Filing bankruptcy at 44 - Loser Story
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Rob Castellano

Rob Castellano

Aug 9, 2026

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#Defeat

Filing bankruptcy at 44

Signed the papers on Thursday. Chapter 7. The trustee meeting was eleven minutes long. Eleven minutes to close out twenty years of trying to build something. My landscaping compan…

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In short

At 44, I filed bankruptcy after losing contracts and equipment at my landscaping company. Eleven minutes with a trustee closed out years of effort. I am still carrying the shame, even while trying to be present for my kids.

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