Creative Slash

The dream we were all sold was going out on your own. Your own clients, your own hours, your name on the door.
But what if freedom looks different once you've lived that dream for a while?
In this episode, we talk with designer and CROP founder Matt Dawson about his first-ever CROP Field Trip to Cleveland, his guitars and records, and a band that sounds like Weezer and the Pixies had a baby. 
Underneath it is a bigger story. After seven years of running his own thing, Matt realized his priorities had changed. He wanted more time with his family, evenings that actually ended, and room to get excited about design again. 
He began to see that freedom can mean a lot of things. Sometimes it's your name on the door. Sometimes it's a steady in-house job, a team that logs off at five, and the choice to say yes only to the work you actually want.
It is part gear talk, part record-store hang, and part permission slip to stop curating yourself.
In this episode, we talk about:
Choosing a day job on purpose after seven years on his own, and why real freedom turned out to be saying yes only to the work he actually wants.
Letting go of the logo-only feed and how posting records and guitars has led to better conversations with clients.
Taking a group of designers on a field trip to Cleveland including a behind-the-scenes tour with the Guardians creative team and what to do with 10,000 bobbleheads that came back not quite right.
A Kurt Cobain Jaguar he hopes to be buried with plus Dustin's Strat versus Silver Sky showdown and why Fender picked now to defend the Strat shape.
A mystery question from Jason Craig that ends with a hotel door, an orange, and a running text thread between two friends.
Whether you're freelancing, in-house, or quietly wondering if your priorities have shifted, this one is a reminder that careers don't run in a straight line. As Matt puts it, you can't lay your career on tracing paper over somebody else's and expect it to match up.
ABOUT THE CREATIVE
Matt Dawson is a designer and creative director based in Austin, Texas, and the person behind Stay Gray Ponyboy. His work centers on brand identities and logo systems, for clients that have included Disney, Jeep, Adobe, Under Armour, the Atlanta Braves, and Toyota.
He is also the founder of CROP, a creative conference he runs with his wife in Austin. For the past decade CROP has brought creative people together, and this fall it added Field Trip, a smaller, hang-out-first event in Cleveland. The next CROP conference is April 29 and 30, 2027.
When he isn't designing, he might be creating something on his Jaguar, playing with his band LCLS, or checking another ballpark off his list.
Website
https://www.staygrayponyboy.com
Instagram
https://www.instagram.com/staygrayponyboy
CROP
https://www.cropcons.com
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

Most of us were told the same thing. Make something every day, share it, and the people will come.
But what happens when you do exactly that for years, the numbers stall, the platforms change the deal, and the thing you love starts to feel like homework for an algorithm?
In this episode, we talk with illustrator, teacher, and author Tom Froese about building a very public career as a self-described introvert. It starts with camera presence and resting dad face, then turns into a bigger conversation about owning your audience, scaling back, and why any of us spend our lives making commercial art in the first place.
It is part career audit, part wardrobe therapy, and part airport-gate conversation that wanders into ghosts, aliens, and faith.
In this episode, we talk about:
Why Tom is pulling everything under one roof after years of spreading himself across Skillshare, YouTube, Patreon, Instagram, Substack, and a podcast, and why every channel now has to point somewhere.
Why he moved his daily drawing practice off Instagram and onto Substack to protect it, especially once the joy started to erode.
Resting dad face, eyebrow pencils, and the plaid shirt uniform and why being on camera means playing a slightly stylized version of yourself.
Why "if you build it, they will come" may not hold anymore including what Tom thinks actually works now, and Dustin's case for owning your list instead of renting an audience.
Aliens, ghosts, and the spiritual realm and a candid conversation about faith, doubt, and doing your work for a reason bigger than money.
Whether you draw every day, quietly wonder if social media is still worth it, or just want permission to make the one-brush version of your thing, this one comes back to a question Tom asks his own students. You're spending most of your adult life making commercial art. Why?
ABOUT THE CREATIVE
Tom Froese is an illustrator, teacher, and writer based in British Columbia, Canada. His work borrows from printmaking, with limited colors, overprints, and letterpress-style texture, and it shows up in maps, editorial work, and picture books.
He is one of Skillshare's top teachers and has taught more than 150,000 students. His book Drawing Is Important: How to Start a Lifelong Daily Drawing Practice came out this spring from Rockport. It is not a how-to-draw book. It is a why-to-draw book.
Website
https://www.tomfroese.com
Drawing Is Important
https://www.tomfroese.com/book
Classes and Drawing Club
https://www.commercialartistry.com
Substack
https://mrtomfroese.substack.com
Instagram
https://www.instagram.com/mrtomfroese
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

Most people see a slackline, a motorcycle, or a recurve bow and think, “That’s not me.”
Chris DeLorenzo sees the same things and signs up for lessons. He taught himself to slackline one summer. He has a motorcycle license he has never used. For a while, he wondered if he was quietly training for the apocalypse.
In this episode, we talk with Chris about his years as lead designer and art director at Johnny Cupcakes, his move into illustration for places like The New York Times, and the 500-foot mural that now greets people flying into Boston. But the real conversation is about curiosity, what happens to it when life gets busier and more settled, and knowing when your work is already good enough to stand behind.
It is part career history, part client-wrangling masterclass, and part three guys talking about French chore jackets for longer than anyone planned.
In this episode, we talk about:
Why you should ask a designer for all their working files and how digging through Clark Orr’s messy Illustrator files taught Chris more than any class.
How Johnny Cupcakes kept everything limited and still made payroll, including the tiered system that split the collectors from people who just wanted a good shirt.
Why the same drawing is worth more on a wall than on a T-shirt and how mocking up the work you want to do got Chris an email from The New York Times.
The time Chris told Dustin the RetroSupply logo was better the first time and why a little confidence in the pitch can save everyone a round of revisions.
Whether drawing flowers is a cop-out, especially when the thing people already find beautiful is the thing you keep coming back to.
Whether you are a designer drifting toward illustration, an illustrator with too many hobbies, or someone who keeps saying “that’s not me,” this one is a good nudge. Curiosity is a practice. You are allowed to try the thing before you decide who you are.
ABOUT THE CREATIVE
Chris DeLorenzo is an illustrator based in Massachusetts, known for simple, bold work built on line, flowers, and hands. He spent about six years as lead designer and art director at Johnny Cupcakes before going out on his own, and this year marks ten years of working for himself.
His work has appeared in The New York Times and The Atlantic, and it shows up all over Boston, including a 500-foot mural at Logan Airport. He also designed RetroSupply’s original logo, which is still in use today.
Website
https://www.chrisdelorenzo.com
Shop
https://www.chrisdelorenzo.com/shop
Instagram
https://www.instagram.com/chrisdelorenzo
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

Van Berkemeyer has built two separate creative careers: one as an illustrator and designer, one as a musician who's had real viral hits and industry attention.
He says neither one ever actually felt like arriving.
In this episode, Brad and Dustin talk with Van about growing up on a small farm in rural Texas, working as a cowboy on an Oklahoma ranch as a teenager, and building BerkMade, his illustration and design studio, alongside a music career as Van Andrew. The surface topic is juggling two creative disciplines. The real conversation is about something every working artist runs into eventually: chasing a peak, hitting it, and finding out it doesn't fix anything.
It's part career retrospective, part cigar-lounge philosophy session, and part reminder that the goalpost never stops moving, no matter which craft you're chasing it in.
In this episode, we talk about:
Why success in one creative discipline doesn't transfer the lesson to the next, and how Van's found the same empty feeling chasing wins in both illustration and music.
The shoe-shopping analogy for chasing achievement, and why finally getting the thing you wanted for years lasts about as long as a new pair of shoes.
What's actually real about a creative's social media persona, and why the people who look most confident online are often the most different in person.
Why "jack of all trades" doesn't have to mean master of none, and how Van thinks about splitting real creative capacity across two disciplines without feeling like he's failing at both.
Aliens, ice walls, and why Van isn't (technically) a flat earther — a tangent Brad and Dustin promise is "a safe space."
Whatever discipline you work in, this episode keeps circling back to the same question every working creative eventually asks: once you get the thing you thought you wanted, then what? Van's answer, four and a half years sober and building two careers instead of chasing one high, might be the most useful part of the whole conversation.
ABOUT THE CREATIVE
Van Berkemeyer is an illustrator and designer based in Nashville, Tennessee, working under the name BerkMade. He grew up on a small farm in rural Texas and spent his teenage years working as a cowboy on an Oklahoma ranch before building two separate creative careers: illustration and design as BerkMade, and music as Van Andrew.
Alongside his design work, Van has had real success in music, including a song that went viral and hit number two on iTunes, and a stint as a contestant on The Voice. He's four and a half years sober and spends most of his downtime on his Harley, at the cigar lounge, or playing volleyball.
BerkMade (Illustration & Design)
Instagram
https://www.instagram.com/berkmade/
Van Andrew (Music)
Website
https://www.vanandrewmusic.com/
Instagram
https://www.instagram.com/vanandrewofficial/
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

A 99-pack of beer sounds like a joke. It's about as tall as Shaq and weighs eighty pounds. When Christian Helms described it to his mom, she said she didn't get it.
A few months later, she called to ask if he'd seen what Austin Beerworks did.
In this episode, we talk with Christian Helms, founder and creative director of Helms Workshop in Austin, about the 99-pack, Howler Brothers, a week living with Modest Mouse's Isaac Brock, and a career built mostly on naive optimism. Underneath the stories is a bigger conversation. Why is the funniest idea in the room so often the most human one? Why do you have to understand something better than anyone before you can make it surprising? And why would he rather hire a great person than a great portfolio?
It is part design history, part Southern storytelling, and part confession from a man with two giant wind chimes and a painted bunting at his feeder.
In this episode, we talk about:
Getting chased out of a McDonald's with a broom as a Pentagram intern, and why just being in the room while Michael Bierut presents is a master class.
How the 99-pack actually happened including the rule he still works by: take the joke you make at the bar with the client and make it real the next day.
Why creativity is a skill, not a gift and the Edward de Bono exercise that can turn a hospital logo into a vehicle.
Why AI and focus groups pull you toward the same place especially when the whole point of a brand is to not look like everything else in the category.
How years of Lyme disease finally broke his micromanaging habit and why he's hired the third-best portfolio in the stack more times than he can count.
Whether you run a studio, work in one, or just want your ideas to stop looking like everyone else's, this one's worth your time. The weird idea is usually the right one. Someone just has to be brave enough to make it real.
ABOUT THE CREATIVE
Christian Helms is the founder and creative director of Helms Workshop, a branding agency in Austin, Texas, focused on consumer goods and hospitality. The studio has built brands for Austin Beerworks, Howler Brothers, Tecovas, and plenty of the places that make Austin feel like Austin.
He grew up in small-town North Carolina, studied journalism and creative writing at UNC, went on to Portfolio Center in Atlanta, and interned at Pentagram under Michael Bierut. In Austin he fell in with the Decoder Ring crew, making music posters for the bands he was already seeing four or five nights a week.
These days he reads a lot of Southern noir, keeps boiled peanuts in the freezer, and is writing a book on branding.
Website
https://helmsworkshop.com
Instagram
https://www.instagram.com/tchristianhelms
Studio Instagram
https://www.instagram.com/helms_workshop
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