Start up a Dynasty and select your Alma Mater as a decent 5 or 6 star team (I choose Ohio State). Make sure you select a head coaching job for the same team that you set your Alma Mater as. To make this achievement a lot easier and less time consuming, I recommend creating a custom schedule and scheduling some games with lower-ranked teams.
If you choose to simulate, make sure you have Autosave turned OFF. This way if you lose when simulating you can always revert back to the old save and try again. Continue through the season and win the BSC bowl to unlock the achievement.