Introducing Jonathan Gilbert
Jonathan works in Portland, Maine for an employee-owned company called Qualpay. Jon went to his first WordPress event in 2016 and has been hooked on WordPress and its community ever since. When not working, Jon enjoys hiking, traveling, cooking, and hanging out with his cats and wife.
Tara: This is Hallway Chats, where we meet people who use WordPress.
Liam: We ask questions, and our guests share their stories, ideas and perspectives.
Tara: And now the conversation begins. This is episode 92.
Tara: Welcome to Hallway Chats. I’m Tara Claeys.
Liam: And I’m Liam Dempsey. Today, we’re joined by Jonathan Gilbert. Jonathan works in Portland, Maine for an employee-owned company called Qualpay. Jon went to his first WordPress event in 2016 and has been hooked on WordPress and its community ever since. When not working, Jon enjoys hiking, traveling, cooking, and hanging out with his cats and wife. Welcome, Jonathan.
Jonathan: Hey, thank you, guys. Thank you for having me on the show. I’m very grateful to be here.
Tara: Hey, it’s great to have you here, Jonathan. Can you tell us more about yourself?
Jonathan: Yeah. I work for an employee-owned company called Qualpay. We’re based in San Matheo, California. I’m personally based in Portland, Maine as one of two remote employees out on the east coast. We’re a solution provider for WordPress and we create payments platform that helps developers earn additional revenue by providing a service that their customers need. We help merchants by providing the most updated tech in modern payment features to help their business grow. My job is to get developers and software providers to use our platform by offering it as a value-added service to their core offering. I’ve been having a lot of fun doing that in the WordPress community so far. It’s been a really tremendous experience meeting these people.
Tara: How much of what you’re doing is number-related? You have to know a lot about accounting and that type of thing? Or is it more coding and programming?
Jonathan: That’s really interesting. I have to know quite a bit about pricing and so forth but the people who work with me don’t. We have some pretty easy calculators that we use kind of to take the load off of our partner’s back and kind of do the thinking for them. For me, there’s a couple of quick calculations that I need to be able to do but I also have to understand– I can’t code myself but I have to understand and talk about code, and certainly, we’re API-based and so it’s important to be able to communicate why our services are valuable to a developer and a merchant. It’s a little bit of both, a little bit of being able to run some numbers but also having at least a remedial understanding of how programming works.
Tara: Yeah. What is your background then?
Jonathan: My background is actually in business. I went to business school to become originally a sports agent. I went to the University of Massachusetts to the school that the McCormicks founded, who is the father of support management. I graduated high school right around the time when Jerry Macguire came out and–
Tara: Ahh. “Show me the money.”
Jonathan: Yeah, exactly. I was like, “I really want to work in sports.” And then I first started working for Michael Phelps’ agent, Peter Carlyle and through that, I learned a lot about how non-profits work and– but I found the most thrilling part for me was kind of putting these presentations together where we would figure, what’s a good fit for Michael Phelps in terms of products that he should endorse? And what kind of values can he help communicate with these brands and create a perfect match? My favorite part was always when we were talking to those interesting companies and how we could help them kind of communicate the interesting things about their companies through sports, something that everyone can relate to.
Tara: That sounds like it must have been kind of fun.
Jonathan: It was a lot of fun, yeah. The part of the company that I worked for was Olympic and action sports. It was also during kind of the takeoff of a lot of these snowboarders and skiers like Hannah Teter and Shaun White. It was really cool to be around and get a free couple pairs of gloves here and there and some goggles. Yeah, it was a lot of fun.
Tara: Did you get some autographs too?
Jonathan: I did, yeah. Actually, when I was in college, I volunteered for the X Games and I worked in the Bagel Bites tent and I got to work with Tony Hawk. I basically was just cooking bagels back and forth but he was there signing autographs and a really cool guy to hang out with.
Tara: That’s really fun. What’s your trajectory from there to working on WordPress software?
Jonathan: Originally, I started working for the support management piece and then I went into a field called experimental marketing, which we were creating these experiences for brands and so forth like these Gillette shaving experiences with Michael Phelps or things along those lines. In 2006, I ended up leaving the company to go travel around Australia and kind of backpack around for a year. And when I did that, I came home and I started temping for a company called PowerPay which was just this payments platform. I just became really interested in how payments were connected to software companies and I just kind of understood that as a very important part of the software company’s business. You’d have these shopping sites, you created these e-commerce platforms, but you also needed to connect payments to it in order to get that license, in order to accept funds on their site. It just became fascinating about how that world unraveled. And recently, when joining Qualpay a few years ago, I was very drawn to it because I saw Stripe being this company that had this beautiful documentation and this great solution that a lot of developers liked. And I was like, “Wow. Wouldn’t it be great to work for a company that had these features but also had kind of an affiliate program so developers could earn revenue for doing this?” And I came across Qualpay and the first thing that we were kind of needing about this company and where we should kind of embark upon for e-commerce platforms, and either we wanted to do an open-source platform because we wanted people to play with our tools and to build stuff with them. So I checked out a WordPress event and I was really blown away by the community and really just how people treat each other. It’s a very interesting community where everybody is like a bit of a tinkerer. And solutions become popular not because you dump a bunch of money into advertising, it’s really this group of peers reviewing peers and helping each other out. I was really blown away by the fact that I was visiting these hosting company tables, Bluehost, GoDaddy sitting right next to each other, and they were getting along so well. They’d have a customer going from one booth to the other booth at this WordCamp. And they were competitors but everybody was helping each other. It’s very, almost, socialistic to the extent where it’s all for the greater good. If you’re not succeeding by helping everybody, you’re not really helping everyone. Just seeing other people lift each other up and seeing just the inter-connectedness of everybody, I just came away being– just had this overwhelming sense of happiness and I just felt so energized from the community.
Tara: Yeah. I would think that would be a big draw. I haven’t really thought about it too much but as a vendor, as a provider to the community, that would be, I guess, a really big draw to sell to this community because your competition is also your colleague’s. I know it’s like that from the agency perspective but I never really thought about it from the perspective of the hosting companies and that type of thing. That’s really interesting. And now, make a note of the time, Liam, Liam’s Zoom has frozen so he cannot unmute himself which could be a story for an episode when I’m hosting and Liam can’t make it. We can just pretend that that happened, but in fact, Liam is here, but we need to stop this Zoom call because he’s hosting it, and restart with a new Zoom link.
Liam: Jonathan. I want to ask you about your role at Qualpay. It says you’re not a coder but you have to be able to talk about it and you have to know what your company skill does, what it doesn’t do, what it plays nice with, and what it plays very perhaps poorly with if it plays poorly with anything. Talk to me about getting your head around that. Because if you’re coming from a non-technical position and you have to learn to talk tech, there’s a learning curve there and there’s a confidence issue. That first, “I’m going to show these people how to do it.” And they say, “Oh yeah, well, how about this?” And then you say, “Oh.” What was that like? What was that process like for you?
Liam: So all the PCI compliances there.
Liam: Let me talk over you because I want to talk about Maine. [laughter] I’ve never been and it’s on my bucket list of places to go. Tell us a little bit about Portland, how big it is? You said you’re into hiking so can you walk out of your house and hike or do you have to drive to the edge of Portland? I don’t even know if that’s driving to the edge of a city of 800,000 or are there four people that live in Portland, you wave to them as you walk out. Tell us a little bit about hiking and living in Maine?
Jonathan: Maine’s got about a million people. Greater Portland has about 250,000. Most of the people are kind of where I’m living right now in this bottom part. I can tell you, one of my favorite parts about Maine is the local supermarket that we go to is called Hannaford. There’s three of them right next to my house. Two of them overlook the ocean and one of them overlooks a 10-mile nature reserve. Portland itself is very vibrant food, beer, and coffee town. Three favorite things.
Liam: That about covers it for me, too. I’m done.
Jonathan: Exactly. So there’s all kinds of running trails, walking trails, and biking trails within two miles of where I live in downtown. It’s very easy for me to be connected to nature and to leave and go see a little wooded forest. And that’s what I really appreciate, growing up by the water is being able to get out quickly and take a look at the ocean and smell the sea salts and hear the seagulls.
Liam: So you grew up there?
Jonathan: Yeah, I grew up about 15 miles south in a small town called Saco.
Liam: And you talked about going to see the ocean, to smell the salt, and to look at the seagulls. I’m guessing since you didn’t mention play in the water that it’s a bit cold and no one goes swimming up there or how does that work?
Jonathan: It is a bit cold. I actually surf in Maine. You’ve got to use a wet suit for most of the year but there are some pretty intense surfers out here who surf all the way into January, February because that’s when the biggest waves are. I am not that bold. I surf until November. 46 degrees, 45 degrees is cold as I’ll allow the water to be around me.
Liam: Yeah, that’s cold. I was watching a documentary recently about some guys who go surfing in the Arctic circle so that they can surf under the Aurora Borealis. And while the footage looked awesome, they had to like clear ice away from the edge of the shore to get in to go surfing. Colder than I’d like.
Jonathan: The funny part about surfing, it’s like, when you’re in the water, that’s alright. Yeah, you get splashed in the face, you get a little ice cream headache, every once in a while. But the hardest part is actually getting out from the ocean and out of your wetsuit into your car. Those five minutes are– and it can take longer because your body is a little numb and it’s so hard to wiggle out. The colder it is, the harder your wetsuit is to get out of.
Tara: What is the tech community like there, that remote place?
Jonathan: It’s actually a pretty big tech community. We actually do a lot in pet healthcare. There’s a company called Idexx that’s the largest veterinarian supply company in the world. They’re the ones who come up with heart medications and how to identify parasites and so forth. It’s a two-billion-dollar company, it’s downtown in Portland. We also have a pretty vibrant startup community as well with a lot of ocean-based products. We have some people who do kind of scientific marine stuff. You have people– one of the biggest companies out here was a lobster company that ships all around the world. These two kids that grew up from a high school around here. I don’t know if they hit 30 yet and they’re probably making few millions of dollars a year in profits. We do have a nice little tech community and a lot of it’s connected to marine sciences or pet sciences.
Tara: Okay. I want to ask you about success, especially talking sort of about quality of life where you live and appreciation for nature and that kind of thing. How do you define success professionally and personally, mixture of the two, or if you want to focus on one? What does success mean to you?
Jonathan: That’s something that continues to change for me. When I was a kid, I grew up on Welfare. So as a kid, most of my goals in life were about making enough money to buy a house and to have a cool car. Once I, at the end of my 20s, started making money and I got to buy a house, I realized that the next thing that you want is a campsite and this or that. Whenever you buy something, that satisfaction happens for a moment and then you want something more. When I think about personal success and when I reflect back on the things that made me happy and made me who I am, it’s been about these collections of these experiences that I’ve been a part of. It’s traveling, hiking the Appalachian Trail, backpacking through Australia, being part of sports teams. When I think about the things that have shaped me, it’s always been through experiences that have made me be uncomfortable or vulnerable in the people I’ve met through these journeys. Now when I think of success, I’m kind of, how can I showcase more gratitude? How can I be happy with what I have so I don’t want more? How can I keep evolving and put myself out there and keep meeting people who help enrich my life and help me understand common things that we’re all going through and things that can help us make us better?
Tara: I love the idea of not only being grateful but not wanting more. I just finished reading the book The Company of One, and it talks a lot about the idea in our society of success and never maxing out, just always trying to learn more and always improving on your revenue and that type of thing, and growing your business. You might not need that. He talks about a friend of his who basically works until he makes enough money to sustain him for the rest of the year and then stops working so he can go skiing or do whatever. The idea of understanding that you don’t always need more, it goes against the grain of, I think, our culture in a lot of ways but it’s a brilliant relief to realize that that’s okay, so I love that definition, thanks for sharing.
Liam: I wanted to ask a question about it. You said it’s about asking yourself, “How can I showcase more gratitude?” What did you mean by that?
Jonathan: It’s being able to internalize what makes you happy and also the things that you have and being mindful of the things that you have. For me, when I wake up in the morning, I try to say, “What’s one thing that you love about your wife? What’s one thing you love about your work? What’s also something that you love about yourself?” It’s reminding yourself of these little things that can help you be a little bit more happy with what you have as opposed to what you don’t have.
Liam: Do you ask yourself those three questions when you’re still in bed or is that when you’re brushing your teeth or when you’re having the coffee? When does that awareness of the emphasis on gratitude?
Jonathan: I try to do it the first thing I do when I wake up or it’s part of my meditation practice. Sometimes when someone cuts me off when I’m driving in my car, it’s not thinking about the person who cut me off, it’s thinking about how lucky I am that I have a car that I’m driving.
Liam: Yeah, especially in America.
Tara: For sure. Thanks for sharing that. How do you apply that idea in other ways? In your work and your interaction with your community? Do you have sort of gratitude?
Jonathan: I listen to this really great podcast by someone names Rich Roll and he had a guest named James Clear who talks about habits. A habit is a set of behaviors that you use to solve recurring problems. And if you think about your own persona, all we are is a story. When we think of ourselves, it’s a collection of all of our experiences. That’s really all we are. When you think about the person that you want to be, you can think about little behaviors that you can put together to kind of reinforce that persona. I want to be a healthy person in terms of my own health for my body, so I make sure I exercise five days a week. I want to practice being more grateful and mindful so I meditate. I also need to become smarter and to understand how people are also dealing with these problems maybe better than I am. It’s reading books from peers, it’s reading people’s Twitter feeds on WordPress and understanding how some of these people solve the same challenges that I’m going through it can make me a better person.
Tara: Yeah, that Atomic Habits is another book I’ve read recently and it had a big impact on me. Thanks for mentioning that one, too. So many things. How you define yourself instead of just saying you want to aspire to something, saying, “I am a healthy person.” And it helps you be that. For sure, yeah, absolutely.
Liam: Jonathan, what’s been your biggest challenge to date or what is your biggest challenge and how are you working it or how did you fix it, how did you overcome it if it’s–?
Jonathan: Yeah, it’s something I’m still working on. Being a new company, especially in a payment space where there’s a lot of other companies here, and especially in WordPress where Stripe and Paypal have been the overwhelming favorite for what people use. Because in a lot of senses, people have always thought about payment as kind of a means to an end. It’s like, “I’ve almost finished your site, connected your e-commerce software. Go sign up for the Stripe account because it’s easy to set up and I can just hand this off to you and kind of wash my hands of it.” And getting people to kind of understand that, your clients for one, are looking for you as a recommendation in the products and services that you offer. A lot of people think about when they design a site, “I’m going to resell them an SSL certificate, I’m going to resell them web hosting. I’m going to recommend this e-commerce platform and so forth.” And if you can help them make that very last step, which is choosing a payment processor for them, it’s a great way to earn recurring revenue for one and two, it’s a great way for them to save their pricing because the flat rate one size fits all pricing doesn’t work for everyone and there’s a lot of reasons why certain merchants should use it and certain merchants shouldn’t use it. And I’ve noticed that this community, because they have overwhelming use of Stripe and PayPal, people don’t have as much of an understanding about the impact of payments. So it’s been a really challenging thing for me but a really fun thing for me to educate people on why pricing matters, what kind of decisions do you think of when setting up someone’s payment processing, how do you sell payment processing, and so forth. I really enjoyed how open people are about talking, about their pinpoints and so forth. To me, it’s how can I further educate people on payments and help them empower their clients.
Liam: Do you see that more as a communication challenge that you’re facing or is that as an education challenge?
Jonathan: It’s a little bit of both. Pins can be so complicated. You can get so deep into the weeds. It’s really just first educating these people that this is something that you can’t use to earn revenue on. To me, it’s more of an educational thing.
Liam: Okay. Let me ask you another one of our signature questions and it’s about advice. You’ve talked a lot about the practices that you have to try to be a better person and I wonder if you can share with us some advice that you’ve received or gleaned or read and successfully implemented in your life? Some advice that’s made a big difference. What is that advice?
Jonathan: When I actually graduated college, someone gave me this old book from Dale Carnegie, How to Win Friends And Influence People.
Jonathan: There’s this really profound part where he was talking about the favorite sound that anybody can hear is the sound of their own name. When you meet people, keep repeating their name, but mostly, it’s a life lesson on how to be compassionate with your speech and how to kind of make people know that they’re important by asking questions about them. That really helps me when I’m at networking events, it’s always– I think everyone gets a little anxious when they don’t know people. And just being kind and asking questions is a great way to kind of open people up, to really get an understanding of what people are about.
Liam: Yeah, that’s certainly been my experience as well at conferences and meetups and tech events, is paying a little extra attention to what the people who we’re meeting, what their name is, and making a little extra effort to try to remember it. And then when we see them later in the day, to be able to say, “Oh, hey, Jonathan. How are you? How’s your day been?”, “Oh, you remember my name. Wow, thanks. Yeah.” The value of hearing your name, I never thought I heard it phrased that way but that’s really interesting.
Jonathan: Yeah. One of the things that I love about the WordPress community so much is how much people put an effort in because they know that there are people who are very introverted. Before, one of the WordCamps, I think it was WordCamp Miami last year, someone put this PSA about the Pacman approach. If you’re in a circle, you shold always leave a little bit of a circle open for somebody to come in because it’s hard to break into a circle. If a bunch of people are talking and there’s a lot of people who just want to be a part of that conversation. I think the etiquette that people use at WordPress events, it really warms my heart.
Tara: I love that. I’ve never heard that Pacman approach or description. That’s really cool. I love that. I’m going to remember that next time. And I also loved Pacman but I don’t play any video games anymore.
Liam: We’ll save that for another day.
Tara: Yes, for sure. Jonathan, it’s been great having you with us today. Thanks for telling us more about yourself and what you do, and your history, just really loved getting to know you a little bit and hope to meet you at a WordCamp. Can you tell us where you can be found online?
Jonathan: Yeah. My personal Twitter is @prefont and you can find information about Qualpay at Qualpay.com.
Liam: Jonathan, thank you so much for joining us out here on our virtual hallway today, it’s been a real pleasure getting to know you and I look forward to trying to get up to Maine and get that ticked off my bucket list before too many years more.
Jonathan: Yeah, pleased do it.
Liam: Definitely, I will, I will.
Tara: Thanks for joining us.
Jonathan: Thanks for having me.
Tara: If you like what we’re doing here – meeting new people in our WordPress community – we invite you to tell others about it. We’re on iTunes and at hallwaychats.com.
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