A couple of guys I worked for at in a small company were geniuses at petty fraud. They knew exactly how to rip people off for just a little bit less than it would take to go after them.
They would routinely purchase things from small vendors, and after a few trust-gaining orders that were paid perfectly on time, they would run up maybe 8000-10000 on credit and then simply not pay. Months of phone calls, threats, etc. would follow, but they knew if they ever got cornered, at worst, they might have to pay the original amount plus some interest. Often enough, a vendor would simply give up and write it off, and these douche-nozzles would be 10k ahead.
They played the same game with customers. They would never deliver what was promised. They knew to limit written commitments and would promise the world verbally. Customers would have to go after them for weeks or months to get anything out of them. Again, the worst they had to do was deliver as promised eventually. But a few customers would settle for less just to make the hassle go away and these dick-heads would profit from the difference.
My own personal limit was when I realized that they were not depositing my Simple IRA contribution into my account. I'm not talking about the employer contribution - I'm talking about the payroll deduction that (supposedly) went from my wages into the IRA. They held the contributions for 5-6 months or more. This, of course, is illegal. They thought, as 'employers' they were naturally smarter and superior to us mere 'employees' and that they not only had a perfect right to use the cash as the saw fit, but that we were too ignorant to notice it. They were wrong. I compiled a complete history of pay-stubs and bank statements and sent it off to the Department of Labor. Again, however, they way the law is, they only had to catch up the contributions plus some interest. So they were really not any worse off than if they had borrowed the cash legitimately. Plus, if no one would have turned them in they may never have paid and pocketed that cash as well. (They were so pissed when they got busted - they thought it was disgusting that anyone would betray them and turn them in).
You may very well ask at this point why I worked for such garbage. These thinks are only clear in hindsight. They played themselves as struggling businessmen trying desperately to keep the company going and keep us all employed. The hints trickled in over time, and when we all finally realized what these guys were really about it was largely too late.
It did finally catch up with them, sort of. Enough customer and vendors had them litigated into a corner. But then they simply went out of business - dissolved the corporation or whatever it is they do. They held no personal liability (and they paid themselves very well in salary the whole time).
There's a lot more to this, particularly what happened when I tried to call them on their bullshit behavior. I don't have time for the details, but it nearly cost me my career and worse.