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Hiring for personality instead of skill. I wanted to be a cool, fun, hip startup founder and hire people who seem really cool, but that ended up being a mistake because being a fun person doesn't mean you can do the job. I had to let several people go because they just didn't have the skills to back up their personality.
Not doing something for the fear of making a mistake. Do your research, understand the pros and cons, but do not let fear of failure hold you back from doing anything at all.
Kind of the same thing here. I wasted a couple months "working" on this with an old colleague. He's a sharp guy and had great insight when we did connect; it was the getting him on the phone part that was the problem. I finally realized this isn't a priority for him and more or less cut him out. We hadn't formalized anything, so it wasn't a big deal, but it was still annoying because he approached me about teaming up after seeing a post I'd made about it, not the other way around. I was really excited by the prospect and now feel like it was a completely avoidable waste of time. Whatever though. Onward and upward.
Not firing quick enough
I wish someone would say this to my boss. There were several people on our team who should have been fired sooner than they were. And it really did have an impact on the whole team.
Leaving a large firm for a startup was a deliberate decision. The firm is performing well, but I did not fully account for how much of the total compensation package I discounted in exchange for a title. That title aligns more directly with progression in the RIA space rather than the broker dealer space. While there is broad interest in talent with broker dealer backgrounds, I am seeing the strongest traction from RIAs, which aligns with my current role and focus. Although much of my experience has been with institutional and high net worth clients within a broker dealer environment, broker dealers tend to show less interest unless the role is financial consultant, individual contributor, or sales focused.