Everyone tells you to build websites for free to “gain experience.”
That’s exactly how you train clients to devalue your work forever.
Here’s what I learned building a web design agency from scratch over 16 years ago. And more importantly, what I’d do differently if I was starting in 2025.
The real first step nobody talks about
Before I even thought about going solo, I spent years learning the ropes at another agency. I had two mentors there who I still call when I’m stuck on something today.
They didn’t just teach me about web design and marketing. They helped shape my entire perspective on business.
Here’s the thing: You can absolutely learn everything on your own. YouTube University is real. But if I hadn’t had those mentors in the beginning? The ride would’ve been way rougher.
Find someone who’s already where you want to be. Buy them coffee. Pick their brain. Most successful people are surprisingly generous with their knowledge if you approach them right.
Why your first website better not suck
Your agency website isn’t just another project. It’s your entire credibility wrapped up in pixels and code.
When I built my first iteration of Connective Web Design, I slaved over every detail. The portfolio was barren. The case studies were non-existent. But that site had to look like a million bucks because it was literally all I had.
A web developer’s site needs to set the bar for what you’re capable of. Period.
Think about it: Would you hire a personal trainer who’s out of shape? A financial advisor who’s broke? Your website is your fitness level in digital form.
I spent weeks on that first site. Launched it to the world. And then… nothing.
Turns out “build it and they will come” is complete bullshit.
The microsite strategy that actually worked
While waiting for clients to magically appear (spoiler: they didn’t), I decided to build a second site.
Back then, I was reading all these case studies about microsites. The theory was that people convert better on a website dedicated to one specific thing rather than a site that does that thing plus 47 other services.
Since SEO was going to be a primary offering (I had a legit knack for it), I built a microsite just for SEO services. Called it Linear SEO or something equally forgettable.
Did it bring in clients? Not really. But it did three crucial things:
- Built my confidence with another completed project
- Gave me something else to add to my portfolio
- Taught me that splitting your efforts across multiple properties is usually a mistake
I eventually killed that microsite and doubled down on one property. But that “failed” project was worth its weight in education.
Your brother’s construction company doesn’t count
Everyone says to build websites for friends and family for experience. Here’s what they don’t tell you: Those aren’t real projects.
My brother’s construction company needed a website update. Could be better optimized for search. And I could do it without dealing with actual client feedback.
It was a comfy, no-pressure situation. Which is exactly why it didn’t prepare me for real client work.
Real clients have opinions. Deadlines. Scope creep. Payment delays. Communication issues. Your cousin’s dog grooming business won’t teach you any of that.
But here’s what that project did do: It gave me another portfolio piece and started building my confidence. Sometimes that’s enough.
The $500 website sweet spot
I was willing to work for pennies. Not free – that’s important – but damn close.
My first paying jobs came from referrals. I had a couple friends who really wanted to see me succeed. For the price I was charging and coming from trusted recommendations, landing those first jobs wasn’t that hard.
I built websites for:
- A hair stylist
- A snow removal company
- A horse photographer (who’s still a client today, actually)
Here’s the key: I poured my soul into those $500 websites like they were $50,000 projects.
Why? Because doing great work for one type of business is how you accidentally find your specialties. All the niches we focus on today? They weren’t planned. We just did great work and people noticed.
The most embarrassing thing that actually worked
When I wasn’t drowning in referral work (all three projects), I did something that still makes me cringe.
I walked into businesses and pitched owners face-to-face.
Looking back, it was freaking awful. Awkward. Embarrassing. But you know what? I landed jobs that way.
And you wonder why most web designers stay broke? They’re not willing to do the uncomfortable stuff.
Cold outreach in 2025 looks different (thankfully). But the principle remains: You have to be willing to do uncomfortable things when you’re starting out.
Those face-to-face rejections taught me how to talk about what I do. How to identify who actually needs help. How to feel comfortable calling myself a web design business when my “business” was just me and a laptop.
The skills nobody mentions (that nearly killed me)
Building websites is maybe 30% of running a web design business. The other 70% is stuff like:
- Sending invoices that actually get paid
- Managing scope creep without losing clients
- Tracking time without wanting to throw your computer out the window
- Keeping books that won’t make your accountant cry
- Writing contracts that protect you from nightmare clients
I became obsessed with nailing every aspect of the business. If I was going to send invoices, what’s the actual best way? If I’m working with outside help, what’s the smartest deal structure?
Most of what I learned came from actually doing it wrong first. There’s no YouTube video that prepares you for your first client who ghosts you after you’ve done 80% of the work.
Playing the long game while broke
Relying on referrals and face-to-face awkwardness wasn’t sustainable. I needed inbound leads or I’d be stuck in feast-or-famine mode forever.
So I started blogging. A lot.
Every article was a line in the water. Each URL was a chance for Google to find my site and send customers my way. Some of those original posts from over a decade ago still bring in work today.
I didn’t realize back then how massive content marketing would become for us. It’s now a primary service and a huge chunk of our revenue.
Social media for introverts who’d rather die
Social media didn’t (and still doesn’t) come naturally to me. I’m an introvert who’d rather code in a dark room than network at events.
But I created accounts on every platform active at the time and forced myself to be active. Not just posting – actually engaging with people.
This built two things:
- Skills I could eventually charge for
- A network that would send me work for years
The discomfort was worth it. Social media management became another major service offering.
The Google Ads money pit
Once I wasn’t completely broke and living deposit to deposit, I dove into Google Ads (AdWords back then).
I wasted a stupid amount of money in the beginning. Like, threw-it-straight-out-the-window wasted. I vowed to quit so many times.
But eventually, my account became so optimized I could predictably turn ads on, win clients, and get a positive return. My largest clients ever actually came from paid search.
And yes, it became another primary service we offer. Seeing a pattern here?
What I’d do differently in 2025
Starting a web design business today is both easier and harder than when I did it.
Easier because:
- AI tools can 10x your productivity
- No-code platforms let you build faster
- Remote work is normalized
- Online education is everywhere
Harder because:
- Everyone and their mom is a “web designer”
- Clients expect more for less
- AI is commoditizing basic web design
- The barrier to entry is basically zero
If I was starting today, here’s what I’d focus on:
- Pick a specific problem you solve: Don’t be a “web designer.” Be the person who builds conversion-focused sites for SaaS startups. Or the expert in membership sites for course creators. Specificity wins.
- Charge real money from day one: That $500 website sweet spot? Make it $1,500 minimum. You’ll attract better clients and build a real business faster.
- Build in public: Document everything. Share your wins, losses, and lessons learned. This builds authority faster than any portfolio.
- Focus on recurring revenue: One-off website projects are a rollercoaster. Add maintenance plans, hosting, and ongoing optimization from the start.
- Learn the business stuff first: The technical skills are the easy part. Master client communication, project management, and sales. That’s what actually matters.
Here’s what it all comes down to
Looking back, success wasn’t about having the perfect plan or the best technical skills.
It was about three simple things:
First, just doing it. Even when I had no idea what I was doing. Even when that meant awkward door-to-door sales that made me want to crawl under a rock.
Second, learning from people who’d already figured it out. Those mentors saved me years of painful mistakes.
Third, being willing to look stupid while figuring it out. Every successful agency owner has a collection of embarrassing stories from their early days.
Here’s the thing: The people who make it aren’t necessarily the most talented. They’re just the ones who didn’t quit when it got hard.
Don’t overthink it. Dive in the deep end and force yourself to swim.
And seriously – don’t underestimate how much the people close to you can help along the way. My first three clients came from friends who wanted to see me succeed. That momentum carried me through the brutal early days.
Starting a web design business is hard. Building it into something sustainable is harder. But if you’re willing to do the uncomfortable work that most won’t do?
Believe me when I say this: It’s absolutely worth it.
