"If I'm down three with 30 seconds left, is it better to take the three or easier to take the two and attempt to foul a bad free-throw shooter and get another possession?"
The former hedge fund analyst was inspired to create Khan Academy after leading countless math-tutoring sessions with his many young cousins.
As Khan's tutoring began to take over his life, he began posting his explanations of common math and science ideas on YouTube.
Eventually, he dropped the hedge fund job and began working full time in 2009 on what turned out to be Khan Academy.
After $3.5 million in seed money from Google and the Bill and Melinda Gates Foundation, Khan has 37 full-time employees and has produced over 3,500 videos answering questions ranging from traditional algebra concepts to more current topics, like "Why Europe is worried about the Greek debt crisis?"
The Khan Academy YouTube channel has over 212 million views to date.
One of those watching with interest is a certain NBA superstar in Miami.
James has been a Khan Academy regular, asking questions on topics that include the chances of making 10 consecutive free throws and the odds of hitting a 3-pointer versus three straight free throws.
So how did James, who didn't attend college, become interested in Khan's program?
"We got an email from one of the folks in his team saying: 'We want to figure out a way we can work together,' " Khan said. "And he really was curious about some of these questions."
James wanted to use his profile to encourage his fans to learn something new, Khan says. The eight questions currently on the site are just the beginning. Khan says he expects more contributions from the Miami star.
"When he has time, he sends us stuff, and we'll come up with questions for him to pick, too," Khan says. “He said something to the effect of, ‘If Michael Jordan told me and my friends to study harder, we would have, so I’m going to tell kids to study harder.’ This Khan Academy stuff is not going to generate a ton of money or a ton of fame. James is doing it because he genuinely thinks that it’s worth it.”
The academy is looking to branch out into other sports -- they've invited other athletes to submit questions but have yet to incorporate another star like James. Khan hopes we'll start seeing fuel-mileage questions from NASCAR drivers, angle-of-impact questions from golfers or thoughts on when to go for it on 4th-and-short from NFL players.
"We want to do as many of these as we can," he says.
Check out a Khan Academy video with LeBron below: