Leo Barry was everywhere during AFL Grand Final week this year. With a Sydney Swans scarf draped around his neck, you could be mistaken for thinking he is employed full time in the club’s marketing department.

In truth, Barry always has a lot on his plate. From the moment he was drafted by the Swans, he has been on the run. The Swans relocated him to Sydney, placing him in boarding school out of the limelight of Melbourne. Soon enough, he cracked the big time, becoming a premiership player and an All-Australian defender.

But away from the football pitch, “Leaping Leo” was preparing for his next career. A career that has ultimately led to him part-managing some $500 million in funds across the ASX small cap universe.

In this edition of Success and More Interesting Stuff, Leo and I discuss what happened next and how he transformed himself from a football legend to a finance superstar.

TIME CODES

0:00 - Intro1:54 - Move from football to finance6:53 - Early life14:22 - Lessons from a career at the swans24:05 - Beginning of career in finance33:36 - Lessons from a career in finance47:40 - Future of Leo and Fairview51:21 - Outro