"We (my partner Dave and I) had to put money into the business. We both had pretty low personal burn rates at the time and were making a decent amount of money ($100k salaries + annual pre-tax profit of about 25%) and we were able to bonus out most of the money. It was tough to loan the company after tax dollars to make payroll, but we did it a few times. I remember the Hyperion one being big enough that the check I wrote was really uncomfortable. Re: tips on how to deal with this better - my biggest realization is embodied in the John Galt quote - recognize the unimportance of suffering. You are going to suffer. It's going to be hard. But it ultimately doesn't matter to the universe. So - do all the things you need to do to calm yourself down (sleep, meditate, talk to a trusted partner or SO) and then tackle the issue directly and try to work through it until you get to the other side." - Brad Feld