Usain Bolt is a Jamaican sprinter who ran a time of 9.58s, with an average speed of 23.35 mph. Damn, that’s fast!

In this line, the “cool shit” is the songs coming from other rappers, while the “nerd shit” is his own music. He’s saying he’ll make their music lame and his music cool

Like Lupe, President Obama is also from Chicago. .

Often referenced in his catalogue, “Chilly” is Lupe’s friend and co-founder of his record label, First and Fifteenth. He was sentenced to nearly 50 years in prison after being busted for carrying 6 kilos of heroin

Anthony Kiedis is the lead singer of the band Red Hot Chili Peppers

Enemy of the State, the mixtape on which this song is on, is free

Also relates to the theme of this song/verse, many of the references in this song are referring to school, financial aid application is usually done during senior year of high school to prepare/pay for college.

Very clever metaphor. To not be able to bring something to one’s court means that you cannot compete with them. A subpoena is mandated court appearance, as a witness or otherwise

This also still refers to the school references that he has been making in the previous lines. His says his name is on the arenas, and one type of arena is a basketball gym, with a court. If his name is on it, the court “belongs” to him.

Lupe is the explains that he’s the “dean” of the school of hard knocks. A dean is “a person with significant authority over a specific academic unit, or over a specific area of concern, or both”

Lupe could also be referring to the Islamic term, Deen. Which translates in to “religion”, but also refers to the path Muslims follow to stay on the righteous path. So, it’s another double entendre

OR, a reference to the song “Hard Knock Life” by Jay-Z, because Jay-Z was the one that helped sign Lupe and put him on the map.

Using the metaphor of a car race to explain that he’s always a winner, while the opposition is always sitting in the pit stops. This could mean that the other rappers are always resting, or it could mean that they’re so far behind, that they won’t catch up

Referring to the movie Bill & Ted’s Excellent Adventure, in which a guy from San Dimas, California creates a time-traveling phone booth to go back in time to ensure the formation of the band “Wyld Stallyns”

From the movie The Machinist