Podcast: From developer to entrepreneur with Raygun and Simple Programmer

| 27 min. (5747 words)

CEO and Co-Founder of Raygun John-Daniel Trask and host of the Simple Programmer Podcast John Sonmez discuss how to manage the transition from a developer to entrepreneur.

Most developers aim to become entrepreneurs at some point in their career and the amount of information regarding that transition is still scarce.

This podcast has great tips on the entrepreneurial mindset in the technology industry. Whether you have a fledgling project or a full scale SaaS company, these two experienced developers-turned-entrepreneurs discuss what it takes to find a niche and make it yours.

Listen to the full podcast below:

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Full transcription

John Sonmez: Welcome to the Simple Programmer Podcast, making complex programming simple and fast.

With everything from career advice to philosophy, John Sonmez will show you everything you need.

It’s the Simple Programmer Podcast.

Announcer: Welcome to the Simple Programmer Podcast, a short mix of career advice, philosophy, and soft skills from successful author and software development John Sonmez.

John Sonmez: Hey, what’s up? John Sonmez here from Simple Programmer.com, and I got an interview for you today. Today I am interviewing John-Daniel Trask, who is actually the founder, one of the founders of raygun.com. And it’s a platform I haven’t actually used myself, but I know a lot of developers, I know a lot of you out there in the audience have used, and I’ve heard a lot of good things about it, and I thought it was just interesting to have John on here or John-Daniel on here because he also has a lot of experience.

He has over 25 years of software development experience. He’s actually running a company and still doing some coding, which is definitely difficult to do. I stopped doing coding when I started writing Simple Programmer, so I don’t know how he’s doing it.

And just, you know, the story, I know a lot of you are interested in building a company and going and making the transition from software developer to entrepreneur. And so, I thought it would just be interesting to talk a little bit about that and maybe some of the future trends I think that John-Daniel is also more up to date on some of the existing trends that are happening in the software development field than I am because he’s following that very closely.

So, welcome, John-Daniel, JD. It’s a pleasure to meet you [inaudible 00:03:16].

John-Daniel: Yeah, well, I’ll just say me still programming is much to the frustration of most of the team still at Raygun. It’s all right. I’m chief bot creator, and, yeah, and hacky code guy now, but, yeah, thanks very much for having me on, John. I appreciate it.

What does Raygun do?

John Sonmez: Yeah, yeah. No, it’s good. I’m glad to have you here. So maybe if you wanna give like kind of a brief intro of who you are and what you do. And then maybe we can talk a little bit about your story.

John-Daniel: Yeah, sure. So, yeah, I’m the Co-Founder. So, my business partner is a chap by the name of Jeremy Boyd. He’s our CTO and a Microsoft regional director to boot. And we co-founded Raygun actually before we called it Raygun many years ago. And then we launched this product, which was a software crash reporting solution that we called Raygun, and it got really, really popular, which was really, really awesome to see. And then we sort of broadened out into today.

We sort of consider ourselves a full, what we call a software intelligence platform, which is tracking everything your users are engaging within your software, tracking the performance that they have, the experience they have, and tracking the software errors, and building up a full sort of story around that with dashboards and alerting and all of that stuff. So, it’s really sort of helping software developers better understand the software that they have and making sure their users are experiencing it, how they’re intended to experience it.

So, I’m now based in Seattle. Our company is actually headquartered in Wellington, New Zealand, which is why I have a bit of a funny accent. But I’ve moved to Seattle to help build out our sales and customer success teams over here. So, I’ve been in America now for about a year and enjoying it over here.

And as you mentioned, I still do a little bit of coding just to try and sort of keep the skill sharp and play around things on the weekend, but I don’t tend to write too much code these days on the core Raygun product much to the benefit of our customers. But I like, I love programming. I consider myself living at that intersection of sort of basically software and business, you know, and I’m always trying to decide which street I wanna be going down.

John Sonmez: Yeah, yeah. That’s a common problem I think you know, a lot of developers face especially in their career. But it’s kind of funny, like it’s really hard to run a business I think and then, and still be…I know a few people that have had to give up the coding because they just couldn’t do it. They couldn’t run the business and do that.

John-Daniel: Yeah. And that’s definitely been a challenge. I sort of phased it out. We bootstrapped our business initially, and was one of those ones where I’d spend a certain period of time writing code, and then slowly less and less of that time to the point, like I say now, it’s pretty rare that I actually write code. I do still review things like GitHub pull requests from time to time, and I really enjoy, you know, connecting with the team on that. In particular, I like…I’m big on software performance.

Maybe it’s a function of age where I sit there and kind of go how do we handle these multi-gigahertz boxes with many gigs of RAM. And this stuff seems to go slower than when I had a 48625, like. So, you know, I like to bring a performance [inaudible 00:06:29] to what we’re doing.

John Sonmez: Yeah. Yeah. I’ve always want…I do…that does boggle my mind today when I think about how, you know, especially when I’ve got, you know, got a new laptop here, and I boot it up, and I’m like, how is this…it doesn’t feel like it’s that much faster. I mean, the technology’s come so far, yet we keep on needing beefier and beefier machines. I mean, will we ever get to that point where it’s just gonna be like, okay, you know, I’m trying to think of another industry where it’s like, it just doesn’t matter. We’ve got so much power that like, you know, everything just runs instantly, but we never got there yet. So.

John-Daniel: Always striving, always striving, yeah.

John Sonmez:: It’s the gamers. It’s the games.

John-Daniel: Yeah. I mean, I sort of…you know, I use…it was one of those things to try and transition away from coding. I use a MacBook Pro 13 inch for work. I find the 13-inch machine is small enough that it kind of forces me just to focus on email. I always say that, you know, the EMC always stands for Chief Email Officer. But at home I have, you know, the whole multi-monitor thing, the grunty PC, and it’s got Visual Studio and all the crazy stuff in there, and whatnot. But, yeah, this was almost a forcing function to make sure that I focus just on business tasks.

The evolution of Raygun

John Sonmez:: Yeah, yeah. No, that makes sense. So, tell me a little bit about the story, like how did you make the transition, and what…I mean, did you set out to create a company? Was that kind of your aspiration? Did this start off just as a side project and then it became something more or what was kind of the beginnings?

John-Daniel: Yeah, it’s a good question. I am…I guess I was one of those weird kids that kind of knew what they wanted to do from a very early age. So, I probably knew when I was about nine years old that I wanted to own and run a software company. I’d sort of started coding when I was nine years old, and to me, I use this analogy all the time, but to me, it was like discovering a box of Lego bricks that had an infinite number of bricks. It was up to me on how the heck I was gonna put it all together. And I liked that. I’ve always liked the idea of being able to leverage technology to achieve more, to amplify your capability, and in a lot of ways, I see that as being the same in business. In business, you’re sort of trying to bring together a group of people on a shared mission to achieve more than you could achieve yourself. So, I kind of go, “Well, if I can combine one level of amplification with another level of amplification, then that’s a lot of amplification.” So, I’ve always been on that intersection.

My father, well, my parents, they ran their own business from home. My aunties and uncles ran their own businesses. So, it was always sort of in my blood to do it. And then I took the traditional route and I went to university, got a degree, you know. I started an IT services company in Wellington, New Zealand, where I met my now business partner. And, you know, his comment to me was, even when they hired me and he was like, “These guys considered you a flight risk from day one.” No, yeah. I was pretty upfront that I wanted to go do my thing, but I also wanted to see how a normal business operated. And I learned a hell of a lot there and met a lot of people in the industry, learned a lot more about professional software development. But I’d run a bunch of small businesses as side projects all through high school, university, and things like that. So, the one we have today was a lot more planned out than the side projects.

Developer skills meets entrepreneurial endeavours

John Sonmez:: I see. Okay, that makes sense. Yeah, it’s kind of funny that a lot of…I mean, but, you know, a lot of companies are sometimes wary of hiring someone that has entrepreneurial, but I always tell that, you know, I always tell the developers that I talk to that like don’t worry about that. Like, find the company that wants to hire the entrepreneurs because they know that they may only have you for three years, but you’re gonna be working harder for them or doing more and doing better things for them than someone who’s maybe a lifer, that doesn’t have that kind of motivation. So, you know, I tend to tell them [inaudible 00:10:40] don’t shy away from it. Just let them know your ambitions, you know.

John-Daniel: Yeah, absolutely. Well, at the business that I joined, which was called Intergen, they were still run by their founders. So, the three directors were the founders of the business, and that, I think, meant that they didn’t shy away from it because they just saw in me exactly what they had themselves. And I was sort of, you know, I was setting up this office here in Seattle and I’ve taken the same approach with bringing people in. And so, I always say, “We want people with an entrepreneurial mindset because, especially when you’re starting out or you’re smaller, you don’t want people pigeonholed into you do X, you know.” You need them to be saying, “Hang on a minute. We’re not doing this part of the business very well. I thought this process wasn’t working so well. Did you think about this?” And you know, I love that. I kind of imagine myself surrounded by droids.

John Sonmez: Yeah, yeah. So how did it start out then? How did you…? So, you said you planned out this business. Did you…? And you bootstrapped it. So, how did that work? How did you get your first customers? How did you come up with…? I mean, did you have the idea and then build from that idea? What…did you have an existing audience to be able to sell or market to?

John-Daniel: Yeah, we didn’t have a particular audience, or none that was sort of, of significance. We decided that…my business partner and I wanted to sort of leave and start a business. We wanted it to be a product business because, you know, in services, it was one of those cases where sometimes you’d really want to do the right thing, you know, but budgets run out or, you know, it doesn’t fit a timeline. And so, building a product sort of felt more like we could bring more of a craft to what we were doing and be, you know, in control of our own destiny. So, what we did was we bootstrapped because basically we don’t have a whole lot of money. I’d saved up enough money in the three years that I worked in the industry to make sure that I could afford to not take a salary for, I think I going up to about 18 months of not needing a salary.

And we were quite fortunate actually that Microsoft New Zealand came to the party on literally day one. I mentioned my business partner’s regional director, and so he had a great relationship with them. And so, they actually gave us, from memory, it was about a quarter of a million-dollar contract to build out a sort of “best of breed” modern web application to try and demonstrate to developers worldwide how they should approach building modern wave applications on the Microsoft stack. And so, without us actually planning to have that as effectively seed capital, that was a huge blessing on day one and helped us immensely. And then with that capital, we then had the freedom I guess to build out our first product, which was an object relational mapper called LightSpeed and built, you know, got our online store up and humming, which was great.

So, Microsoft was hugely supportive of us in the genesis of our business really. But that’s the hardest thing I think sometimes going into business is that it’s so not exact. It’s not mathematical. It’s like, you know, some of these things come out of relationships or, you know, we…even in sales here, you know, just had a customer yesterday who was like, “Oh yeah, I’m ready to move on that colossal deal that we talked about in September that I, you know, [inaudible 00:14:19] anyway.” Those sorts of things, which it can really test your nerves and commitment, you know, early on, but, yeah, so that’s how we kind of got started.

Managing the transition from developer to entrepreneur effectively

John Sonmez:: Okay, okay. And then so you started with the object relational mapper. And then now the current product that you have, the raygun.io. I know I’d seen the first iteration when you first came out with it. How did that transition go? Was that just another product that…

John-Daniel: Yeah, initially it was just another product. And just before we keep going because I know Nick on our marketing team is going to stab me if I don’t correct it. We dropped the IO.

John Sonmez:: Oh. Okay, I see. There you go.

John-Daniel: It’s just Raygun now. It’s all right. I still have all our swag that still has IO on it, sort of retro brand. So, we actually bought the dot com, and we moved over to that. Raygunstill works, but, yeah, we dropped that. So, yeah, we built it as just another product, but something that we…based on our experience back at Intergen actually, where we kind of noticed that really good software developers would tend to write some code to send themselves emails when things went wrong with their software.

John Sonmez: I’ve done that.

John-Daniel: Yeah, yeah. Well, there always seems to be two sets of software developers, and I was gonna say this shouldn’t sound like a criticism, but it is, which is some that wanna know when something goes wrong so they can fix it, and then the other ones who are like, “The last thing I wanna know is what’s going wrong with my software.” And so, but the problem was, is that if you just email it yourself, error messages or stack traces, inevitably, you’d get a bunch of noise in there. You’d set up an inbox rule to send it a folder, you’d slowly desensitize yourself to it because it was usually not active errors that you needed to deal with. And suddenly, you’d end up where you were missing, you know, the credit card system was failing, and you didn’t notice.

So, we kind of wanted to build a whole workflow around that for ourselves, and ended up building out the Raygun product to do that, where, you know, you get a virtual inbox online. We do error grouping. So, you might have 10 million errors, but only actually have say, 18 bugs. So, you’ll only deal with 18 things. We wanna know how many users are affected. Just because one user has a shitty Chrome plug in that spammed you with 10,000 errors doesn’t mean that it’s worth fixing when there’s another error that maybe affects 500 users but only occurred 500 times, you know, things like that, and give you all the context of the developer and how to fix things quickly.

So, we kind of built it for ourselves. We put it out there. We had tremendous interest from day one, and then a month after we launched it, people started contacting us saying, “Hey, guys, do you want us to do a case study for you? We think this is fantastic.” And I was kind of like, “Well, you know, I’ve never had people contact us offering to do a case study. That seems pretty different. Normally you’ve got to try and put the legwork in yourself on that.” So, we kind of knew something was a bit different. And then sort of, I think, it was three to six months later, a mid-sized U.S. tech company tried to acquire the company just because they wanted the Raygun product. We obviously turned that down, but that sort of caused Jeremy and I to sit bolt upright in our chairs and kind of go, “Well, you know, there seems to be something going on here. Maybe we should focus our efforts.”

And so, we did, and then we added, like I say, real user performance monitoring. We have full mobile support, and you know, I don’t wanna turn into a feature list, but, you know, it’s a pretty mature platform now. It’s been on the market for several years used by some massive companies. So, you know, it’s been…I have no doubt it’s gonna turn into one of those stories of the 10-year overnight success.

John Sonmez:: Exactly, yeah. How big are you guys now as far as like employees and [inaudible 00:18:09] company?

John-Daniel: So, we’re about 40 people now in the business. We’ve just moved offices both in Seattle and New Zealand to support probably a headcount of around 100, and things are still growing really well. We just had our strongest month of growth in February, which was great. But, yeah, it’s been a fun ride. And the interesting thing for me is because it’s a cloud hosted service, we do provide an on-prem option, but, you know, everybody’s on the cloud one, is I mentioned I love performance. And so, this has become one of those things, where we deal with billions and billions of inbound messages every hour. And so suddenly, hey, maybe if I can shave 100 milliseconds off something, that can compound up to a pretty massive win. And so, I love talking with the team now about all the software performance optimization work that we can be putting in all over the place to make sure that providing the services is done as inexpensively as possible while being super reliable.

The future of the software development hiring process

John Sonmez:: Right. Yeah, that makes sense. That’s a good opportunity there that’s you get those opportunities of scale. I was gonna ask, you know, maybe to shift things a little bit since I kind of wanted to get your kind of view. You know, you’re probably doing some hiring, too, of software developers and just, you know, have a pretty good pulse in the industry. What do you think, what are your thoughts on kind of software development, the future? I know there’s a lot of fears. It seems like a kind of a strange of a fear to me, but…of software developer jobs going away, of being automated away. I’m not so sure about that, but I don’t know. What do you think about where we’re sitting right now, I guess, in this field?

John-Daniel: Yeah, I mean, I definitely don’t think our jobs are going away in any hurry. You know, I just read an article yesterday saying that Facebook was gonna down tools and rework their bot framework for Messenger. I never really used it, but the idea being that you can use Facebook Messenger to chat with a bot and ask it questions, and it’s kind of like, I don’t know if you use things like Siri or Alexa, but given that they struggle to answer even some of the most basic questions, I’m not convinced that we’re gonna end up automating away software development in any hurry. Or at the very least, if we do, I’m sure my business in terms of tracking software faults will skyrocket.

But, yeah, I think we’ve got a long way to go on some of that, and I wouldn’t worry about it. I would say that I think there’s a lot of people in our industry that actually don’t appreciate how wonderful things have been for software developers now for quite a long time. I mean, we had the 2008 GFC. Certainly, sort of impacted a lot of people, but we haven’t really seen any massive downturn in the tech industry since the dotcom bubble burst, and you know, when you sit there, and you read on Hacker News and sites like that about people on this, they’re actually on pretty significant salaries. And that’s not a bad thing. I’m not saying we should bring them down, but I don’t think…it’s been good, and people should appreciate the good times, and they should stash a bit of their cash probably during those times, you know, to make the most of when times might not be so good. I mean, I remember being blown away, and this is New Zealand numbers, but, you know, I think started as a graduate software developer where I was just shy, my salary was just shy of the average household income in New Zealand, you know. And you’re like, oh, actually you’re doing pretty well.

So, I don’t think people should be super worried. I think they would just plan for a rainy day. Things can’t go up and up forever even though we try. I would say one of the things, and this is not necessarily something for the audience to be too, maybe, too concerned about, but I was chatting with a friend of mine recently who’s in a management role of a software team but was also a software developer, still codes a bit for fun. And we were sort of chatting, and I sort of said, “I somewhat feel like the new stuff around machine learning and AI, with things like TensorFlow and stuff like that, it could be at that point where this is the boat I’m gonna miss.” And if all my skillset is to be diminished and its value in sort of 5 to 10 years’ time because this is the first time I haven’t actively had a need to personally learn the stuff and use it. So that’s what I kind of playing around with at home. So, I think as long as people keep their skillset up to speed and whatnot, they’ll be fine.

John Sonmez: Yeah. Yeah, that makes a lot of sense. Well, I mean today too, like you said, I haven’t really looked in…learned machine learning and that skillset, and now, I mean, there’s a whole bunch of the ones that are coming out, you know. I mean, I just heard someone just email me and said that they’re working on embedded systems for drones, and drone…I was like, “Oh, yeah. I guess that makes sense.” But we’ve kind of hit this point where there’s like this explosion where you can’t really keep up to date on everything anymore. You used to be able to, right? I mean, sort of, like, you know, like 10 years ago, you could kind of know like most…keep your thumb on kind of everything that was going on, but I think today it’s pretty difficult.

John-Daniel: It’s certainly become a super broad industry. I mean, I think it was in the late ’90s maybe. I remember reading somebody’s thing where it’s like, “You know, I used to know every single Win32 API,” you know. Just like nobody, nobody does that. No one knows that sort of stuff anymore, but, I mean, it’s one of those things. So just keeping your skills reasonably fresh and looking for new ways of thinking about things. The biggest challenge that I usually find is actually applying the filter for what to fed and what do I really need to get into, you know. For all I know maybe this machine learning stuff is just gonna like, you know, be worthless in five years’ time and there’ll be a whole new breakthrough and you need to learn it that way. Who knows?

Maintaining a deep knowledge base

John Sonmez: Yeah. Yeah, that’s funny about the Win32. Well, you know, back in the day, it was like I used to do C++ development, and it was like to be a good developer, you need to know the insides and outsides of everything in C++ and STL and you just like we’re really good at it. And today, it’s not that at all, like having really deep knowledge in the language is, like, useful, but it’s not the defining characteristic. To me, like the defining characteristic today is to be able to integrate a bunch of different technologies and quickly learn things because you don’t have that. Like, there’s no point in mastering Win32 API or anything to that level because it’s all changing and there’s so much, there’s so many moving pieces now I’ve found, but…

John-Daniel: Yeah. No, I totally agree. When I first got started with, I think it was .NET 1.0. So, most of the time I code in C# these days if I am coding, but I remember getting the box, you know, back when software came in a box and being like, “Okay, I’m gonna go through here…” And I was like, “Oh, man. I’ve got a whole poster of the name spaces and the [inaudible 00:25:31] library. Better put that up on the wall. I kind of need that guy, you know.” But I did this at home, too, and I can assure you, that did not spark the romance when you brought the ladies home. What’s that poster? Well, let me tell you, yeah.

John Sonmez: I started this project the same thing when .NET 1.0 came out, right? I started this project, and I opened, made this Visual Studio project, and I was going through, and I was gonna use, you know, every single object, every single function call, right, in the dot. I just practice it so that I would know it all in this example. How do you use this thing, you know? And so, I went through every name space. And I got like through like maybe halfway through the entire .NET framework making example code for every single one before I gave up on it, but it just seems…now I look at it, like if someone told me they were doing that, I would say they’ve been wasting their time, but…

John-Daniel: Absolutely.

John Sonmez: I was the king first for a little bit there. I had like…you know, I was like, anyone could ask me anything about .NET framework, and I was like, “Oh, I know exactly how to use this.”

John-Daniel: Yeah, yeah. Well, see, I blithely steal a friend’s joke for this, but, you know, but my business partner, Jeremy, he is just an absolute software wizard, you know. And I sort of say, “Well, why did you become the CEO?” And it’s like, because I was the s** coder out of the pair, so I drew the CEO card. But you know, he is a machine. He likes things like getting on a plane and not having Wi-Fi on the plane so he can just code even more and not be distracted. And I’m like, “Man, if I didn’t have the internet, I can maybe hash out a full loaf or two for you, but we’re done there.”

How can we find out more about Raygun?

John Sonmez: Yeah, yeah. Cool. So, I guess, you know, where can people go if they wanna find out more about what you’ve got here with Raygun?

John-Daniel: Yeah, well, they can go to raygun.com. We have a free 14-day trial like I mentioned. It works with everything out there, mobile and web and backend and all of that good stuff. So, you know, whenever I say that I normally get somebody who goes, “Oh, yeah, well, I wrote a Cobalt app, do you support Cobalt?” And it’s like, “We don’t support Cobalt, but if there was enough demand, we would.” We support about 20, 25 different languages and platforms today. So, there’s quite a lot of coverage. Most of those are on GitHub as well the provider piece. And so, they can sign up, give it a whirl. Seriously, it just one of those things that usually takes 5 to 10 minutes to get set up. So, it’s not a challenge to get running.

John Sonmez: Okay. And then do they put…is it like instrumentation that they put into their code or are these, your APIs in order to call, like instead of like kind of how ELMA, that kind of thing?

John-Daniel: Yeah. So, we provide an SDK. You integrate it in a few lines of code and that gives you 99% of what we do. There’s some extra things that we can do, deployment tracking. So, if you’ve got things like say Octopus Deploy set up, and you’re pushing builds out, you can ping our endpoint, and that allows us to start telling you things like, hey, this new version that you have, has introduced these new errors, and you’ve had these regressions and whatnot. So, you can start telling the difference, the health between versions and deployments. You can attach real user information. So, if you wanted to understand who exactly of your users was having issues, you can do that with Raygun with a little bit of extra instrumentation.

So, we use Raygun to track Raygun, right? So, like if somebody gets in touch with us and says, “I’ve had this problem,” we can just jump in and look at their account and be like, “Oh, yeah, I can see, you had this 500 error like 3 minutes ago. Okay, cool. Well, a software developer can fix that in no time and push out another deployment,” which fixed it up for them. So, it sort of changes the whole dynamic. But generally speaking, sub 10 minutes to sort of do integration, the SDK, and be up and running.

John Sonmez: Okay, yeah. That sounds good. Sounds like it’s worth taking a shot and trying it out. I remember trying to code up something similar on my own when I was doing the same thing, like you said, with emailing myself. So, I got smarter and created a database and started shooting the stuff there, and I was trying to match up stack traces, and…but you know, it sounds like you’ve got that already going, so this is kind of…I would have loved to have this, you know, when I was still writing code about maybe six or seven years ago when I was trying to tackle this, so.

John-Daniel: Yeah. No, that was one of those ones where I also wish it was around. I mean, the thing I like, and I’m sorry this sounds sales pitchy, but it’s just hearing from my, you know, fellow engineers who are like that you know, we can’t imagine not using a tool like this now in our stack, you know. And we get that sort of feedback every day, and we rely heavily on that ourselves, you know, to change our whole way that we deliver software, but, yeah, it’s pretty valuable.

John Sonmez: Well, thank you, JD. I appreciate you taking the time, and I appreciate your insights. And hopefully, you’ll continue to grow and hopefully to still be able to do a little bit of coding at least.

John-Daniel: I hope to keep coding. Yeah, there’s just so much cool stuff out there. Like I say, I still feel like an unlimited piece Lego set, which is just waiting for me to tinker around with it, you know. So, I love it. I love software.

John Sonmez: Yeah. All right. Well, thanks again, and I’ll talk to you later.

John-Daniel: Thanks very much for having me. Bye.

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