I was always curious about this too. Sam Altman sold Loopt for less than all the funding he got, and yet he still says in multiple places that he was able to pocket a couple million.
The Loopt deal seemed sketchy from the get go. And was one of the first concrete tangible things that made me start to think YC isn't much different than the rest of Silicon Valley in not being a meritocracy, the opposite frequently.
Loopt was effectively dead in the water when it got bought. It was a geo location app. But it got bought by Green Dot. A frequently despised (look at their reviews) finance/prepaid card company. Loopt and Green Dot happen to share connections like Sequoia. Once Loopt is acquired, nothing is done with it. Or its tech. I highly doubt they would want to spend $40M+ to acquihire however many people came over, and not even the founder. Unless Sam did?
I hate turning this into a rant, but YC's treatment of Maciej [Cegłowski]/Pinboard and the way they took back their word..eh I could say harsher things, but I'll regret it. But their handling of the community supposedly choosing a few people for F3 last year was not cool. YC seemed just like the rest of SV. https://news.ycombinator.com/item?id=11633270 is an example of the incident.
That makes me think even more firmly that the Loopt deal was done by connected people exchanging hand shakes and favors.
