About Podcast

The guy sold longboards, princess dresses, tungsten rings, and hoverboards out of the same warehouse. Then he built the largest ninja warrior gym in the world.

Wally Roskelly has been on American Ninja Warrior three times, took first place Masters gold at the World Ninja Games, and has started more businesses than most people have had jobs. He sat down with Stu at a live retreat recording to talk about all of it — the wins, the near-million-dollar hoverboard disaster, and why he says he'll never sell his gym even at breakeven.

What he covers:

→ Quitting an $11/hour insurance gig to start his own agency (same product, completely different feeling)

→ How he spotted a supply-and-demand gap in longboards and turned a bedroom full of 100 boards into a fulfillment operation with 250 drop shippers

→ Wiring $7,000 to a stranger in China for princess dresses. They sold out in two days.

→ Ordering $450K worth of hoverboards, watching the second container get stopped at the California port, and making about $4,000 total on the deal

→ Getting on Ninja Warrior (90,000 applicants, 600 spots) and building a backyard course that turned into a real gym

→ 4,000 people showing up on opening day of a gym that didn't have a single ad running

→ His obsessive market research process — including months of sitting in competitors' parking lots counting foot traffic

→ Why community and belonging drive retention better than any marketing you could run

→ 1,003 pull-ups in 5 hours at age 45 (nearly double David Goggins' pace)

→ The adoption story he rarely tells publicly

CONNECT WITH WALLY

Instagram: @wallyroskelly

CONNECT WITH STU

Instagram: @stu

Website: https://startupswithstu.com