Levi Nunnink CTO of Droplr

(Joel Beasley at 00:00:00) Today, we are talking to Levi, the founder and CTO of Droplr, and we discuss the journey from team member to company leader, the importance of soft skills when managing diverse teams, and speaking up to combat depression in the startup community. All of this right here, right now on the Modern CTO podcast. Here we go. This is the Modern CTO podcast. Dude, Droplr.

(Joel Beasley at 00:00:36) Is that how you say it? That's how you pronounce it?

(Levi at 00:00:38) Yes. Yeah. Well done.

(Joel Beasley at 00:00:40) It's beautiful. You got the purple going on. Makes me want to trust you. I like Droplr. It's a beautiful brand.

(Joel Beasley at 00:00:47) You have all the content on there that's right. You're doing this right. Clearly, this is not your first go at this.

(Levi at 00:00:56) Well, thank you. That's really nice. Yeah. I wouldn't say it's taken us a little while to learn the right way to do things, but yeah, I'm happy we're still able to be working on it and, you know, making it better all the time. We're not done. We're still working on a new release as we speak that I'm pretty excited about too.

(Joel Beasley at 00:01:17) Oh, what's going on in the new release?

(Levi at 00:01:19) You know, it's mostly kind of a user interface refresh on some of our apps. We're trying to—you know, a really important thing for us is simplicity. Right? So we've come to the conclusion that we can make things even simpler while not removing features, but just make it easier to expose certain features. And our kind of goal with Droplr is we want it to feel like it's just a part of your system.

(Levi at 00:01:44) You know? So we're doing some stuff to make it feel like it's just kind of built right into the Mac experience. Like, it should be something that just is a feature of OS X. That's kind of how I've always believed it, and Windows as well. So, yeah, we're doing some stuff that probably in about a month or so should be rolling out. I'm pretty excited about it.

(Joel Beasley at 00:02:05) That'd be a nice acquisition. Right? You position yourself like you belong, and then they come knocking.

(Levi at 00:02:10) Oh, yeah. Hey. I didn't even thought of that. That's a great idea.

(Joel Beasley at 00:02:13) Yeah. You thought of that. Come on now. I love the voice of your brand too. On your content, you know, "Code makes the world go round," and then you're like, "Well, it doesn't literally make the earth..." I can't even speak. "Earth rotate." Jake's going to edit this up, so it's going to be great.

(Levi at 00:02:32) Oh, no. No worries.

(Joel Beasley at 00:02:33) Who does that? Are you responsible for that?

(Levi at 00:02:36) You know, I used to do—I actually love writing personally, but today, we have some great people in charge of that. So Philip and Ula are kind of in our marketing group. Ula is—she's a great copywriter, and she does a lot of our blogging. Nicole is also someone who's done some great blogging in the past for us too. So it's generally a team effort.

(Levi at 00:03:02) Really, if someone wants to write for our site, anyone on the team or even if you're not on the team, we'd love to publish your stuff as long as it's, you know, kind of within where, you know, what we're interested in.

(Joel Beasley at 00:03:15) It's got to be somewhat relevant.

(Levi at 00:03:17) Yeah. It can't be just cat photos or something.

(Joel Beasley at 00:03:19) Oh, I'll scratch that off the list then, I guess.

(Levi at 00:03:23) I don't know. Maybe there's a venue for that. But yeah. So we have probably about four people who write somewhat regularly on our blog.

(Joel Beasley at 00:03:32) Are you writing at all on your blog still?

(Levi at 00:03:35) You know, gosh. Blogs are one of those things that I have moments of inspiration where I'm like, I'm going to dedicate myself to writing more and doing more. I write a lot, but it's mostly just kind of, you know, I'll have ideas for stuff, but I take too long to publish it, and then, you know, it gets going. I actually—it's interesting. For being a CTO, I find writing about technical stuff really, really boring.

(Joel Beasley at 00:04:04) Oh, yeah.

(Levi at 00:04:04) It's I don't know why that—you know, we have some engineers who write amazing technical articles, and I enjoy reading them. I love it. But for me to sit down, it has to have that kind of right inspiration, and rarely is that something that I feel like, you know, usually it ends up being about something completely unrelated to tech that I want to write about.

(Joel Beasley at 00:04:26) Well, that's fine. If that's where your brain wants to go, that's you just listening to yourself. Right?

(Levi at 00:04:32) Yeah. Yeah.

(Joel Beasley at 00:04:33) You don't have to write around tech. I'm telling you right now, I took a vote from the—I will speak on behalf of the industry as a whole. You can write about whatever you'd like, Levi.

(Levi at 00:04:41) Well, thank you. I appreciate that.

(Joel Beasley at 00:04:43) I just got his permission. And you speak—I've got this awesome picture on my screen in front of me here of you speaking with a Droplr shirt on. What was that talk about?

(Levi at 00:04:53) Yeah. So the times I've, you know, kind of spoken representing Droplr, we've done some pitching at some accelerators. We were a part of the Portland Incubator Experiment up in Portland, obviously. And we had an opportunity to kind of pitch our product there to a fairly wide audience. It's similar to a lot of different incubators like Y Combinator, Techstars, and stuff like that.

(Levi at 00:05:20) So that was a fairly large audience to get to pitch Droplr to. You know, in other things, I'll accept any opportunity to speak generally on tech or, you know, stuff like—I love actually really talking to younger developers. I think that's always interesting because, you know, I've been programming for quite a while now, and there's so many things I've learned along the way that I wish someone had just told me when I started. Even just like what kind of company should I work for? Should I work for a startup?

(Levi at 00:05:49) Should I work for a big enterprise? You know, those are things that you can—depending on who you are and what your aptitude is, you can be really happy in one of those and have a great career. But if you pick the wrong one, you might, you know, do really poorly. I started my career working for, you know, a very large IT company, and I was pretty unhappy for four years.

(Joel Beasley at 00:06:12) What company is that?

(Levi at 00:06:14) It was a health care company here in California. Yeah.

(Joel Beasley at 00:06:16) That doesn't sound super exciting to begin with.

(Levi at 00:06:20) You know, on the one hand, if you look at it on paper, it was a great job. Right? I was 17 when I got hired there. You know, good money, good benefits, and all that kind of stuff. So it seemed, you know, when I thought of from that perspective, I thought, well, of course, you know, this is an amazing opportunity.

(Levi at 00:06:38) But what I learned about myself over that period is, like, that's just not a good fit for me. Not that that's a bad decision for many developers. You know, they could have great careers doing that. But for me, I knew. Yeah.

(Joel Beasley at 00:06:51) I just—

(Levi at 00:06:52) I couldn't succeed doing that. So yeah. And I think thinking about that as you're starting off your career is always an interesting thing to do as a developer. Like, you know, where am I going to be the most successful?

(Joel Beasley at 00:07:05) How did you get to Riskalyze?

(Levi at 00:07:06) Riskalyze. Yeah, that's—Riskalyze is an interesting kind of connection. So this was just through a mutual friend. So where I live is a small town called Auburn, California. I'm not sure if—do you live—are you on the East Coast?

(Joel Beasley at 00:07:23) Yeah. I'm in Florida, but I have been out to Bend. Anyway, I saw someone in your profile up at Bend. I was like, Oh, yeah. I've been out there. They had some waterfalls, I think, I was hiking. I did some waterfalls. Yeah. All right. So that's the right spot.

(Joel Beasley at 00:07:36) Yeah.

(Levi at 00:07:38) Yeah. Yeah. It's been a great town. But so I live in Auburn, California, which is probably—it's about two hours out of San Francisco and about an hour out of Tahoe. But it's a really small town. We have about 30,000 people here. So the actual, you know, the tech pool is pretty small. So it's a small tech world. Right? And so I just had a mutual connection through a mutual friend with the now, you know, CEO of Riskalyze, Aaron Klein, who's an amazing entrepreneur.

(Levi at 00:08:12) And, you know, we ended up just kind of meeting. We shared an office space together. We were both kind of subletting an office. And he had this technology that he was considering bringing to market, which is what developed into Riskalyze. And so we all kind of got together and we're like, hey, let's try building this thing. And so, yeah, that was—I worked for Riskalyze for two years, started off as a co-founder there as the director of engineering. And, you know, my background, it definitely lends itself well to kind of those early stage startups.

(Levi at 00:08:47) Mostly, you know, my background was originally in art. And, you know, I love—I started off as a graphic designer or visual web designer.

(Joel Beasley at 00:08:53) I'm happy to dribble up right now, by the way.

(Levi at 00:08:55) Yeah. Thanks. Yeah.

(Joel Beasley at 00:08:57) I'm not—

(Levi at 00:08:57) You know, I haven't—I don't maintain those skills as much as, you know, I'd like to these days. But I kind of stumbled into programming out of necessity. And that was where, you know, that actually is pretty helpful if you can have someone who can actually program something and, you know, design an interface somewhat competently. It's helpful at that stage of a company where you don't have to employ, you know, you can have just one person doing it. So we did a lot of, like, interface prototyping, really quick iterations on different ideas in that early stage for about two years, until we were able to build kind of the core product of what they have today.

(Levi at 00:09:35) And, you know, the product itself has completely blown up. They've launched amazing stuff. They're a company I'm still good friends with all of them. And we get together for, you know, for lunch.

(Joel Beasley at 00:09:49) You follow them as they want to. Oh, really?

(Levi at 00:09:50) Oh, so you've heard of them before. Yeah.

(Joel Beasley at 00:09:52) Oh, I followed them day one. I've done integration with them. Really?

(Levi at 00:09:56) Okay. So you have some background then in fintech. I think I remember that.

(Joel Beasley at 00:10:00) Yeah. I built software—financial software for a large firm in Tampa. Okay. And one of the things that we did was an integration with Riskalyze. Oh, wow.

(Joel Beasley at 00:10:13) That was a lot of stuff. Yeah. So I went through—it was, what, three years ago-ish. So, you know, I forget who I was talking to and everything like that. But it was easy, had good docs and everything, good support, and it was a very simplistic integration.

(Levi at 00:10:32) Yeah. Yeah. Their CTO is a guy named Matt Pistone, and he's a good friend of mine. And he's—I mean, he's, you know, he's a genius. They're doing a lot of really complicated stuff. Matt himself is a Berkeley physics grad, just knows math insanely well. And he's doing such an amazing job just scaling that engineering team. And it's just really a treat to see what's happening with that company. They're a solid—I mean, that company is just—someone who's just, you know, I look at just the leadership there as just inspirational in such a big way to me.

(Joel Beasley at 00:11:11) So how big is your team right now at Droplr?

(Levi at 00:11:14) So we're—we've added a couple people, so I think that brings us to around close to 20 people total. About half of that—a little more than half of that's engineering.

(Joel Beasley at 00:11:26) And are you growing off your cash flow or investor capital or a little mix of both? Or how are you growing?

(Levi at 00:11:33) Mix of both. Yeah. So we're—you know, we've raised money, and, but we're also—you know, we have a decent amount of cash flow. So we're trying to—you know, our aim is to be a profitable, very capital-efficient company. And we're managing to do that. And so we've never done the biggest kind of hiring. The scaling we did was last year where we had some initial investment and used that to scale up our engineering team.

(Joel Beasley at 00:12:04) I'll look at that. In one of your screenshots, they used your art from your Dribbble. Yeah. That's amazing. I'm—I'm sorry. I loved it.

(Levi at 00:12:14) Awesome.

(Joel Beasley at 00:12:16) I want to tell people, like, what I'm seeing right now with Droplr, what it is, because, you know, we say or talk about how cool it is, your growth. You could do everything with it. I didn't even know you could do this. So you could take screenshots, screencast, you can draw on it. It sits—it kind of lives in your menu bar. It looks like a native thing that should just belong there. Right? Right now, it's sitting next to my little Postgres elephant. And this is awesome, man.

(Levi at 00:12:44) Well, thank you so much. Yeah.

(Joel Beasley at 00:12:46) You don't need to do anything else. So right now, it's—I take a screenshot—I just grabbed it to check before the show. Right? And I'm loving it because the workflow before this is take the screenshot, it auto goes to Dropbox with the name, and then I have to go copy the link. And this looks like it's—and then if I want to do a screencast or something completely different, I'm in QuickTime and doing a screencast and then exporting it to make it smaller so it's not insane big.

(Joel Beasley at 00:13:16) And then putting it in Dropbox, maybe for the upload, copy the link, and paste it to someone. This looks like—and I'm drawing on it with Preview. Right? I get Preview open real fast. Just circle something in red. This looks like it's got just—it's like everything, boom, boom, boom, boom, boom.

(Levi at 00:13:30) Oh, thanks. Yeah. We built it to be as simple as possible because we think we have the best chance of getting into people's workflows by removing steps and just kind of making it something you can do with—kind of making it muscle memory, I guess, is the way we look at it. So it's a product, you know, we use all the time as a team. And that helps us to kind of, I think, hopefully make good decisions about, you know, how to build new features and add them in. You know, if it's something that we can actually use ourselves, then we know we've generally nailed it.

(Joel Beasley at 00:14:03) Have you read the book Hooked: How to Build Habit-Forming Products?

(Levi at 00:14:08) You know, I haven't. Who wrote that? That sounds interesting.

(Joel Beasley at 00:14:11) Yeah. One of our guests did. His name is Nir. Okay. N-I-R is his first name. E-Y-A-L is his last name. Okay. And the book is called Hooked: How to Build Habit-Forming Products, and it essentially is talking about—I thought you just quoted essentially part of that book. Yeah. You want to get into—we're humans, we're heavily—if you think about what we do on an everyday, we're pretty basic.

(Joel Beasley at 00:14:35) We do very similar things. We eat very similar things. We have very similar routines all to each other. And in our own lives, we have those same routines. And so the best products are products that actually pay attention to that and then hook into our habits. Right?

(Levi at 00:14:49) Yep.

(Joel Beasley at 00:14:49) Because those are the ones we can't live without. Everyone's screenshotting all the time. Screenshotting is a human behavior that we do every single day. Yeah. Right?

(Joel Beasley at 00:14:57) And so you're hooking into that.

(Levi at 00:14:59) Yeah, that's a really interesting way of thinking about it. And it's actually, you know, I think a lot of people don't really think of simplicity as a competitive advantage. You know, it's been interesting because we're still a small company. We're still fairly early stage. You know, when people hear Droplr, they kind of put us in the category of Dropbox or Box or these big enterprise companies that are down the road. And when we started off, when we first got funding and really kicked this thing into gear, those are the companies we would always look at. What are they doing? How are they marketing themselves?

(Levi at 00:15:35) And what I came to realize was that a company at the scale of where we're at, even if we're somewhat directly competitive, even if our names sound similar, we have a way different—we have the luxury of being insanely simple. Whereas the bigger you get, the less, you know, the more complex you become. And actually, the more difficult your product just kind of inherently becomes. It's really hard to maintain simplicity as you scale.

(Joel Beasley at 00:16:05) Have you heard of Peter Drucker? He talks about that.

(Levi at 00:16:08) I have the name. I know Peter Drucker, but I'm not familiar with him talking about that.

(Joel Beasley at 00:16:13) He talks about it in biz—you know, he was way older. He's since passed, but he was like a huge authority on management in, you know, the past fifty years. And he talks about the larger you grow, the bigger the internal mass becomes, the more cost it takes to manage. So the more people you have, the more expense and time you spend managing it. And like, that's the same with codebase and everything.

(Levi at 00:16:36) Yeah. Oh, absolutely. That's—I mean, that's actually an interesting, you know, I think your background is, if I remember correctly, you started off as a developer and kind of transitioned to a CTO, right?

(Joel Beasley at 00:16:48) Yes. Yes.

(Levi at 00:16:48) Yeah. I mean, and that's the—I think for me, having the same experience, you know, I've been a developer for many years and, you know, for the last, I don't know, five years have been more in the role of the CTO. And that's, you know, that's an interesting transition. And it can be challenging just because all of a sudden you have to think about things. It almost becomes, you know, all of your issues go from being technical challenges to almost like sociological challenges.

(Levi at 00:17:16) You know, thinking about, okay, how do people interact? How is this specific group of people going to interact? You know, you have to start thinking about, well, how do I choose a technology that fits the team I have or connects with this customer as opposed to, you know, just the things that you, the way you think as a developer, almost sometimes becomes a hindrance as a CTO.

(Joel Beasley at 00:17:38) It absolutely does. It is a complete transit—you know, I'm over here smiling at Jake and Jackie right now who are watching the call because this is, we just did today, we just sent the final book cover and the whole book and everything to print. And this is the entire book. It's going from developer to CTO and all the non-programming things that you have to look like, all the human parts, like everything that I was so frustrated because I'd read these scrum books, I'd read these project—no one talks about the all the human stuff. There was a complete white space. You know?

(Levi at 00:18:09) Yeah. And it is interesting. You know, there's been so much, you know, thinking about diversity and everything in tech these days. But there's also, you know, the interesting thing about teams is every human being is pretty different. And when you get a group of diverse individuals together into a room to work together, they all, you know, it's not like they naturally gravitate towards scrum or agile programming or something like that.

(Levi at 00:18:39) You know, every group of people works together differently for some really different reasons. You know, it could be that they like each other, you know, or maybe they just have, you know, personalities that grate on each other. And necessarily, like, you know, certain processes aren't gonna help that. You know, it's, I don't know, it is a very interesting challenge to try to just, you know, and I'm only doing it on a very small scale. Right? Now, once your team gets to hundreds, that's, you know, that's a whole other insane challenge that I, you know, I'm sure it's gonna be like, you know, throw out the book and relearn everything again at that point.

(Joel Beasley at 00:19:16) Well, I'm interest—I've, so people write into me all the time now. This is what I love about, I didn't know this was kind of like a surprise, a little hidden gem about doing this whole show and the book and everything. People write to me daily with their experiences. Oh, I read your content on this and I tried it. And I was like, oh, now I have some responsibility with what I'm putting out here. People are doing what I, what I'm, what I'm sharing. I'm not necessarily telling people exactly like what to do specifically like ABCD.

(Joel Beasley at 00:19:46) I share my experience and my story around a topic and then it's they understand like how I'm thinking about it, right? So it's, oh, man, it's this responsibility now. So, like, I'll get emails from the people with, that are just them and their cofounder up to people that have 600 employees at their company and they're going to a thousand employees.

(Joel Beasley at 00:20:09) And it's interesting how these principles—it's the same principles, but everybody's kind of understanding them, putting their own spin on them, and then able to use them. I'm like, this is crazy.

(Levi at 00:20:18) Yeah. And it's, I mean, the starting, you know, you, you know, CTO and a cofounder, right? Usually, that's how kind of a lot of startups will kick things off, or some kind of combination of that. You know, if things go well, which everyone wants to plan for, like, your job is gonna change as a CTO drastically over the course of, you know, the business.

(Levi at 00:20:38) And I think that's, you know, that's something that can be kind of scary. Right? Or that there's not a lot of resources that tell you, like, how do I be a good CTO? You know? I think it's awesome that you're asking this question and providing resources on that because this is kind of a unique role that there's, I feel like, there's less resources on than, say, how to be a good CEO.

(Joel Beasley at 00:21:02) Right. Oh, that's the thing. If you look at books, like, if this is when I decided to do this, I went and searched the books, like CTO books. There's been like five, maybe, books written on the topic and they're all old. And then you go to CEO, there's like 10,000, chief marketing, 10,000, growth hacking, like it's insane the amount of content on it. And if you try to go from developer to CTO, there's like nothing. Like, all right, well, we'll write this out, you know?

(Levi at 00:21:29) Yeah. It's interesting. I mean, that experience, you know, for me, it's exhilarating. It also can be a little bit depressing at times. I remember, you know, so once when we scaled our team, right, a lot of the things that I was used to doing that were, I actually enjoyed doing, you know, usually when you start off as a CTO, but you're really like the programmer, right, in a small company. So your job is to ship stuff really quick, you know, be kind of the hero who comes in and, you know, delivers, hits the deploy button, makes a bunch of people happy. And that can be a really fun—especially if you're a good programmer, that can be a really fun experience. But you have less of that as your engineering team grows. And I remember some mornings, you know, when we were initially scaling, just coming in and feeling just like this cloud of gloom over me because I was like, I can't program today. You know?

(Levi at 00:22:25) I have to have someone else do this now. And that could even be a problem, you know, that can even be a problem if you're jumping in and still trying to do what you used to do. That's disempowering to the people who, you know, you brought on to do that work for you. And, you know, so that was something that I had to learn.

(Joel Beasley at 00:22:41) Well, you made the transition successfully.

(Levi at 00:22:43) Oh, thank you.

(Joel Beasley at 00:22:46) You have. There's so I get the mix of everyone, right? I get, I was curious to check out CTO job postings because I was writing an article on how to write a job posting for a CTO, right? And so I was looking at all the job postings, and I was like, alright, I'm gonna reach out to some of these people. And there were, I would say, a good, I reached out to about 10 people. I'd say three or four of them were programmers, CTOs that the company had gotten to 10 or 20 people, and they didn't know about the—they didn't wanna be a CTO anymore. They wanted to go back down into product and be like a product lead because they didn't know what to do.

(Levi at 00:23:24) Yeah. I think, and I think that's perfectly, you know, if that's what you're good at, if that's what you're great at, that's a great thing to recognize. A 100%. You know, there's like absolutely no shame in that because it is, you know, it is challenging like to, I don't know. For me, as I've grown in this, I've realized, you know, things that, even parts of my personality that were not a problem as a programmer can actually become problems as a CTO, as you get more and more into leadership.

(Levi at 00:23:57) So, you know, for example, example is if you're someone who prides yourself on being like, you know, a harmonious team member or someone who is very affable and wants to just, you know, kind of do the job and then, you know, do what you're asked to do and then do it really well and make everyone happy. You know, that can actually be a big hindrance once you kind of get up into leadership. It's a great quality to have as a team member. But if you get into leadership, you're actually required to be someone who might, you know, make some people upset by the decisions you make, you know, or you're going to have to be strongly opinionated and say no a lot of the time.

(Levi at 00:24:42) And that, that's just, it's interesting how it puts you through—you have to do a lot of self-analysis through this process of going, okay, you know, I can't lean back into these qualities that have made me a good programmer necessarily. I have to develop some new ones or find some new ways of approaching problems and be okay with, you know, doing things that I, you know, would have, that I'm uncomfortable with.

(Joel Beasley at 00:25:10) Right. So, like, when you're a leader and you're a team leader of programming, you're very confident. You have a lot of experience. And you know the stack you wanna use. You know the tools you wanna use. You can build a team around that because you have that pillar of the programming experience. The moment you have to move out of leading that team to leading a broader team, you have to refind your pillar. You know? You have to develop it with understanding how people work and how to manage people. And I agree with what you said. If you're a cofounder CTO and you get to that point where you're like, look, I don't wanna be the CTO. I'm in love with product, and you've learned that about yourself. Congratulations, man. Welcome to the next step of life. Go be the cofounder slash head of product. Awesome.

(Levi at 00:25:53) Yeah. And there's, I mean, that's, that actually means that you probably have a lot of really exciting opportunities too, if that's who you are. You know, if you're someone who can get a company successfully from zero to 10, that's a great quality to have. And it means you can probably work on a lot of exciting ideas. I don't know. It's, I'm a big fan of 37signals. I know you had Ryan.

(Joel Beasley at 00:26:18) Ryan. Yeah.

(Levi at 00:26:19) Ryan. Yeah. Yeah. And they do a lot of, you know, they've done a lot of, you know, kind of challenging orthodoxy over the years that they've been around. And, you know, you can build a very interesting company with a small team. You can actually do it and take investment and, you know, because then you have responsibilities to, you know, your investors to grow and increase value and all that stuff. You know, if you're someone who loves building product and is very capable of building product, you've got a lot of options. There's a lot you can do and build really interesting companies. Maybe they're not, you know, VC funded or maybe they have a different kind of structure, as far as the way that the things are financially set up. But, man, you know, I look at, you know, what Basecamp has done, and I admire that so much, you know, how they've somewhat, they bootstrapped themselves to this amazing business that's so long-lived.

(Joel Beasley at 00:27:18) And they stay so lean too.

(Levi at 00:27:20) Yeah. And maintaining a lean, you know, a lean company. You know, bigger companies are big by necessity. And, you know, smaller companies, I think, you know, in my experience, are so fun to work for. You know, the smaller something is, the more, you know, agile you become, the easier it is to transition, make changes, and just have a better time doing what you're doing. You know, like we were talking about earlier that, you know, the less time you're going to spend managing, the more time you're going to spend actually doing things. So, yeah, I mean, I guess all this goes to say, if you're someone who doesn't want to manage a huge company, then, like, you actually have some pretty good options for yourself.

(Joel Beasley at 00:28:00) So the, we're doing this new thing, right? We're excited about it. We're putting together a tour, my friend.

(Levi at 00:28:07) Okay.

(Joel Beasley at 00:28:09) So when we come out to California, we want you to come speak with us on our little tour. We're basically going to do the Modern CTO Show live, right? But we're going to have three people. You have like a little DJ, some music, and it's going to be this sort of like South by Southwest half Q and A. So like the local CS students can come and ask you questions because, like, you're someone who's done it and you got it and you're in the zone. You're the man, right? And it's going to be a lot of fun, a little story sharing, a little Q and A from the audience. And there's going to be three guests and all experts just like you. And then I'm gonna host it. And we're gonna put it up at either the local college or a local incubator. And we're gonna do 14 cities, and we're starting the tour later this year. We're really excited.

(Levi at 00:28:59) Yeah. Love to. Thank you so much.

(Joel Beasley at 00:29:01) Yeah. Because that'd be so, we're actually, we're all excited about it, right? And so I got an illustrator to start sketching up, like, how we're gonna do it in the stage and what it's gonna look like so that we can, you know, build it all up in the cities. And so we brought in some really cool people to help us organize it and put it together because we have, we have all these relationships, Levi, and all these, then we started to notice they're grouping. Like, we got, we got relationships, you know, California, Boston, New York. And then we started looking through our past guests. We're like, man, we have relationships everywhere. That's cool. Meet everybody. Like, because I keep wanting to go, like, I want to go fly out and meet you. And I want to go to New York City. We've got, like, two of the Forbes 30 Under 30 guys doing some crazy AI stuff in New York City. I, like, I wanna go hang out with them. And I wanna go hang out with you and check out the drop—like, I wanna go hang out with people. And if I keep, if I go do all these independent trips, like, let's find an excuse. And we were like, let's do it. Let's do a Modern CTO tour.

(Levi at 00:29:56) That's a great idea. That's awesome.

(Joel Beasley at 00:29:59) You pumped about it?

(Levi at 00:30:00) Yeah. Absolutely.

(Joel Beasley at 00:30:01) It's gonna be so great. I'm so excited. I really want to know about serverless technology. You talked about it. You're using it. And I gotta be honest with you, I don't understand it. And I figured I could go research it or I could just have an expert explain it to me. I prefer that.

(Levi at 00:30:20) Okay, great. Yeah, so serverless technology is something we've kind of embraced over the past year at Droplr. We're not completely serverless.

(Levi at 00:30:29) We still run servers. They're all in the cloud. But serverless is interesting. So I'm always a little bit—I try to push back on new technologies just because I think there's risks involved with that. But really what I've found with serverless technology, and I can kind of explain a little bit how it works, is that it removes a ton of barriers from developers writing code to getting stuff out into production, stuff that's really functional and works well.

(Levi at 00:30:58) So essentially what serverless is is taking—instead of me writing code, wrapping it in, figuring out how I'm going to deploy it up onto a server, maybe I'm going to use some kind of Linux environment or whatever—it basically just allows me to write code and put it in the cloud, and I don't have to worry about scaling it at all. If it doesn't have to be running, it's only running when it needs to be, right?

(Levi at 00:31:27) So if I wanted to write a really simple piece of functionality that would let a visitor to my website upload an image, I could write that. And then serverless technology will let me just deploy this out into the cloud, and it will give a URL that someone can hit. And I don't have to worry about, is this going to be—what kind of uptime is this going to have? Is this going to automatically scale? It'll just scale up to however many it needs to be and shut it down when it's not being used.

(Levi at 00:31:55) So it's a way—there's all kinds of names for it. The one we use is Amazon Lambda. That's what we use pretty heavily. I think Google calls theirs Cloud Functions. I think Azure has a version of this too.

(Levi at 00:32:08) But it really takes away a lot of the headaches of trying to write scalable services for developers because you just know, hey, it's going to scale up. It's going to do this much. I can track how these things are being used through these awesome dashboards that AWS provides you. I can see how they're doing as far as response time and all this kind of stuff.

(Levi at 00:32:33) And deploying is basically—I type a single command, my function gets updated to the latest version, and it's instantaneous. So I'm a pretty big fan of that. And that's really our technology of choice for new services as we kind of develop stuff in Droplr. And based on my experience, I would pick it again on any other project.

(Levi at 00:32:59) I recommend a lot of developers to check it out. I think it'll make your lives kind of easier in a lot of ways.

(Joel Beasley at 00:33:07) Yeah, you super interest me. Did you go to the AWS conference this year?

(Levi at 00:33:12) We didn't. Maybe next year, though. I think it's probably about time we started descending. We use a ton of their services, so.

(Joel Beasley at 00:33:20) Right? I use AWS heavily, and I haven't ever been to the conference, but I keep seeing pictures of it and I'm like, oh my goodness, it's like a city. They take over.

(Joel Beasley at 00:33:29) Their conference is huge.

(Levi at 00:33:31) Yeah. Yeah. They're an amazing company. The stuff they do is inspiring and kind of mind-blowing, the amount of technology they give you.

(Joel Beasley at 00:33:40) Yeah. I'm interested. I'm always watching them, Google, Musk. I'm like, who's taking over the world? Who wins?

(Joel Beasley at 00:33:48) Right now, they're in their own spaces, right? Because there's plenty to eat for everyone. But oh, man, I kind of see that gap closing. They're all going out. I can't buy a Google Home on Amazon, right? It's like, oh, that's awesome. You go to Verizon and then Google's shoving Verizon Homes down you when you're trying to buy an iPhone. It's like, oh, man.

(Joel Beasley at 00:34:07) What's happening? It's crazy.

(Levi at 00:34:09) Yeah, they're definitely—yeah. Google and Amazon and, I mean, these companies are insane, the amount of tech they're leveraging and bringing out to the masses. So it's a little scary.

(Joel Beasley at 00:34:19) Well, and then, come on, we know it's a data game too because there's all machine learning, and whoever has the biggest mountain of data and can process it the best, they win.

(Levi at 00:34:30) Yeah. Yeah. That's a whole other—I mean, and that's maybe where Google has the edge, but I wouldn't count—

(Joel Beasley at 00:34:35) They do have the edge on data right now a little bit. Oh, that's interesting. That's true. I wonder how far Google attracts you into Amazon. Because Amazon has all your product purchases, right?

(Levi at 00:34:45) Yeah. That's true.

(Joel Beasley at 00:34:46) They're going to know—yeah, they're going to know more about your diet, but then Google has your search history and they have your location data. Well, I think Amazon probably has got a pretty good pin on your location data too now. Yeah. But it's like, I don't know, who wins the full profile data, right?

(Levi at 00:35:02) Yeah. Yeah. Oh, man. I know. It's—I actually switched to DuckDuckGo a little while ago. I tried to, just because it was getting scary how well Google started to know me. And—

(Joel Beasley at 00:35:17) I've had—

(Levi at 00:35:18) I've had to go back to Google on numerous occasions. I love the idea of DuckDuckGo, but—

(Joel Beasley at 00:35:23) What's DuckDuckGo?

(Levi at 00:35:24) So DuckDuckGo is like the—it's like the "we don't," it's like the "we're not evil" search engine, you know, that we don't track you, we don't try to retarget your data, all this kind of stuff. And it's a great search engine. But yeah, that's the interesting thing. Google, with all their personalization stuff, with all the things they know about you, uses that to bring amazingly relevant search results to you. So by respecting your privacy, DuckDuckGo has a harder time surfacing extremely relevant search results.

(Levi at 00:35:58) So it's this weird conundrum.

(Joel Beasley at 00:36:00) Right? So did you ever get to the point where you actually made it your default tab?

(Levi at 00:36:05) I did. And some of—yeah. And some of my machines, I have it as my default tab.

(Joel Beasley at 00:36:10) And then you start yelling at it. You don't know me well enough. These results are horrible. Stupid privacy. Let's go back to Google. You know me. Hey, buddy. How are you? It's been a while, Google.

(Levi at 00:36:19) Exactly. You know me so well, Google.

(Joel Beasley at 00:36:22) Before, like, Alexa will start counseling me one day. Joel, this is the third day you have been slightly down. I'm not down. Yeah.

(Levi at 00:36:32) Yeah. Well, so who knows more about you? Because you have Google Home and Alexa. Which one is able to speak more directly to you, would you say?

(Joel Beasley at 00:36:42) I don't talk to Google.

(Levi at 00:36:43) Okay.

(Joel Beasley at 00:36:44) Okay. I haven't. Google's like the awkward stepchild in the corner. Every once in a while it speaks up and I'm like, shut up.

(Levi at 00:36:56) Go back to your corner, Google.

(Joel Beasley at 00:36:57) Yeah, go back to your corner. Yeah. So it's—I don't know. I'll tell you what, I love the human connection to speaking to Alexa. And I love that it's integrated with—oh, I do this thing with my wife, right? So there's an Alexa in my kitchen at home and there's an Alexa at my office, and I can say, Alexa, like, play "I'm Gonna Get You"—like a play, a song with lyrics, "I'm gonna get you" on my kitchen. And then it'll be like, I'm watching you. My wife's sitting there making dinner. Like, I'm watching you.

(Joel Beasley at 00:37:29) And I'll be on my way home, or she'll send me a song back. It's like, I miss you. And then I'll send her, like, Michael Bublé, "I'm Coming Home" right back to her. And we keep hijacking the Amazon. It's a great relationship.

(Levi at 00:37:42) That's pretty amazing. Yeah. Yeah, it's—

(Joel Beasley at 00:37:45) It's fun. You can do intercoms with them too. A lot of people don't know that.

(Levi at 00:37:48) Really? Okay. Okay. Yeah, see, and I—as I remember, Alexa is fairly affordable too.

(Joel Beasley at 00:37:56) Yeah, like, less than $100 for the full version.

(Levi at 00:37:58) See, they're smart. They're—we just for Christmas got Kindle Fires for our kids. And they're so affordable, and they're actually fairly good machines for what they do. And I was like, well, Amazon is definitely doing some stuff as, like, a market grab here because this is insanely affordable, and it's a pretty good product.

(Joel Beasley at 00:38:23) Yeah. I know the guy that launched—that was responsible. Like, Amazon went and plucked him to develop the team and launch the Kindle.

(Levi at 00:38:29) Really? Okay.

(Joel Beasley at 00:38:30) Yeah. Super cool dude. And then he did that. There was a lot of success with that. And then they made him head of, like, international sales for Amazon.

(Joel Beasley at 00:38:38) Oh, wow.

(Levi at 00:38:39) Okay. Cool. Congratulations. So you're good with that. Yeah.

(Levi at 00:38:43) Right?

(Joel Beasley at 00:38:44) Yeah. So that's cool. So I'm going to call them up and be like, hey, you guys want to sponsor the tour?

(Levi at 00:38:49) There you go.

(Joel Beasley at 00:38:50) There you go. Oh, man. This is—I love talking to you, Levi. When are you speaking at conference next?

(Levi at 00:38:57) You know, I don't really actively look for that. Generally, if there's an opportunity that comes up, I'm happy to. But most of the time, if I'm doing something speaking, it's generally kind of smaller, like at a company talking about some technology or something like that. But I really do—it is enjoyable to step out and talk about something other than tech or, not necessarily tech, but yeah, talk about more kind of the human side, I guess, of the business.

(Joel Beasley at 00:39:29) Yeah. Well, we'll—I'm going to—you know, after the episode and everything, I'm going to keep you in mind, put a note on you for a marquee for that. So when that opportunity comes up with us and I need some perspective on one of these human things, I'm going to tap you for some information.

(Levi at 00:39:45) Awesome. I'd be happy to.

(Joel Beasley at 00:39:46) Yeah. So you'll speak at, like, a small company about this—oh, you know who you—you hear Gary Vaynerchuk?

(Levi at 00:39:54) Yeah. Yeah. Okay.

(Joel Beasley at 00:39:54) So he's been—I like to listen to him for some advice on marketing. And oh, by the way, do you have a press person at Droplr?

(Levi at 00:40:05) Well, Ula, actually, is a good press contact. I could put you in touch with her.

(Joel Beasley at 00:40:11) Yeah. So we got a press person, right? Jenny. She's awesome. Dude, when all their—their whole job is just about getting press and they do their job and then you're everywhere.

(Joel Beasley at 00:40:25) Okay. I'm saying it as, like, a suggestion because I was—you know, a lot of people, they think, oh, I'm going to go do some advertising or some direct business development. Like, all that's great, but man, the press needs experts. Yeah. So, you know, you're a smart guy.

(Joel Beasley at 00:40:43) You should have someone watching out for press stuff for you because you would just, like, catch on fire, man.

(Levi at 00:40:48) That's an interesting idea. I'll talk to—yeah. Yeah. Jenny did a great job. I had the pleasure to interact with her. And yeah, that's a very good idea.

(Joel Beasley at 00:40:58) Yeah. It's working. I'm just trying to share because the whole point of this show is to share to help. Like, everything in the book is a blog post somewhere that I wrote. I just tied it together as a book.

(Joel Beasley at 00:41:06) So I'm not—I'm doing it to help people because I, and yourself, we kind of struggled and fought through to figure it out. And if you get thousands of people who are struggling through to figure it out, it's like this next generation coming up below us is going to have to go through the same thing.

(Levi at 00:41:21) Exactly. Exactly.

(Joel Beasley at 00:41:22) Like, let's help them out a bit. Let's give them a ball. Let's—I also do the book, you know? Say, hey, look, go read this. You'll be a step ahead of me.

(Levi at 00:41:29) Yeah. No. That's awesome. That's a great idea. And yeah, I think that there is such a void in that, and it's a great opportunity to kind of just speak to people who, you know, yeah, the next generation on that.

(Joel Beasley at 00:41:43) Yeah. So Gary V was talking about, like, tech startup suicide rates.

(Levi at 00:41:49) Really?

(Joel Beasley at 00:41:50) Yeah. Have you heard him talk about this?

(Levi at 00:41:52) No. I haven't. That sounds harrowing.

(Joel Beasley at 00:41:54) Yeah. I know. So a couple of people that he knew, some tech founders and stuff like that, you know, they killed themselves. And so he's become, like, this advocate for preventing that. And he brings it up through his content and talking about it.

(Joel Beasley at 00:42:11) And I'm like, you know, I could see that happening because people they take other people's money. I've—look, in my startups, I had, you know, big ups and downs, you know, like, real low moments, real high moments. And I'm like, you know what? That's, like, that's a thing.

(Joel Beasley at 00:42:24) And I'm glad that he's addressing it, and, you know, it should just be talked about at some degree if it's happened. Right?

(Levi at 00:42:33) Yeah. I think that—again, that doesn't surprise me that that happens. You know, the experience of doing a startup, especially once you get investors involved—it's, there's so much pressure. It can definitely, you know—I've lost friends through this, you know, relationships. Just the toll it can take on you as a person and just the stress it can put you under is sometimes just—it's really, really difficult, and it's terrible that people feel so trapped that, you know, they would resort to something like suicide.

(Levi at 00:43:07) But it needn't be. I think there's help and there's answers in those situations. You know, nothing is ever that drastic. But—

(Joel Beasley at 00:43:18) Right. And so I'm feeling like, you know, the thought popped up in my heart, in my mind, like, bring it up, right? And I wanted to bring it up. But at the same time, when I went to go bring it up and kind of talk about it with you, I found myself sidestepping and, like, awkwardly feeling like we don't know how to—I don't know how to talk about that.

(Levi at 00:43:37) Yeah.

(Joel Beasley at 00:43:37) Right? Like, I don't know how to bring it up to say, hey, you know, if you're feeling this way, you know, there's some resources you could seek out, you know, something of that nature. Because it's just—I guess it just takes practice of me kind of talking about it so it's not awkward. I mean, I know we tend to, like, shy—my internalness was, like, shy away from it, you know, but I just kind of wanted to—there's my first go at it, Levi.

(Levi at 00:43:58) Well, I think it's great. I think, you know, one of the things that, you know—if you're someone looking on the outside looking in at the world of startups, right, and I know this is certainly something that I experienced, right? You just see the success stories. You know, you see the exponential growth graphs because that's what companies want to put front and center, right? We don't talk about failures. We don't talk about the real challenges that we're dealing with. We're talking about how great we're doing. Everything's awesome.

(Levi at 00:44:26) You know, everything's going great. So when you actually get into that—in every company, when you start talking to people, every company has gone through real challenges. Every company that's still around is currently going through real challenges. You know?

(Levi at 00:44:41) Yeah. I know that I'm sure, you know, even someone like Slack, right? Amazing success story. I'm sure they have things that are keeping them up at night right now. They have things that are deeply concerning to them that they're worried about.

(Levi at 00:44:53) So at any stage of your company, you are faced with some definite challenges that can be extremely stressful. And sometimes, you know, if you can't think of the answer, you feel like you're alone. Right? You feel like, well, man, I'm just not like these other companies who are just blowing up. I'm a loser.

(Levi at 00:45:08) I'm, you know, I've made so many mistakes. And that's where you can start getting into some really dark places. And depression is a real thing. And just because some people don't publicize that, I guarantee you a lot of CTOs and founders are struggling with that sort of stuff.

(Joel Beasley at 00:45:30) So I'm just gonna share real quick. Like, I just wrote this down. I'm gonna share a little tip of how I dealt with it.

(Levi at 00:45:38) Okay. Yeah.

(Joel Beasley at 00:45:38) Right? Because whoever's listening, like, I dealt with it through moving faster. Like, so I found, you know, when you're depressed by definition, like, you slow down. Right?

(Joel Beasley at 00:45:49) So, you know, just a little physics, invert it, speed it back up. Right? So when I'm really busy and I'm going around, I'm talking to people, I'm making things happen, you know, some of the worst days for me, Levi, even today, like just as a human, is the weekend. Interesting. It's hard.

(Joel Beasley at 00:46:06) And so I had to figure it out. So I started this show and I would buzz. You know, I'd be talking to people, two, three people a day on a show. And then in between that, doing micro calls, I'm talking to eight to ten people a day with a team around me, high energy. We're going. We're making things happen. We're getting numbers. Things that like, life's exciting. Like, it's real good. We're on this energy high.

(Joel Beasley at 00:46:26) Saturday morning hits. Boom. Yeah. You know, I'm up 5:36 in the morning. I got nothing to do. And I'm just sitting there like, what do I do? So I took some intentional planning from me to pack my Saturdays and Sundays with different segments of the day to keep myself moving in different chunks. Like, so I go to the office twice on Saturday, but at two different times because I come home for lunch with my family, which I don't get to do during the week. And so I do morning walks with my family.

(Joel Beasley at 00:46:54) Then I go into work, knock some work out, work on a certain type of project. Then I go home, have some lunch, hang out, you know, bounce my daughter up and down. Like, you know, get some—I'm like, I know you got some smiles in there. I'm kinda like shaking her and tickling. Like, it's awkward because you're shaking and tickling. And I hear the word shaken baby syndrome. I'm like, how much is too much? I like the smiles, but sometimes some drool starts happening. I'm like, alright, stop. No more shaking the baby. So then I'm back at work and then I take my family out for an evening or something or another.

(Joel Beasley at 00:47:30) So it took like—the point I'm making is it didn't happen automatically. The high got started because of the work because everything got so busy with the work. And then when I noticed the lows, I said I have to do something about this. I didn't just accept it and say, okay, I'm gonna be depressed every weekend. I didn't accept it. I said, no, I'm gonna get my weekends faster. I'm gonna speed it up and be productive. And then even when I don't want to, stay productive. And so that's kind of how I dealt with the most recent experience of mine with slowing down and getting a little depressed.

(Levi at 00:48:02) Yeah. That's great. I think every person is different and we all kind of react differently. But at least doing that introspection on yourself and figuring out, okay, how can I address this problem? You know, how can I not just wallow in this is great?

(Levi at 00:48:18) You know, for me personally, my therapy is yard work. So we have, you know, we live in the trees up here. And so the yard is constantly getting pine needles on it and leaves are falling and all this kind of stuff. So every weekend, like, I just go out, you know, put on a podcast or something and then just spend hours raking or chopping wood or whatever. And it's so therapeutic for me, just that experience. But, you know, just finding those things that help you get you out of those ruts, I think, are super important. Just even as a human being, not just as a CTO, but, you know, life can be hard.

(Joel Beasley at 00:49:02) We have to—

(Levi at 00:49:03) We have to learn how to deal with these things.

(Joel Beasley at 00:49:05) Right? I'm a big fan of music. I play music, guitar, drums. So that's one of my go-to reset buttons. Or something's not right. What do I need to do? All right. Go hit my reset pattern. Right. We write code, right?

(Joel Beasley at 00:49:20) We write these routines or these functions or whatever you want to call them. We write these repeatable events in the form of text. And then those tools get used as needed. So in your life, we need a tool for a mental reset. And my mental reset routine's like, alright. Something's wrong. Let's go play some music, clear my mind, and get started again. Yours is yard work. So I'm sure your family loves that. You have the best yard. There's fountains and every different color. You got a giant elephant shaped bush in the front yard.

(Levi at 00:49:51) No. It's a bad day.

(Joel Beasley at 00:49:52) You're like, no, I'm relaxed. Oh, man. This is so great.

(Joel Beasley at 00:50:02) Alright. So you're driving down the road. Hypothetical. Right? So you're driving down the road in your town, small town. You're at a stoplight. You look over to the right. Okay. Instantly your car breaks down. Okay. In the lane next to you, there's a gentleman in a Tesla and it's Elon Musk. He rolls his window down. He says, Levi, you need a ride. And you're like, yes. Yes, I do.

(Joel Beasley at 00:50:26) So he's got flamethrowers in the trunk. You go around the back of the car, right? You get in the passenger side and he's got a time machine there, right? The passenger seat is a time machine.

(Levi at 00:50:36) Okay.

(Joel Beasley at 00:50:37) Right? And he goes, you're going to go for twenty-five seconds. You're going to go ten years in the past and get to give yourself one piece of advice. What are you going to tell yourself?

(Levi at 00:50:47) Okay. Oh, man. So, okay, I'm going to give a really—I'm going to give maybe just a couple quick answers. But the first thing I would say to myself, maybe ten years is too long, or too short, but I remember when Apple stock was $10 a share. That was when I was first getting into programming. And I was like, man, if I just bought some Apple stock at that point. But that's the ultimate selfish answer. Right?

(Joel Beasley at 00:51:16) I love this stuff because you can help more people with more money. Sure. Right?

(Levi at 00:51:20) Yeah. That's the theory. But I—that's how I would explain it.

(Joel Beasley at 00:51:26) Evil.

(Levi at 00:51:29) I think I would have told myself back then to be entrepreneurial, to start earlier. You know, I had a lot of product ideas for years that I didn't really execute on. And it took me a while—for about six years, I spent time just kind of doing freelance programming, you know, subcontracting and consulting. And that is one part of my career that if I had the opportunity, I would have said, just go build something, you know, that would be a much better investment of my time. I learned a lot during that time, but I wish I'd spent that time building something that was more long lasting.

(Joel Beasley at 00:52:13) That is absolutely excellent advice. Your previous self thanks you, by the way.

(Levi at 00:52:18) That was actually the advice that got you to start Droplr because we've got the whole paradigm.

(Joel Beasley at 00:52:19) Yeah. Oh, man. This has been so much fun hanging out and talking with you, man.

(Levi at 00:52:29) Thank you so much. Yeah. Thank you again. And, you know, best wishes on the continued success of the podcast and the book. I'm excited for you.

(Joel Beasley at 00:52:43) Thank you so much for listening to the Modern CTO podcast. Share this, get the word out. Thank you guys so much. I couldn't do it without you. I appreciate it. You guys are the absolute best.