“It might be a tax law partner in a big firm, but that's so extraordinarily unlikely because they already have clients that they're servicing. They're part of a partnership. They're kind of bought in. They kind of have dedicated their lives to that path. It could be somebody who's doing tax at an accounting firm, but it's a very similar. It's a professional services role and they're on that path. They have clients they're, they enjoy like a relatively good living. And what draws somebody into that kind of career path is it's a known path and it's relatively predictable and they are not dispositionally typically going to be the kinds of people who are like, oh, I know what I'm going to do. I'm going to do a tech startup and kind of roll the dice and see if they can make it work because the opportunity cost of doing that would be so significant.”
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