How I Grew My Newsletter Engineering Leadership to 165k Subscribers in 3 Years
In this 30‑minute retrospective, Gregor Ojstersek, founder of the Engineering Leadership Newsletter, walks through the three‑year journey of building a Substack‑based newsletter from a side‑project to a community of 165,000 subscribers and 1,504 paid members. He shares concrete metrics (208 articles, 312 K words, 28 guides/templates, 10.6 M views, readers in 195 countries) and outlines the evolution of his content strategy, platform choices, and product offerings. Starting as a senior engineer, he was motivated to fill a gap in resources for new engineering managers, initially publishing a React/Gatsby blog before fully committing to Substack. He describes early struggles with low traction and self‑doubt, the pivotal shift to frequent LinkedIn posting and community collaboration, and the subsequent growth phases (0‑6 months, 6‑12 months, 12‑18 months, 18‑24 months, and the final year). Key milestones include launching a paid tier, a senior‑engineer‑to‑lead course, increasing article length to 2,000+ words, and moving to a twice‑weekly cadence. Throughout, he emphasizes consistency, quality, collaboration, and the challenge engineers face in selling their expertise. He concludes with a forward‑looking goal: to make the newsletter the go‑to resource for engineers and engineering leaders, continuously improving content usefulness.
Chapters
Starting the newsletter 3 years ago has been one of the best decisions I have made. Over this time, I have discovered a passion for writing, and the only regret I have is that I didn't start writing earlier. If you don't know me yet, my name is Gregor Ojstersek. I am the founder of Engineering Leadership Newsletter, and in this video, I'll be sharing my 3-year journey writing it. All right, let's first start a little bit about statistics over the past 3 years of writing the newsletter. So I, I wrote over 208 articles over the course of 3 years. So the first 2 years were at least 1 article per week, and the last year it was 2 articles per week. I've been also able to create 28 guides, templates, and infographics. These are all templates, these are all helpful for engineers and also engineering leaders to be able to do great work on a day-to-day basis. These are also all of the, all of the things that I'm using on a daily basis as well. Interestingly, there has been more than 312K words written, so that, that is kind of like equivalent to 5 engineering books with the length of 200 and 250 pages. We've been able to go to 165K subscribers, 1,504 paid subscribers. We also have readers from 195 countries, which is really amazing. And there has been total 10.6 million views, which is really, really amazing. Some of the most important, uh, medias has been Substack, of course LinkedIn, and then also Reddit, obviously also X as well, and then Google as well. Now let's talk about a little bit why I started with writing online. So this is an interesting story, and you know, when I— in my career, I grew, started as a software engineer, then became a senior software engineer, then grew to become a team lead, engineering manager, head of engineering, VP engineering, and then CTO. In the middle of like being from head of engineering, VP of engineering I was thinking like, hey, I'll eventually get to the CTO role eventually, right? And what is, what is going to be the next, next step for me? And I was thinking, okay, CTO is the last step in the engineering organizations, right? What's, what's going to be the next for me? But then I was thinking like, okay, maybe, you know, I like to help others, I like to help people inside of the team, inside of my organization. Inside of the company. I mean, I like to level them up, I like to make everyone around me better. I was thinking like, why should not also like try to help people outside of the company as well? And that's when I started to post actively on LinkedIn. I started first with 2 times a week and then also sending out 1 newsletter every week as well. But yeah, I didn't have an idea that this, this is going to become what it is today. And Yeah, I'm really grateful that it, it has become what it has become today. Now let's talk about a little bit how I picked the topic. Um, yeah, when I grew from senior software engineer and then to team lead and later engineering manager, I made a lot of mistakes, and there weren't like a lot of resources available, particularly just for people that I have just started with engineering management and I was struggling. I made a lot of mistakes. You know, I learned a lot from them and I wanted to share those resources that, you know, me personally would find it really extremely helpful when I was in that position. And that's how it started. I wanted to help as many people as possible to become great engineering leaders, help them to make that successful transition, and then also be able to thrive in the roles as well. All right, let's talk a little bit about how I started with the newsletter. So, uh, you know, maybe probably a lot of you guys don't know, but first, basically the idea of having a newsletter was more kind of like a secondary. I was first having a blog. It was built with React and Gatsby. And, um, yeah, funnily enough, I was basically more doing development than actually writing. And, um, yeah, I was trying to perfect my platform, but instead I should have been perfecting my writing instead. I was having a newsletter on Substack as well, but the reason why I had it was because I wanted to have the functionality of sending emails and that only. I had this, this basically blog to be on my primary domain and then just use the newsletter to send also the newsletter. What I did was I added the full blog post here and then do like a quick, quick preview of what this blog post is going to be, and then add the link to the full article. But that, that eventually this, this has changed its courses, and I decided to go fully on just with the newsletter. This is probably around 7, 8 months, maybe 9 months, 10 months when I started. And yeah, that was one of the best decisions I have made. So yeah, this is how I started, and it was really amazing decision to have my newsletter on Substack. And yeah, I couldn't recommend that more. All right, let's first talk a little bit about, you know, when I first started writing online, the feeling is not good enough is very real. Yeah, this is unfortunately the case, and I needed quite a long time in order to become semi-comfortable with writing online, you know. Adding comments to LinkedIn posts, writing LinkedIn posts. But still, you know, to this day, I still feel like a lot of times like, hey, this is not good enough, this could be better, you know, what is everyone going to think about me posting this, and so on. But the thing is, it's a lot of it is in our heads. And the more, the more you post, easier it gets, but it will never get, you know, completely out of our heads. That's my feeling, because that's, that's exactly how it is with me, right? I still have regularly feelings— 3 years of writing online and I still have regularly feelings like it's not good enough, you know, this is not something that is up to my standard, I'm not feeling comfortable publishing this out there, maybe I'm not feeling too as an expert in this particular topic and so on. But, you know, I still publish and so on and nothing bad has really happened over the course of 3 years which has been really, really amazing. Only great things. So yeah, let's go to the next thing, which is let's first talk about my progression over first 6 months on blog and also newsletter. So the thing is, you know, I started posting on LinkedIn and also 2 times a week on LinkedIn and once a week on the newsletter. And yeah, there wasn't a lot of traction in the first 6 months, but the reason for that was that I just posted and then I sent out a newsletter and posted a LinkedIn post, and then I just closed everything down until I send out the next, our next article or the next LinkedIn post. I didn't really kind of like put myself in the community. I didn't try to get to know other people who are trying to do similar stuff than I am. I was trying to be kind of like a lone wolf doing my own thing, but yeah, it doesn't work really well like that. I think in anything that we are doing, collaborating and growing together with others is going to be so much better and so much better way to progress than, you know, you just trying to learn everything yourself, you're trying to progress, you're trying to grow yourself, and so on. And yeah, I needed a lot of time so that, you know, riding online became a bit more comfortable to me. And yeah, I always had doubts, you know, but I kept going. And because, you know, it was also a bit of a challenge for me because it was a new thing, and I was trying to see what is needed in order to get better at this. So yeah, I kept going. I had the knowledge, I had like a lot of knowledge from my career over about 9, 9+ years, 10 years of my experience in the engineering industry and also had the motivation to share knowledge. So I kept doing that. But yeah, over this first 6 months there wasn't a lot of traction. I learned a lot over this, this time. And yeah, now let's, let's go to, to where there was a sign that maybe this potentially might be something that, that is going to be, uh, you know, worth pursuing forward. So yeah, let's talk about 6 to 12 months. Uh, I grew from 200 to 15,000 subscribers, and I decided after 6 months that I'm going to start posting on LinkedIn 3 to 4 times a week. And also soon after, about, I think it was maybe 2 months after, I started to do daily LinkedIn posts as well. And that's where I put myself more in the community. I started to connect with other people that were on the similar path than I am. I was also very lucky at that time because a lot of people were starting their newsletters at that time. There was kind of like a really big amount of people starting their engineering newsletters at this time. And what really worked well is that I met people who were also in the similar path than I am. Helped each other, we did collaborations, we supported each other, we were all learning together to get better and so on. And yeah, as I mentioned before, growing and helping others and working together, that is going to be so much better than you trying to be a lone wolf and trying to learn everything on your own. So this has been the progression for 6 to 12 months and Yeah, I remember April, I think it was, yeah, April 2023, uh, I grew from 200 to 1,000 in one month. This was 800, uh, and this was amazing. This, this was really, really awesome. And yeah, this was kind of like the first, first signs that, hey, yeah, maybe, maybe that I'm onto something here. And, um, yeah, let's, let's, let's keep going. Okay, so let's go, let's talk about from 12 to 18 months. Yeah, this was a time where I saw amazing growth at that time. As I mentioned before, a lot of new people were starting their engineering newsletters at that time. And, you know, at this time even more, even more people started and so on. I think I remember at this time, like, LinkedIn feed was actually filled with either people posting about their newsletters, how they started the newsletter, sharing the articles and so on. So yeah, this was a time where I became also a lot more, how do I say, I increased the quality as well of the articles. I also added more illustrations and added my signature personal branding to it as well. And I also started the course Senior Engineer to Lead: Grow and Thrive in the Role. That has shown to be a really, really great decision. So yeah, I always have this, this time a good, good reminder. Of myself. And yeah, that's where I really knew. And then also when I had the first successful course, this, this was really amazing time that, that told me that, hey, I'm on to something here and I want to keep, keep doing this. Okay, listen, so let's talk about 18 to 24 months. I went from 50,000 to 77,000 subscribers. I really started to, to get a hang of the process of my writing style. And I really built consistency over time. So I was writing for 2 years every day, basically every day, and also every week. I didn't miss, I didn't miss an article for over 2 years. And still, even to this, to this day, I haven't missed out an article on a weekly basis. And I built that self-confidence over this time that, yeah, I can be consistent, I can consistently write articles. And I really enjoy doing this. This is what I found out after 18 to 24 months, that I really like doing researching, I like doing, I like writing, and I also like to learn new things and also share what I'm learning as well. So I like to get better as an engineering leader and then also help as many people as possible along the way as well. So over these 2 years, I built consistency, I built the cadence of regular sending out a newsletter every week. And then also I grew my paid subscribers to about 550 over, over that time. Now let's talk about, uh, the last, the last one year of writing the, the Engineering Leadership newsletter. So over this time, at the 2-year mark, so that was the October 2024, I decided that I'm going to start sending 2 newsletter articles per week, not only one. So that was one paid article and one free. And I remember this, you know, feeling very nervous about it. And I know I wanted to present myself as being confident in it and that, you know, everything is going to be great and so on. But I know feeling very nervous inside about that paid subscription, that paid newsletter, additional paid newsletter article every week. Which got me thinking like, hey, I don't want to feel like I'm a salesperson. I'm trying to be selling something to others. I think that's something that is deeply rooted inside us as engineers and engineering leaders. It's hard, it's hard for us to sell, and it's hard for us to charge for our work. But what I found out is that nothing really bad has happened, only amazingly good things. So I'm really happy that I went through it and I started with the paid newsletter article per week. And yeah, this has been— then I saw the biggest growth at this time in my paid subscribers and also in my overall subscribers as well. And that's also the time where I didn't pursue an additional full-time role. So I've been now working— I don't work full-time roles anymore for a full year. And that has been also very, very interesting for me, especially because, you know, you find yourself, you can do so much different stuff in terms of, you know, when you're— this opportunity, this particular thing, you know, that sounds interesting. This particular thing may be a good thing for me to pursue. And you need to really prioritize what is going to be the best, you know, for you and also what kind of vision you want to have for yourself and also for your 1 year, 2 year, 3 years and so on. So, um, yeah, that's when I decided that, hey, I want to focus on a lot more on, on two core things, which is being better as an engineering leader. How can I be the best engineering leader as possible? And then also, how can I help the most people as I can? And in this time, I've been able to grow paid subscribers to 1,504. And I also focused a lot more on quality. I've increased the length of articles to more than 2,000 words per article at the moment, and also focusing a lot more on sharing experience, not just theory. And yeah, also doing a lot of collaborations with other professionals and also sharing my insights on various different topics. I think the combination of those two is working, working pretty well. And I'm also constantly talking with many engineers and also engineering leaders and I did two articles which are kind of like a product of that, which I got and which I gathered many different insights from different professionals, and I shared all of them in, in two of those articles. So yeah, this time has been a lot more focusing on, on overall quality and making sure that I continuously improve articles, and I continuously try to look for more useful articles as much as possible. And that is going to be my goal for the future as well, is how can I, how can I make this newsletter to be as useful, to be the most useful as possible, to be the go-to resource for both engineers and also engineering leaders to become, you know, as great engineering leaders as possible. That is going to be my goal moving forward. So yeah, I hope this was interesting for you. Yeah, I'm really excited to see where this is going to, to go in in the future. As I mentioned in the beginning, it's been really amazing 3 years of writing this newsletter, and I, you know, the only regret I have is that I didn't start with it earlier. That is the only thing. So yeah, I hope this was interesting and potentially also helpful. Yeah, that's it. That's it for today. Thank you for watching, and I'll see you on the next one.
