In this episode of JackQuisitions, Jack catches up with Chris Barr, who returns with a hard but valuable update: his most recent deal is officially dead. After months of diligence, capital invested, and a strong connection with the sellers, Chris made the tough call to walk away when the risk profile jumped too high. What could have been a dream business became a cautionary tale about what happens when books don’t line up, multiples stop making sense, and the juice just isn’t worth the squeeze.
Chris shares the emotional side of killing a deal, why it sometimes feels like “paying tuition” in the acquisitions school of hard knocks, and the critical lessons he’ll carry into his next LOI. From working capital debates to due diligence missteps, this conversation is a masterclass in knowing when to say no—without losing sight of the bigger goal.
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💼 Special Thanks to First Internet Bank!
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🎙 Host: Jack Carr — https://x.com/thehvacjack
🎙 Guest: Chris Barr
📈 Keywords: small business acquisitions, dead deals, due diligence, working capital, risk mitigation, sunk cost lessons, acquisition strategy, ETA, service business growth
📌 Disclaimer: Some links may include UTM parameters or affiliate relationships, meaning we may earn a commission if you make a purchase. Episodes may feature sponsors, but all o
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Jackquisitions Newsletter — Your favorite source for how to buy small businesses. Real insights, smart strategies, zero gurus.
🖊️ Sign up HERE for more insights
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