zlacker

You are correct, failing upward was the wrong word choice once I realized Loopt didn't crash and burn but actually had a ho hum exit. Definitely not a 'failure'.

If I could, I'd rephrase my question of what makes him stand out from all the other thousands of people who have sold companies for ~10m net? From an outside perspective it looks like the biggest success of his career pre-open AI was getting PaulG to like him a lot.

Hence why I'm asking if others can vouch for him being brilliant or something.

>>VirusN+(OP)
"Failure" is still a fair description. Companies that raise that much money usually don't collapse outright. Instead the investors engineer an exit, partly because it returns some money but mostly because it looks better and solidifies relationships both with founders and acquirers.

sold companies for ~10m net

We don't know the exact numbers for this particular case, but you can be sure people lost money. Raising $30m doesn't mean the company was valued at $30m; it means the company was valued at much more. For example if you took $30m in a typical Series A round you'd be valued at $150m. If you then sold for a third of that...