Overflow Podcast S1:E14
Coming Soon

Keegan Leary

From San Francisco, United States and Full Stack Developer, Keegan, who is known online as Web Bae, made the transition from military service to a full stack developer focusing on extending Webflow's capabilities especially with JavaScript and teaching others how to do the same.

About this episode

In this episode, we'll discuss everything from life in a submarine to the importance of defining project requirements and scope with clients plus the benefits of smaller projects for learning faster and getting paid sooner.



Matthew Munger: Hey, Keegan, it's a pleasure to speak with you today.

Keegan Leary: Thanks for having me, man.

Matthew Munger: So to get us started, why don't you quickly introduce yourself so that those who may not know you yet get to know a little bit about you.

Keegan Leary: My name's Keegan. I go by Web Bay online. I have been using Webflow for a little over a year now. Mostly my identity is tied up in my military career. I was in the military for 10 years as a submarine officer, but got out of that and really had been wanting to learn how to code and so that's– I started with Webflow and kind of got my hands on JavaScript, and that's been my main focus in the last year.

San Francisco, United States

Matthew Munger: Where are you located?

Keegan Leary: I'm in San Francisco. I'm in a neighborhood called Lower Pac Heights.

Matthew Munger: Very cool. What do you like about living there in San Francisco?

Keegan Leary: I grew up south of here in Palo Alto or Menlo Park, if you're familiar with the area, and I've just always loved California. I love that we have access to the beach and the mountains and all the outdoor stuff. There's a lot of great food here in San Francisco too that I enjoy.

But mostly it's for the California weather and the outdoors, that sort of thing. I did live in Hawaii for three years too. So I could easily be convinced to move back to Hawaii, but those are kind of the two places on my radar are California and Hawaii.

Matthew Munger: When you go out of the house and you're not working, where do you like to go visit? You mentioned nature. Where do you like to go?

Keegan Leary: So just north of the city is Marin. They have a lot of nice trails over there. My girlfriend lives in Oakland, so we spend a lot of time on the trails in the East Bay as well. We're both training for a marathon and then a 50k and then a 50-miler. So a lot of my time is spent running these days if I'm not at the computer. But yeah, there's trails all over the place and South Bay has some mountains with trails on it. I'm very close to Golden Gate Park, I'm over in Golden Gate Park as far as the outdoors go. And then I enjoy Tahoe as well. I'm heading up to Tahoe this weekend to get some snow.

Matthew Munger: And what about just around town, outside of running and nature, what do you like to do?

Keegan Leary: I like to go out to eat. It's probably one of the main things, so lots of restaurants.

Matthew Munger: Give us some tips.

Keegan Leary: I live pretty close to Japan town, so there's, I think it's called like Mara Fuku Ramen or something. That's a good ramen spot. Lots of good sushi over there too. I like to cook, so I make my own pasta. I make my own breads and that sort of thing. Eating, running, and Webflow. That's kind of like my 3 activities, I guess.


Matthew Munger: What does your workspace look like?

Keegan Leary: I do all my work on a 16-inch laptop for the most part. I have one of these wide screen monitors. So I have in front of me my laptop and then my microphone set up with the little interface. I don't know, I have a light here. My bed is right over there. So I definitely got the home office thing going on. 

I like to move around too. I do a lot of work from my couch. I have a nice easy chair. I found a La-Z-Boy on the street, so I do a lot of coding in that easy chair. I have two other chairs that I got for 200 bucks on Craigslist that are Pottery Barn. Really big, I like big comfy things. My workspace is like, I have in my bedroom my desk, but I prefer to hop around through the apartment as the day goes on. Change it up a little bit.

USS Louisville

Matthew Munger: Do you have any interesting objects that are near you, maybe that have a story behind them?

Keegan Leary: I’ve got this– It's a Louisville Slugger bat. So the submarine I was on was called the USS Louisville. And the crew signs it and gives you a nice little message and stuff. So this reminds me of a lot of terrible but also wonderful times that I had on the submarine.

Matthew Munger: How big is the crew?

Keegan Leary: It's anywhere from 115 to 140 or 150, depending on what we're doing and how long we're going out for. The longest I spent without feet on dry land was 45 days. They try to get you in port every 30 days or so, but it depends, you know. If you're on a mission, then you might just be out until the mission is complete kind of thing.

Matthew Munger: Wow.

Keegan Leary: We did a six month deployment where we skipped around through Asia. We had port calls in Japan and Singapore and Guam, Okinawa, those places.

Matthew Munger: That sounds like quite the experience. What's it like, life on a submarine?

Keegan Leary: It becomes very routine. The days kind of all blend together and become the same day in and day out. You know, there's different stuff. So the way we do it is we divide a day. It used to run on an 18-hour schedule, and they would divide that into three. So you would stand, there were six hour watches.

There's essentially three teams on board. You have a day watch, a swing shift, and then we call it the mids watch. So you have three different shifts on board. You're standing watch one of those shifts, and then after that is the time that you support the on-watch shift.

So if they need relief to go to a meeting or to use the bathroom or to eat food or whatever, then you're standing by. And then you have six hours supposedly to sleep. When you take steel and submerge it in salt water, a lot of things break. So a lot of your time gets spent making sure things are fixed or dealing with problems. We did move to a 24-hour day cycle as well, though, to try to be more in sync with circadian rhythm.

Matthew Munger: Right.

Keegan Leary: I think that helped. But an eight-hour watch is quite long, so, yeah.

Matthew Munger: Yeah. Because you're on eight hours of active watch and then eight hours kind of on call after that.

Keegan Leary: Mm-hmm. And that downtime is often spent doing, you know, you have a lot of normal administrative work emails and luckily you can only get emails internally when you're underwater. We maybe have a cycle where we come up and we call it copying the broadcast, where we download a bunch of messages from satellite and they tell us all the stuff we need to be doing out there. It's pretty wild. Like just for us to send a two megabyte image from the middle of the Pacific Ocean, it can actually be rough. Especially if we're at periscope depth and we're getting waves slapping over our antenna. Then it'll just log off the whole system and you'll have to reboot kind of thing. So it's pretty wild, it really is. Yeah.

Matthew Munger: Wow.

Keegan Leary: People always wanna know how deep it can go, and I'm not allowed to tell that, but it's pretty accurate on Wikipedia. If you just look it up on Wikipedia.

Matthew Munger: How does the depth affect you and your body?

Keegan Leary: Not too much. When we're rapidly changing depth, you can feel that pressure change, like when you're in an airplane. So you just kind of pop your ears and that sort of thing. One of the interesting things, the pressure that we feel in the hull affects the partial pressure of oxygen and carbon dioxide in the hull. Depending on the time of day, how many people are awake and what we're doing. If we're running drills, the atmosphere inside the submarine fluctuates pretty wildly and it's really important, every 15 minutes I would check the logs. We might have to increase our oxygen bleed or start another CO2 scrubber.

That was, to me, kind of the most interesting part was how to maintain the atmosphere. Sometimes the oxygen will get low, then people are getting woozy and tired and that sort of thing. So maintaining atmosphere is very interesting to me. It's pretty cool, all the stuff you learn in Physics 101 class comes into play when you contain 140 human beings in a steel cylinder. 

Matthew Munger: Wanna stay alive. You wanna be able to breathe

Keegan Leary: Yeah. For sure.


Matthew Munger: When you're not running or coding, what do you like to do?

Keegan Leary: I'm a little bit late to the game, but I'm working on my sourdough right now. I like going to shows. I like comedy, so I'll go to comedy shows, a lot of stuff in the city to check out. I'm going to a show called Tech Roast tomorrow where they just roast tech workers. Check out their Instagram if you haven't. They're pretty funny.

Matthew Munger: Tech Roast.


Matthew Munger: We may have already covered this, but is there anything that would surprise people to learn about you?

Keegan Leary: Yeah. The submarine is always– the military career is always the good one. Kind of the places I've lived is an interesting one. I lived on the east coast in Charleston, South Carolina for a year. I lived in upstate New York for a year. I lived in Hawaii for three years. I lived in Ottawa, Canada for two years, those are some things. I can do a handstand. What else is there?

Matthew Munger: How long can you hold that handstand?

Keegan Leary: Back when I was really working on it, I would time out to like a minute or two. So I can hold it for quite a bit, but I don't do it as often anymore, I suppose.

Usually it's like when I'm hanging out with little kids and little kids get rambunctious and run around and want to show me all the cool tricks they know. I'm like, well “Watch this trick.” And it always impresses the little kids for sure, yeah.


Matthew Munger: What is your day-to-day role and how would you describe what you do?

Keegan Leary: It feels kind of all over the place. But, you know, every day in Webflow what I like doing is using custom code to kind of unlock new features in Webflow, or to do things that Webflow doesn't have native capability for at the moment. And by doing that, actually I've really been able to dig into the meat of HTML and CSS and JavaScript, which has been really good for my personal learning.

A lot of the stuff I've learned from Webflow applies in React and when I'm building serverless, kind software kind of stuff. But my day-to-day role, back to your original question, is just open the laptop. If I have client work, then I usually focus on my client work.

If I have extra time, then it's either filming YouTube or coming up with an idea for YouTube, and just building little applications or extensions and trying different things out and seeing what I can learn.

Matthew Munger: For your client work, since you consider yourself more of a developer, are you working with a designer or do people come to you with designs?

Keegan Leary: People almost always come to me with designs. Sometimes they have some cool things that don't really fit well on web and so it's good for me because it always presents a unique challenge.

Like, “Okay, how can I get this to work?” But at some point, here has to be me discussing with a designer, “Can we do it this way,” or that sort of thing.

Matthew Munger: I'm curious, what are some of those other kinds of artifacts that clients try to come to you with? Do you still Photoshop files? I mean, what are we talking?

Keegan Leary: I've gotten everything. Yeah. Xd, Photoshop, Figma. What else? I have one client who likes to send me copy on a Word document and then transfer it over.

Matthew Munger: So no design, just the content?

Keegan Leary: Yeah, a lot of times it'll just be, “Here's a website that I like. Can we create something similar?” I actually like that a lot. If I can artfully steal, I guess, a design from a website.

So different things like that. I'm working with one client right now. It's been a learning experience for both of us as far as specifying project requirements. I've found since day one that the most useful skill is being able to articulate project requirements and define scope.

Small projects

Matthew Munger: So around that, do you have any advice for others in the community? Like how do you control scope creep, or how do you really define those requirements well upfront?

Keegan Leary: Yeah, for me, I wish I had stayed with smaller projects. I was eager to take on larger projects and I wish I had just been able to tell myself, “Deal with smaller client projects first,” because I had just gotten out of the military. I didn't want to get her a “real job” in air quotes. I was just freelancing, so I was on Upwork. And on Upwork it can be tough, a little bit of a race to the bottom. But it was great for my skill development just to be able to take small projects and then move to another project. Because to have a large project, it can really suck away your time and you'll be spending a lot of time on things that I think you could learn faster just by having a lot of smaller projects. That's my one big piece of advice for myself is just take the small projects and don't worry about getting these really large scale projects from the start.

Matthew Munger: Right, because those can kind of seem glamorous. But yeah, start with small projects that give you bite-sized challenges that you just keep leveling up and layering your skillset.

Keegan Leary: Yeah. And also just getting paid. Like it's easier to get paid faster. When you have a larger project it's a little of a stretch. I can remember one project. It was definitely a stretch for me. If I logged my time and looked at my hourly rate for that, it was way under minimum wage for sure.

Matthew Munger: Right. And then to wait months for the payout.

Keegan Leary: Yeah.


Matthew Munger: What would you say excites you and motivates you about what you're doing?

Keegan Leary: This is fun. I love development because it feels like anything is possible, and I really like the feeling of building something and putting it out to the world like, “Look what I did.” Or like, “I built a thing.” So what excites me is that with just a laptop you can do that. There's so many good resources out there to learn. You don't need a super powerful laptop or anything. So that's what's motivating for me is just building things and it's just really satisfying.

Matthew Munger: Yeah. The entry requirements are lower than a lot of other professions.

Keegan Leary: Mm-hmm. I really like the idea of being able to travel and not being tied to a specific location for work. I do miss going into the office and bantering with people and that sort of thing. So there's some degree of that that is needed, and I have really been enjoying contracting with Finsweet in that regard. Because it does give me a team to interact with and all that. When I was just freelancing by myself, it was definitely a lonely endeavor.

Matthew Munger: So finding those places where you can either work with others or just kind of get that contact?

Keegan Leary: Yeah. And Twitter's been good too, using Twitter and meeting people. I feel like I'm building a professional network that I didn't really have when I was in the military, which was just a gigantic organization. It feels like I'm actually able to develop some pretty meaningful connections through there.


Matthew Munger: What is a resource that you think more people in the community should know about?

Keegan Leary: In the Webflow Community, we have Webflow Conf once a year, but I'm not a huge fan of just going to conferences for the sake of sitting through boring seminars. More for trying to network and setting up stuff with people ahead of time.

So trying to meet my Twitter friends in person is really what I'm doing. Curating your Twitter feed can help a lot too. You know, my Twitter feed is pretty Webflow-heavy. I make sure to have some JavaScript experts. To me, what’s really helped me grow in Webflow is by focusing on stuff that's not just Webflow as well.

Matthew Munger: Yeah, absolutely. There's an area you're interested in, or there are people you want to collaborate with in the future, it doesn't mean that you need to have the exact same skills as they do.

Keegan Leary: Yeah.

Matthew Munger: Often, you want those complimentary skills to be able to collaborate in the future.


Matthew Munger: Okay, within the Webflow community, who is someone that inspires you?

Keegan Leary: Oh, a ton, but it's easy to call out Alex Iglesias here. Just really impressed by the tools that he builds and the quality of his coding. He's like my hero in the Webflow Community for sure. As well as Joe Krug. So Joe Krug, I just got to meet a lot of the Finsweet team at last Webflow Comf, and it was pretty unique, the team that he's built, just like of people around the world, around Webflow,

Matthew Munger: Yeah.

Keegan Leary: So as far as a business hero, that would be Joe Krug. And then I love Tim Rick's content. I'm definitely heavily inspired by his stuff.

Matthew Munger: Absolutely.

Keegan Leary: I like how he's so good at design and development, so he can do both. To me, how he makes all his tutorials beautiful and succinct, very inspiring.


Matthew Munger: And then lastly, is there any other advice that you would like to share other than your one earlier of start with small projects?

Keegan Leary: You know, there's a lot of unexpected benefits that come from being more active on Twitter and YouTube. I'm not telling everybody you have to start a Twitter or you have to like, be active on YouTube, I would give it as advice. I've gotten jobs through Twitter, people are like,”Hey, we have this JavaScript bug. Anybody know?” And somebody will tag me. And all of a sudden I've got a week of work in the bank kind of thing. So, it just kind of compounds it, it helps you meet people. So sharing what you're building. What inspired me to do that was the Austin Kleon series of books, I think it's called, “How to Steal Like an Artist” is one of them, and some books like that. So those books are quick reads and pretty inspiring.


Matthew Munger: You never know. All right. If anyone in the community would like to reach out to connect with you, Keegan, how can they do that?

Keegan Leary: Twitter's the easiest way. Web is Bay is my Twitter handle. I'm on YouTube. You can search Keegan Leary, and Google, like I'm all over the place. Look for the orange background or the schmuck in the uniform, and that's probably me.