I've made this mistake three times now and I'm done learning it the hard way. We hired people with impressive resumes from well-known companies. They knew how things were supposed to work at scale. They'd seen mature processes and sophisticated systems. I thought that experience would help us level up. What actually happened each time was a mismatch. They were used to having support functions we don't have. They wanted to build teams before we had the revenue to support headcount. They expected clarity and structure that doesn't exist at our stage. They were frustrated and we were frustrated. The best hires we've made are people who've worked in messy, scrappy environments. Maybe they were at a startup that failed. Maybe they were in a small team inside a bigger company that operated like a startup. They know how to function without perfect information, without dedicated support, without clear career ladders. Experience matters but context matters more. Someone who was great in one environment can struggle in another. I now specifically ask candidates about times they operated with limited resources and ambiguity. Their comfort with that tells me more than their resume.