One thing that can really catch founders out is “scale appropriate resourcing”.
What this means is that it’s very different to run a tiny business compared a very large business, but founders can get in a nasty situation where they find someone who’s worked for a very large business and think, “ah great, they can really help me because they’ve been through this journey and built something big!”, so they bring them on board and find out that that person was AMAZING at working in a business with £25m of venture capital money in the bank, and where the business just bloated it’s headcount to a few hundred people, but pretty useless in a business that is so small if someone doesn’t remember to pick up the milk from Asda on the way to work no one can drink any tea that tea.
The reason for this is that how you lead, strategise, manage, and operate, changes as you go through different stages of maturation and the skills you need within the change as well. But weirdly very successful personnel from businesses that have “made it” often don’t know they’re a great fit and when everyone finds out, it’s too late.