Jaiden’s journey into web design started with a curious moment — overhearing a friend talk about building a website. A few Google searches later, he was experimenting with a site for his dad’s business (which, fun fact, still isn’t live nearly a decade later). From that spark came a business that’s grown from $250 websites on Squarespace to custom WordPress builds backed by a small but mighty team.
In this interview, Jaiden shares how a $60 pack of business cards marked the “profitable from day one” start of his business, why sitemapping is his secret weapon in the design process, and the one piece of advice that keeps him focused on what matters most — building a business that supports his life, not the other way around.
What got you into WordPress and how long have you been using it?
I’ve been working with WordPress since about 2020. I’m definitely more of a designer and strategist than a developer, but over the years I’ve been lucky to work alongside some incredibly talented developers who help bring my designs to life.
Before 2020, we built most of our sites on Wix. I can’t knock it too much; it kept the lights on for five years. But as our projects grew in scale and complexity, we started hitting a lot of ceilings. Simple features clients wanted just weren’t possible, and it was frustrating to feel like the “professional” but have to say no because of a platform limitation.
So in 2020, I set out to learn WordPress and partnered with a developer who does fantastic work. Now, we have far more flexibility — from plugins to hosting to custom features — which means we can create exactly what works for both me and my clients.
What part of the website creation process is your favorite to work on and why?
I love the sitemapping and wireframing stage, it’s like laying out the blueprint for how people will move through a site. There’s something satisfying about organizing information in a way that just makes sense. But honestly, nothing beats the design phase, when all those ideas and plans come to life on the screen. That’s the moment it stops being a concept and starts feeling real.
What motivated you to start your own business, and what keeps you going when things get tough?
Back in 2015, I was hanging out with some friends when I overheard one of them talking about building a website with Squarespace. For some reason, that instantly caught my attention. Later that day, I went home, looked it up, and decided to try building a site for my dad’s business.
I like to joke that he was my worst client – nearly ten years later, that site still hasn’t launched.
Not long after, I mentioned to another friend that I was experimenting with websites, and he suggested we start offering them to businesses. We gave it a shot, and our very first website sold for $250. We even called ourselves “profitable” from day one because our business cards cost $60, the domain was $20, and Squarespace hosting was $120.
From there, we gradually increased our prices, saw the demand in our area, and realized this could be more than just a weekend side project; it could be a real business.
When things get tough, I think back to those early days: the $250 website, the excitement of our first sale, the fact that we had no idea what we were doing but did it anyway. That perspective reminds me how far we’ve come and why it’s worth pushing forward.
What do you do to keep a healthy work/life balance as a business owner?
Being a business owner is tricky because your business isn’t just your job, it’s part of your life. Sometimes the lines blur a little too much… like when it’s 9 p.m. and you’re still checking work emails. (Guilty!)
I think it’s okay to occasionally work late or on a weekend, as long as you’re enjoying it and it’s not coming at the expense of your family or your own well-being.
One thing that’s helped me is having a dedicated phone for work. Not just a separate number, a completely separate phone I can leave in my office to create that physical separation. I’m also trying to be more intentional with my time: tracking my tasks, checking things off, and then stepping away so I can actually enjoy my time off knowing I’ve done my best.
At the end of the day, it’s about finding what works for you and your family and sticking to it.
What’s the best piece of advice you’ve ever gotten and how has it affected your business?
I’ve gotten a ton of great advice over the years. The problem is, my brain loves to overthink things, so half the time it gets buried under a pile of “what ifs” and “maybes.”
But one piece has always stuck: prioritize what’s important to you. If your family is your priority, you’ll figure out how to make everything else fit around it. Same with your health — or whatever matters most to you.
At the end of the day, what’s the point of all this if you’re not doing what you want and what makes you happy?
So when I catch myself chasing shiny objects or getting excited about the next “big” business idea, I try to zoom out and ask, “Does this support my priorities?” If the answer’s no, it’s easier to let it go.
What’s a book every agency owner should read?
Profit First by Mike Michalowicz
What’s your favorite podcast to listen to?
What’s a WordPress plugin more people should know about?
FluentSupport, Pie Calendar, CheckView
What’s your favorite tool, accessory, or gadget on your desk?
Logi MX Brio. I was sick of webcams always looking bad, but this one is fantastic.
What’s your favorite non-WordPress tool or software?
I would have to say ClickUp. I’m using it to organize all parts of my business and having it in one place helps me stick to it better.
