You can find Ryan on LinkedIn or Twitter. This is our recent interview with him, as part of our Kinsta Kingpin series.

Q1: What is your background, & how did you first get involved with WordPress?

Before WordPress, I worked as a System Administrator for a health care network. It was a Microsoft world *shudder* in a big corporation and while I didn’t hate what I did for work, I didn’t particularly love it either and started playing with some open-source software in my spare time.

A friend asked me to build him a website and I stumbled onto WordPress. I knew enough PHP to be dangerous and was really familiar with server stacks, so I put something together that he was really happy with.

That little project turned into many, and then I started to notice a pattern. The same people who I built websites for kept coming back and asking for help over and over again, and their requests were all pretty similar.

I figured there may be a business opportunity if I could establish a baseline set of services and charge a monthly fee, and sure enough, it worked! About a year after putting up a website for WordPress support services, I left my job and started working on WP Site Care full time. That was 5 years ago in May.

Q2: What should readers know about all the stuff you’re doing in WordPress these days?

I run WP Site Care. We’re a WordPress support company that specializes in helping small businesses and pro bloggers. We’ve worked with lots of customers over the years. From people just starting out to Fortune 50 corporations, but we’ve found the scrappy small businesses are the ones we’re able to help the most. Partially because our skills fit well there, but also because we’re a small business too. So we know what it’s like.

WP Site Care
WP Site Care

Earlier this year we also launched our first product, Cookbook. It’s for managing recipes in WordPress and we’ve been really happy with how things have gone so far.

Q3: What challenges did you face in getting to where you are now professionally?

How long is this interview supposed to be? There have been many. Like, honestly more than I could even start to list here, so I’ll just highlight my biggest challenge.

My biggest challenge has been myself. Making the transition from a full-time technician to someone who is supposed to be a leader has been a long journey for me. I’ve learned so much about myself and my own strengths and weaknesses as we’ve grown WP Site Care, and I’m incredibly grateful for what we’ve been able to accomplish. But most of our challenges have ultimately been a result of me lacking knowledge or confidence, or the chops to navigate something new or unexpected.

Q4: Has anything surprised you while coming up in the WordPress world?

Definitely. When I first started working with WordPress the laid back vibe and grassroots feel was very charming. The only problem, that I didn’t notice at first, is that there was a baseline level of professionalism missing in a lot of online interactions that resulted in people not following up, or saying things that wouldn’t otherwise be acceptable in a more professional forum, or downright rude or offensive.

Granted, those interactions were certainly not the norm and having participated in a lot of online communities I’d say WordPress is still one of the best around. It’s probably because I held it to such a high standard that the ugly parts stood out and surprised me so much.

I was also surprised by just how much of a global reach WordPress really has. It’s incredible and seems to be a truly global CMS.

Q5: What does the future look like for you in the WordPress world?

In terms of specifics, I wouldn’t even try to guess what’s on the horizon. I have some guesses, but that’s all they are.

As far as high level goes, WordPress will ultimately be what we make it, and I’m hopeful we can continue to improve it and build an ecosystem that supports lots of small businesses for many years to come.

Q6: What do you look for in a WordPress host?

Ownership and self-awareness. I know it’s kind of a weird answer but I’ll explain it, I promise.

I’m super familiar with what’s required to run technical and customer service infrastructure at scale, and it isn’t easy. Bad things are probably going to happen eventually no matter which host I choose.

That said, a host that owns it when they screw up and follows through with making corrections speaks volumes to me. Patterns of poor performance, bad customer service, or skirting blame are all huge red flags and signals that I should avoid that host.

Also, it’s disingenuous for every host to claim they’re the absolute best. They very well may be great at a specific set of things, and they should communicate those things directly to customers. I love a host that tells people they’re the best at X, rather than simply saying anything they can to bring one more person through the front door. Not only is it not cool, it also usually ends up burning the host and the customer eventually.

Q7: What do you enjoy doing when you’re away from your laptop?

I love to play golf, hang out with my 3 boys playing LEGO, and I’m an obnoxious Utah Jazz fan.

Q8: Whom should we interview next & why?

You should interview Nathan Tyler. He’s one of the most thoughtful people I know in WordPress, and has some really hot takes on the state of Girl Scout cookies.

Brian Jackson

Brian has a huge passion for WordPress, has been using it for over a decade, and even develops a couple of premium plugins. Brian enjoys blogging, movies, and hiking. Connect with Brian on Twitter.