About Video

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

CHAPTERS

00:00 – Intro

02:15 – Selling insurance at $11/hour and hating every second of it

06:30 – The longboard shop, the first sale, and 250 drop shippers

12:45 – Princess dresses from China ($7K wire to a stranger)

17:00 – The hoverboard deal that should've made $1M each

22:30 – Getting on American Ninja Warrior

28:00 – From backyard obstacle course to the world's largest ninja gym

35:15 – 4,000 people on opening day

40:00 – "I will never sell this business as long as I live"

43:30 – Free Play app and raising capital

47:00 – The hardest moment of his life

52:00 – Progress is the key to happiness

55:00 – How he stays stress-free as a serial entrepreneur

58:00 – Q&A

#entrepreneur #startups #ninjawarrior #americanninjawarrior #businesslessons #serialentrepreneur #smallbusiness #founderstory

Timestamps are estimated from transcript flow. Swap to actual timecodes before publishing.