earnesti parent
I'm not sure that VC's will be investing in the company of a failed entrepreneur. At least something should have changed to make the company "better". In Gumroads case the truth was that the money would be pretty much gone, the company is not going to be valuable. He didn't raise this time from VC's, but from clueless retail investors, which is quite a different thing.
As a strong counterpoint, Adam Neumann lost $16B of Softbank's money and walked away with almost a billion of it himself personally. [0]
He later raised 350m from A16Z[1], so this is not universally true and in fact is a pretty big counterpoint. Adam Neumann is about the worst founder you can fund (Maybe SBF is worse) and can still command vast sums from top tier VCs.
[0]https://www.calcalistech.com/ctechnews/article/a8vuka5hj [1] https://www.google.com/search?q=adam+newman+new+company+fund...
As best I can tell VCs largely attribute their 99% failure rate to largely random chance rather than their own inability to pick winners - so the failure of an entrepreneur is not a particularly strong mark against them and a weaker mark than the fact they got funding in the first place.
> I'm not sure that VC's will be investing in the company of a failed entrepreneur
Andreessen Horowitz has entered the chat with a $350M check for Adam Neumann