One startup I was working with had an amazing technology and a really sharp entrepreneur, Barry (not their real name). As they moved from the technology development stage into the market development stage, Barry and I discussed implementing the Abunden Framework to help with hiring and building the team. At that point, Barry was very busy building a prototype and talking with a prospect about a big contract. As he was so busy, he did not want to spend the time on "non-critical" tasks at that point.
As we were getting together about once a month to talk, we parted ways and looked forward to our next meeting. By the time we got together again, he had hired an acquaintance of his, Jack, to be his CEO. Jack was a very good sales person, but for a couple of reasons, Jack was not a good fit. Jack was not a natural CEO personality and did not have much experience in this role. Further, and perhaps more critically, Jack was not a fit culturally.
By the time Barry figured all this out, he was so committed to Jack in front of customers, employees and advisors, he did not want to admit the error. Barry decised to move forward with Jack despite the problems. In the short run, the decision cost the company $2 million in funding that I had connected to the company. In the longer run, the company floundered for several years and another company took over the technology for a fraction of the value that was originally envisioned.
All of these problems were avoidable problems, but required Barry to spend some time and effort ahead of his early key hires to build the foundation for his business.