Short excerpt from a James Sinclair YouTube video advising startup founders not to accept investment from difficult or disrespectful investors. Sinclair warns that accepting such investors causes long-term harm (they remain on the cap table and compound problems), and that founders often later regret specific investor relationships.
Chapters
You are a startup founder and you're raising money and the person you're raising money from is a prick. Run as fast as you can. I get it. The way you're thinking it is, I'd rather have 1050, 100K from a prick than no K from no one. Money solves problems. Money solves everything. I know you're going to tell me you have drag along proxy suppression. I know you're going to tell me that you can manage them. I know you're going to tell me that at least when you get going you'll have money and you'll be able to deal with it down the line. You cannot if the person you're talking to is being unreasonable or onerous in their requirements of what they're asking you to produce. If they aren't giving you the same respect that you're giving them, if they don't treat this like an equitable relationship, they are getting as much from you as you are getting from them. It only compounds and you can never get them off your cap table. You ask any successful founder what they regret the most and they'll just tell you a name. Good luck.