He doesn't sound like he is interested in startups. He has a kid, a big time draw, he says he is going to work 20 hours a week contracting on the side, a big time draw, he wants expensive benefits, a big money draw from the company hurting its runway and making the founders waste time fundraising more often, he gets told he can take unlimited vacation yet decides he'll still hold them to the 15 number, so the extra freedom you get at a smaller younger company isn't even used by him, he says he is saving up for a house, a big distraction from just paying for food and rent, etc..
Someone scrimping and saving every penny and working a side job is not going to grab some hardware that helps them work, or take a cab when they need it to get to an important meeting, or work overnight, etc. they are going to scrimp and save and be less effective and clock out ASAP each day to do their contracting or spend time with their kid.
It doesn't really surprise me that he then considers joining a C round company the same as joining a freshly funded YC company and that he thinks both will just sell to a talent acquisition. And that he doesn't think a smaller earlier company gives him a lot more independence and control over what happens to the company. You can find a lot of founders who definitely will not go for a talent acquisition, which you would do if you are going for a big win. And joining a later round at the same equity means much less upside for the big win. You aren't going to be part of as many big valuation increases. But if you aren't putting a lot into the startup and are spending time on kids, contacting on the side, saving up for a house, I kind of doubt you are going for a big win at your company anyway.
It's OK if you aren't going for a big win, but should you join a startup if you aren't? Should you say joining a startup is a bad idea when you are intentionally making all the choices that make it a bad idea? I don't think he's really in a position to even understand the cost benefits of more cash/benefits vs. more equity and more runway and better startup performance since he doesn't care about the startup's performance, so of course he prefers more cash/benefits.
Someone scrimping and saving every penny and working a side job is not going to grab some hardware that helps them work, or take a cab when they need it to get to an important meeting, or work overnight, etc. they are going to scrimp and save and be less effective and clock out ASAP each day to do their contracting or spend time with their kid.
It doesn't really surprise me that he then considers joining a C round company the same as joining a freshly funded YC company and that he thinks both will just sell to a talent acquisition. And that he doesn't think a smaller earlier company gives him a lot more independence and control over what happens to the company. You can find a lot of founders who definitely will not go for a talent acquisition, which you would do if you are going for a big win. And joining a later round at the same equity means much less upside for the big win. You aren't going to be part of as many big valuation increases. But if you aren't putting a lot into the startup and are spending time on kids, contacting on the side, saving up for a house, I kind of doubt you are going for a big win at your company anyway.
It's OK if you aren't going for a big win, but should you join a startup if you aren't? Should you say joining a startup is a bad idea when you are intentionally making all the choices that make it a bad idea? I don't think he's really in a position to even understand the cost benefits of more cash/benefits vs. more equity and more runway and better startup performance since he doesn't care about the startup's performance, so of course he prefers more cash/benefits.