At a Glance
- Almost every senior equipment finance professional carries a small inventory of deals that returned a normal financial outcome but never closed psychologically
- These are not the deals that lost money — those resolve. The ones that don’t resolve are the deals where judgment was overridden by deference, fatigue, or pipeline pressure
- The 2 AM deals are a leading indicator of organizational dysfunction, not personal weakness. They cluster around specific committees, specific cycles, and specific organizational pressures
- Senior leaders who acknowledge their own 2 AM deals — rather than performing certainty in committee — produce stronger judgment culture across their teams
The Deal Is Not What You Think It Is
The first thing to understand about the deal an equipment finance professional thinks about at 2 AM is that it is almost never the largest loss in the portfolio. The catastrophic deals — the fraud cases, the bankruptcy concentration, the residual collapse — those resolve. There is a write-down, a workout, a post-mortem, a lesson. The pain has a shape.
The deals that do not resolve are different. They are usually mid-sized. They are often credit-approved with a thin majority. They sometimes perform exactly as expected. The financial outcome is unremarkable. What makes them stick is that the senior banker in the room knew the deal was wrong and approved it anyway. According to Secured Research, 71% of equipment finance professionals at the SVP level and above can identify a specific transaction they wish they had pushed back on more forcefully — almost none of which resulted in a documented loss.
