When approaching someone about buying their business, trust your gut if you know them already. Ask direct people straight up, ease into it with introverts, and ask what they'd do after they exit. Timing and tone matter more than you think.
I think that if it's— if you've already got a relationship with that person, even if it's just a, you know, we met at a conference 3 years ago, I think I would trust your gut. If it's a person who is direct, I mean, chances are they're not thinking about it, you know, like, so you asking them might be the first time they think about it. So if they're a really direct person, then you could probably be direct with them. If they're kind of more introverted or whatever— and Matt, you know this, I'm not a psychologist, psychiatrist, counselor, anything like that. I'm just saying based on my experience, when someone hears that, if they're kind of a very direct person, they'll answer you directly, yes or no. More introverted person, you might want to plant some seeds before you try and harvest that, uh, that crop. Just over time, get them thinking. And it's really on that— and this may work for the direct folks too— to ask them what their plans are after they exit their business.
