Across 5 funding rounds, Crunchbase lists Loopt as having raised $39 million and then was acquired (acqui-hired?) for $43 million. He didn't create any multiples of value for his investors. Loopt wasn't a breakout hit like so many other YC startups have been. It was certainly one of the first interesting location-based apps in the App Store, but soon was surrounded by other location-based apps and never really appeared to surface and gain traction.
Obviously Sam runs YC now and has dramatically improved it, but in the lens of being an entrepreneur, isn't he still essentially unproven, and not a success story in the startup world?
A lot of "heroes" in this world are fairly fraudulent. Worse, some went from young tech luminaries to older VC sharks with questionable ethics like Mark Andreeson.
I think coding and tech, in general, is mostly a meritocracy, but on the business end its practically the lottery. Right time, right place and other luck of the draws determine financial success just as much as the merit of the product, if not more so.