The failures teach more than the wins, but nobody wants to post them. From what we've seen advising on the financing side, the recurring threads are: EBITDA add-backs that looked fine in diligence but didn't hold up once the new owner was actually running the business, working capital cushions that were too thin to survive a rough first two quarters, and transition plans that quietly assumed the seller would stay hands-on longer than they actually did. The diligence gap is usually less about the historical financials and more about operational risk — who really holds the customer relationships, how key-person-dependent the business is, and whether the team sticks around post-close.

@redacted‌ excellenty articulated