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Flourish Management Monthly Partner Letter · Investment Committee Directive
Macro Strategy · Mar 2026 · 3 Min Read

The Math of Never Taking a 30% Loss

A 30% loss takes a 43% gain just to break even. A 50% loss takes a 100% gain. Here is how mechanical collars protect compounding.

Most investors focus entirely on upside returns. They look for stocks that can double or funds that promise 25% annual gains.

Warren Buffett’s famous Rule #1 is simple: 'Never lose money.' Rule #2 is: 'Never forget Rule #1.'

That sounds like a clever soundbite, but it is rooted in unforgiving geometric mathematics. Loss recovery is not symmetrical:

  • If you lose 10%, you need an 11% gain to break even.
  • If you lose 25%, you need a 33% gain to break even.
  • If you lose 30%, you need a 43% gain to break even.
  • If you lose 50%, you need a 100% gain just to get back to zero.

When you suffer a 40% loss, compounding stops. At an 8% historical return, it takes six full years of work just to recover your starting principal.

How Collars Defend the Compounding Engine

By using systematic options collars—selling covered calls to purchase protective puts—we place a hard legal floor at 10% below market value. If a black swan shock crashes the broader index by 35%, our account value is capped at a 10% decline.

Recovering from a 10% drawdown takes months, not years. By cutting off the left tail of catastrophic losses, capital compounds uninterrupted for decades.

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Flourish Execution Standard · Principal Portfolio Implementation

How Flourish Adopts This Best Practice

Flourish establishes mechanical collar structures on all held equity positions, eliminating catastrophic drawdowns to preserve long-term capital compounding.

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Flourish Investment Committee

General Partner Desk · Flourish Management LLC

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