►EXECUTIVE SUMMARY 1) BUYER FATIGUE IS A DEAL KILLER — AND THIS HARVARD MBA FELL RIGHT INTO IT: Months of searching, deal after deal falling through, and when the clock was running out he circled back to a business he'd already passed on. That's not conviction — that's desperation wearing a suit. Search fatigue makes smart people do dumb things with seven-figure checks. 2) HE BOUGHT A "MANUFACTURING" BUSINESS THAT WAS ACTUALLY A JOB SHOP — AND THAT DISTINCTION COST HIM EVERYTHING: Tool and die, good revenue, solid margins on paper. But manufacturing means repeatable inputs and predictable outputs. A job shop means your revenue walks out the door every night with one key employee. Confuse the two and you're buying a house of cards at manufacturing multiples. 3) THE KEY EMPLOYEE WAS ALREADY CO-LOCATED WITH THE #1 CUSTOMER — AND NOBODY ASKED WHY: The top client was being serviced by a single employee working out of a facility next to that customer, not at the main shop. That's not an operational quirk — that's an exit strategy. The second-gen seller knew that employee was about to bolt and take 50% of EBITDA with him. That's deal sense, not accounting — and no QoE report will flag it if you're not asking the right questions. 4) THE SELLER KNEW EXACTLY WHAT WAS COMING — AND CLOSED ANYWAY: When something catastrophic happens three months after close, that's not bad luck. After 16 years of deals, Elliott's rule is simple: sellers always know more than they're telling you. The real due diligence question isn't "are the numbers right?" — it's "why is this person really selling?" 5) YOU NEED A DOMAIN EXPERT OR YOU'RE GAMBLING BLIND: All the Harvard pedigree and financial acumen in the world won't save you in a bespoke industry you've never operated in. If you're writing a seven-figure check in tool and die, manufacturing, or any niche sector without someone in the room who's lived that business — you're not doing diligence, you're doing guesswork.