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Utah CTO Show: “Chase Mathewson – CTO at Huckabuy” — Show Notes

Podcast Description

Podcast Title: Utah CTO Show

Host: Brett Flake and Kristopher Jenkins

Guest: Chase Mathewson

Summary

Brett Flake sits down with Huckabuy CTO, Chase Mathewson, to discuss Chase’s career journey in the technology industry. Chase talks about his experience starting out with no formal engineering education, learning on the job, and finding dynamic leadership roles in startup environments that eventually led to more formal leadership roles.  Finally he explains his experience today, at Huckabuy, where he is working on a product he believes in.

Listen to the full episode here.

What You’ll Learn in This Episode

  • There are pros and cons to gaining a formal education (as a developer)
  • Most people feel like an imposter in the first job of their career
  • Startups can be a chaotic place, and a great way to grow into leadership
  • A good mentor is key, but you can learn something from most people
  • Find a product you believe in and work there

Time Stamped Highlights

[0:08] How Huckabuy CTO Got Started In The Tech Industry

Brett: Alright, welcome to the Utah CTO Show. I’m Brett, we’re missing Kris today, but we’ll catch you next time, and I’m here today with Chase Mathewson, who’s the CTO of Huckabuy welcome Chase. 

Chase: Hey, thanks for having me. 

Brett: We’re super happy to have you. Let’s just go ahead and get started here. 

Can you tell me about how you got started in the technology industry? 

Chase: Yeah, you know, it wasn’t something I actually planned out. So if you go way back, I wanted to be an animator. I wanted to go to Disney or something, and I quickly found out that design is a very hard field. I just wanted to do art — I love drawing. And so that got me just far enough to realize that wasn’t going to quite work out. Going into animation as a primary goal was hard — you know, it’s not like there was an animation studio down the street. So I started doing graphic design, and then that got me close to web pages, and after collaborating with a couple of people I ended up with a partner, we were running just a two man freelancing shop, and he got a big job out in Seattle. He said to me one day, “Hey, you know, if you want to teach yourself to code, you can keep doing this by yourself but I’m out of here.” So, I studied a lot over the next four weeks before he left town and the rest has just been taking on more and more challenges after that. It started with a lot of web design and I started coding some HTML and I was like, “Okay, I understand how to deploy a site. Okay, now I can do the CSS on that, I can make it dynamic.” I got into JavaScript, and then it turned into programming. 

Brett: That’s really interesting. I kind of have a similar background with drawing and art. I loved it as a hobby as a kid but then when it comes down to like being on the individual contributor level for design and stuff it’s definitely…you have to be very dedicated to it. But I got into programming pretty early on, and I think that it’s that creative background that really drives that and I don’t know if that’s how it feels for you.

Chase: Absolutely. I mean, I don’t know if it’s a good thing but some people have said like looking at my code I just like the way it looks — as opposed to the way it runs — that’s why I’m not sure it’s a great thing but, you know, you still look at things in a different way sometimes it is that creativity is the ability to take a different vantage or just think about things from a perspective that you might not look at it from if you came from a hard computer science background. If that was your goal, and you were all about efficiency and algorithms, you’re going to make something different than if you’re thinking about visuals. So for me, product was a perfect fit. I just fell right into that. You know, when people are saying “Oh well where do you want to specialize, do you want to be further on the back end or do you want to be more on the front end?” It was an easy choice for me because I was always thinking about the visuals and what the experience was like, and then the code was just something I had to learn how to do to make what I had in my head happen. 

Brett: Right, that makes sense. That’s interesting. I actually just recently discovered product, and was like, “Oh, this is actually where I fit in” Until recently I was a developer, but primarily an individual contributor there, and then a little bit of management, and then moved into product management. So you were a freelance web developer, your partner kind of took off to Seattle, and did you continue to grow that business, or what made you move away from that? 

Chase: Yeah, eventually became too much for too little. Yeah. Back at the time, you were quite young. At the time I was like, you know, 19-20 still trying to decide if this is truly where I’m going right. I did have that trim of all the animation and stuff, but you know, these were things we had taken on just, you know, we were good friends. And it was kind of side money and then as it came time to start paying bills and eventually long story short, I went and got a job.

[4:21] Chase’s First Job and The Imposter Syndrome

Brett: What was that like starting out your first job?

Chase: Oh, intimidating, people throw around the imposter syndrome line a lot and I carried that with me for a while, and probably still do, depending where you’re talking to me about. It was hard because I had no idea what I was coming in from, I wasn’t sure if anything that I learned would carry with me right because I had just done all this part stuff and you know I had a little bit of a computer background, just being a nerd, but I wasn’t sure if you know I was just hamstrung for my entire career I had no idea what to expect and every time I failed or struggled I attributed that to my weird start. I didn’t feel like I had the wind at my back, so to speak. 

Brett: Yeah, you’re gonna spin that in a more positive light. You’re just scrappy right?

Chase: Yeah, I mean, I would now.

[4:41] The Value of Formal Education vs. On-The-Job Experience

Brett: Yeah. So did you have any sort of formal education in technology or in the product space?

Chase: No,  like I said I was just looking into that artistic side of things. I’d started a little bit at the U of U wanting to do that. So it was just really this full body punch into the deep end. And I worked for a couple of startups, and luckily enough, in a startup world, enough things change and the needs are so rapid that as long as I was willing to be flexible, I managed to get the experiences I needed to round myself out pretty quick. 

Brett: That’s great. Similarly, I was moving from position to position just trying to get that experience. I did finally finish a degree program, but ultimately it was the job experience that got me to where I wanted to go I think. I think a lot of people out here, especially developers and people in product, like all those jobs you can do on your own without having to have the formal education and be an excellent contributor. Do you feel the same way? 

Chase: Yeah, I mean there’s pros and cons. You’ve got to make up for those cons because those turn into your weaknesses, and then it has strengths — the pros and you got to lean into those a bit. You know, someone on my team just joined who just finished her degree. And she has the ability to pick things up so quickly, because of that foundation. And I remember some things, you know, I remember the first time I ever had to interact with the database. And that was a three-month long process for me just to feel comfortable because I had never really seen the periphery of that knowledge space, right? So all that domain knowledge to me it was like, every time I learned something new I thought, “Oh geez I, I must not know anything.” Having the formalized education gives you some boundaries to what you know and what you don’t know. 

It helps you understand when you’re done learning. So in her case, she came on board and learned really quick and I don’t know that I could attribute this to education directly, but then there’s some rigidity that comes with that thought process of “Okay, I need to learn this new thing. You know what are the modules, what are the tutorials or what are the exercises I should be going through?” And sometimes I wish I could just throw everybody in the pool like I had in the past or like a lot of self-starters. 

Brett: Like “No, just try and fix this problem,” right?

Chase: Yeah. Ship it and if it works, that’s great, and if it doesn’t, that’s how you learn.

[7:29] Working at a Startup: The Pros and Cons (But Mostly Pros)

Brett: Awesome. So you’ve had a lot of experience in startups, it sounds like. Tell me about that a little bit, the good and the bad. 

Chase: Yeah. I mean really I don’t like to think about the bad, I mean definitely there were some companies that had turns that weren’t good for the business, and there were events that got stressful you know that’s just kind of startup life, but really I just look back and I think of all the people who taught me things being in the trenches with people, I think in a startup is the best way to learn. I can think of all these times I spent like a 12 hour day just working, working, working and then you got that success, and it’s fun. It’s exciting. I remember a weekend hit, at some point in my career, and I was disappointed. Once my career got to that point I thought “Wow this is strange.” I remember work being hard. I remember it being something you had to do. And then it’s like my career hit this point where I thought, “No this is where I want to be and I almost don’t want the weekend to come.” And I would work over the weekend in startups. “Startup” really for me, I think if I was to sum it up, I’d say it’s a challenge. It’s fun and it’s meaningful and all of that for me creates this feedback loop. That’s why I like startups. 

I’ve been at companies that stayed small, I like that. A couple of companies back, I was at InVision App, and when I  started there I think when we were at 50 employees. By the time I departed we were somewhere around 350. Before that, at LeadPages, I was the first engineer there in The States, and then when I left there, I think we were around 200.  And so, watching that growth factor kick in — I really like the startup from like zero to 100. Then once you get past 100, you start leaving what would be that scrappier time — that more impactful dangerous, riskier time. When more people get involved, bureaucracy starts to happen. And those things aren’t bad. They’re necessary, but I think for me, that’s why I look at startups with such kind of idealism. You know your work matters, there’s no boundaries — it’s challenging. But like I said, that’s really how I got my start and still try to grow.

[9:46] Changing Structures At Startups Enable Opportunities For More Individuals to Be Leaders

Brett: Absolutely. It just seems like it’s you know it’s a lot more challenging. There’s a lot less structure, and a lot of times have to define your own role in some ways. But then it can be more fulfilling on the other side of that.

Chase: Yeah, I think so I think the lack of structure allows for a lot more leadership, you know, individuals can lead. It’s like, “Are you in management, or are you a leader, or are you an individual contributor?” The roles are much more dynamic.

Brett: Yeah, it feels good. That’s funny. I was just thinking along the lines of a startup experience that I had where there wasn’t really necessarily formal leadership in place in our team and so there’s kind of this gap in, you know, communicating with the other departments and such. And I kind of naturally filled this leadership role that kind of needed to be there. And, and not ever having like the actual formal title, you know, I kind of took up this, it was almost more like a relationship management type thing for the other engineers because somehow I ended up being the more socially capable engineer, which to me is a joke, because I struggle with that for sure but like most engineers do I’m sure.

Chase: Yeah, it’s still something that affects me.

Brett: But yeah, I think, that was an interesting challenge and coming away from that, you know, it was very fulfilling as well. Kind of like, oh I accomplished something with my team and we focused on each other’s strengths and it was a good way to solve some of those problems.

[11:23] The Power of A Good Mentor

Brett:  InVision App, you started when there were 50 employees — that’s wild. So I imagine, over the course of that time that your role evolved or changed considerably?

Chase: I started out doing product management and — talk about change — that only lasted about a month. So up until then, kind of like you described, I had taken these informal leadership roles, either as a team lead, or sometimes as a product manager/UX person because of my design background, and I really just loved it. And my last role had been really strong on the product management side, but I’m still an engineer, so I had the privilege of giving myself my own tickets to go work on. But I started to see a lot of value in making the right choices. Early on, and I think with that, for me, it made me desire that role officially. I wanted to spend the majority of my time doing product management because I just saw that I could bring more value there for the business, and I just must have gotten really lucky, going into Envision and applying, so they brought me on for that. And, you know, we were just about to enter our hyper-growth phase. At that time, I think we had maybe 20 engineers, and they more or less all reported directly to the VP. So there was a management area in engineering, I came in with another product manager at the time, and just that management, that oversight, that ability to connect team to team or to align, or pull feedback, being a technical product manager, it just wasn’t very long before people were like, “Oh yeah this is great.” And, you know, the CEO, caught wind of it was like, “Look, I think we want to have a director of engineering anyway and you’re becoming that as a de facto thing so let’s just make it an interim thing. No pressure.” And I was stressed. So now the 20 people reported to me. And over the course of about a year to a year and a half we grew from 20 to about 100 and over that period of time I had leads, and I had product managers who were helping me but I was still technically the report for that many people. Then we grew out of that. I finally got some structure, and then I got to learn how to manage managers. I had an amazing mentor there, Bjorn Freeman Benson. That was probably the best experience I’ll ever have. He was one of the greatest teachers I’ve ever had the pleasure to work with. 

Brett: Yeah. And that’s awesome the, you know, it’s interesting you bring that up, you know the role of mentors is definitely something that we talk about a lot about on the Utah CTO Show, and it can’t be understated. Sometimes that just happens naturally, because of the roles that you have at your company and is that essentially how that happened with Bjorn?

Chase: Um, yeah. I’m sure if he had it his way he would have brought in a track team from people he’d worked with before, but the relationships were there the roles were there, and it was like “Okay, let’s see if I can work with you.” And I hope I was an absorbing sponge, you know, looking back I always just wish I could have just had another minute or another week with a good mentor, because I try to mentor my team now, and I still keep my eye out, or people who I can learn from and different little ways, but when you find a mentor who can teach you in many aspects all at once. I think it’s just really empowering. I hope it was pleasurable on both sides, you know, I like mentoring. Watching somebody grow and seeing, maybe seeing my past mistakes and them not being as big of mistakes, or helping them learn from my mistakes that they don’t make their own, to me, it’s really rewarding. So I hope that happened. 

Another thing that was interesting about  InVision is we were completely distributed. So you talked about the socializing of an engineer, it was like The Taming of the Shrew for me. It’’s like okay, “You’re used to sitting, not only being an engineer in front of a screen all day, but now you’re also in a situation where everybody’s located in different places so you can even be face-to-face a lot of times.” I think that was the unique lesson that I really got from him he was just technically brilliant but he also saw a lot of social skills, almost social engineering, I would dare say, I really think that that’s what makes the good mentor relationship, from the mentees side is just what you can learn, that’s unique to that person that you uniquely need and anytime you post, stars align. Then you’re really going to run into a really high value exchange. 

Brett: Yeah, there’s like a secret recipe to having the right problem to solve and having the right person to help mentor you at the same time. 

Chase: Yeah. And, you know, I always look for that. Like I said before, and it’s really easy to find somebody that can teach you an individual lesson. And I think you really have to look for people that you might not disagree with but who have a really strong strength that you can pull from. That’s what I try to remember, I go to places where I’m weak, and I look for people that are strong there to try to pull lessons from. But you know, when they’re just the person you report to, in your same field, in your same vertical within a company, and if you get lucky, a lot of those checkboxes get checked all at once. 

Brett: It seems like I’ve been really lucky lately, with that. 

[17:05] Work for a Place Where You Believe In The Product

Brett: Yeah.  InVision App is a great product, like, a lot of our audience has probably used it, maybe you can tell me a little bit about having a product that you believe in and having that be different than contrast that with maybe a situation where you didn’t have a product that you believed in or something.

Chase: Well you know that’s funny, because I don’t think I’ve believed more in a product than what I’ve been working on with Huckabuy. When I was at  InVision, there were times where I struggled to really attach to what we were doing, because  InVision does a lot of different things. You go in and you try to play, or if you were on the inside and you can see all the different teams and all the different projects we had, it was kind of a broad scope. And we hadn’t gotten really deep — at least in the time that I was there — we were so busy trying to build new things and release new features that there wasn’t a lot of deep technology built. You know, we get a feature working, we try to scale it up, we move on and we build something new. Whereas, in my role right now, my team is laser-focused on the technology, and we don’t even have the UI for it. So when I was at  InVision, I loved the UI. I would really miss being the product manager, just because I couldn’t sit on the design meetings anymore and I couldn’t see all the different UX discussions. The user base for that product is huge and it’s a product for building products, so you’ve got this wonderful exchange where the people you’re building it for can see the product and like the product and then they’re all product people so their opinion means more to you —and that was great. Whereas now, sometimes we’ll be working on stuff for a couple of months, and it’s just this technology piece that you never put a UI in front of, and that’s probably what I enjoy the most. Right? 

Brett: The magic behind the scenes. 

Chase: Yeah, you know I like it when you have a product that other people find impressive; that’s obviously really fun. But when you talk about being able to connect to things, for me it’s the investment and the challenge. I think sometimes a UI, it’s almost like a low hanging fruit. You can say, “Oh look at this cool UI. Look at the way this dashboard shows up or this animation works on the floor,” and it can look really cool, and everybody can get the warm fuzzies, and then you look at your usage numbers, and they’re just not there. So, that happened a few times throughout my career where I would do these big redesigns and everybody was really excited and I was like —  

Brett: Yeahit’s disheartening. It’s painful. 

Chase: Oh yeah, I remember months of time going into redesigns and app overhauls and then we’d release it, and almost immediately the feedback would tell us we missed the mark.

Brett: Yeah, or just the general disinterest in it or something you know and it’s like, “Oh, I thought this was gonna be a thing. They hyped it up so much.”

Chase: Well, and it might be amazing, right? You and your team might have really made something cool, but maybe the business alignment wasn’t there, maybe you had done a really great UI for something that people didn’t want to engage in, or it wasn’t the atomic action that they really needed to get out of your offering. 

Brett: Yeah, it would have worked better for a different customer base or something. 

Chase: Yeah exactly. So, for me those things really used to draw me in but now I look at things like the technology that’s underlying everything else — some of the more core directions, because then those things don’t go away. And as I invest in them over time, it tends to ramp up my engagement, rather than have these peaks and valleys, it’s a little more of an investor’s portfolio than a traders portfolio, if that makes sense. 

Brett: Yeah. Yeah, no, that does make sense.

[20:35] What Huckabuy is Doing To Change The SEO World and Help Out Developers

Brett: So, before we end here I’d like to get in a little bit of questions about Huckabuy itself. SEO is not, in terms of the technology sector, it’s not a new problem. You know, this goes back to 1995 when Google first started and stuff. What are you guys doing to shake things up? 

Chase: Oh man. Yeah, you’ll have to make sure to ask me a question so I don’t talk too much about it. But, you know, when you look at it from the market, or you look at it from the people and the stakeholders, it’s really common that you can find developers that don’t really invest a lot of time in SEO. It’s often an afterthought or it’s a ticket they have to handle, because it came from another department or then you’ll find people who are really invested in it, but they don’t have their hands on the steering wheel, they’re not able to go at it from the perspective of having their own dev team and making it a priority. So it’s a really nice market space to be in because there’s a lot of need for innovation there. 

When you look at the SEO problem on the web, you gotta look at it from Google’s perspective. How do they get the most information that’s accurate, and what would they rather have: more information, or would they rather have less information in terms of accuracy? And you can look and see Google’s more or less about quantity before they are about quality. If you’re somebody that they’re trying to index, you want both. You don’t want to sacrifice the quality of your content or maybe the caliber, or the right keywords and all of that stuff. And so technically, when it comes to solving these problems, it’s about your platform. It’s about your deliverability, it’s about balancing what you want to do for the robots versus what you want to do for the users. Working at Huckabuy, one of our things that we like to say around the office is: “The number one visitor of your website is a robot, and it’s Google,” because until they come and index it, you’re not going to get that content in front of users. 

We’re looking into everything that Google makes available, or says they want to support. They’re really big on structured data recently, so we have a product for that. Two years ago they offered dynamic rendering, and so we have an offering for that. And then we’re trying to combine that with what the actual implementers need — so trying to make the right points of ingress and remove these things that a lot of people want to do but they can’t do. And so now instead of, you know, making a bunch of tickets to your development team over the course of one or many quarters, you can just use the product to get it done. So, I guess, as you can tell, there’s a lot of different aspects to it, and it is an old problem, and agencies dominate the space, there’s not a lot of products out there, and if they do exist, they’re just products that tell you what work you need to ask your agency to do, but not a lot of products actually move the needle for you. And from a technologist perspective, that’s what really keeps me interested in what we’re building. 

Brett: Yeah, absolutely. Yeah, it seems like if you can find some, some particular segment of a problem that everyone else finds tedious, you can build a product around that, or a service around that, and that can really take off. Huckabuy just recently got some funding, you guys obviously have people who are interested and you’re doing well. So it sounds like maybe you found that piece of that niche piece of technology that people don’t want to do themselves. That’s really good. 

Chase: Yeah I think so and I think, for us on the engineering side of things, it’s a real joy because we’ve all been in those seats, and we’ve had those requests made of us. And, you know, we all have thought “Do we really have to lose a cycle to this.” And so, building a tool that we know is taking the eyerolls out of the engineering teams out there, kind of helps us have some motivation behind it. It’s not a business motivation, it’s something that really touches us in the heart. 

Brett: Right. Yeah, we can’t forget the human element so that makes sense.

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