When Deals Get Weird: Stories You Don't See in the CIM
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Show notes
Nathan Rust, Lutz Lehmann, Troy Pospisil, Jeremy Segal, Patrick Mumman, Tej Brahmbhatt, George Helock, and Angie Astle
A background check killed a deal a week before close, after the QoE and the IT and cyber diligence were already done. George Helock's fix: run background checks on everyone with money tied into the business, and ask for them at the NDA stage.
Recorded live at DealMax, this episode collects eight deal surprises the CIM never shows. Troy Pospisil was told revenue-by-customer data didn't exist, asked how the company invoiced, and pulled eight years of it off a late-'80s IBM. Jeremy Segal lost a deal at signing to a co-founder who was never fully on board. Angie Astle's first acquisition was heading toward bankruptcy mid-diligence, so Chugach bought the bank's debt and took ownership through Chapter 11.
George's lesson is about timing: the request that can kill a deal should go out first, not in the final week. DealRoom Diligence lets you create, assign, and track every request from day one and connect findings directly to the diligence data, so red flags surface while you can still walk away early. See how it works: click here.