October 23, 2025

Ryan Sheckler: I Could Have Done More with That Million | Forward Progress

Skateboarding and reality TV star Ryan Sheckler reflects on his evolving relationship with money, including earning his first $100K before he could drive and “wasting” more than $1M with material things like bottle service, penthouse suites and private jet flights. Sheckler also talks of current business interests, including Sandlot Times, Palm Springs Surf Club and a potential deal involving a chain of tattoo shops.

Also available on Apple Podcasts ↗