Reminiscences of a Shrub Operator

Reminiscences of a Shrub Operator

Round-Tripping Not Allowed

Plus: Grift Arbitrage & Portfolio Review

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Le Shrub
Oct 11, 2025
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The “Round-tripping” and Circularity that is taking place in the AI ecosystem is evident to everyone but a blind monkey.

“Round-tripping” is widely understood to be a practice where companies inflate their top lines through reciprocal deals that don’t always create real economic value (you can read again “The Scorpion and The Frog”).

But there is a far worse type of “Round-tripping” where retail and professional investors are guilty alike:

  • “Round-tripping” of Profits after a great run

We don’t need to go far behind in history to find examples:

  • The “Ponzi bros” of 2021 that rode the zero-revenue stocks during the “Covid Bubble”, didn’t book gains along the way and waited until now to break-even IF they were lucky.

  • The “Commodity bros” of 2022 that rode the Commodity stocks during the “Ukraine War”, didn’t book gains along the way and waited until now to break-even IF they were lucky.

This is where I hope we are different.

It doesn’t matter if it’s a Stock, a Call Option, a Put Option or a SPAC:

  • When it doubles, we take off half, make the trade “free” and give thanks.

It’s important to “Give Thanks”. The Market doesn’t owe you anything, yet she has gifted you profits. You book some and you give thanks. Ingratitude and arrogance will blind-sight you into “round-tripping” your P&L…

… and Round-tripping is NOT allowed in Shrubstack.

As simple as that.

Portfolio Review - The “Freebird” Basket

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