The general rule for startups is to innovate in product space and not in the mechanics of running (and taxing of) the business. This will put a startup at the disadvantage of FAMGA. But that is only one of many disadvantages.
The irony of this CFO example is that the innovation was ethics, run it by a lawyer, and the conventional wisdom was unethical, to backdate the options. But irony notwithstanding, the law won out.
If your inner voice says you and your C corporation might be getting away with something then you should probably run that by a lawyer. If that something involves someone else not knowing something else (the essence of fraud) you definitely should run that by a lawyer or just follow the general rule.
The irony of this CFO example is that the innovation was ethics, run it by a lawyer, and the conventional wisdom was unethical, to backdate the options. But irony notwithstanding, the law won out.
If your inner voice says you and your C corporation might be getting away with something then you should probably run that by a lawyer. If that something involves someone else not knowing something else (the essence of fraud) you definitely should run that by a lawyer or just follow the general rule.