Software Developers Journey Podcast

#183 Karl Hughes from mechanical engineering to self taught dev, technical writer and CEO


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Karl Hughes 0:00
If you're not the point where you can charge for your work, maybe don't have any samples that are already out there, start writing on medium or dev to or start your own blog, whatever you prefer, just start getting some tutorials, basic stuff out there. Then the next level like is well for me was like starting to subcontract and actually move beyond these community programs and into like, direct relationships with clients. So I started finding companies that didn't have a committee writing program didn't have the bandwidth to like, edit this stuff in house that needed that sort of that level of help. And I started talking with them about like, Could I do that? Could I just find writers for you and edit them, make sure they're up to speed and then pass it over your way. And in order to do that I had to raise the rates a bit, but I also was raising like the level of service quite a bit to.

Tim Bourguignon 0:51
Hello, and welcome to developer's journey to podcast, bringing you the making of stories of successful software developers to help you on your upcoming journey. I'm your host, Tim bourguignon. On this episode 183 is wondering DC three already received call you call He's a former software engineer and startup CTO, former because he left software development to start a technical writing business called draft dot Dev. Carl and I have something very special in common, right around the same time in 2018, we each created a tool to create call for proposals for technical conferences, and we kind of have been in contact ever since. And both tools still live in parallel. You probably know mine already. I've advertised a couple time here. ccfp.com. But if you don't know calls, it's a CFP, land.com. And maybe we'll talk about that as some call welcomed afternoon.

Karl Hughes 1:47
It's great to be here, Tim, it's always fun to reconnect, because we have so many similar interests. Yes, we do. Yes, we will. I'm

Tim Bourguignon 1:53
sure we'll come to that in a minute for sure. But before we come to your story, I want to thank the terrific listeners who support the show every month, you are keeping the dev journey lights up. If you would like to join this fine crew and help me spend more time on finding phenomenal guests, then editing audio tracks, please go to our website, Dev journey dot info and click on the Support me on Patreon button. Even the smallest contributions are giant steps toward a sustainable dev journey. journey. Thank you. And now back to today's guest, the show exists to help the listeners understand what's your story look like? And imagine how to shape your own future. As always, let's go back to your beginnings. Where would you place to start off your directory?

Karl Hughes 2:43
This is a great question. I love that you lead with it. So I would actually place it way back when I was a kid, I spent countless hours playing with Legos and renting architecture books like house architecture books from the library and copying the designs that I saw there. This is the you know, the sort of design and nerdy side of me that like from the time I was five, six years old, I was doing this and I kind of thought I even that young, I wanted to be an architecture engineer some kind of design type job. Obviously, I didn't know all the intricacies especially didn't know anything about software engineering, or computer engineering, because that was this was you know, 30 years ago now. So that stuff was barely you know, registering on my brain. But at the same time, I knew I really liked that sort of creative blend of both design and logical sort of problem solving. And so throughout high school and into college that kind of shaped a lot of my career path to be honest, like I took physics in high school. And then in college, I went and studied mechanical engineering. The other thing that really shaped my journey though, which kind of leads to where I met with draft is writing. So one of my favorite sort of hobbies besides school and this sort of like, I don't know, mechanical side of my brain that wants to design things was writing. And so I got into like AP English in high school, and then college, my friends and I would sit around that I had a lot of English major friends, I was always kind of drawn to creative types. And so they would sit around at night and do these short story. We call them like short story competitions, although I wouldn't really say they were that competitive, what we do is we write down a list of words for each other, and then pass them around. So I'd give 10 words to my neighbor, and they'd give 10 words to me and we go around a circle, we had to write a short story that involve those 10 words in like two hours, then we come back together. And you know, of course, we're drinking a little were enjoying the like laughing about each other's ideas and stories. And we share this and that was kind of formative thing is well that sort of got me on this like idea that writing can be fun. It isn't always just work and like that laborious thing you have to do for school, like writing school essays was never exactly my favorite but like there is a creative side of writing. And so anyway, I think those two early experiences really formed informed where I went my career and then what happened is I got into as I got into college and I started doing internships in mechanical engineering. I realized how big In slow and boring, most of the companies you can work for in mechanical engineering are. So I've worked at like GE and Siemens, and a company that tested coal power plants. And it was just, I mean, they were fine jobs. Like from a, you know, objective standpoint, it was great pay good benefits, good work life balance, but like, it was super boring. Most of the time, you're just kind of crunching numbers in Excel. And I don't know, sitting around like taking data. And I kind of looked at the career progression in those companies and realized that's just really not for me. So that got me interested in startups, which sort of as I started learning about them, this is this will put this back about 1012 years. So this is about the time that like Facebook and Twitter are starting to get really big. And people are thinking about software startups as a whole new, a new world online, startups were really getting big things like WordPress and Ruby on Rails, were starting to pick up a lot of steam. And that was allowing people to build software faster with fewer, like less knowledge of code, to be honest, like you didn't have to know how a compiler work just to get something on the internet. And that was a big sort of step in the progression of allowing people to get out there and start building stuff and including myself. And so that's where I started learning to self teaching mostly, and Stack Overflow was a thing back then. But that was about it. There was not the there's not the free code camps and great online tools there are today. And so I just started hacking away building stuff. And eventually that got me into like, looking like I could build enough that a couple clients, local businesses hired me to build their WordPress sites. And then that got me enough to where company hired me out of school to help them run a little college news blog and write the code for it. And so it was I just had, like, it was a very weird journey, the whole thing like it was it felt very even now looking back, it's not very, like directed. I had a path at it for about a year at a time. And then it shifted about a free year. And I think I've carried that onto my career. So anyway, that's probably a good intro. I think there's a lot to go from.

Tim Bourguignon 6:55
Just just gonna be back to one point, did you consider something else? You weren't into this mechanical engineering path more or less? And suddenly one of the options open to to go toward WordPress, Ruby on Rails doing website development? Do you consider something else? That's

Karl Hughes 7:10
so the problem was how to say this is not a great student, I took a long time to go through college, but I really liked I liked the working aspect, usually like more than the study aspect. Like I've never been a big fan of rote memorization. And like all that I like application of technical ideas. So what I took about six years to get my undergrad degree, which in the US is typically for and some of that was because I was working a lot. I went part time a couple of years. But anyway, I sort of had this intro into things like programming later in my college career. And I was far enough through that degree where I was like, I should just finish this up. Like it was a slog, the last two years were like mentally very, I was checked out of school. And I was not doing that great in my mechanical engineering classes. But I was like freelancing as a web developer, and I was building and making money, building real company websites, like, I was like, this is way more interesting and fun than the like stuff I have to study just to get this degree. But I did think to myself, like, you know, in the long run, when I look back in a few years, maybe I do want to go back to a bigger company. And maybe they do need me to have a degree. So for me, it was kind of like checking that box just to be safe. I think there's a side of me that's a little bit risk averse that wanted to make sure that that was there's a good backup plan if this whole crazy web thing didn't work.

Tim Bourguignon 8:25
risk averse, and then you went full into startups.

Karl Hughes 8:30
But I didn't go off and like start my own company right out of college, you know. And so like you think about like, actually, this is one of the the second startup I joined the founders were right out of college, they started in college, they started pitching to investors that basically when as they graduated, they got on Shark Tank, they raised a ton of money. They hired me, then, you know, I was one of the first employees. But I didn't have that level of gumption to be honest, like, I was not that like, able to, I didn't have in my mind this picture of Oh, I could be an entrepreneur that starts a business right out of school, I was not quite there yet. I also, you know, financially wasn't there yet, either. And I was kind of not quite at that point where I felt confident enough to like go pitch investors and sell it. So, you know, different people have different levels of risk aversion, right. Like there's the really conservative one that's like, must get a steady nine to five job at a huge fortune 500. And, you know, you'll be there set for life, right? And then there's kind of somebody in the middle like myself, who's like, I like to work at startups, but I didn't know if I wanted to start working right away. You know, it's a really risky job to make. So yeah, I don't know if this is a git commit to your whole point of this podcast. Like everybody's journey is different. And it doesn't have to be quite as black and white as you might think. You don't have to be Mark Zuckerberg to go, like want to work with a slightly riskier environment in a startup, but you also don't have to go full corporate forever. So there's there's a lot of room to shift around.

Tim Bourguignon 9:53
3 million colors in between, I would say,

Karl Hughes 9:56
right. Yeah, exactly. And then there's there's also things this has also been A formative thing for me is like having side projects. And this is kind of where we actually touch, you know, overlap in our careers most like sci fi land I started a few years ago as a side project while I was working as a engineering leader at a startup. And it's like, I just had a little bit of time on nights and weekends, I thought it was interesting. I was doing some speaking I'm sure your journey. So it was like the one of the things that I think a lot of entrepreneurs these days are realizing is that they've got the skills and the tools available to start building stuff on their own. Even if they never make a real business out of it. Like CFP land is never going to pay my bills. It's a nice fun side project. And it you know, it paid for itself right now, which is the that's all I'm trying to get to like, even Yeah, I'm not paying for it more than it's paying for itself. So that's all it needs to do. But yeah, it is. It doesn't mean you have to like just because you start a side project doesn't mean you ever have to go full time on it. That has to be your your life's work.

Tim Bourguignon 10:55
Absolutely. Welcome back to the startup thing, I'd like to roll by a little bit. How did you ramp up from doing some freelancing and websites on the side and being I'm going to put Here are quotes here attractive enough to a startup to be the first employee?

Karl Hughes 11:12
Okay. So the trick that I learned early in my career is that small companies, this includes like the small companies I freelance for and the startups I worked for, hire almost entirely based on trust and their network. So in other words, if you want to work for a small company, you need to meet people that work there, or that could introduce you to people that this is maybe a fault in small companies. But the truth is, most small business owners are not great at hiring and evaluating people. So they sort of operate off of trust. And they say like, well, if so and so trust Carl, then you must be a decent guy. And that's all I really need. You know, it's like, they don't know what they want, technically. So they're just like, honestly, if we can trust you, that's that's it. So realizing that was like one of the probably one of the keys to my career, honestly, because that's how I got every job with startups, because I met the founders, either outside of work, or we had mutual connections. And then it's honestly been the reason that our, my, my agency now draft IDEV has done so well is that I just use the connections I built over the last 10 years of working with startups to start it off and get it going. And then those turned into other connections. And that's just kind of snowballed, but kind of to give a really concrete, how did I get those first freelancing clients and how to get that first job. Couple things like I started just telling people at on campus that I was a web developer now. You know, build one website, I'm a web developer doubt like, this is the there's probably something to be said, like, my ego is maybe too high. That's my life. But whatever, you kind of have to overcome that. So I knew that like with WordPress, there are so many good plugins, themes and things like that, that I could probably hack together just about any basic, you know, company website, like if I was not building intricate applications here. So I just started telling people, yeah, I can do blogs and local websites and stuff. And then so my friends who worked at different local businesses started introducing me to like charities and nonprofits and small businesses, and that that sort of like, brought it in, of course, I was way under charging, because I was a college student, I didn't need much money anyway. And what I was kind of doing was learning while I built. So in other words, I'd take a contract and say, look, it's going to take me two or three months to do the whole thing, I'm gonna have several checkpoints along the way. And at those checkpoints, you're gonna pay me x and y, you know, whatever these numbers. And so I just kind of put those checkpoints in my mind said, I don't care how many hours it takes for me to get there, I'm gonna build this thing by this day, because I told this person that would, and they're gonna pay me this much. And that's gonna keep me you know, like, fed till the next one. And that was basically how I did it. And, you know, again, like I was in college, they didn't have a worst case, I was gonna move back home with my parents, right? It was not or go get a job, it was not the end of the world if I failed at it. And that was a luxury that I know, a lot of people don't have. But at the same time, when you get that luxury, you gotta take advantage of it, you know. So that was my approach. And you know, as you do that, you get better, I get better. And I eventually got good enough at building these, like, blogs. And I built like a campus blog and operated that with some friends never made any money on it. But it was like a lot of good experience. And that sort of got me into that first startup where they were, this was like, this is perfect timing, and also the power of like, just going out there and meeting people. It's like, this company was a college classified ads platform. And I was building a college news site at my college. They happen to be looking into at the moment that I sent them a cold email, they happen to be looking into adding college news to their, their campus classifieds. So this kid who's like, got no work experience, but has built a campus blog and has 30 or 40 writers, these working with, like friends, you know, and just like, casually doing this thing comes to them and says, I want to do this, I'm basically going to work for next to nothing, because I'm like, right out of college. Like I'm just looking for my first job. And they're like, Yeah, sure, let's do it. And they started me on contract. And then they moved me to full time as we got as I got a little like more embedded and better. And then that sort of opened up new opportunities down the road got me to Chicago as well. This is maybe a pre pandemic thing, but like getting into a city where there was lots of startup activity was really key to building the next relationships and getting into slightly more ambitious and faster growing startups. had more funding and things like that.

Tim Bourguignon 15:02
I haven't feeling you have a couple of networking tips don't use leaves.

Karl Hughes 15:06
Yeah, a couple. So big one is staying in touch. I think a lot of people. So this happens all the time, I'll tell you the the bad versus the good. The bad approach to networking is you meet somebody, once you talk to them once you send them an email once, and then that's it, or you get coffee with them once. That's the end of that relationship. You never follow up with them again, and you get a this happens, like Bootcamp grads, so I speak a lot of local area developer boot camps. And well, I suppose after I speak, a few of the students will come up and ask me questions. And they'll a couple of scheduled coffee, which is great. I love meeting students and helping encourage them. And then what happens is almost none of them ever follow up, they get a job, they forget about old car, which is fine, right? Like I'm not expecting them to. But what the differentiator, what I've done is stayed in touch intentionally with a pretty big list of people. So 50 to 100, people, depending on the year kind of fluctuates, a bit of people that want to just touch base with every six months, at least, and maybe more. And having that list. And being intentional about staying in touch with them opens up so many opportunities that I mean, you just you can't like I can't even express like that couldn't count them. There's just so many ways that's helped it, for example, my second job. So after I'd worked the first startup in Chicago, I started going to startup pitch competitions and meeting people and hearing about what was being built and who's getting funding and all this, I'm learning so much. And then I reached out to one of the founders after one of these pitch competitions, I said, Hey, look, this is a cool idea, I would love to just meet you and hear more, got coffee with them stayed in touch for I think three to six months. And then finally they were at a point where they could hire an engineer. And that was the first person that thought of, again, it goes back to like, trust and staying in touch. It was not like one meeting, it was not like coming up and shaking their hand after that does not work. You have to stay in touch with people if you do want to build a real relationship and actually, like, you know, have that two way help each other out.

Tim Bourguignon 16:53
This is so true. This is so true. The the the incredible exchange that I've had was within the first batch of guests on this podcast is incredible. So I'm dating a little bit of something four years ago. And I need to do that with more people. I haven't been diligent and doing that with each and every one of them. But then to go back to it because the first 50 guests, I really sit in touch with them. And it's works wonders, yeah, we're discussing things and at some point, some something will happen. And if it's the right link, or the right hint at the right moment for what you were doing, or if it's the right person that suggested in an interview network VR, those connections and unblock something, you never know what it's going to be. But it's absolutely fantastic. Yeah.

Karl Hughes 17:37
And you think your jobs are like the jobs that you want, as an engineer, like the more senior you get, the more options you have. And the more picky you can be and should be in generally speaking. And so as you get more senior, like, do you want to go work for a company who you know, no one and you have no idea what it's really like, you're just basing it all on the job description where of course they're selling you on the benefits of it like? Or do you want to go pick a place to work just based purely on salary, because very few devs really do usually we're all like doing fine on like, you know, we're making our minimum. So like, that's not a problem, the extra 10 grand a year that you make, and I'm making this sound very casual to make that much money because that is a big deal to some people. But generally speaking in Europe, in the US that few that small difference in like the best job versus the worst shop does not change your lifestyle. It's just money that's gonna pad your bank account. And so you really need to make decisions about where you go based on like, do you trust the people who work there? And is it a really good environment? Can they tell you it's a good environment? So like, now, if I were to go ask if I needed a job, I would go to those people on my list. And I'd be like, hey, just you know, so you know, I'm kind of looking around. Anybody you've heard good things about that would be interested in talking kind of in this area? And like, I mean, that would just be I would not, there's no way I'd be like cold applications. It just doesn't make sense anymore. So I think it just completely shifts the mindset of how you do job searching. Once you've got this connection list that you can kind of keep in touch with and you've got relationships with you didn't just meet once, and then drop them off the face of the clip.

Tim Bourguignon 18:59
Have you been diligent about this list from the get go? Or? Pretty much?

Karl Hughes 19:03
Yeah, yeah, like for the last at least, I think it was probably I started after right after college. And because I kind of realized I was moving from Tennessee where I had lots of connections to Chicago where I had almost none. And I thought a couple things. One is I would stay in touch with some of these people from my time in Tennessee, because it was a little startup network I built but also I wanted to keep in touch with the people I've met in Chicago and I you know, I don't know, I just felt like careers are long. And it's easy to look at the next two or three years and think that's all that matters. But really what matters is 30 years and I think too many people just focus on that two or three years, instead of zooming back out and saying what's going to be really valuable in 10 years for me or 20 years and if you do that you think like yeah, the people that's the most valuable thing.

Tim Bourguignon 19:50
Absolutely. Can Stop smiling. This is what I've been preaching for years. So

Karl Hughes 19:55
I know I probably too much on a pedestal here ranting but like this exists get like, I think this

Tim Bourguignon 20:01
is what you know, every time I read

Karl Hughes 20:02
a thread on Reddit about how awful the like, I don't know, these hoops are for developers to go through, like the coding interview, like coding tests, and all this BS, I've never had to do one of those I've never had one for a job actually took, I've done them for jobs. I never took that, like, I just weren't good fits. And so like, I'm terrible at those things. Like, I don't know how to sort of link list and stuff like that stuff that like, I'd look up on StackOverflow the moment it came up in a job, so I, yeah, I just don't I don't

Tim Bourguignon 20:30
care. How can you do your day job without being able to sort of list? It's,

Karl Hughes 20:34
it's never come up where I didn't have the internet to ask, you know, this is a good look, this is partly why I wasn't a good student. Like I'm probably not a great rule follower in those kinds of like, when I don't see the point of the, the game that we're playing, and you know, everybody's different. So like, some people love those things, and they're gonna do really well on those kinds of interview tests. And they're gonna, they also probably did really well in their college exams. And that's fine, right? Like, use that to your advantage. I kind of don't want to put my story out there and make it seem like this is the only way. It is one way. I would say for people who are more networkers and relationship builders and less, maybe into the heavy math of software and computer engineering. Maybe this is the way this is the leverage point you use. But for others, this may not be right.

Tim Bourguignon 21:18
Absolutely, absolutely. So So take us slowly toward the draft a Dev, what happened between this startup world risk, not aversion, but not completely risk friendly, and somehow making your own company?

Tim Bourguignon 21:32
Yeah, well, so I've now worked at before starting draft, I worked at three startups in Chicago, one right out of college, and other one a couple years after that. And then a couple, two or three years after that. Another one, they were all pretty early stage under 30. People, I was the first employee that the second two. So like, I was joining really early, and then you know, kind of grew with the company, what happened was, as I that second one I grew, I started as a software engineer, and then kind of grew with the literally grew with the company, because like they tried hiring some outside managers to kind of work over me. And they just, I don't think they were a good fit for between the founders and those people and then just kind of moved on quickly. So like I ended up kind of getting promoted into like this head of engineering role as somebody who was like, barely, I feel like I was barely a competent engineer. But like, again, it was more about like, Carl was pretty good. Or they saw that I was pretty good at keeping the team motivated, hiring people building relationships. And those were really the things that mattered more at that point for their like growth and for the building a team than the like pure technical things, because we could hire pure technical people who could like fill in those gaps that I didn't know. But it was not easy to hire like a manager who was bought into the company, and like cared about it and wanted to get the right people in and make them successful. So I think that's one thing that I that kind of helped a lot is getting this like outsized opportunity with this really small company. And what that did was kind of put me in a position where now I can go to a future startup and say, like, Look, I've led a team, I've hired a team of engineers and an early stage company, if you want to do that, I can do that. And so that's kind of what happened in the next one. So we got hired to do that for them in both. The other thing that was critical, again, to me starting a business was seeing the early days, what it's really like for founders early on the good and the bad of it, and seeing the things that they honestly the things we did wrong. And both those two startups were really helpful and instructive. We did some things well, but we also did a lot of things where we wasted a lot of engineering cycles building too much. We hired poorly on lots of friends at different times, had to let people go. So like going through the process of firing people was I mean, I hate to say this is really helpful to go through because it's very painful, and it hurts and it sucks and like nobody wants to do it, but you have to as a manager. So getting that experience early in my career was helpful from like a growth standpoint. So anyway, all that kind of led me to feel like I could do this. It's just a matter of like finding the right idea and the right time. And so CFP land, actually, for a couple of years as I was like doing on the side, I thought about maybe I tried to find a way to make it into some kind of consulting business, right, you know, help people speak at conferences, or help engineers learn to speak better, or something like that. I didn't know. So those ideas all went through my head, I played around to some of them. I had a bunch of interviews with like potential customers. As I was working again, I was working these day jobs, but I would do this on the side. And that was a good experience. But I realized that market was just too small and then COVID hit. And that really shut down the whole conference thing for a while. I mean, you know, we're coming back to it now. And I don't know about you. But like, see a few ads traffic was doing really well in January. It was like our biggest month, and then the pandemic started to pick up. And by March, it had just dove off a cliff like there was no element conferences are canceled. Nobody's interested in this. Like we got bigger stuff going on, you know, and all the all the audience, the dev rel teams that were subscribed, a lot of them are getting let go because like the companies are cutting down and not sure if they're gonna raise funding. It was just everything was up in the air. And so I was like, this is not going to be the way I get out. started a company. Not the right moment. No, not the right time. Yeah, there's so much in in startups. That is timing. I think this gets under undervalued by a lot of founders that think, Oh, if I just built better features than Facebook, I could do what they do. And that's not the way it works. The way it works is you had to be in the right place in the right time in history, the internet had to be ready for Facebook. Like it wasn't quite ready at mainstream adoption for MySpace, Facebook hit at just the right time with just the right audience of college students to be Right Place Right Time. That's so much of it. Now. I think they did good things. They're good. From like, early on there. I don't know if it's a good company now. But early on, I think they had some you know, good people in there that were smart and learn how to build things. But like, the tech was not revolutionary. It was a lot of PHP scripts, you know, stuff that anybody could have built but right time Right Place Right network was way more important. So So anyway, yeah, that and that's where draft that that it was like right time, right place.

Tim Bourguignon 26:34
So what made it being the right time, the right place with the right idea? Okay,

Karl Hughes 26:38
so the, what happened was COVID Hit the startup I was working for was not in a great funding position. It was unfortunate timing. We were planning on raising money that summer, right after right after everything shut down. And so that was not a good time to try to raise money. So we sort of looked at it and like said, we need to sort of cut budget down to the minimum. So myself and the other engineers went down to halftime, we had to let a lot of people go, it was I mean, it was tough. I mean, I personally, I was not as effective as a lot of people. So I don't want to say it was like, the hardest thing ever, like I was a little less worried, because again, I had this network to fall back on, I had savings. Because my I mean, my wife and I both work have worked for a long time. And so we were in an OK, spot. Plus my good thing, my son's daycare shut down for a while anyway, so I had to take care of him too. So going down in hours was nice for a while. So went down in hours. And then as things started to kind of loosen up and get a little better. I started to ask like, what do I want to do next? Like, this is not a great, you know, I can't work 20 hours a week forever. And so I started writing freelance, because I had done this on the side just for fun. Whenever companies would reach out and ask like, Hey, would you read a technical article about this tool we're building or this thing that you use that we're interested in? So I started doing more of that. And I started just picking up like, two or three articles a week, maybe sometimes, which is, you know, depending on the how much? Yeah, I mean, depending on the complexity was doable. Sometimes some bigger articles, I'd only be able to do one a week, but some do two or three. And I just started seeing like, well, what if I just like cobbled together like a living off of writing these freelance articles, that was literally my plan was like, maybe I'll just do this for a while and see what you know, like, do it for a year, see if I like it, and then go get a job, you know, it was like, kind of want a break, do something different. And then within two or three months, I mean, it was so fast. I had way more demand than I could service myself to start raising prices, hiring people acting like an agency, like I was just like, well, let's just do it. Let's just see what happens. And then I transitioned off my old job pretty quickly. I think by August last year, I was full time on draft out Dev and starting by September in October to hire other writers. By November, December, I hired an editor, January, she went full time. And then now we have seven full time people and 120 writers that are contractors and another five or six contractor editors and tech reviewers like It's nuts. I mean, they're the it was again, this was timing, purely timing. Like I'm not saying that I wasn't like I was a pretty good writer, but like the ability to then hire other people to write and editors and stuff. I had not done any of that. So a lot of this is learning on the fly. And it was just right time, right place the market and even we're doing a good job of it so far.

Tim Bourguignon 29:10
Seems like

Karl Hughes 29:12
I don't know if so far, it seems good. I mean, you know, this is it's a service business. So like there's a limit to how fast we can realistically grow and add clients. There's kind of limits to maybe how big we can get or maybe there's limits to how much we can charge realistically and keep the things running. And so like as your costs are, and I'm learning all this stuff about like running a real business. And I still feel like I have no idea what I'm doing. But it's fun. It's worth learning.

Tim Bourguignon 29:36
I have so many questions. First and foremost, what kind of articles do you write?

Karl Hughes 29:42
So what we do is we write technical content for software engineers by software engineers. And it's usually for companies, their developer tools, companies. So think like CI CD platforms, testing tools, automation platforms, a little bit in the low code space too and a lot in the Kubernetes space right now. So it's companies that build tools for developers, and every one of these companies wants to write more technical content, but their engineers are busy building the actual platform. So the question that comes up is, these companies say like, well, how are we going to double our output of content. So we can compete with these big companies like Digital Ocean who's putting out hundreds of articles a month, or aka or somebody like that, who's got this whole content engine going. And that's where we come in, we augment their team and just say, like, look, we'll bring in some, we'll find some freelance writers, we'll also add editorial oversight and tech reviews to make sure that they know their stuff. And that way, they're getting really high quality, regular technical content without having to manage a whole team of freelancers and edit all their stuff. It works really well for like the startups to midsize companies, mostly that we work with, we're now starting to kind of push into a little bit of enterprise work, too. But they Yeah, that's kind of the core use case for our content.

Tim Bourguignon 30:48
Okay, okay. Did you get to write still? Oh, are you full time managing? And yeah,

Karl Hughes 30:53
not really, I think, last article I wrote for a client was maybe in July or so. And that was one of that I just like wanted to write like that every night, I can pick one up whenever I want. That's kind of fun. When I have time, right now, the challenge has been that we're hiring, we've hired a lot of people. So we've gone from, I mean, again, the team has grown a ton. So the full time hires take a lot of work with me one on one to make sure that they've got everything they need. Because we've grown and things have changed so much our documentation is not great. And so I'm like, a lot of times just recording a loom video, this is how I do it. Now, please do it and then write it down. Which is not ideal, like, but this is like what it isn't really company like this. So you know, a lot of hiring onboarding is now my job. And then sales calls are still my day. And then, you know, whenever there's a client that has a some kind of bigger issue comes up, you know, those kind of get rolled up to me to make sure we're handling it the best way possible.

Tim Bourguignon 31:44
Homage homage network leveraging have you been doing to get this this business started?

Karl Hughes 31:49
So early on, it was huge. A lot of our I mean, probably three quarters of the first, you know, like batch of clients were personal introductions, I knew a couple of a couple of people who had worked in developer marketing and developer relations that had they were consultants. And so they had clients who would need things like this often. And so they send me their clients. And so when I went to I had referral agreements with and have still with one of them. And then the other thing was, I just started reaching out to these companies that I was freelance writing for, and saying, like, you know, what are the challenges you have around managing all these freelancers? Because what would happen is I would do an article and they were like, This is awesome. We barely had to edit it. And I was like, that makes me feel really good. Like, I know, it's like, okay, I'm good at something. That's awesome. And then they would say, like, you know, could you do more pieces? And I'm like, Well, realistically, no, I can't do more. But maybe I started kind of pitching them on, maybe I could hire some other people do this and see what how that goes. And like, not many of them carried over to be clients for us at draft, maybe one or two. But probably all of them introduced me to people later, who then did. So what was interesting there is that, like, they knew I was trustworthy. This again, goes back to that network thing. They knew I was trustworthy, and could do this work, and was doing it well for other people. So even though they hadn't directly worked with my agency, they were willing to like say, Yeah, Carl is good. And this is something that you could reach out to.

Tim Bourguignon 33:14
So yeah, that's very interesting. Have you been hired to do more really deep down technical documentations. And really, not just this, this marketing level marketing stuff, but going deep? So

Karl Hughes 33:26
early on, we tried all sorts of stuff, or I tried, essentially, because I didn't know what where we would land as far as like, what kind of services we would offer, how limited they would be. So I did try some of that early on. What I realized was that the thing that I wanted to do with this business in any business is make it very repeatable and not dependent on me entirely. Now, it is still, but like we're working, you know, I'm slowly working my way out of more and more. So it's getting closer to where I could take a couple of weeks off if I wanted, and it would still run. That's like the goal, right? It's like, as a business owner, it's like, it's not easy yet. Yeah, I'm not quite there yet. Now. The big thing is like right now, if I took a couple weeks off, all new business would stop because nobody else takes sales calls. Nobody else closes clients. So working on that, but But yeah, so like, and that's not actually actually wouldn't be the end of the world. I think for the most part, our team could handle most of the ongoing work with existing clients, which is awesome. But you know, it's a lot of work to get to where you have people who can also grow the business, not just run it, and that that's what I'm learning now. So yeah, it's,

Tim Bourguignon 34:27
it is going deeper and deeper, going deeper. And that was all on you at the beginning.

Karl Hughes 34:31
Okay, so the way I've approached this is initially I started trying to offer whatever people would pay me for, I'd write for engineering teams that wanted to like, show how great they were. So I'd like kind of go straight for their engineers, like pair with them on articles. Basically, I would do this kind of like deep dives and like basically first round tech docs for a company. And then I would do like these sort of high level articles and tutorials and integrations and stuff like that. And what happened was I realized some kinds of this some of this kind of content was it'd be easy to write off or have other engineers write, some of it was going to be super hard to hire people to write and to execute at the level I was doing. So what I started to do is eliminate the things that were going to be really hard for other people to do and concentrate on the things that would be easy for me to pass to someone else, because I knew that was the only way this was going to grow beyond just be freelancing. So in doing that, I kind of gravitated towards the marketing focused articles. Now, their educational marketing, like I think marketing gets a there is a dirty word and engineering circles, but I don't think it has to be. And I think that if you are writing really great content, it can just be helpful content that just keeps you in front of engineers. So good example, this, again, I'll bring them up, because they're big enough that you've heard of them, like digital ocean does a great job with this, they have like three or 4000 technical articles that are essentially written for marketing purposes. But you would not necessarily know that because they are actually just really helpful pieces of technical content that show engineers how to solve how to set up a Linux server that runs or whatever. And of course, like they're gonna mention, DigitalOcean is a way that you could do that. But like it, even if you didn't use them, it would be helpful. And so by doing this over the years, I think they've been doing it for at least five or six years, probably longer, they've now built up this organic traffic source of engineers looking for problems and solutions. And they're always going to be in the first page for certain ones. And that brings them in tons and tons of business. And they don't have to, like go hard sell and send cold emails and do like, you know, scammy pop ups and stuff. Like they're just giving good content. That's kind of what we gravitate towards. And the sort of thing that we're most useful for with teams that want to reach developers in a very authentic way.

Tim Bourguignon 36:38
Is that sound the best bit of sweet articles that you find when you have something really interesting? And right at the end, the last paragraph smells like like a tool or something. Who wrote this again? And now you take the sword and say, oh, okay, yeah, that's obvious. But the rest was very interesting to me.

Karl Hughes 36:57
I mean, at the end of the day, like, what happens is these companies are funding, they're giving money to software engineers to write this stuff. They're funding engineers to learn and share their knowledge. So for us to like we do now we only do accredited writing. And so what that means is all the 120 writers that work with us, their day job is being an engineer, or freelancer, consultant. And at nights and weekends, they're getting to write this content, get their name out there. And so whenever they apply for that next job, whenever that is, they've got like tons of source material, they can show they actually know things. It's like one thing when you tell an employer, oh, yeah, I know how to use React, but it can't show you any code. So you're gonna have to do a code test on me. So totally different thing. If you say, Yeah, I know how to use React. Here's five articles, I wrote on these advanced react topics for either draft or your personal blog, or whatever. And I think that's been huge. I mean, I actually always put this on my resume, like, instead of just saying, I know how to do something, I write a whole blog post about that topic. And then I link to it in my resume. And now everybody's PDF resume. So you can just do like rich links and stuff. And that's always gotten a lot of comments from people. Again, I haven't done many cold, like, you know, pitches for jobs. But like, even the ones that are warm, they want to see a resume just to check that box. And they're always like, Oh, I love that, you know, he had all this reading material that could like dig in and like, see, does Karl actually know his stuff? And can he communicate about it. And so anyway, that's kind of what we try to, like, you know, we're business, we have to make money and all that. But like, at the same time, like, we're also getting to help engineers advance their careers. So I love when there's like a bit of a positive, you know, going, it always makes me feel a little better about anything, where it's like, you know, I don't know running a business, it's like, it can be very cold at times, it's like you do have to look at the numbers you does have to make sense. It like financially has to work. But at the same time, like we're giving a lot of good opportunities to people. And that makes me feel really

Tim Bourguignon 38:38
good. Before we come to the end of the interview. Do you still code?

Karl Hughes 38:40
Do you still have time rarely, just for fun, usually, like so actually, we we have a very small sort of web application for draft dot dev writers to use to accept assignments. And and it's a very small kind of low code thing. But I do still do some work on that for fun. It's a nice, nice night and weekends thing. Yeah, I don't know, Tim, if I'm going to go back to being a full time coder. Again, I think about it. And I'm like, I could but also like, we'll see. I don't know if this may be, you know, I think I want my career to keep turning like I'm okay with these twists and turns every few years. And so I hope it keeps twisting and turning. I hope, you know, in five more years, I'm like doing something completely different. And we can talk about that again.

Tim Bourguignon 39:23
I don't want to call it but I will I think that ship has sailed. You're going somewhere else? Yeah. I mean, when you put your fingers into low code that's already a sign you are more interested into doing something creating something and not necessarily code. And what you're doing is more of that.

Karl Hughes 39:41
Yeah. Well, the other thing that I didn't maybe I didn't appreciate till I actually got started with this is that once a business gets to a certain size, like where we're at where I have a full team doing a lot of the day to day as the kind of leader there my role shifts completely like I'm not trying I'm not worrying about every assignment that goes through our system. Instead I'm pulling back and I'm saying, Okay, how many editors do we need? How many writers do we need? Who needs the resources to get there? Like, how much money do we need to give to each of these teams to make sure they can do their jobs? Well, and it's like, it's kind of fun in a similar way to engineering where you're kind of zooming out of like it, it reminds me actually of playing like SimCity, or something, or one of those things like resource allocation games, where you're like, constantly tweaking knobs to figure out like, Okay, what will keep my city from burning down and like, but also make sure we have money in the bank? Like, that's literally what it feels like. Now, it's a little more like real, because at the end of the day, like, if we do it, if I do it wrong, like, Yeah, I'm in big trouble. You know, like, I'm up for a lot of issues there. declaring bankruptcy is not a fun or easy thing to do. But it's still like, you have to kind of have a little fun with it. And you do have to think like, Okay, this is mine to experiment with a bit like to be, you know, take cautious risks or calculate risks. And that part is kind of fun. That reminds me of that part of engineering where you're like designing a system, and you're thinking, what are the trade offs? What are the pros and cons, these different approaches?

Tim Bourguignon 40:59
Absolutely. And I have this various pictures of the very first SimCity. In my mind, we had this Godzilla coming out of the water, and he couldn't be nowadays a giant Coronavirus, rolling.

Karl Hughes 41:10
Exactly. That's, it's totally true. Because you don't know what's going to you can tweak all the knobs you want. But if disasters are turned on, anything can happen. And like you're you're basically like trying to and I'm doing this all the time with the team like saying like, you know, yeah, we want to, we want to make sure everybody like gets paid as much as possible. But if we don't reserve some cash in the bank for when Godzilla comes, like, we're all gonna lose our jobs. We don't want that either. So there's like this trade off. We're all like making in our minds about like, you know, you maximize for profits today? Or do you hold on to stuff to make sure we can run for a year without having new clients or something like that? When disaster strikes? Yeah, there's no right answers. It's really hard. But it's also the part that you have to just embrace and get good at, if you're going to run like a business more than just you freelancing.

Tim Bourguignon 41:59
Did you find some other ways you had to make some extra cash flows and not just have this ordering or route business, but have something else that might be a bit less time relevant, and then going up and down with it with the mood?

Karl Hughes 42:11
Yeah, that's a good question, there's probably ways to do that I'll kind of be to be perfectly honest, part of the reason that I went with draft as a business model was that I did not have enough money in the bank where I could sit for a year, make no money and building like a SaaS product where people would subscribe for a year and, you know, like, just make money, just running the software. Like that sounds great in theory, but the years that it usually takes to build up to a level where you can make a living are very hard to fund on your own unless you're independently wealthy, or you've sold a business maybe, or you have a spouse who just does really well, and you can live off their means. And I don't have quite at that level, yet my career. So the truth is, like I had six months of like, if I made nothing for six months, I'd be fine. And that was like it. And so it's like, I needed to make something pretty soon. And it needed to be getting closer to my you know, I still don't pull down what I did as a CTO to start up maybe, but like, it needs to be closer to that need to be something that like he's getting to where I can help pay some of the bills and all that. So anyway, that was a big constraint. And that was part of the reason that we went with or that I went with draft as it is where we are the service business, it's very people dependent. You know, the nice thing is clients pay us upfront, and then we can pay writers after they do the work. So there's a bit of a like, cash flow system there that makes it doable, like where we can self fund it. But at the same time, you know, there's because we don't have external funding, there's limits to how quickly we can hire full time people. And that sometimes causes like, constraints on how quickly we can grow. That's just a reality of like, being in the situation. So you just you're again, the lovers, you're tweaking them, you're making changes, you're saying, What do I want to do? There's no right answers, and nobody can tell you what to do fun, but also really scary and challenging at times.

Tim Bourguignon 43:51
I believe it fully. So let's go to a word of advice. I have been tweaking this in my mind, turning the knobs and saying how can I formulate that? Let's imagine a developer writing as fun writing is something I could do. You mentioned doing that in the evening and sometimes on weekends and, and maybe make a couple bucks here and there. What what will be your playbook to say, Okay, I need to ramp up all the way to, I'm going to be able to make money at some point, what will be the major milestones?

Karl Hughes 44:16
Yeah, so for me the milestones were initially just getting like a base of like, I don't know, five or six, like places you could pitch article ideas to, and they would consistently like you figured out what they wanted and could say yes to, there's actually a great list, I'll send it over in the for a link later. It's called Community writing programs, and actually help maintain it now. Because I built my own list and the guy who's building this list, he also had a similar ones, we merged them together, and now we're working on it together. But basically, it's a list of companies that pay software engineers to write content, like we do with draft I mean, it's it's like the same like we're on that list too. But like a lot of our clients have or and people we don't work with have their own community writing programs. So this is a great place to start. Aren't you can kind of apply to those programs, get your feet wet writing some for pay. If you don't, if you're not the point where you can charge for your work, maybe don't have any samples that are already out there, start writing on medium or dev to or start your own blog, whatever you prefer, just start getting some tutorials, basic stuff out there, then the next level like is, well, for me, it was like starting to subcontract and actually move beyond these community programs and into like, direct relationships with clients. So I started finding companies that didn't have a community writing program that didn't have the bandwidth to like, edit this stuff in house that needed that sort of that level of help. And I started talking with them about like, Could I do that, could I just find writers for you and edit them, make sure they're up to speed and then pass it over your way. And in order to do that, I had to raise the rates a bit. But I also was raising like the level of service quite a bit too. And also, as we started, you know, as I started hiring other writers, it became more scalable, a company could instead of like, because I have limited time. So like, if I'm writing all the articles, I can only do so many a month, maybe it's seven to eight a month or something. Whereas if I'm hiring five or six writers, we now have upped our capacity to 10 to 20 a month maybe. And that's kind of what we've done is just slowly over time up capacity that makes us more valuable to companies that want to scale up their content more. And now we're doing anywhere from like, four articles a month with smaller clients up to I think 30 a month with some bigger ones or 20 a month, some bigger ones. Yeah. So it's, I mean, like the, the volume we can now do is makes us really rare and valuable, because not many companies have that level of capacity for software engineer writers. So that took a long time to build to and like a lot of little steps happen in between and mistakes and false starts and everything. But that was kind of the basic progression.

Tim Bourguignon 46:41
Awesome. Thank you very much for sharing all this. Thanks, Tim. So, Carl, where are we at the best place to find you online started discussion, maybe find draft, but then I suppose non draft?

Karl Hughes 46:54
Yeah, draft is easy to remember, I love the domain name. I think that one's getting not getting as much use as it could because it's nice and short. And it also speaks right to developers. It just I like it. So draft devs are the company. And then if you want to connect with me, personally, I'm happy to have you know, love to chat on Twitter is usually the medium I go for. So at Carlisle Hughes. And then it's Carl with a K. So we'll put the link, Eric. Sure. And then you can also email me Carl at draft dot Dev. And yeah, if you ever want to write obviously, we're always taking applications and most of our writers have some experience before they come to us. But so if you've written a few pieces in the past, you want to try working with us. That'd be awesome. We work you pair you up with a tech reviewer and editor. So you're gonna get a lot of feedback on your work, which is helpful for people who are, you know, newer to writing but maybe experienced in development. And we've got, you know, anywhere from like 30 to 100 topics coming each week for writers to pick from. So there's a ton of like, yeah, a ton of options of things you can write. So we'd love to have people apply and that's draft dot dev slash write if you want to go there.

Tim Bourguignon 47:59
Duly noted, and we'll put it in the show notes. Great Call. Thank you very much.

Karl Hughes 48:04
Thanks, Tim. Good catching up.

Tim Bourguignon 48:06
Here wasn't the end. This has been another episode of Devil's journey with each other next week. Bye. Thanks a lot for tuning in. I hope you have enjoyed this week's episode. If you liked the show, please share rate and review. It helps more listeners discover those stories. You can find the links to all the platforms to show appears on our website, Dev journey dot info, slash subscribe. Creating the show every week takes a lot of time, energy, and of course money. Would you please help me continue bringing out those inspiring stories every week by pledging a small monthly donation, you'll find our patreon link at Dev journey dot info slash donate. And finally don't hesitate to reach out and tell me how this week story is shaping your future. You can find me on Twitter at @timothep ti m o t h e p or per email info at Dev journey dot info. Talk to you soon.