>Yours is probably a textbook case of someone needing a partner who has a better idea of where that line is seat of the pants wise. I've never needed that it comes naturally.
My life partner, actually, is sort of stepping into the role you describe. It's hard for me letting go, but I'm far more likely to be okay with my partner taking that role than some random sleazebag. I mean, her background is more technical than mine; which is a downside in that role (though an upside for me actually following. Like most technical people, I have a hard time accepting leaders who don't have a technical background.) but eh, hiring for that role is really hard; judging from my past, when it comes to evaluating business people? I'm worse than random.
But it's still ultimately my business, and ultimately mistakes (or unethical decisions) made by that business are still my responsibility. Perhaps I will feel differently if someday I'm no longer the majority shareholder? (my partner is vesting in over time, so I am still the majority shareholder by quite a bit..)
But it's probably good that it's her; we have a lot of shared values and cultural background, and ultimately I see her as a good person, so while she's probably not the best businessperson available, she might be the best at working with me.
>I simply weigh the downside to any decision vs. the upside. It's almost automatic. After a while your brain just works that way.
Yeah, but almost nobody weighs moral concerns as zero. I mean, for an extreme example, you wouldn't murder someone for money even if you were certain you wouldn't get caught, and wouldn't face any negative consequences save those you imposed yourself.
(I'm not claiming that 'sharp' business practices are anything like murder; I'm just pointing out that you have the same line I have, even if yours isn't quite in the same place as mine. Almost nobody does a pure cost benefit analysis with no ethical or moral overlay.)