Simulated Sports & E-Sports ... two things that I have zero interest in now, but 25 years ago I was involved in some iteration of the two.
I was in college in the mid-90's. Video games were exploding in popularity, especially among young college kids with nothing but a shit ton of time on our hands. I sucked at video games. So instead of playing them, I handicapped them. I created Madden Leagues, set matchups, made lines and booked the action at -120. Even offered insurance on their bets.
In most cases students would play the games, in some cases we ran simulations.
I should have recognized the potential.