It's clear that DHH has some bias against success.
Quite on the contrary I and many others think of him as extremely successful:
Profitable since year 2 IIRC
Have built nice products that you can pay for by money (instead of by privacy)
Well known for a certain web framework that 100 000s of developers use and many love.
I'd even go so far as to say he influenced (not shaped though) our entire industry by showing how web development should be done in a world filled with ugliness like: old enterprise Java, old Spring, old Asp.Net webforms, old PHP etc.