Bootstrapped by people that work in the industry, and just needed tools to be less about learning how to use the tool and more about getting the thing done.
Make the tool work for you.
To make doing that 1 thing a 5-minute job not a 5-hour job.
Security is everything, if it's not secure don't use it.
Somethings don't need to cost a fortune, especially if most of the work is done on your own servers.
You should be able to choose when and how often to upgrade without worry that it's going to take down everything.
You shouldn't need someone to train you on how to use the system.