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October 6, 2022 · 17 min read

Season 2, Ep. 6 – No software is better than no software.’s Director of Engineering (and Janitor), Wade Williams

Sure, you have someone at the helm of your engineering department. But do you have someone that used to be a professional waterskier? Probably not, and we promise that’s just one of the amazing things you’ll learn about our Director of Engineering and sometimes janitor, Wade Williams, in this episode.


Read transcript

Faith (00:04):

Welcome to your staff interview, Wade.

Wade (00:08):


Faith (00:08):

I’m very excited. I’m gonna pretend like I have no idea what it is that you do so that I can ask the right questions. But we’re doing these interviews because I think folks are interested to see kind of who’s behind the scenes here and what they think about every day, kind of their primary focus, and how they got here. So I guess to start, Wade Williams, what is your job here? What do you do at

Wade (00:35):

I typically tell people that I’m the janitor, so kind of jump around a lot and make sure the wheels are staying on for most of the app things. I guess technically, I direct the engineering team.

Faith (00:51):

Specifically on the engineering team. But he also does some janitorial duties across teams as well.

Wade (00:58):

Yeah, for sure. And I mean at, at this point, like we’ve got whatever, three other folks on the engineering team and going on two product folks. So you know, I try and keep up with the workload on the engineering side, but I’m also like just running around and coordinating and in and outta meetings and trying to keep the ball moving forward on all angles. So whatever needs done, that’s what I’m doing.

Faith (01:27):

I feel like you have been in the Gun circle well before my time. And one day we just needed an engineering leader, and the next day, you were here. So I’m sure there’s a story there. How did you find yourself at Gun?

Wade (01:45):

It was a circuitous route to say the least. I worked at a startup down in Arizona for like five years, which is a different complicated story. But surprised to say, I bailed out of there and went to Nepal for like three months.

Faith (02:04):

I didn’t know that.

Wade (02:05):

Yeah, this was like 2016. And I had seen Gun in like 2013, when it was like a bug bounty page with like, hey, do this here. As much money you could make, thought it was cool. It was interesting. The branding was on point for 2013, I guess some parchment paper background, geomorphic whatever. 

Faith (02:27):

Yes. You can find it on way, way back if you’re very curious.

Wade (02:30):

So I wound up, I don’t even remember what the process was at that point, but I reached out to whomever, however it worked—and wound up talking to Megan in or about early summer 2016, I guess, and wound up going through the process that existed then, which was less structured than it is now.

Faith (02:59):

Yeah, it’s very different.

Wade (03:01):

Yeah, it was. I only got like five or six people fired from projects for just not doing what they were supposed to be doing, and there was just a lot of waste. There was also a really big disaster project that I was on with Gun that I had to try and save in the 11th hour after people had screwed it up royally for months. That was really fun.

 Faith (03:26):

So you’ve been running around with the mop bucket for many years. Your janitor rule is not new.

Wade (03:32):

No, it’s not. Basically, you know, you read the linchpin thing from Seth Godin, it’s like, okay, well I guess I just need to keep the wheels on. That’s kind of the move.

Faith (03:43):

So you came on basically like inherited v1 of the app as we know it today, and then built out our engineering team and that was 2019? 2020.

Wade (03:58):

Yeah, the app, the first commit was made in August of 2019, and did a lot with Jordan Shots back in the day. And I’m in a Slack with him and we kind of chatter back and forth now and then. He’s like, Hey, you should do this project for Gun. And I’m like, No, why would I do that? And he is like, Hey, you should really do it. And I’m like, No. And then he wound up—so I have a Slack team that’s like a local—it’s basically like people that I’ve worked with in the past—and the local tech meetup group is all in there, and there’s like channel for like the local tech meetup group. And so Jordan gets in there and publishes this thing where it’s like, I’ve got this job that I need somebody to take over for me. And it has like, it’s this tech and that tech and that tech and that tech and it’s like everything that I know perfectly, it’s like the perfect description. 

Faith (04:50):

He was obviously ready for you. He knew you were in there. 

Wade (04:53):


Faith (04:53):

He just wanted to publicly—

Wade (04:56):

Yeah, publicly shame me into taking the gig. Yeah. In my own Slack team. Yeah.

Faith (05:00):

Oh my God. Is he—he’s near you? I didn’t realize that you guys were—

Wade (05:03):

He’s up in Montana. I saw him last year. (Faith: Ok.) He’s like seven hours away, but—

Faith (05:09):

Which, out west, is close.

Wade (05:11):

Yeah. I mean, Salt Lake’s like four hours, so I guess that’d be closer. But yeah, I met him for the first time in— IRL last year.

Faith (05:19):

Wow. Big moment. 

Wade (05:21):

I’ve worked with Jordan since 2016 on Gun projects, so it was kind of like—

Faith (05:25):


Wade (05:27):

So anyway, yeah, he posted in my Slack team about this job that was like the perfect tech fit for stuff that I know, and I was like, Okay, Jordan, fine. What is it? And he is like, It’s gone. And I’m like, that’s not what I wanted. God. I’m like, fine, I’ll look at it.

Faith (05:45):

And here you are.

Wad (05:48):


Faith (05:49):

So you built out our engineering team, as I remember it, pretty quickly. Like I think you were a lone wolf for a couple months. And then Regis and Richie joined in short order, is that right?

Wade (06:00):

Yeah, so I started—I picked up the app like end of February, beginning of March, 2020—just right about pandemic moments. So that was cool. And then we had a Nashville dev, Tim Warren, come on for a couple months to do some of the front end work. And then by the time that we had the company infrastructure set up so you could like sign up as a company, I think was September, and promptly use that to go find our engineering team. So we posted one job for, I think it was a UX engineer is the way that we framed that one, and 15 people applied. I interviewed most of them a varying quality, but the top three folks we wound up hiring over the course of, I think we brought Regis and Richie on end of September beginning October. And then Steve came on, I wanna say like January of 21 or so.

Faith (07:02):

I feel like the sentiment on the team is that our engineering team is really unique. I feel like we move really fast, especially given kind of the resources. What do you think makes our engineering team unique?

Wade (07:19):

Yeah, so I don’t think our engineering team’s necessarily unique. I think we just kind of adhere to a few principles that work pretty good. So there’s kind of a lot of research on this, if you take the time to dive into it. There’s a, a couple novelized versions of like how to do things correctly. The super dev-relevant one is called the Phoenix Project, which tells a story about some impossible situation that somebody gets put in charge of this project that’s a complete disaster and has to rescue it. And they do that through basically lead manufacturing principles. And the Phoenix project is effectively the goal, which is another novel, but the goal is around actual manufacturing at like a auto parts plant and theory of constraints and you know, which machine on the floor is taking all the time and making everything go slower? And then don’t context switch that machine, and just keep it going at maximal capacity, like eliminating the constraint. And if you’re, you know, retooling that one machine three times a day, then you have how much downtime and you didn’t make any parts. So that kind of translated into: DevOps looks like kind of what our process looks like, which, you know, we do one week iterations. We put the issues in on Friday, we kind of go over Monday and make the final cut and then go for the week. And at the end of the week, most of the things in that milestone are done. Some of ’em aren’t. And we make the call on whether or not those things are gonna go into the next week. But you know, everybody’s encouraged to try and finish one issue a day. If you’re doing one issue a day, then you’re making progress. We’ve got three to four people, depending on how you wanna count. ‘Cause I’m frankly not very useful in my janitorial role right now as far as like actually moving the milestone forward. But you know, you can knock out the one issue a day. Then we’ve got somewhere in between 15 and 20 issues being done a week and that’s a pretty good clip.

Faith (09:19):

Yeah. In my mind you’re like a Jedi master in that you know a lot about many different things. And so I’m curious how you got started in engineering. Like was this a lifelong career thing? It sounds like maybe—

Wade (09:35):

No. The circuitous route, the serpentine route through the neutral zone. So, I had a pretty good start. My mom worked at the Apple store in the 80s, and so I like learned to spell on an Apple computer. You know, I had a lot of experience withcomputers in general. Windows 95 came out, that was cool. The internet. (Faith: Yeah.) And then I would just sit around in like the late 90s and view source on webpages and figure out how to do that stuff. I also had an HTML class in high school in like ’99-2000.

Faith (10:12):

That’s very progressive.

Wade (10:14):

Yeah. I went to a pretty good high school: private, all boys, Catholic, super awesome. (Faith: Nice.) Then I went to Florida to be a professional water skier, got a water ski scholarship, and did that for like 10 years. But I majored in computer science in college, so I had that going for me, and I kind of kept up with it, you know, I was doing websites the whole time, and ran a pretty big water ski coaching forum website thing and like built custom software to do video coaching before YouTube existed. So I was always keeping busy with it just on my own projects and what have you. 

Faith (10:56):

Is that how you learned how to fix a boat?

Wade (10:59):

Something like that? Yeah. No, I grew up on a pond, so like, I’ve been around boats forever. Like forever. Like, I was on 27 foot sailboat on the ocean before I could walk, so…

Faith (11:13):

Hmm. As you do.

Wade (11:14):

Yeah. So I basically ended my water ski career and went back to Boston for one winter and lost my freaking mind because it goes dark at like four o’clock in the afternoon in the middle of the winter. (Faith: Oh yeah.) And so I started talking with some recruiters in Boston and wound up like—just the dumbest stories ever—but the CTO for this company in Arizona lives in Marblehead, Massachusetts. And so I wound up interviewing with him and getting hired to go to Arizona, even though he still lived in Massachusetts. (Faith: Yeah.) ‘Cause an absentee CTO is—well, you have the in-house team in Arizona and we’ll just have the CTO in Boston. And so it’s the funniest stuff ever because yeah, it was a really good experience, because we could—we did a bunch of different things and got a lot of good experience with like varying technologies and problems and, you know, white labeling a web app is kind of a whole like, swath of problems.

Like the CTO would be on a Zoom—it wasn’t even Zoom, like—this is so bad. Back in the day—it’s amazing anything even works—but the technology that we had to deal with even 10 years ago is so silly. So there was this—I forget what the name of it is—but there was like this tiny video thing that you could just open up and have a video call with people on, but it was like in the web browser and it didn’t work good. So we would have these things around the office, so the CTO could just like jump in, and so the screen would just be on over there, and suddenly he pops up—

Faith (12:59):

What in the world? 

Wade (13:00):

“Hey, guys, what’s going on?” It’s so weird.

Faith (13:02):

Surely it’s easier to just move to Arizona.

Wade (13:05):

Yeah. So I did a bunch of work there, left, started doing things with Gun, and then I wound up buying this this web app called, Sprintly, that we had used back in the day to like run our sprint process in Arizona. So I wound up buying that and did some work there for a few years. It’s still operating in production, but that’s like another whole swath of stuff. It’s like a fully blown SAS software that’s up and running with all of its warts and good things and problems and not problems and what have you. So I mean, a lot of my experience is just self-taught and do it from doing it. But technically, I got that computer science degree. The startup that I worked for in Arizona was really interesting because, you know, it was a big hype machine. And, and we worked with a lot of big clients from BMW to like Peterbilt trucks and Domino’s Pizza and what have you. And every one of those needed their own little snowflake solutions, and we had really poor product management, which is kind of why I started doing product management after that—because it became pretty clear to me after a few years at that startup that it doesn’t really matter how good you build something, if it’s the wrong thing.

Faith (14:37):

Right. You remind me a lot of the engineering version of my brother. Like, my brother will walk into my house, and there’s a perfectly good chair or something, and he’ll be like, “This doesn’t look sturdy!” and like bangs it against the wall until it breaks. And he is like, “See, that wasn’t well built.”  I feel like generally, you’ve got an eye for that stuff too, where it’s like, yeah, you’re right. It’s not well built. Like it might look pretty, but it’s not gonna do the thing it’s supposed to, long term. So, equal parts of that and like pushing on things until they break, poking holes in shit, and janitorial duties. 

Wade (15:12):

Yeah, for sure. I mean, like I said, you can build something perfectly, but it’s not what you need, then it’s kind of useless. There’s an old quote that’s kind of a deep thought that’s no software is better than no software.

Faith (15:28):

Maybe that’s what we’ll call this episode.

Wade (15:31):

Yeah, there you go. There’s, there’s another good—because some of this stuff is just like esoteric, and you just need to think about it for a long time to make any sense of it—so, no software is better than no software. What I take that to mean is like, if you can solve something with no software, that’s better than not having any software to solve that problem. That’s kind of what that means to me. And so it’s like, is there a way to do this with no code? Is there a way to do this with little code? Is there a process change? Like do we actually have to build that thing? There’s another really good artifact on the internet called The Codeless Code, which is these cones, which is like some Japanese thing where it’s like, here’s this poem riddle thing. And it has no explanation to it. You basically just think about it and come up with your own meaning.

Faith (16:21):

Yeah. It’s like therapy! 

So somebody’s listening, and they’re like, you know, I’m technical, I’ve been kind of on the ground building products for the last, you know, however many years, but what Wade does sounds really interesting. Like, I would love to be in more of like a tech lead or DevOps kind of space. What advice would you have for somebody who wants to do what you do, other than don’t do it?

Wade (16:56):

There’s this meme that I have— I keep a folder on my desktop called Important Things, which is where I keep all my gifs and my memes—and so right here, software development, short answer, name and describe the five key phases of software development. And it’s like: denial, bargaining, anger, depression, and acceptance.

Faith (17:23):

Seems accurate.

Wade (17:27):

The advice is definitely be prepared for failure, because it will happen every day. But I think the most important thing is just do stuff, right? Like a lot of—I’ve looked at probably thousands of resumes, and just the number of people who don’t have any example of them doing anything in the real world on the internet is just shocking, because apparently you’re trying to be a software developer, so perhaps you should develop some software, and put it on the internet where people can see it, so that it proves that you actually know what you’re talking about. And honestly, that’s where most of my experience comes from. Personal projects that, you know, I’ve taken and tried to try to turn into a business and make some sort of money with. Which, you know, not that I’ve been hugely successful at it, but the best way to learn is through doing, in my opinion. Like you can watch YouTube videos and you can go to a code camp and that will give you some something, but put something on the internet in production, and keep it running for a long time is by far—I’ve got stuff that I built in 2005 that’s still running on the internet, which is kind of crazy. And it’s like, sure, is it performing perfectly? No, but if you look at my profile on the internet, it looks like I know what I’m doing. Hopefully. Maybe. It probably doesn’t, but you can definitely see that I do stuff!

Faith (19:00):

That you knew what you were doing in 2005 at least. Yeah, sounds like almost a piece of advice within that advice is like, don’t wait for somebody to pay you for a chance to learn how to do things. ‘Cause I feel like a lot of the sentiment now is like, I need to find an entry level job so I can learn all this stuff on the job. And it’s like, well, why not take on something on your own and learn as you go.

Wade (19:27):

Yeah, for sure. And I mean, it’s also just about how motivated you want to be, and I think if you’re trying to get hired, the more motivated that you look, the the better it is, for sure. I mean, if I wasn’t working with Gun, I have no fewer than seven projects I could be working on right now. Some of which would pay me, some of which might pay me, some of which are like completely not gonna pay me. But—

Faith (19:52):

But they might be fun.

Wade (19:53):

Yeah, it’s super interesting, and I’ll learn something that I can use in the future. You don’t—I think people think they need to ask permission in order to do stuff, and it’s like, no, just do stuff. Like asking for forgiveness is far better, but like, it’s not even like you are gonna have to get forgiven for going out and doing something on the internet, you know? And so much of software development is just reading the F-ing manual—RTFM, as we say. Like the documentation’s all on the internet, for basically everything. I don’t think that there’s a lot of documentation that isn’t on the internet for anything, really. And all these tools that we use in software development are all the docs around the internet. So like, go figure out how to use it, go spin up docker in production, get pwned, have everything burned to the ground and fix it. Like that’s what it takes to get the experience. I mean, you know, managing people is kind of a different thing, but in my experience, it’s just more about trying to do the best job you can and get the things working so that people are happy with it, and making sure they don’t burn down. And any kind of preventative maintenance that you can do to prevent bad things from happening is good, but a lot of times you gotta step on that landmine before you know it’s there. So.

Faith (21:14):

Well, Wade, speaking of the internet, can people find you on the internet, if they have questions for you? 

Wade (21:19):

I mean, they can. They can find me on the internet.

Faith (21:24):

Great. We can leave it there and say if you’re smart enough to find Wade…

Wade (21:30):

My name’s Wade Williams. It shouldn’t be that hard.

Faith (21:33):

Well, this is so much fun. I’m thrilled to have some nuggets about your professional journey—other than that time that your car got stolen and burned. So this has been really enlightening for me, and hopefully people enjoy listening. So—appreciate your time.


Thanks, Faith.

Faith (21:52):

Thanks, Wade!