We don't often have the chance to see into pro skaters' family lives. Besides the familiar story of pros leaving home in their teens or growing up in rough situations, disconnected from their families, a lot of pros just don't want to publicly share their families. (Trust us, we've tried.) So we were excited when Eli offered to let us tag along with him and his mom for a day and ask them embarrassing questions about their mother-son dynamic (including her reaction to Eli skating the Playboy mansion). Eli's mom, Joan Ryan, is an accomplished artist and teacher at the Art Institute of Boston. She's made graphics for Eli's former clothing brand and his current board brand Becky, and they've collaborated on legit paintings and artwork as well. Watch for a glimpse inside Eli's new place in Manhattan and to see some of Joan's artwork at the Townley Gallery in Tribeca. It's one thing to see a pro produce boards with scantily clad women on them, but finding out that his mom paints some of those pin-up graphics is way more interesting.