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My wife ran her own business, and a lot of her time was spent chasing up people like this and it was so frustrating. A lot of small business owners do everything themselves, so having to re-issue invoices and chase them up if they weren't paid was a real pain. She didn't mess about though, of they didn't pay and didn't communicate she would engage a debt-collection company. She also knew some of her clients were also small businesses and would work out a payment plan or extra time if they needed it. But some deliberately strung her along till the last minute.
I had the opposite experience. I worked for a guy who easily could have retired years before, but kept working because he liked the continuous puzzles he had to deal with.
His books were an absolute mess. His daughter tried her damndest to handle the accounting, but it was a losing battle (the staff wasn’t affected, because there were never any payroll problems). He often forgot to charge customers, and when he did eventually send a bill, the rate was significantly less than what a competitor would charge. He just didn’t care about that part of the business because he didn’t need the money.