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?
I think I've learned a lot from working closely with entrepreneurs that run massively successful companies that's worth sharing.
If you disagree, no one is making you watch this. You're free to hit the back button.