Josh Hall has a bone to pick with us. If one phrase sums up his whole run, from metal-band drummer to laid-off cabinet maker to agency owner to selling that agency in 2020, it’s slow and steady, baby.
And we took the name first 🐢😏
Josh built In Transit Studios, his web design agency in Columbus, Ohio, over a decade. Then, as it’s profitable, he did something most agency owners never do… He sold it! The buyer was one of his own students, a designer he’d coached who was leaving his role as a pastor. Since then, Josh has become one of the biggest names in the space: Web Designer Pro®, a community of 2,000+ designers, the #1 podcast in web design, and millions of YouTube views.
His whole message fits in one line. A web design business should give you freedom and a life you love. And no one wants to buy a job.
In this episode, Jake and John sit down with a friend of eight-plus years to talk about where freedom actually comes from, the two habits that built his agency, and why the AI panic looks a lot like the Wix panic of 2016.
Key Takeaways
- “Freelancer is a fancy term for a job.” Freedom comes from building a real business: a team, processes, and recurring revenue, so everything stops relying on you.
- Care and communication beat competence. Josh’s best client told him, “You made us feel like we were your only client.” His sites were okay at the time. His follow-up was elite.
- Roughly 75% of web designers won’t communicate like they should. Replying within 24 hours and sending updates when there’s nothing new puts you ahead of most of the field.
- Test before you leap. Build a couple of sites for your warm market, keep the day job, and pay attention to whether you enjoy the actual work. Some people make better employees, and that’s fine.
- The AI panic is the Wix panic of 2016 with better tools. DIYers don’t know what they don’t know: SEO, conversion, accessibility, optimization, messaging. The mess still becomes a pro’s project.
- You have to enjoy every phase. The designer chasing $50K MRR in six months gets sold a fantasy. The one who likes the work compounds.
Episode at a Glance
Josh walks through a decade of building In Transit Studios, the coffee meeting with Elegant Themes that accidentally launched his teaching career, the moment a $4,000 website sale made him feel nothing, and the quick decision to sell to one of his own students. Then the conversation turns to AI, and why all roads still lead to websites.
Action step: Reply to every client within 24 hours on weekdays this week, and send one progress note on a project with nothing new to report: “We didn’t get to this yet, it’s on tap for Monday.” That single habit puts you ahead of most of the field.
Main idea: A web design business should give you freedom and a life you love. That freedom comes from building a real business around the work: team, process, recurring revenue, and relationships strong enough to survive any new tool.
Why it matters: The tools keep changing. Templates, page builders, Wix, now AI. The pros who survive every wave are the ones clients trust to own the problem, communicate constantly, and genuinely care.
Quick tool: The non-notification update. A short, unprompted progress note to a client, even when there’s no progress. It costs five minutes and builds more trust than a better design.
Listen & Subscribe
Podcast page: https://artillerymedia.com/podcast/
Apple Podcasts: https://podcasts.apple.com/us/podcast/slow-steady-a-podcast-by-artillery/id1840249614
Spotify: https://open.spotify.com/show/37ZzVcI8N7xnEDqkap2vCW?si=70b138e65b8c42ca
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Contact us: https://artillerymedia.com/contact/
About Josh Hall
Josh is a web design business coach, podcast host, and web agency founder based in Columbus, Ohio. He built and scaled his own agency for over a decade before selling it in 2020 to teach other web designers how to build businesses that give them freedom and a life they love.
- Built In Transit Studios from a side hustle into a six-figure agency over ten years, then sold it in 2020 to one of his own students
- Founded Web Designer Pro®, a courses + community + coaching platform with 2,000+ members
- Hosts the #1 podcast in web design, with 900k+ downloads
- 4.1M+ views on YouTube and nine online courses, mostly on the business side of web design
- Started as a drummer in a metal band and a cabinet maker. Hasn’t had a job since 2009
- Work-from-home husband and dad of 3 littles, 5 counting the Golden Retrievers
His definition of slow and steady: “Few fun tasks/projects per week and a pretty open calendar.”
Web Designer Pro®: https://webdesignerpro.com
Josh’s podcast: https://joshhall.co/podcast
Josh on YouTube: https://joshhall.co/youtube
All of Josh’s links: https://joshhall.co/media
Highlights & Timestamps
00:00–04:30: The Name He Wishes He’d Taken
Josh airs his public grievance about the Slow & Steady name, and the guys talk about the student who got baited by a “$50K MRR in six months” promise.
04:30–07:00: Drummer, Cabinet Maker, Accidental Entrepreneur
Laid off in 2009, Photoshop for album art, and the festival question (“who does your artwork?”) that started a business.
07:00–13:00: A Coffee That Became a Teaching Career
The meetup with Elegant Themes’ content manager, writing for the blog, courses out-earning the agency, and the $4,000 website sale that made him feel nothing.
13:00–16:00: Freelancer Is a Fancy Term for a Job
Twenty-three projects right before his first child was born, the job description no one would take, and the assets that made the agency sellable.
16:00–25:50: Why Musicians Make Good Entrepreneurs
Piano lessons, discipline, the electric guitar as an AI analogy, and the couple in the Philippines now supporting their family with 100 web design clients.
25:50–35:15: Starting From Zero
Quick wins and momentum, warm-market-first sales, why you shouldn’t burn the ships, and Jake’s white cowboy hat.
35:15–40:15: The Two Secret Weapons
“You made us feel like we were your only client.” Genuine care, relentless communication, and why the five-out-of-ten designer wins.
40:15–49:07: AI Is the New Nephew
The Wix déjà vu, the client who destroyed years of SEO with a DIY AI build, frog-boil pricing, and where to find Josh.
The Accidental Entrepreneur
Josh never planned any of this.
He was a drummer in a metal band and a cabinet maker by day. In 2009, the cabinet job disappeared. He’d always liked art and design, so he picked up Photoshop and started making his band’s t-shirts and album covers.
Then someone at a festival asked who did the artwork. He said, “I did.” They wanted to hire him.
“I could make money doing something I love to do. I thought I was such a unicorn.”
He wasn’t, and he knows it. A whole generation of musicians took the same road into design, Jake and John included. The band was the training ground: build a product, run a marketing campaign, refine the craft, make referral partners, handle conflict, put on a show.
Josh still wanted a design job at first. Then he did the math. He’d made $30,000 on the side while entry-level jobs paid $40,000 for 50 hours a week downtown. Low expenses, no risk to speak of, and skills that were already earning.
He went for it. In his words, he’s been unhirable ever since.
A Coffee, a Blog, and a Buyer in the Audience
The teaching started small. A local high school had a mentor program, and Josh loved sitting down with the students who cared.
Then came the fateful coffee. Josh found out the content manager for Elegant Themes, the company behind Divi, lived in Columbus. He invited him out, no agenda, just to say he loved the product that powered his almost-six-figure business. He walked out with an invitation to write for one of the biggest blogs in WordPress.
That led to a YouTube channel, then courses, then three years of building a personal brand alongside the agency. And slowly, the balance tipped.
“I sold a four thousand dollar website and I just didn’t feel anything. It was kind of like a red flag moment.”
He wasn’t burned out. He loved his clients. But the courses were out-earning the agency, and when COVID hit, he made about $60,000 in course sales in six weeks. He knew he couldn’t run two businesses at once.
So he sold. The buyer was Eric, one of his own students, a strong communicator who was leaving his role as a pastor. Josh’s logic: if you can pastor a church, you can run a web design business. Different personalities, constant content, all the same stuff.
The whole decision took weeks, and it worked because of what came before it. Ten years of slow and steady built something worth buying, and the teaching built trust with the person who bought it.
Freelancer Is a Fancy Term for a Job
Ask Josh where designers get freedom wrong and he starts with a distinction most people skip.
“Problem with being a freelancer is it is a fancy term for a job. So everything relies on you.”
He learned it the hard way. Right before his first child was born, he was carrying 23 active projects alone. “If you wrote my job description down, no one would want to take that job. For like a million dollars.”
That stress started his scaling. He got over his control tendencies, brought in a small team of subcontractors, and turned the work into a business. And when it came time to sell, that structure was the leverage: processes, a client list, recurring revenue from hosting and maintenance, and a support network that could transfer with it.
A freelancer sells hours. A business owner builds assets.
Nobody buys hours.
Care and Communication Beat Competence
Josh recently asked one of his first great clients why they hired such a new designer back in 2012. The answer stuck with him.
“You made us feel like we were your only client.”
His websites were okay at that point. His two secret weapons had nothing to do with design. He truthfully cared about the client’s result, and he communicated like a wild man.
He puts a number on it, too: “Probably 75% listening to this right now are not going to communicate like they should.” The bar is low. Reply within 24 hours on a weekday. Send a monthly newsletter. And send the non-notification update: “We didn’t get a chance to work on this, but it’s on tap for Monday and we’ll get to it.” Easy peasy, his words.
John frames it as the seven-out-of-ten designer beating the ten-out-of-ten through communication, on-time delivery, and staying on budget. Josh raises him: the five-out-of-ten can do it.
It’s the same instinct behind John picking up every band’s set lists and drink cups after a show. The sound guys and promoters remember. Small separators, done every time, become the reputation.
Competence gets you in the game. Care and communication win it.
AI Is the New Nephew
Ask Josh if AI scares him and he tells you about Wix.
A decade ago, a client left him to build his own site with a DIY builder, then asked if Josh was worried the whole industry was about to disappear. The result across the market: terrible websites, and serious business owners coming back to professionals.
AI is the same movie with better effects. Just last week, a Web Designer Pro member watched a client destroy their SEO with a DIY rebuild in Claude. “Years of authority building gone like that.”
Josh is careful about where the blame goes. The tool did what it was asked. The DIYer didn’t know what to ask. They don’t know the ins and outs of SEO, conversion, accessibility, optimization, or messaging. You don’t know what you don’t know.
That’s why every wave of DIY tools ends the same way: “I’m so done with it. Whatever it costs, you just do it.” Sunk-cost DIYers become the best clients.
John’s version: clients used to say “my nephew built our website.” Then it was the guy from church, or the guy in the band. “AI is the new nephew in 2026.”
None of this makes AI a toy. We built the new artillerymedia.com with Claude in the loop, and it let us snipe on accessibility, compression, and speed faster than we ever have. The tool is real. It rewards people who already know what good looks like.
All roads still lead to websites. That part didn’t change.
Call to Action
Want a website team that makes you feel like their only client?
Start here: https://artillerymedia.com/contact/
Show Credits
Hosts: Jake Kramer & John Wooten
Guest: Josh Hall (Web Designer Pro®, https://webdesignerpro.com)
Produced by: ARTILLERY, Lincoln, Nebraska
Slow & Steady — A Podcast by ARTILLERY 🎧
https://artillerymedia.com/podcast/
