A Developer Who Does It All
Kevin Leary is one of those rare developers who’s just as comfortable diving into analytics and design as he is refactoring code. I caught up with Kevin for a fast-moving conversation that covered AI, web development, and how a career that started with graphic design and assembly code led him to running his own successful consultancy.
On Learning to Learn
Kevin studied both computer science and graphic design at Champlain College and got his start working for agencies in the Boston area. What stood out to me was his mindset: he wasn’t afraid to pivot or jump across disciplines. In fact, that curiosity helped him go independent.
“I like to jump from design to dev to analytics. At first I thought that wasn’t a good thing, but I realized that’s what drives me.”
That ability to synthesize across disciplines is what makes Kevin’s work so effective today—he’s not just building sites, he’s helping clients improve performance and user experience in measurable ways.
How Kevin Thinks About AI
We had a great moment in the interview where Kevin described how he approaches conversations about AI with clients:
“I talk to clients about AI almost the same way I talk about any technology. First, what do you want to do? What are your goals? Then we figure out if AI helps with that.”
It’s refreshing to hear that kind of clarity. Kevin uses AI daily in his own coding workflow but is careful not to overhype it. He points out that without a deep knowledge of the codebase, AI-generated code can actually slow you down. That honesty is something a lot of developers (and clients) can relate to.
WordPress, Spam, and Smart Use Cases
One AI use case Kevin mentioned was especially clever: he used OpenAI’s API to score contact form submissions for spam instead of relying on captchas or Cloudflare Turnstile. By scoring messages and reviewing their accuracy before putting the filter in place, he created a custom, client-friendly solution to a very real problem.
Hosting That Doesn’t Waste Your Time
We also talked a bit about Kinsta, and Kevin didn’t hold back:
“I always say this to everybody: the amount of time you’ll save by spending an extra $200–300 a year is so astronomically higher than the amount of time it’ll take if you go with the cheaper option.”
He’s been a fan since 2016 and still recommends Kinsta today because, as he puts it, it just works. We’ll take it!
Who Kevin Works With
If you’re running a custom-built WordPress site that originated with an agency and now needs ongoing performance, analytics, and UX improvements—Kevin’s your guy. He’s happiest working with companies who already value good design and want to keep improving.
Full Transcript
Kevin Leary (00:00)
I talk to clients about AI almost the same way I talk about any technology. First, what do you want to do? What are your goals? And then once you determine what we’re setting out to do, maybe AI is good to do it. But the red flag for me is if someone comes in and says, we have to use AI because that’s what’s going on. Everyone else is doing it because there are a lot of cases where it doesn’t really make sense. But for me, I’d say I use it day to day just because I think that is where
coding is going. So you kind of have to learn how to work with it. You definitely can improve your workflow, but it’s also a little bit eye opening to see that you still really do need a deep knowledge of the code base that you’re working in. Because sometimes one or two things are off, and if you can’t find that, it may end up taking more time than if you had just written something yourself.
Roger Williams (00:38)
Okay.
Hey everybody, it’s Roger with Kinsta. Today I’m joined with a new friend, Kevin. Hey Kevin, how are you?
Kevin Leary (00:52)
Good, how are you Roger?
Roger Williams (00:53)
You know, I’m doing really well. It’s the middle of the week. Things are cruising along. So I’m pretty happy with stuff. I’m excited to be on this call with you and learn more about you from looking at your website. You you’ve got a huge variety of technologies that you’re involved in. So, you know, to like get us started here, can you kind of tell us how you got into the web and big data and AI stuff?
Kevin Leary (01:16)
Yeah, definitely. So, I mean, I’ve always been a programmer, more or less. I went to school for graphic design and computer science, did a little bit of work during college at an agency. And then I worked at a couple of agencies in the Boston area. They were very good, very great. I liked working there, but I found that like, I like to jump around from role to role too much for an agency. And at first I thought, well, maybe this isn’t good. Maybe I should just focus on development. But then I realized that’s kind of what
drives me almost, like the ability to jump from design to dev to analytics. And that’s where I sort of decided to go off on my own and pursue all of those things. So I’d say to answer how I got into WordPress, way, way back, I just was poking around with CMSes. And I saw it, and I was hooked, basically. I could just see that it’s very interesting to see how the themes are set up, to dissect them, things like that. And then with
Roger Williams (02:02)
Okay.
Kevin Leary (02:09)
BigQuery and data warehousing stuff. I got into that by way of originally working with Segment, which I believe now they’re owned by Twilio. But it was before the new GA had the event-based stuff. It was just an approach that made sense to me to be able to track a business event when this happens, another one when this happens, another one when this happens. So I set that up, connected it to BigQuery way, way back. I think it was like 2014.
maybe, 2012, 2013. And that was really valuable. And so that kind of steered me towards using analytics to help measure how effective that design and dev work was. I think that, is that a good explanation? I that covers it.
Roger Williams (02:52)
Yeah, no,
no, so I want to go back and dig into things here a little bit. So you said you’ve always been a programmer. Did you go to college or school for any computer science or anything?
Kevin Leary (03:01)
I did, I went to Champlain College in Brentwood, Tidumon.
Roger Williams (03:05)
Okay, and you studied comp sci and got all into assembly code and everything?
Kevin Leary (03:10)
Yeah, was kind of it was like a hybrid, almost self created program where it was half graphic design and then it was half computer science.
Roger Williams (03:17)
Okay, very cool. Anything from that experience that you still kind of pull from today?
Kevin Leary (03:23)
I mean, to be honest, maybe not at college, but one thing I learned then was like to really know how to do things well, you’ve learned on your own. I do a lot of reading, any new topic I’ll dive in and try to understand it first before I work with it, which is sometimes hard because often you have to dive right into it. But yeah, learning to learn, guess you would say, which is a little bit cheesy, but it’s really ultimately what, what I came out with.
Roger Williams (03:47)
No, absolutely. I think a lot of times people go to higher education and they have like a direct goal in mind. And maybe sometimes they get disenchanted because it is really about learning how to learn. At least that was my experience as well. As you were starting to work with agencies, what kind of work were you on? Were these like enterprise level sites, small medium sized businesses?
Kevin Leary (04:00)
Sorry.
I’d say medium, not too much enterprise right away, but medium to large businesses at some of them. There were some design sites that I did from scratch with a brand that was like, I’d say smaller, more or less. And then my dev skills were a little bit stronger. that was where I was put. That’s where I did well. ⁓ But yeah, at the time it was like Symphony apps. There was really no WordPress at the agency.
Roger Williams (04:28)
Thanks a lot.
Kevin Leary (04:34)
It was like jQuery was new, not to point out how old I am, guess, but yeah, that was the case. Actually, the first agency job I had, I remember I went in and I was like, gosh, I got this thing jQuery. And I remember the developer there was like, no, I’m using Scriptaculous. It’s way better. And anytime I mention that, people are like, what’s Scriptaculous? Nobody knows what it is.
Roger Williams (04:34)
Okay.
There’s a giveaway.
you
⁓
Exactly, All right, very cool. then fast forwarding, it sounds like you’ve got some squirrel syndrome, which I suffer from as well. I like to go after the shiny new things and try all the things. As you started your own business, how did you start finding clients initially and have you niched down as it were?
Kevin Leary (05:14)
Yeah, too. I guess in terms of the squirrely scenario, too, it’s more, I guess, that I find that if you want, let’s say you’re trying to increase leads on a site. You can do it with design, but it’s only a piece of it. You can do it with analytics, but it’s only a piece of it. If you know how to code, you can look in and see maybe people on an Android phone are having issues with this. It’s sort of all dove into all of it to gear it towards like,
making those things better and when you can do all of them, great. But it’s all encompassed in that too. It’s not necessarily some of the things are not new. They’re just in that space. But yeah, sorry, what was the other part of the question? Second one?
Roger Williams (05:52)
Well, so then
as you figured out that you wanted to go out on your own, what were some of the first steps to get that really started and cemented?
Kevin Leary (05:57)
yeah.
So initially, did it outside of sort of pulled back my hours at agencies and worked a lot of night and weekend hours to build it up because it would be very hard to do a hard switch to it. But initially, a lot of it was SEO. So it’s pretty good at it. Could rank pretty well locally for things like Boston WordPress Developer and other stuff like that. And then the real, probably the larger clients that
have been great to work with in their more long term. A lot of those came from that original agency work 10 years down the road. Like they just reach out and they’re like, you know, we worked together on this. I don’t know if you remember, if you’re available and that that’s probably the best source of work referrals to be honest. Yeah.
Roger Williams (06:40)
Okay, absolutely.
Yeah, when people have worked with you and have an idea of what you can do and how you operate, that’s always a big bonus. Fast forward to today. I’d be remiss not to bring up AI. It’s everybody’s favorite subject. I take it at this point, you’re well over the hurdle of should we be using AI? Where are you?
Kevin Leary (06:53)
Yeah.
Roger Williams (07:01)
focusing your efforts and how do you talk to clients about AI?
Kevin Leary (07:05)
I talk to clients about AI almost the same way I talk about any technology. First, what do you want to do? What are your goals? And then once you determine what we’re setting out to do, maybe AI is good to do it. But the red flag for me is if someone comes in and says, we have to use AI because that’s what’s going on. Everyone else is doing it because there are a lot of cases where it doesn’t really make sense. But for me, I’d say I use it day to day just because I think that is where
coding is going. So you kind of have to learn how to work with it. You definitely can improve your workflow, but it’s also a little bit eye opening to see that you still really do need a deep knowledge of the code base that you’re working in. Because sometimes one or two things are off, and if you can’t find that, it may end up taking more time than if you had just written something yourself. ⁓
Roger Williams (07:44)
Okay.
That makes sense.
Absolutely. I run into the same thing where I’ll get it to write something and it just doesn’t feel right. And I’m talking about text, not not code even. And I’ll just end up using it as like a blueprint instead of what I’m actually going to end up with. So that that’s really cool. When it comes to like WordPress and AI. Are you seeing any solutions yet that are
Kevin Leary (08:08)
Yeah.
Roger Williams (08:17)
that are either client facing or customer facing that you’re implementing.
Kevin Leary (08:20)
Yeah, there’s one that I wrote about recently that’s kind of interesting. I won’t mention who because it’d be best to do that. But spam with gravity forms is a big problem. Anyone who has a form on any WordPress site, it’s rampant. It’s almost impossible to block it. But because it’s a low-volume site, there’s not too many submissions going into this contact form. We used OpenAI APIs to basically just say, hey, here’s the message. Does it look like spam to you?
give it a score of 1 to 100. And then based on that, what we did initially was it just put the score at the top so the internal team could review it and see, like, is this effective? We found it once. It was really good. So now we replaced, what is it, Cloudflare turnstile with this AI approach. It works well so far. I guess the thing is, like, you know, it works well until the AI bots figure out how to beat the AI spam filters.
Roger Williams (09:13)
you
Kevin Leary (09:13)
And then I
guess you’re in this big loop, right, where they just go back and forth. But for now, yeah, it does work pretty well. Also, lot of content creation, too. This is pretty common.
Roger Williams (09:20)
Excellent, excellent.
Definitely. As you’re implementing WordPress sites, I’d be remiss to not bring up and mention Kinsta for hosting. Is there anything specific about working with Kinsta that you really appreciate?
Kevin Leary (09:34)
Yeah, definitely. First, I’ll say it. I have no incentive to say this, right? But I really like Kinsta I started using it way back. I don’t know when it was founded. I could be wrong about this, but I think it was 2016 or 17 for a site that’s still online today. It’s proto.life. And they don’t publish articles anymore, but it was great, to be honest. At that time, a lot of people, was WP Engine was the only default. And there’s still both.
Roger Williams (09:47)
Okay, yeah.
Kevin Leary (10:03)
great, but Kinsta’s been, since then, very fast. Site hasn’t really went down the server in any way. And anytime there’s an issue, it’s easy to get a response from it. I would say the big thing I tell people, it’s actually what I recommend, to be totally honest, on Reddit. If somebody’s wondering about a host, it is who I recommend. A lot of the feedback you get is, could get a site for $5 or $10 elsewhere.
Roger Williams (10:21)
Excellent.
Kevin Leary (10:26)
I always say this to everybody, the amount of time you will save by just spending an extra $200, $300 a year is so astronomically higher than the amount of time it will take if you go with the cheaper option that it’s just, for me, it’s a no-brainer, to be honest. And that sounds very promotional, but it is not. It’s totally 100 % honest.
Roger Williams (10:44)
Ha
No, and I appreciate that you were not primed in any way. But I’m with you on that, managed aspect of having somebody there who’s watching the servers and if there is an issue, resolving it, having backups that actually work, it’s priceless. And then having support that can actually answer your questions and get things figured out for you. Kevin, I like to keep these short and sweet. This has been…
Really an enlightening conversation. I appreciate your time. If people want to get in touch with you, if they want to hire you, what are the best ways for them to reach out?
Kevin Leary (11:16)
Yeah, definitely. So kevinleary.net is the best place to go. You can submit the form there. And it doesn’t have AI spam blocking yet, but it might soon. And also just hello at kevinleary.net is another email that you can write a chat on.
Roger Williams (11:31)
Excellent. And as far as like ideal customers, who do you enjoy working with the most?
Kevin Leary (11:37)
I would say my sweet spot, so you mentioned the niche before, I didn’t really mention it, but to be honest, I inherit a lot of custom built agency sites. So maybe somebody pays a lot for a brand and they get the brand online, but then they want to maintain that and grow leads, try to get more business coming through, try to make it more effective at achieving those goals. That’s probably my sweet spot, I think, because I can set up analytics.
help with the design of certain flows, develop it out, build it, see it grow, and then iterate on it.
Roger Williams (12:10)
Excellent, excellent. All right, well, Kevin, I appreciate your time. I hope that at some point I can have you back and we can talk more about some SEO and some AI and all the fun stuff. Thanks. Yeah, yeah, you’re welcome. All right, Kevin, we’ll talk to you soon.
Kevin Leary (12:18)
Yeah, I’d to. Yeah, I’d love to. Thanks again for reaching out, too. It’s been great.
Sounds good. Bye, Roger.