Stephen Woolsey - be a cockroach: you can survive anything
About Stephen
Stephen Woolsey has built creative agencies, toured Jordan Peterson and Theo Von, and co-founded Pawn & Co, East 9th Brewing, Good Times Tech and Ballers Clubhouse. His operating philosophy, tested by the biggest hospitality lease in Melbourne's history signed four weeks before lockdown: be a cockroach.
Stephen Woolsey has built creative agencies, toured Jordan Peterson and Theo Von, opened one of Melbourne's most talked-about bars, signed the biggest hospitality lease in the city's history four weeks before lockdown, and lost a house and millions of dollars along the way. His advice on how to survive all of it: be a cockroach.
Stephen walks through how a floppy disk and a hungover all-nighter got him through his one and only year of uni, how a chance meeting at Big Brother auditions turned into a 20-year business partnership with Josh Lefers, and how "everything's for sale" became the concept behind Pawn & Co, right down to the grand piano someone bought off the DJ booth. Then comes the harder part: signing the lease on a 2,500 square metre venue in January 2020, watching the brewing business collapse under COVID, and rebuilding while banks called in their money.
He gets honest about what he'd change, what resilience actually costs, and the three life lessons he's learned the hard way: being ruthless about who you surround yourself with, learning to respect risk instead of running on pure optimism, and knowing when more stops being more.
What's covered · 16 chapters
- 00:00Cold open: the cockroach theory
- 00:35Welcome to Life After Launch, introducing Stephen Woolsey
- 04:56Growing up, acting, and learning to love rejection
- 09:16Competitiveness, imposter syndrome, and outworking everyone
- 15:36From Big Dog Creative to touring Jordan Peterson and Theo Von
- 19:46Meeting Josh Lefers and the TV shows that started it all
- 23:39Building Pawn & Co and the story of the $5,000 piano
- 26:39Launching Good Times Tech and East 9th Brewing
- 30:39COVID hits: losing the brewing business, a house, and millions
- 41:16Signing the Ballers Clubhouse lease weeks before lockdown, and building through it
- 55:44Scaling Ballers, Good Times Tech, and the plan to go global
- 1:12:17Building systems, working with AI, and staying frictionless for the customer
- 1:17:23Life lesson 1: be careful who you surround yourself with
- 1:22:11Life lesson 2: respecting risk instead of running on pure optimism
- 1:26:07Life lesson 3: more is more, and knowing when enough is enough
- 1:38:23Closing thoughts + outro