Q: "...What's the hardest lesson for a startup CEO to understand?
Answer: "Time and time again, it is the lesson of the true cost of the under-hire. The CEO fills a role out of desperation, or recruits a buddy who is not quite the right fit but will do for now, and then that person in turn takes the organization down the wrong paths, hires the wrong people, et cetera.... My advice to CEOs is to hire the very best, act as if your life depended on every person you bring on your team, and put a ton of cycles into finding, referencing, recruiting, and retaining those people."
Yes yes yes. You may have heard most of this before, but there are good old adages for startup hiring. Try to hire people better than you, always search, hire slow, fire quick and work with people that can wear many hats. You can't always find the right person for the job and for existing relationships, and only a culture of diversity and tolerance can overcome this fact. There are moments for hiring people you trust, but you can't forget to forsee their role and its consequences. First hires are the top of a pyramid, the bottom slowly grows over the years, founders may leave, but always hire employees that can also manage growing teams.
These are great things to learn, but you have to experience them. Its an unforgiving job that takes a great deal out of you and your relationships. You are only a first-time CEO once. Its fun, but inevitably painful the first time. Second (and so on) time is a charm. Getting to the been there, done that, lets you spend your energy on the more rewarding work.