Most founders wait until the bank calls or payroll is tight to think about restructuring. By then, your options have already shrunk.

After working with distressed small-to-mid-size businesses, there are three numbers I check first — before looking at anything else:

1. Cash runway in weeks, not months. If you don't know exactly how many weeks of payroll + fixed costs you can cover with cash on hand, you're flying blind. Most owners think in "months" because it feels less scary. Recalculate in weeks.

2. Debt service coverage ratio. Take your operating cash flow and divide by your total debt payments (principal + interest) for the period. Below 1.0 means you're covering debt with new borrowing, not earnings — a warning sign long before default.

3. Gross margin trend over the last 6 months, not the last quarter. A single bad quarter can be noise. A steady downward slope over 6 months means your cost structure or pricing is broken, and no amount of "more sales" fixes that alone.

If any of these are flashing red, restructuring isn't a last resort — it's the fastest path back to control. It usually means renegotiating terms, cutting the right costs (not just any costs), and rebuilding a plan around what the business can actually sustain.

Happy to answer questions on any of these in the comments.