In the following sentence:
Unless your work is pro-bono, you should make sure that your customers keep you in shoe leather.
What does "keeping someone in shoe leather" means?
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StoneyB over at ELL answered your question rather well:
The phrase at hand, keep you in shoe leather, means, literally, to provide you enough revenue to pay for maintaining your shoes—more generally, to cover the costs of keeping your business open and maintaining the value of your capital investment.
More interesting information about the phrase can be found at the full answer.