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?
My belief is that there's a large chunk of building a company that I will never learn or understand without becoming a founder myself. Maybe that's 50% of success. However, for the other 50%, I can actually learn things better than many founders because they have a sample size of one or two or three startups that they have started, while I can look across fifty or a hundred companies that I am intimately involved in and analyze what is different between the ones that become huge and the ones that do not. I think this cross-sectional pattern matching is what makes a lot of VCs and investors sources of good advice (in some startup topics) even though they might not have built huge companies themselves.
Maybe that's 50% of success of being a football manager. I can learn more than other football managers because I can watch lots of football games on Sky Sports.
That's why many top premiership teams hire their managers by finding the people who watch the most football games on TV.
EDIT: I'm sure there's plenty here who have been in more startups than me, but in the 4 or so I've been in, I've heard conversations between founders and investors plenty of times.
Often little of what comes out of the founders mouth is based in reality. Sometimes they're not seeing reality as it really is, sometimes they're painting a rosier picture, sometimes they're outright lying, sometimes they're tired and not thinking straight, sometimes they've got obsessed by something utterly irrelevant. Sometimes they're not actually listening to the staff, or not even asking the right questions.
As a VC or researcher or whatever, you're not actually playing the game. You're not on the team, you're not on the field, you're not even on the side-lines. You're seeing a different game than's being played.
I think it's actually the opposite: if there's a good founder/investor relationship, the investor is an extended part of the team, is sometimes on the field (helping close job candidates or doing customer intros), and is often trying to help from the side-lines. Not all founder/investor relationships are this good, but some are.
To use your analogy, the founders are football players, and investors are somewhere between "football fan" and "football coach", but probably a lot closer to coach than fan. It's true that neither coaches nor fans are actually on the field playing the game, but coaches have way more insider info. For example, they watch players practice and have a deeper understanding of what each player can and cannot do, they know which players might be nursing injuries, how to motivate different types of players, etc. That doesn't mean a great coach could be a great quarterback, but I think lots of players would agree that a great coach knows a lot about how to become a better football player despite not being a football player themselves. (And to extend the analogy, I think coaches are good at helping players improve despite the fact that some players might lie or make excuses or paint rosy pictures or whatever.)