.
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Sep 16, 2026 · 6 min read
Why a founder’s exit can turn an owner into a lender, plus the investing blind spot that can survive a successful business sale.
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Sep 11, 2026 · 4 min read
Why I use cash flow to fund a longer-term bet, and why more deals don’t always mean more diversification.
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Sep 10, 2026 · 6 min read
Why a $100M franchise system is not $100M of franchisor revenue, plus the recurring service opportunity that can remain after a restaurant closes.
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Sep 4, 2026 · 6 min read
Why a $100M portfolio can still feel empty, plus the simplicity premium hiding beneath the polished complexity of alternative investments.
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Aug 28, 2026 · 6 min read
Why $500K of income can become a trap, plus the ownership math that changes a 20-year career.
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Aug 20, 2026 · 6 min read
Why a $10M exit can trigger a bad allocation, plus the illiquidity premium Jeremy Roll refuses to waive.
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Aug 14, 2026 · 8 min read
Why a $500 million paper fortune wasn't real liquidity, plus the venture math that can tolerate 80% zeros while waiting for a 100x outlier.
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Aug 12, 2026 · 5 min read
Almost every private investment you've been shown puts you in the same position.
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Aug 5, 2026 · 7 min read
70% of people haven't talked to a living soul about money in a year, plus the $20 experiment that still works even when you force people into it.
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Aug 1, 2026 · 6 min read
A $30,000 Christmas week that cost nothing out of pocket, and why chasing airline status is mostly a waste of your time.
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Jul 22, 2026 · 5 min read
The $44M founder who won't take a vacation, and why the hardest part of an exit has nothing to do with the deal.
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Jul 16, 2026 · 4 min read
The tax strategies behind eight and nine-figure exits, and what a decade of 27% IRRs going to zero taught him.
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Jul 14, 2026 · 5 min read
A founder who built an eight-figure company around the life he wanted, and a fund manager who moved to Costa Rica with three kids and runs her whole business from a laptop.
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Jul 3, 2026 · 4 min read
What 8,000 HNW investors actually buy, plus a live panel on where they're putting capital now.
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Jul 1, 2026 · 4 min read
Issue #25 - Two quick wins from the platform this quarter, and one new development behind them.
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Jun 22, 2026 · 7 min read
Issue #24 - Anyone with a spreadsheet and some capital can buy a business. The hard part is everything that comes after, and almost none of it lives in the numbers you underwrote.
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