Ep. 024 – Travis Robertson – Taking More Swings Before You Feel Ready

This episode caught me off guard.

Travis Robertson has done things that are, honestly, a little intimidating. Not just successful creative intimidating but hey-I-watched-you-in-movies-as-a-kid intimidating. The kind of stuff that makes you wonder if you’re qualified to be in the room.

So yeah, I was a little nervous.

But less than a minute after meeting him, it felt like talking to an old buddy.

And as we talked the cool stuff he's done Travis kept talking about how he just… tried things.

He wanted to be in movies. He saw an ad in the back of the newspaper. Faxed in an audition (which already tells you how long ago this was). Months later, it worked. No sacred path. No years of training under a master. Just a willingness to take a swing.

And once you hear that, you start seeing the pattern everywhere. Acting, fighting, and founding his own creative agency. Same underlying belief every time:

This is figureoutable.

What made this such a great conversation wasn't how impressive Travis is (although he definitely is impressive), it's how human he is about it. Self-deprecating. Curious. Not precious about his wins. Somewhere along the way, the intimidation faded and turned into permission.

The big takeaway was: most of us don’t try enough stuff.

Here’s some of what we talk about:

• Why trying things beats waiting to feel ready
• How early wins quietly change what feels possible
• Letting go of linear career stories
• Hiring for taste and curiosity (not perfect résumés)
• And yeah, we talk some about AI (is it even possible to avoid these days)

If you’ve been telling yourself stories about who gets to do meaningful work, this episode is for you.

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Brad Woodard

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

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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