Aug 20, 2026 · 6 min read
This week on Mechanics of Money: Jeremy Roll
Why a $10M exit can trigger a bad allocation, plus the illiquidity premium Jeremy Roll refuses to waive.
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Mechanicsof Money
Stop guessing. Start underwriting.
The field guide for high earners becoming sophisticated allocators. Private markets, portfolio construction, tax strategy, and the incentives hiding underneath the headline return.
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From the archive
The latest thinking.
Aug 14, 2026 · 8 min read
This week on Mechanics of Money: Martin Tobias
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
Three seats in a deal, and why almost nobody gets offered more than one
Almost every private investment you've been shown puts you in the same position.
Read the briefing →What gets covered
Money is rarely lost in the headline.
Private markets
Waterfalls, preferred returns, roll-ups, private credit, and the terms that decide who gets paid first.
Capital allocation
Liquidity, concentration, asymmetric bets, and how to make a portfolio work in real life, not just in a spreadsheet.
Tax and incentives
The structures behind tax efficiency, operator behavior, and the gap between a projected return and a durable one.
Wealth behavior
The decisions that look irrational until you account for time, identity, optionality, and what money is actually for.
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