I don’t see that takeaway at all. He didn’t fail because of lack of money. His life is not worse due to spending his savings. He still has a highly valuable skill set and can easily replace that with 1-3 years of working at a company.
If he has $500k, spent $20k living cheaply for a year, I’d bet he would be in a similar position that he is in now and choose to re-enter the workforce after a year of failure.
I think if he had started with more savings, he would have been less bitter about the failure. He still would have been able to take his girlfriend out for dinner.
This complaint made no sense to me. What was his girlfriend doing? Why does she rely on his largess to go out? Is she also a failed indiehacker, or was she using her own income to cover rent and all shared expenses? I think it's irresponsible to take a big risk with someone else's finances, and becoming bitter as you lose that gambit just makes you seem out of touch with reality.
If he has $500k, spent $20k living cheaply for a year, I’d bet he would be in a similar position that he is in now and choose to re-enter the workforce after a year of failure.