At any inflection point in the business, you have lots of options: you can sell, raise more money, raise more and cash out some shares, you can quit, you can ma

At any inflection point in the business, you have lots of options: you can sell, raise more money, raise more and cash out some shares, you can quit, you can make yourself chairman and have your cofoudner run it, you can do nothing and grow it organically, etc., etc. Ah, but this is only true for bootstrapped companies or very early stage companies with little funding. Once you raise a Series A or B, your options are basically to grow as fast as possible or get fired and replaced by someone who will. And this narrowing of options and loss of control is another thing I dislike. A successful bootstrapped company can always go raise money at great terms. But once you do, you can't go back. To be clear, I'm not blaming investors or saying anyone is being cheated. But I do think that many young, naive, overly-optimistic people end up taking a path they wouldn't take if they saw the world a little more realistically. It's the same situation with early startup employees, who almost always get shafted.