Bobby’s journey into WordPress started with a favor for his mom — and snowballed into a full-blown hosting company, a niche agency partnership, and now a growing business that supports agencies with managed WordPress hosting tailored to their needs.
With a deep love for server engineering and an eye for partnerships, Bobby’s built WP Aligned on a foundation of trust, transparency, and a philosophy (from a surprising source): under-promise, & overdeliver.
In this interview, he shares his path from local hosting to agency-focused infrastructure, the lessons that reshaped his leadership, and what’s next as the business grows beyond its founding team.
What got you into WordPress and how long have you been using it?
Back in 2007, my mom signed up with a hosting company, and every problem she had, she would reach out to me. Through it, I learned a lot about hosting, and became fascinated with the industry. So I launched my own hosting company.
I focused on my local area, and here, most businesses don’t even have websites. So I got into building websites as a way to create the need for my hosting services, though I wasn’t, and still am not particularly good at building sites. WordPress was chosen as my framework, and as time marched on, I decided to specialize my hosting into strictly for WordPress.
Later on, I started hosting another person that was like me, and I realized we could do things together to benefit all. That’s when the Hosting Coalition was formed, and we specialized in hosting agencies. In 2021, Tom DeBello joined me, and we rebranded to WP Aligned.
What motivated you to start your own business, and what keeps you going when things get tough?
I’ve loved the hosting world, server engineering, and I’ve always held an entrepreneurial spirit. I enjoy the freedom it gives me. Even on my most stressful days, it’s always proven itself to be worth it.
What’s a hard lesson you learned running your business that’s changed the way you operate?
I’ve worked for several different companies, and had a really long journey, and have learned a lot. The hardest lesson for me in business is that I’ve been a very trusting person.
I’ve believed in people, believed in their mission. Everyone shows you who they are, just give them time. So now, I operate in a clear eyed manner. Now I cross every T, and dot every “i”. I’m still an optimistic person, and I believe in hope, but double check things more now.
What’s the best piece of advice you’ve ever gotten and how has it affected your business?
There’s been so many great pieces of advice, it’s hard to settle on just one.
What really comes to mind though, it isn’t really advice per se, but it’s been something stuck in my brain and my personal MO for the past several years. Around here in the US, we have a Five Guys burger restaurant, and when I ate there for the first time, I didn’t realize that a regular fry was ginormous. After that first visit, I learned that they undersell and overdeliver.
Their model is what I try to replicate in the hosting industry.
As an entrepreneur, what’s your proudest accomplishment?
My proudest accomplishment (and simultaneously the most scary) is that due to growth, we’re on the cusp of needing to hire our first external employee. It scares me because I won’t just be responsible for myself, Tom, and our other internal team.
What’s a book every agency owner should read?
The Lean Startup by Eric Ries
What’s a WordPress plugin more people should know about?
ActivityLog – We need to keep a closer eye on what is happening inside our customer’s sites.
What’s your favorite tool, accessory, or gadget on your desk?
I don’t have a lot on my desk, but my favorite is a custom headphone stand that my sister got me for Christmas that has my gamertag personalized into it.
What’s your favorite non-WordPress tool or software?
Loom, I use it for so much.
