Business IOU field guide

Cash flow and repayment design

Match a note to the cash conversion cycle so a good business is not made fragile by the wrong payment date.

Profit is not payment capacity

A profitable contractor may wait for retainage, a retailer may pay suppliers before selling inventory, and a subscription company may collect well before providing service. An IOU should begin with an operating cash map: when cash leaves, when revenue is invoiced, when it is collected, and which obligations must be paid first.

Design around operating evidence

Monthly amortization is common, but it is not automatically safe. Seasonal businesses may need interest-only periods and principal payments after peak collections. A purchase-order bridge may repay from identified receivables. An equipment note may need a ramp period. The lender should see the assumptions, reporting cadence, and a downside case.

Treat taxes as a fixed cash commitment

For many US businesses and owners, taxes are paid as income is earned through estimated payments. The IRS notes that self-employed individuals, partners, S corporation shareholders, and corporations may need estimated payments during the year. Put those due dates and payroll obligations into the same liquidity model as debt service.