Almost everyone I've seen has thought that Starswirl was Celestia's protege, like Twilight. However, except for a short line by Luna, we have no reason to believe to two ever met. For one thing, the Royal Sisters weren't ruling the ponies at the founding of Equestria, they weren't even mentioned during to play. Therefore, it can logically be assumed that they hadn't been born yet. At the same time, Starswirl already had a GRADUATED APPRENTICE with a job TEACHING. Assuming ponies have the same standards as humans, Starswirl was at least 14 when he taught Clover the Clever, for that is when beards long enough to be notable grow, and he was already known as "the Bearded". Based on Twilight's time as an apprentice, it takes at least 7 years to learn magic, so Starswirl was at least 21 when Equestria was founded. However, a genius like Starswirl would likely have attended some sort of university, putting him closer to his late twenties. Then of course, logically, even a genius doesn't receive an apprentice without several years of experience, most likely putting him closer to 30. And of course, it is likely the life expectancy was lower back then, as it was with humans. Making that about half of his life time, before Equestria was even founded.

3159856 Also remember that even with lower life expectancies, it was still possible that some (very lucky) people could still live up to 80 years. Therefore, Starswirl could have been one of those who lived a long life.

3159987 that's why I said about.

Well according to the latest episodes of MLP. ===Spoiler Alert=== I'm assuming everyone here saw the Season4 Finale.

In that episode we can see a shot where Scorpan, Tirek's brother befriended Starswirl the Bearded. And learn to love the land of Equestria. And afterward he went to Celestia and Luna who banished Tirek in Tartarus. For this to be possible Starswirl and Celestia must lived along side each other. Now this does not necessarily mean they knew each other personally. But you know food for thought.

3433429 don't forget though, Tirek is millennia old, so what would stop Scorpan from sticking around for a few centuries?