"The second lesson of greatness - work your butt off," he said. "In Jamaica, there's a saying - you have to have 10 jobs. One job - you're lazy! Two jobs - you're shuffling now."
Ashley, who has been playing chess since he was 8 and studying the game since he was 15, recalled his failures leading up to the 1991 game that earned him the title of International Chess Federation grand master - one of only more than 1,500 in the world.
"It was the culmination of everything - all the sacrifice, all the hard work, all the love I had received," he said of the seven-year effort that included 24 official games.
Ashley, an author and ESPN commentator, spoke to chess teams organized by the nonprofit After School Activities Partnerships, which is dedicated to engaging students in extracurricular activities, such as chess, debate and Scrabble, as a way to boost academic achievement.
Following his talk, Ashley challenged the players to chess puzzles using his app, Pawn Mower. The app formulates arrangements of pawns for different pieces - such as the queen or a knight - to take out, with the end goal of clearing the board. He projected the app's board from his iPad onto a screen behind the stage, calling individual players to take on Pawn Mower.
Alyssa, a sixth grader at William M. Meredith Elementary School who rapidly solved one of Ashley's pawn puzzles, said the grand master's speech motivated her to play more often.
"You can actually learn a lot from it - not just how to play [chess], but life skills," the 11-year-old said. "But it's really more important to just have fun."
Jowel Ammons, an incoming junior at Pennsylvania State University who started playing at an ASAP chess club 12 years ago, said he found Ashley's words "really touching."
"I thought it was empowering to see someone overcome that many adversities and come this far," Ammons said.
ASAP's chess program director, Ben Cooper, said the nonprofit plans to expand its initiative, even as the Philadelphia School District considers decreasing funding for sports teams and clubs.
"Chess helps students slow down and use the decision-making process," Cooper said. "It's another avenue for students to be a part of a team, a group effort."
Ashley called the benefits of playing chess "self-evident."
"It correlates very highly with critical thinking," Ashley said. "It happens on every single move. It's dynamic. It enhances your approach to things."
Ashley plans to increase global awareness of the game by helping to organize, and competing in, the "Millionaire Chess Open" in Las Vegas in October. Top prize is $100,000.
"That's the next step, to raise the profile of the game," he said. "It's my passion."