In this instructional video, Gregor Ojstersek, founder of the Engineering Leadership newsletter and former CTO, walks viewers through the complete lifecycle of an engineering-focused newsletter. He begins by explaining why writing is valuable—enhancing personal learning, establishing expertise, and advancing a career. He advises creators to write about topics they already know or are actively learning, and to share both theory and personal challenges. To overcome the common fear of publishing, Gregor recommends simply clicking “publish” early and iterating. He stresses the importance of choosing an existing platform (specifically Substack) over building a custom site, and of setting a realistic publishing cadence to build consistency. Growth strategies include active promotion on LinkedIn, Hacker News, Reddit, Daily.dev, and repurposing content on Medium, dev.to, and Hashnode while using canonical links to avoid duplicate SEO issues. He highlights the power of joining a community of like‑minded writers for collaboration and network effects. For monetization, he outlines three pillars: establishing consistent publishing for at least six months, stopping over‑thinking the paid model, and gradually introducing paid features such as gated archives and exclusive articles. He shares his own metrics (150 k readers) and ends with a call to subscribe to his newsletter.
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Starting a newsletter has been one of the greatest decisions I have made, and the only regret I have is that I didn't start with it earlier. I've learned so many different things and cemented my knowledge on various different topics because of it. And also, the most importantly, I have— I've been able to help many people to grow based on, based on my writings as well. If you don't know me, my, my name is Gregor Ojstersek. I am the founder of Engineering Leadership Newsletter.. And in my career, I grew from engineer all the way to CTO. In this video, we'll go over how to start your engineering newsletter, how to grow it, and then also how to monetize it. Okay, let's start with the first one, which is how to start your engineering newsletter. So let's talk about first, why should you start writing? Yeah. The first very important thing is that if you can write about it, you learn, you know it, and you understand it. So when you're writing, you're also learning as well. And you can also reference the topic any time you need. And at the same time, you can also— you basically showcase yourself as an expert in that particular field that you write about. It has helped me immensely to be able to, you know, also progress in my career and also to be able to get buy-ins from stakeholders and also from my team as well. There are so many benefits to it, and I think it's a no-brainer to start doing it because I only see great things about it and the overall return of investment of your time is, I believe personally, is quite big. Okay, so let's go now to the next one, which is what should you write about? I think this is something that many people are wondering. And yeah, I have two recommendations. And the first one is write about something that you're experienced in and you wish to share your knowledge. For example, one of the, one of the motivations behind starting my newsletter is exactly that. It was basically I made a lot of mistakes growing from engineer to manager. And when I started writing and I thought, I thought about different topics, I knew that I wanted to help as many people to, to make less, less mistakes than I did when I was, when I first became a manager. So yeah, that's something that I wanted to, wanted to help with. And the second thing is, what about things that you are learning right now and For example, I intentionally pick sometimes topics that I want to know more and want to understand better of, because I know if I'll be writing about them, then, you know, I'm forced to learn about these topics, and at the same time I'll be also, you know, understanding them more deeply. And then also at the same time, you know, any kind of challenges you faced and how you overcame them, that's always a great, great read, I believe, because I'm a big fan of just not writing just about theory but also about experience as well. Experience, I think, is one of the most interesting things to read for, for many people. So these are my recommendations. Let's go to the next one. Is, yeah, how to overcome the fear of writing online. And I think this is something that is unavoidable to a certain extent. And for me, it took me a long time in order to become semi-comfortable with with writing online. And, you know, still to this day, it's sometimes I feel like the article that I write is not good enough. And also, you know, maybe a LinkedIn post that I post is I feel like, hey, it's, it's not something that I'm pretty— I'm too confident about. So I don't think that that actually entirely you leave it behind, but you kind of like get better and get a better hang of it over time. So my recommendation here is to, you know, even if you, if you feel that it's not perfect, especially in the beginning, you just need to, need to, need to click the publish button and that's it. And it gets, it gets a lot easier over time, I promise. And you get a lot better with it. So you just need to go and you just need to have that first, first initial post, maybe first couple initial posts. And after that, it's going to get a lot easier. Now let's, let's talk about how to start with, with your engineering newsletter. So the first, the first thing is very important is to try to pick the right platform. You know, if you're an engineer, you probably think about, hey, I should try to build my own platform, I should try to build my own blog or a newsletter. But the thing is, when I started writing online, I built I built my, my blog with React and Gatsby. And what, what turned out to actually be the case is that I was, I was actually doing more development than I did writing. So my recommendation is to pick a platform that already has all the functionalities that you need. And of course, my recommendation is Substack because that's also what my newsletter is on, and I think it's a really great platform, not only because it offers all the functionalities that you need, but it's also a great way to give additional visibility to everyone about your articles and so on. The next thing, you want to pick the cadence that you are comfortable with. My recommendation is either, you know, either start with once, once a week, maybe 2 times a week— sorry, 2 times, 2 times a month, or maybe once a month. The important thing here is that you develop consistency, and after that it's going to get a lot easier. After you develop that initial consistency, then you can also like potentially do a little bit more higher cadence of articles. And yeah, the third thing is, you know, write, write, and and more, more writing, right? It's, you know, you— it's hard to know if you're actually writing something good if you don't share it with everyone. You can become— you can be the best, you can create the best articles, but it's going to be hard for you to know that if you don't share it with everyone. So in order to get better, you need to write more. And you need to publish more. And, you know, based on, based on the feedback, you see what's working and, and whatnot. So the wrong way of thinking is if you believe that it's not good enough and you don't publish. But the right way of thinking is, hey, I'll publish anyway and, and I'll see how it goes. For example, like, my first articles that I wrote are totally different than the articles that I wrote, that I write today. So I'm really happy with how I basically progressed over the, over the time, and I try to continuously learn and get better. Okay, let's go to, to the second, second thing, which is how to grow your newsletter. So yeah, you know, what I like to say is you can write the best articles in the world, but if nobody would know about them, it unfortunately won't be perceived that way. So I highly recommend to not only, you know, create an article and that's it, but you also share it with— on social media. And LinkedIn is really great, great for that. So for example, what I do on every Saturday, I create a preview of what's, what's an upcoming newsletter going to be about. And then on Sunday, I also share the snippet of the newsletter. And then I also add a link to the newsletter as well so everyone can, can read it if they, if they would like to. That is the first thing. The second thing is, yeah, be more active on social media as well. You know, the more, the more active you are, the easier it's going to be for everyone to, to know and get to know about your newsletter. I especially recommend LinkedIn because it has worked really, really well for me. Potentially starting with a cadence of 2 times once a week posting on LinkedIn would be a really great additional, additional thing to your, to writing your articles. Now, let's talk about sharing your articles on other platforms as well. As I mentioned, you know, it's, it's not about only about creating great articles, but also making sure that everyone can, can read them and can also find them. So Hacker News and Reddit are really, really great. And also Daily.dev, it's where you can share the links to your articles. Personally, my, my articles have been featured on, on, on, and on one of these platforms multiple times. And then also you can do some article repurposing. For example, if you, if you, if you write on Substack, you can also post it on Medium, uh, dev.to, Hashnode as well. You can repurpose the full article on this, on this medias as well, but the important thing is that you set the canonical link to, to the original article, which is going to be your newsletter. That is how Google can understand that, hey, the original content is published on that, on that domain, and this is basically, this is basically pointing them to, to that particular source. It's how you can avoid any kind of duplicates across multiple sources. But I recommend only doing this if you're going to keep your articles free. If you're going to, if you're going to make the articles paid, it's not a good practice if you also publish the full, full article available on other medias, because then people can also read, read the full articles there. Okay, so let's talk about the fourth thing, which is really important for growing your newsletter. Is, you know, really, you can get better alone yourself as a newsletter writer. It's important that you also have— you find a group of like-minded people who are on a similar path than you are. And that kind of like a group network effect is really, really huge. And if you can find people that are in similar niche that you write about, and connect with them and learn together, help each other. That's gonna be immensely helpful for, for your newsletter. I always like to say that collaborating is a lot better than competing with, with others. And yeah, that, that's my, that's my recommendation. Now, yeah, also you can see, for example, I did a mistake in the beginning when starting my newsletter. I basically, I just posted an article every week and then I completely didn't do anything else. I just left it to be there and I didn't do any kind of actions to try to promote my articles. And I was able to grow from, from 0 to 200 subscribers in 6 months. But then after, after I started to collaborate a lot more with, with other fellow writers and also be more active on social media, that, that's where the real growth started happening. And yeah, that's my, my advice for everyone listening. Now let's talk about monetization. Yeah, there are 3 things I recommend here, and the first one is obviously develop consistency first, because the list— the thing that you don't want to do is you don't want to start a paid newsletter and then you, you end up after some time stop, stop writing articles. So I recommend like for at least like 6 months to develop the consistency of publishing your articles like every, every, every month, every, every week, whatever the cadence you set out to be. And that's going to help you immensely to be, to build that confidence over time. And then, yeah, the second thing is stop overthinking about the paid option. And I think for many engineers, I think many engineers can relate with this, but I also had this, this problem is that I thought that my articles are not good enough to be paid articles, and I was overthinking for far too long. I think I should start with paid options sooner, but Yeah, looking back, you know, as soon as you get over 2,000, 3,000, I would recommend if you have intentions to make your newsletter a paid newsletter, that would be a great way, that would be a great way to start with it. And now let's talk about how to actually start with, what will be the first step. If you would start with a paid engineering newsletter, my recommendation here is to start limiting your, your full archive of posts just to your paid subscribers. That's something that, for example, Substack can— that's a feature that can automatically be done on Substack. And for example, what you can do is you can limit your archive after 1 month, or every article that, that is older, older, more than 1 month is automatically going to become paid. So that, that would be a good, good start. And after that, you see how things are progressing. You can also add more benefits. You can, you can also then additionally create one more, one more article every week or every month that is just going to be for paid subscribers, and so on. And there's many different approaches that you can take. It's all up to you how you wish to move forward. But those three things are going to help you if you are trying to potentially also monetize your engineering newsletter. I hope this, this video has been helpful to you. And yeah, if you enjoyed it, make sure to also check out my newsletter, Engineering Leadership. I send out 2 articles every week, and there are more than 100,000, 150,000 people already reading it. Thank you for watching, and I'll see you on the next one.
