Your pushback = really good point. Personally, I wouldn't recommend that anyone tries to raise $25-$50k, as their odds of hurting a really good relationship will be at about 99%...but I understand what you're saying.
My advice is that if you are thinking about raising under $500k, or only raising money from family and friends, just go through the struggle as a bootstrapper. You'll learn a lot more and probably get further than you would with the friends and family money. Plus you'll still have a place to crash and be welcomed to a warm meal from time to time, if needed.
Of course I say this as someone who was never able to raise capital. So, my bias is what it is. I'm a bootstrapper. Good luck, Rand - wishing you the best!
> If you really don't want to raise money from outsiders, just don't raise money.
This sounds like it’s perpetuating a false binary between VC and bootstrapping. This probably works in VC‘s favor, but not individual founders’ (on average).
PS - Basecamp is another ex of a tech co that raised money from non-VC investor(s) (Bezos) who got dividends—not a payday on an exit.
My only concern would be: is this a one-off use product?
Perhaps if there was a sort of simple CRM to track relationships with influencers, it would make me come back more