[neltnerb]

It gets messy when the other poker players are your mentors and family whom you love and respect, when the money is real, when the amounts to you feel enormous (whether they matter to the investor is a different story), and when losing carries unpredictable emotional and social consequences. And when mentors and family do it you are probably their only bet. It feels like betting other people's money and I totally get how that's a psychological hangup to feel that it is wrong.

I am not being sarcastic or flippant in this, it limits me to not be willing to take advantage of the risk/reward system, but it's somehow deeply tied into my ethics in ways I didn't even really notice until my second startup. And I'm okay with that limitation, but I'll work through it sooner or later and regain my appetite for risk.

Aside from that, many people despise thinking this way about their work. Like me, even though I'm willing to do it. I've met founders who loved negotiation. Like I swear they must have been nightmare children. I hate negotiation, I want people to treat each other fairly and will stick with a good human that does so forever. I suspect those people don't mind ripping off family and friends, much less strangers. It is harsh, and I've seen things, but anecdotes aren't statistics, and that's a huge obvious red flag to me. If the leaders like to do internal negotiation games I just want out. It's just painful to have to deal with being around when you just want to make stuff work.

It's important to talk about ahead of time, and get in writing, but that's also something easily overlooked among family and friends who do not do this kind of thing much. And the downsides need to be honest and clear to avoid mistrust.

Now, after working at two startups and starting three, my third is a consulting company that exclusively does things hourly except in very special circumstances. It's never going to grow fast because it scales as my hours of labor. But I am way more able to pick a price for my labor than decide how to price something that I haven't done yet. I could figure it out, I just kinda don't want to. For now?