Creative Slash

Jason Craig is the type of guy you talk to about freelance work, and suddenly it feels like you’re seeing the whole thing in technicolor for the first time.
This episode gets into the parts of freelancing people usually skip over. Cash flow. Repeat clients. Fast little projects that keep the lights on while the big projects take forever to approve.
Jason also talks about why being easy to work with might be one of the most underrated skills in design. Talent matters, obviously, but so does trust, clarity, momentum, and not making every project feel like a hostage negotiation.
And yes, this conversation also somehow includes the shopping cart etiquette conspiracy, stolen grapes, closeout mustard, murals, chicken bones, and the moral weight of paying someone else to fix your toilet.
IN THIS EPISODE, WE COVER:
• Why steady cash flow matters more than waiting around for perfect projects.
• How to turn small jobs into steady income that comes in year after year.
• Why being easy to work with is a prerequisite to building a stable, low-stress business.
• How personality, weird ideas, murals, merch, and community all become part of the work.
If you freelance, run a studio, or feel stuck between taking every job and waiting for the dream one, this episode will feel painfully useful.
ABOUT THE CREATIVE
Jason Craig is a designer, illustrator, mural artist, and speaker based in Augusta, Georgia. His work spans branding, murals, merchandise, sports, restaurants, events, and plenty of strange creative side quests that somehow make perfect sense once Jason explains them.
His big, kind, and authentic personality has made him a staple of conferences and talks across the country (and an essential merch stand stop).
Visit Jason’s website
Follow Jason on Instagram
Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE
Click here to get the five-part “Off the Record” email series
Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.
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.
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

In this week's episode, we talk with graphic designer, illustrator, lettering artist, and all-around creative entrepreneur Dan Lee.
We've admired Dan's work for years. At Creative South 2026, we finally got to sit down with him, and we walked away struck by his optimism about the creative industry, his genuine love for other creatives, and his impeccable style (he was sporting a Westersen hat from Don Clark's western wear venture — see episode 28).
Here's some of what we get into:
How to leave a "safe" career without feeling like you wasted everything that came before it. Dan has a degree in chemical engineering, and his escape route is a masterclass in transitioning to work you love.
The simple journaling practice Dan uses to turn vague creative ambitions into real projects and clear decisions.
The tested secret to steady creative work. It depends less on constantly finding new clients and more on building relationships that make you the easy choice to come back to.
The one habit that makes clients want to keep working with you. And no, it's not being cheaper, faster, or flashier.
The Shopping Cart Problem. The strangely addictive debate we've been having with everyone about putting your cart back. We think it goes way deeper than shopping carts. You be the judge.
It's a conversation about changing direction, finding your people, serving customers well, and building a creative career without waiting for permission — or following the supposedly correct sequence of steps.
ABOUT DAN LEE
Dan Lee is an artist, writer, illustrator, and designer specializing in hand lettering. A Philly kid now based in Sheridan, Wyoming, he earned bachelor's and master's degrees in chemical engineering, then taught himself to draw words instead. He's the lead artist behind moto lifestyle brand Go Fast Don't Die, and he brings an engineer's eye for structure to compositions that run from four words to a hundred.
Website
Instagram
Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE
Click here to get the five-part “Off the Record” email series
Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.
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.
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

This episode features artist, illustrator, greeting card designer, and licensing powerhouse Kate Smith on what happens when you stop trying to make work that looks “marketable” and start making work that sounds, feels, and thinks like you.
Kate talks about building a creative business from her own weird little ideas, emotional instincts, funny phrases, and need to put more joy into the world. 
That deeply personal approach has turned into a massive licensing career, with her work selling millions of units at retail across cards, gifts, products, and major collections, including Target.
But this conversation is not just about selling a lot of stuff. It’s about how personal work can slowly become financial stability, how licensing can create more freedom, and how building a business around your actual point of view can help you live more of the life you want instead of constantly chasing someone else’s version of success. 
In this episode, you’ll learn:
Why making work that is unmistakably yours is not just a creative luxury. Kate shares how her voice, humor, emotional honesty, and specific way of seeing the world became the foundation of a licensing career that could not have been built by copying what everyone else was doing.
How licensing can turn personal work into long-term stability. Kate talks about landing dream retail opportunities, creating collections for major stores, and learning how repeated licensing wins can slowly build the kind of financial foundation that gives artists more room to live, travel, experiment, and choose.
Why success still comes with a “what’s next?” problem. Even after major retail wins, Kate explains how easy it is to move the goalpost, judge yourself by today’s results, or forget to enjoy the thing you once desperately wanted.
Why joyful art does not always come from a joyful place. Kate’s work often says the thing she needs to hear too, whether that’s “even the sun has its ups and downs” or some tiny phrase that makes life feel a little more survivable.
ABOUT KATE SMITH
Kate Smith is an artist, illustrator, greeting card designer, and creative entrepreneur known for her funny, bright, emotionally honest work that has been licensed across dozens of product categories and sold millions of units at retail.
Her work blends humor, vulnerability, color, and sharply specific phrasing in a way that feels unmistakably her. What started as a small greeting card idea inspired by talking for her dog grew into a creative business spanning stationery, gifts, retail collections, licensing, and art that helps people feel a little more seen.
Visit Kate Smith online
Follow Kate on Instagram
Shop Kate’s work
Explore Kate’s greeting cards
Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE
Click here to get the five-part “Off the Record” email series
Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.
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.
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

This episode features illustrator, author, YouTuber, and accidental Adobe Fresco evangelist Chris Piascik on building a creative career by staying weird, making a lot of work, and refusing to turn art into a fake polished performance.
Chris gets into his 14-year daily drawing project, why YouTube changed his business more than Instagram ever did, how his new book The Accidental Illustrator came together, and why being honest about your process is more valuable than pretending everything is effortless.
It’s funny, loose, and full of the kind of creative advice that only comes from someone who has spent decades making art, shipping projects, reading terrible comments, rollerblading aggressively, and somehow turning all of it into a real career.
In this episode, you’ll learn:
Why consistency doesn’t have to mean becoming a content robot. Chris talks about how his daily drawing project started as a simple structure to help him draw more, then slowly changed the entire direction of his career.
How YouTube creates deeper relationships than faster, scroll-based platforms. Chris shares how his channel helped grow his shop, sell more work, and create a community that actually feels connected to him.
Why leaning into your weirdness is not a branding gimmick. From punk flyers and old cartoons to strange characters, rollerblading, toy design, and Fresco tutorials, Chris shows how your odd little obsessions can become the most valuable part of your work.
ABOUT CHRIS PIASCIK
Chris Piascik is an illustrator, author, designer, and YouTuber known for his bold, funny, weird, character-driven work and his long-running daily drawing project. After drawing every day for 14 years, Chris built a career that spans illustration, lettering, products, online education, YouTube, and his new book The Accidental Illustrator.
He’s also one of the clearest voices online for artists trying to make digital illustration feel more natural, honest, and fun, especially through his work with Adobe Fresco.
Visit Chris Piascik online
Follow Chris on Instagram
Subscribe to Chris on YouTube
Check out The Accidental Illustrator
Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE
Click here to get the five-part “Off the Record” email series
Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.
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.
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

This episode features designer, artist, and Piedmont Brand Company founder Brad Stoneking on building a creative life that doesn't run on chasing algorithms, copying trends, or pretending every designer has to be an influencer.
Brad gets into his work under the name Deadtooth, how personal art differs from professional design, why production work deserves more respect, and how years inside agencies set him up to run a small studio doing serious work for big brands. 
It's funny, blunt, occasionally unhinged, and packed with hard-won advice for designers trying to build something real.
In this episode, you'll learn:
Why visibility isn't the same as momentum (and why posting constantly doesn't build a career).
Why print fundamentals and production skills still matter, especially when so many young designers learn software before craft.
How Brad thinks about long-term clients and why the real work often starts after the logo, once you become the person they trust with everything else.
About Brad Stoneking
Brad is a designer, artist, and founder of Piedmont Brand Company, a small studio that helps brands move fast and make useful, well-built work. He also makes art as Deadtooth, where he gives himself room to go weirder, louder, and more personal than client work allows.
With nearly three decades in design Brad brings a mix of craft, experience, humor, and a healthy distrust of anything that turns creative work into performance instead of practice.
Visit Piedmont Brand
Follow Piedmont Brand on Instagram
Follow Deadtooth on Instagram
Join the Creative Slash Newsletter and Get the 5-Part “Off the Record” email series FREE
Click here to get the five-part “Off the Record” email series
Note: If you're looking for hard-earned advice, resources from top creatives, and the products they can't live without, you're going to love this.
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.
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