In this episode, Brad and Dustin delve into the true meaning of risk and why most creatives have it completely wrong. From quitting safe jobs to launching businesses with no guarantees, they unpack what actually makes something risky.

Brad shares the story of nearly getting knocked out of the game after a big risk went sideways, while Dustin breaks down how false safety in traditional jobs can quietly wreck your career.

Stick around as they talk about risk mitigation, building a creative runway, and the underrated power of placing lot's of small bets.

Whether you’re dreaming of quitting your job or just feeling stuck, this episode will shift how you think about risk, and maybe what’s actually holding you back.

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Brad Woodard

Brad is an illustrator and designer behind Brave the Woods, a full-service studio working with clients like Nickelodeon, Target, USPS, and NASA. His bold, playful style and heart-led storytelling shine through everything from brand campaigns to children’s books.

View Brave the Woods

Dustin Lee

Dustin is the founder of RetroSupply, a shop for retro-inspired brushes, textures, and digital tools used by tens of thousands of creatives — from indie artists to major studios. He shares what it’s really like to run a creative business while keeping it small, weird, and intentional.

View RetroSupply

Credits

Audio/video editing: Clara Wright
Cover art: Brad Woodard
Intro animation: Seth Austin
Intro music: “Snakes and Fire” (Instrumental) by Pär Hagström