Horror Stories / Ass-kickings

November 24, 2025

by a searcher from Columbia University in Santa Fe, NM, USA

I’d like to speak to other searchers / sponsors who bought a business thinking one thing (this is going to be great!) only to have the tables turned (got dragged into a black hole) and lived to tell the tale. If you changed your entire investment philosophy based on your mistakes, bonus points. If you go back far enough, almost every great investor started out in painfully bad situations / investments only to pivot and change how they looked at the world. If this sounds like you, please reach out. I would love to connect with you. Feel free to comment here as well on your situation / how you got through it so the community can get smarter about what to avoid.

Reply by a searcher
from University of Massachusetts at Lowell in Boston, MA, USA

Bought a business that turned out to be complete fraud. Passed through underwriting and a 3rd party evaluation. I'm still (and have been) on the hook for the 7 figure SBA loan. I was forced to build a business from scratch to cover the debt while the lawsuit plays out. Now working on the second acquisition/merger as of this week to hopefully start turning a profit over the debt service. I refuse to lose.

Reply by a searcher
from New York University in San Diego, CA, USA

Where would you like to start ^redacted‌?! ? I personally acquired two businesses before experiencing bankruptcy. Since then, I’ve interviewed 40+ people who have acquired a business and experienced failure within the past 5 years. Those sortie stories & lessons are the basis for my upcoming book “Buyer Beware”.

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