How To Turn Being Unemployable Into a Career with Anthony Wynkoop

Sky King's Mental Playground · Oct 8, 2026 · 1h 2m

Anthony Wynkoop might be the most talented unemployable man in Austin. He's a stand-up comedian who rapped his way through Kill Tony, a musician making everything from indie rock to murder rap, and a hibachi chef who somehow turned cooking fried rice into 90 minutes of crowd work. Now he's stepping into a leadership role in San Francisco, despite admitting he's never held a job for more than a year. Anthony and I unpack the chaos of building a life around multiple creative pursuits instead of one conventional career. We get into the nerves of performing on Kill Tony, the strange money flowing…