
Jed Morris
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Oct 3, 2026
How I went bankrupt after buying a landscaping company because of a personal guarantee.
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Jed MorrisGUEST
And my thought was like, you know, I really, I wanted to like do something that I had experience in.

Jed MorrisGUEST
So for me, that was defense, government contracting, something that was probably heavier in tech.

Jed MorrisGUEST
You know, like for me, like a cybersecurity government contractor would have been a great fit.

Jed MorrisGUEST
um however i did not do that i made plenty of mistakes um i raised a little bit of money from uh people in my network i went out and started searching and you know one of the first biggest mistakes i made along the way was i didn't think i could find a defense contractor especially one that was focused in tech you know within that sba size limit that five million dollars or under and that was a lapse and that was a lapse just because i didn't know like you don't know what you don't know um and i also didn't know that you know with the proper skills and the proper connections, I could raise a lot more money and go buy a bigger company if that was the problem.
14 MINS LATER
Six Real Stories of Small Business Failure with Andrew Hoffman | Halloween
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39:20Andrew HoffmanHOST
yeah thanks jed um hey dana looks like caleb doesn't understand how technology works so you could just take his q a questions and drop them in there for him um uh thanks for that uh so i mean again going back to this idea of like these these like black swan macro trends like type of events um trust and verify protect your downside do what you can to make sure that you're not putting yourself in that over leveraged position yeah uh the next one self-cannibalism eating yourself despite eating your nose to spite your face miguel

Jed MorrisGUEST
And he's actually a really great lead into what I was just talking about, this whole idea of Monday morning quarterback.
8 MINS LATER