A few comments:
1) The PhD takes a huge hit on your opportunity cost.
2008-2014 is 6 years of time; for me, it was the delta between starting my career as a junior engineer and becoming a tech lead at a hot unicorn which let me pivot to a CTO role at a small startup.
2) Academic credentialism has real effects.
This guy did a CS degree at an Ivy in the US. He has been set up for commercial success in the US tech industry through a halo effect you cannot also access unless you gained access to that institutional grooming at the same age. By choosing to do that PHD in EU (and a no name one at that), you forfeited that access.
In my experience, while the effect of this goes down over time, it has extremely strong launch + early compounding effects.
3) Risk tolerance can work to your benefit or against it.
You are working at a FAANG which is the safest and most cash lucrative option. In all likelihood, you have a great WLB and now a great blue chip brand on your resumé. However, the cost of this is that you're generally not going to get access to projects or culture that, by virtue of your participation, set you on an extremely steep growth path.
To get access to that, IMO, there's no real alternative to achieving strong outcomes working at a startup. Of course, that can be hard to do -- how do you figure out which ones are future winners, and how do you get them to let you come on board? I have no great answer rather than early career trial and error (accepting some of it will work out poorly and uncomfortably so).
I wouldn't say that "OP is a beast" per se, but it's much more likely that they have been groomed (working in the right conditions) in ways that you may not have. And yes, startups titles are not comparable to big company titles. It's apples and oranges.
The company he joined is a Series A startup, so absolutely an early stage company where whether you're VP/CXO, you're functionally going to be doing a player/coach role at most with tons of strategy baked in. But I wouldn't call that inflation, per sé. Sure, it's not the equivalent of being an experienced people leader and executive at a big corporation manning a giant organization at its helm. But you are often times in charge with significantly more responsibility and do not have bureaucratic friction and slow pace to hide behind. Doing a startup is just different. It's insanely risky, overall has poor risk adjusted rewards, and often is a magnet for shady characters. But if you can filter out the wheat from the chaff, you get access to the best career opportunities available, bar none.