I'm pretty sure this is a do over story, but it involved a guy who developed a network of rest stops and trucks that simplify trucking in the US. He was in college at a young age as well. There was a chicken and waffles restaurant in each rest stop as well.
Hindsight 20/20 Book 1 by SmokinDriver?
The series is right, but it was book 2 that the chicken and waffles were introduced.
Definitely a good series and well worth reading.
There are three stories with the protagonist and one from an associated character.
https://storiesonline.net/series/1047/hindsight-20-20
