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

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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

When we sat down with Ilana Griffo and Katie Johnson of Goodtype, we expected to talk about typography, online education, and what it’s like to run one of the most recognizable brands in the creative space.

And we did.

But there is so much good stuff underneath that. Funny, inspiring stories and philosophies that will change how you think about your creative business.

In this episode, we talk about:

• How Goodtype grew from an inspiration account into a thriving creative business. Prioritizing what felt like it would bring joy, simple experiments, and the first hires that leveled up their work.
• Why chasing every platform, trend, and opportunity isn't good for anyone. Sometimes it feels like Goodtype is everywhere, but the secret is actually how Ilana and Katie learned to simplify.
• How to define success on your own terms. The phrase has become a little empty but these ladies are doing it by balancing ambition, fulfillment, and work that still feels magical after it becomes your job.

Whether you’re just starting to build your creative business or in the messy middle, trying to figure out what to do, you'll love this episode. Get ready for a conversation full of laughs and a reminder that there isn't a right way to do it.

ABOUT GOODTYPE

Goodtype is a creative education platform, design studio, and global community for lettering artists, designers, and type enthusiasts. Led by Ilana Griffo and Katie Johnson, Goodtype provides courses, events, resources, and inspiration designed to help creatives build meaningful careers doing work they love.

Follow Goodtype on Instagram

Visit Goodtype online

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 episode, we sit down with designer, illustrator, and longtime Creative South community member Jeremy Slagle to talk about building a creative career by following curiosity wherever it leads.

From raising two graphic designers under the same roof to turning a pickleball obsession into real client work, Jeremy shares how some of the biggest opportunities in his career came from personal projects, side interests, and ideas that initially seemed too small to matter.

We talk about the value of creative communities, why portfolios should be filled with real work instead of just class assignments, and how pursuing the things you're genuinely excited about can open doors that strategic career planning never could.

Jeremy also shares his perspective on parenting creative kids, the lessons he's learned from more than three decades in design, and why showing people what you want to be hired for is still one of the most powerful career strategies available.

Along the way, we discuss Creative South, remote work, building expertise through passion projects, and the surprising connection between pickleball and creative entrepreneurship.

About Jeremy Slagle

Jeremy Slagle is a designer, illustrator, and creative director with more than 30 years of experience helping brands tell their stories through thoughtful design and illustration. Based in Columbus, Ohio, he's also an avid pickleball player, longtime Creative South attendee, and passionate advocate for creative community, mentorship, and lifelong learning.

Follow Jeremy on Instagram

Check out Jeremy's website

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

For years, Lenny Terenzi built the kind of creative life designers dream about.

He ran a beloved studio and screen printing shop, taught workshops to hundreds of creatives, spoke at conferences around the country, helped build creative communities, and created work that genuinely impacted people’s careers and lives.

And yet underneath all of it, he secretly felt like he was failing.

In this episode, Lenny opens up about discovering later in life that he had been living with ADHD his entire adult life and didn't know it.

Plus, how that realization completely reframed the way he viewed his career, relationships, burnout, creativity, and self-worth.

“I was fighting a war that I never knew was declared on myself.”

This sentence hit Brad and I hard (and I suspect it does a lot of our listeners as well).

We talk about the hidden ways ADHD can show up in creative lives: unfinished ideas, difficulty crossing the finish line, tying your identity to your work, burnout disguised as laziness, and the exhausting cycle of feeling capable of more while never understanding why certain things feel so impossibly hard.

But this conversation is also about an important reframe of how we define success.

Lenny reflects on shutting down Hey Monkey (the studio and workshop space he spent years building) and why he no longer sees it as a failure simply because it didn’t become a forever business.

Over the years, the studio taught hundreds of people how to screen print, launched careers, created friendships, inspired other studios, and gave people a place to belong creatively.

And maybe that counts for something too.

This episode is for anyone who has:

• Struggled with burnout or creative exhaustion
• Wondered if they’re “lazy” or broken
• Tied too much of their identity to their work
• Felt ashamed of a business, project, or career pivot
• Almost without knowing it, gauge success purely by revenue and profit

It’s an honest conversation about creativity, ego, reinvention, mental health, and learning that the value of the things we build can’t always be measured on a spreadsheet.

Sometimes a project changes your life even if it is not an indestructible empire.

About Lenny Terenzi

Lenny Terenzi is a designer, illustrator, creative director, educator, musician, and longtime creative community builder based in Raleigh/Durham, North Carolina. Known for his bold visual style and irreverent approach to creativity, Lenny has spent decades helping brands and creatives embrace personality, craft, and experimentation.

Follow Lenny on Instagram

Check out Lenny’s website

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 episode, we sit down with legendary illustrator Orlando Arocena (Mexifunk) to talk about building a creative career by leaning into the things other people run away from.

While most designers saw Adobe Illustrator as limiting for hyper-realistic illustration work or something to outsource, Orlando saw an opportunity. He spent decades pushing the software far beyond what people thought it could do.

Eventually, he became known for his coveted work with major films, entertainment brands, and some of the most recognizable vector illustrations in the industry (lots of movie posters look Photoshopped, but they're actually vector, insane, I know).

Along the way, we also dig into highly actionable insights like:

• Why specialization can become your biggest advantage
• The hidden opportunities inside unpopular tools
• What decades of creative work taught Orlando about standing out
• How to build a career around curiosity instead of trends
• And why “breaking the rules” sometimes just means paying closer attention than everyone else

If you've ever wondered whether your weird interests, niche skills, or unconventional path could actually become your advantage, then buckle up because this episode is for you.

(And yes… somehow we also start with colonoscopy stories.)

ABOUT ORLANDO AROCENA (MEXIFUNK)

Orlando Arocena is a Mexican-Cuban-American artist and creative strategist known for his bold, highly detailed vector artwork. A 13-time CLIO recipient and 2025 Emmy Award nominee, Orlando has worked across film, pop culture, gaming, and brand storytelling, bringing more than 30 years of creative experience to his distinctive style.

Follow Orlando Arocena on Behance and 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