đź‘‹ I'm Owen, a New Zealander living in Amsterdam and working as a self-employed writer and creator of digital things! I started out my career as an infrastructure engineer but moved sideways into writing a few years ago.
I went to university and thought that working on servers would be fun, and while I enjoyed a few years working in the budding cloud industry, tinkering with DevOps and helping companies scale beyond their own data centers, I got tired of putting out other people's fires.
During that time I'd always experimented with writing in some form and openly wondered if I'd ever be able to do it full-time. Thanks to being weirdly active on Twitter, I wound up working full-time for The Next Web as an Editor, with my niche in all those developer-focused things that nobody in the industry could really grasp — because they'd never done it.
That was the job of my dreams at the time — I never figured I'd get paid to write full-time! But, it turned out that working for clicks and really driving bulk views is the name of the digital media game and I got really burned out on that. I thought there might be a better way to do it, and ask people for money for my words, since there was some sort of value there.
Fast-forward to now, and I work as a freelance writer, either for clients or for my startup, Charged. We have a blog, weekly newsletter (free), and a weekday briefing (paid), which tries to make technology friendlier for people who want to keep up with the macro changes in the industry, without the advertising or news churn you see on the big sites.
It's been about a year since we started offering paid subscriptions and today we have 350 people onboard for $2,300/mo in recurring revenue. I never thought I'd be able to ask for money directly from readers, but it works!
I worked in the technology media, but I ended up really coming to hate all of its tropes and the sheer amount of noise it generates. If you want to keep up with the industry, you basically need to glue yourself to Twitter all day, check RSS feeds devotedly, or sit there refreshing the front-page of Techcrunch.
Even if you do, you probably won't understand trends or what the hell anything means. Everything is written as quickly as possible because, these days, reporters don't really get the luxury of sitting around and thinking about things or trying to tie together what's going on over long story arcs.
It's exhausting just to think about all of that and I wanted to try and push for a slower alternative. My weekly newsletter had found decent traction, so I floated the idea of a paid newsletter that would update readers much more often, four times a week. That sounded like a scary, but do-able amount of content, and a fun way to help people feel informed each day.
I was surprised by the response! I had expected the majority of people to be uninterested, but instead, 60-70% of people said they'd pay for a service like that — even if it were explicitly just to help keep up, without having advertising crammed down their throats. That settled it and I decided to give it a pilot run.
The problem as always with these things is I actually had a job at that moment: head of digital at VanMoof, a smart-bike brand here in Amsterdam, so it would have to be done outside of work hours. That meant it took much longer to get a prototype out the door, even if it eventually ended up launching somewhat accidentally (more on that later).
Blood, sweat, and tears. One thing I discovered really early on is that nobody was thinking about paid communities or content the way I do: words alone just aren't enough. You need to add value in some other way, be it through a Discord community where you can all hang out, or some other additional benefit that further enhances the conversation.
I looked around at the time, and there was really nothing for this. Newsletters are woefully underserved in general, but what struck me was that there was no coherent way to both charge money for it and get members into a community platform. At the time, Patreon was the best bet, but the “support me” angle doesn't really feel like a good fit for this type of product, so I didn't want to use it.
That meant I needed to build something instead. I hadn't really ever built an entire product on my own, so it took a bunch of time to find the right way to go about developing it. Should I do it in a CMS? On top of something that exists? What language should I use?
I decided that I'd do a rough MVP — done is better than perfect — which would build on top of Craft CMS's flexible base, and extend it to manage the payments part of the experience, sending and reading newsletters for subscribers, as well as getting them into the community. No small feat!
My initial feature set was way more ambitious, but after a series of reality checks, I scoped down to those three things:
It took weeks of choosing tools like NodeJS and React, trying them, ending up feeling defeated in a mess of complexity, and starting again before I settled on true simplicity: Craft CMS and PHP. That was it, and I didn't introduce any more complexity into my app until it was built.
Because I was juggling this alongside a job, I taught myself to get up at 5 am to work on this for as much time as I could before going to work. I am not a morning person, but it was the only way to get quiet, focused time to actually ship something, so I did it.
Frankly, I wish I could say it was like magic and I shipped it into the world after a few sprints, but it took months of chipping away at frustratingly tiny pieces of the app to get anything out the door. It wasn't ever really good enough for me, so I kept rewriting parts of it, never really finishing.
Eventually, after about six months of getting up early, chipping away at it, and slowly making progress, I had a prototype that worked well enough to share with friends.
Eager to get started writing and see what people thought, I seeded it with a few friends and ultra-readers of the newsletter. They loved it — signing up and paying — but wanted to share it around as well!
I wish I could say I had a big, grand launch planned, but it came about somewhat accidentally: someone submitted it to Product Hunt prematurely, and I decided to go all-out and just do it, with the PH team allowing it to be held back for a day while I got my marketing in order.
On launch day, the briefing was listed on Product Hunt and I emailed my entire newsletter list — for the first time ever — to tell them that I'd launched something new, which would help support keeping the weekly edition ad-free as well. I got a lot of feedback that I should offer a free trial, but I stuck with my personal feelings that people should pay up-front but could ask for a refund at any time, because I think having skin in the game as a subscriber makes it more compelling.
At the end of that day, we had results that blew my mind: about 100 people had signed up to pay, providing their credit cards and all. I was committed to that daily newsletter now, so it was serious writing, bug-fixing, and responding to emails for days, just trying to keep on top of things.
Since then, I've really grown it organically in a few different ways:
What I've discovered through all of this is that word of mouth was everything, and people wanted to see social validation: who else reads this and is it any good? Is it worth paying for? I asked some subscribers if they'd consider tweeting about it, so I could embed their tweets in the site, to help with this.
In general, my launch was a little bit of a mess, but overall a success. I had expected to make a small amount of money, but Product Hunt provided a bunch of traction and having an existing audience who trusts my writing already provided a base to build upon.
A lot of products launch these days and what I see founders do repeatedly is throw them out there, and then get disappointed by a lack of response. They haven't spent time building up a reputation, or a small audience who loves what they're doing and are enthused about the person behind it all as well, and I think there's a ton of value in finding those folks.
My logic and inspiration for this came from Kevin Kelly's theory that all a great product needs to succeed is 1,000 true fans, the kind of people who adore what you're doing and want to follow along. My goal with Charged (which I haven't reached yet) is to gain 1,000 superfans, and I'm already a decent way there.
With all of this in mind, I've grown the newsletter to about 340 subscribers in about 18 months and am holding strong there. I've had a bit of churn now that the newsletter has existed for a while and revenue dropped slightly as a result, but in general, I've held steady at this level.
The business model is pretty simple: ask readers for money in exchange for a bunch of really well-considered pieces of analysis, four days a week. There are two plans: $9/month and $90/year (to encourage annual subscribers), and both of them include the same feature set.
Right now, on average, I bring home $2,200 a month consistently from the platform, and my costs to deliver that are broken down into:
It's frustrating how difficult it is to comply with European VAT legislation, and my platform had to keep that in mind when I first built it. I actually geo-detect customers and those in the EU have to pay a little more because I lose up to 21% in VAT for those customers.
If I'm honest, however, it's all held together by spit and sticky-tape right now. The payments system was custom-rolled on top of a third-party Craft integration I purchased, but it was really half-assed on their end and I had to go and re-write a bunch of their code just to keep it stable. Teaches me to trust a third-party package. That's really where I am today. The payment tools I bet on that deliver the Stripe integration are junk, and I built on top of a shaky foundation. I've been trying to balance building new features with re-working the entire platform, and eventually decided I'd stop development on the current tools to transition toward an entirely custom backend. Otherwise I'd end up having to fix other people's crappy code forever.
I don't regret cobbling together a solution at all; it's making me a ton of money every month and delivered a valuable MVP. I would encourage almost all entrepreneurs to just use off-the-shelf bits at first to validate their ideas. My problem, however, is having enough time to move away from that platform now that I've launched it and need to keep serving those users. That's really hard and pretty time-consuming.
I've pivoted my focus a little from the newsletter itself into building a platform for people like me to monetize their content and grow communities around that.
I'll still be writing the newsletter, but I want to build the kind of tool I wanted to use (it still doesn't exist) and basically dogfood it into something others can use too. My MVP will go away and move onto this platform, too. I'm calling it Mailcircle, and it's almost ready for public beta testing which I'm excited about, because paid newsletters are a model that clearly works with the right tools, and I'm convinced they still don't exist today.
In terms of the newsletter, my #1 goal is to get it to 1,000 subscribers, which is when I'd simply be able to focus on that alone. That would be about $8,000 MRR, and allow a bit of breathing room for hiring external help. I want to raise voices other than my own when I can, but it's important to pay people for their work.
My roadblocks are pretty obvious to me at the moment:
I've talked to my subscribers and they've suggested useful features alongside the subscription: an event calendar, or easy ways to view a story timeline in its entirety.
I've made mistakes constantly, I think. If I rewound and did it again, I'd probably launch much later than I did, and add a lot more polish before going public. But, it worked to an extent, and I'm not sure it's useful to dwell on that.
I've largely struggled with my choices of technology and how that pigeonholed me into other decisions in the interim. But I also hadn't really considered how the word would spread or how to drive traffic until later, when I realized that the weekly newsletter and regular blog posts are a key part of that. Essentially, content equals traffic and traffic equals users for a product like this. I got so focused on that 1,000-something words I had to write each day for the newsletter that I forgot to post publicly for months, and that really hurt my user base because it meant the funnel was empty.
So, now I'm getting better at this! I've got a content schedule, so I try to post every other week at minimum, I've started sending my weekly newsletter again, and in order to focus on this thing, I've drastically reduced the amount of freelance work I take.
I'm also a little regretful that I didn't start on the technology part of this sooner. I realized I needed something so I built a hacky solution for myself, but what I hadn't really considered at the time was the broader problem: why is it so hard to make money as a creator, in exchange for a newsletter or community? There are a few solutions, but all of them left me wanting. I didn't realize until recently that maybe I should be the one building that.
Now that I've realized that, I'll have a product soon. But, it's so much lost time and, as always, competitors emerged in the meantime.
A couple of things I learned along the way:
Building a product and launching it to the world is anxiety-inducing, and you should have a way to deal with that. I was crippled by anxiety for months about it not being perfect, and stressed about how I could fix that in the limited time I had available. But that meant I was distracted by the wrong things and found it hard to actually ship much at all. Now that I know this, and understand that anxiety is a thing as a maker, I have strategies for dealing with it.
Your users are more forgiving than you think! All of the anxieties that I had were often unfounded, and people were so much more forgiving than I expected. If you're a one-person-startup, and you talk about that to your users, they totally get that you're human and they surprised me with useful advice almost constantly.
Learn to say sorry. I adopted a policy really early on: if anyone had a problem, I'd give them a refund or a free month. If they hated the product, a full refund. This won so much more karma than I expected, and I quickly got in the habit of saying sorry to people who felt disappointed, found a bug, or whatever else. I think so many people just want to feel heard, and these big giant corporations often don't even apologize even though your internet was down for a week, or whatever, that getting an actual "I'm so sorry about that" goes a long way.
If in doubt, charge more. As a one-person startup, you're a scarce resource. Your time is incredibly valuable and lower prices tend to encourage more complaints or demands from your users. I almost constantly got asked why I didn't charge $1/month to get 10,000 subscribers. It probably would have worked, but that's 10,000 people I now have to offer support to as a solo person, and I just can't justify that.
I always admired Ghost CMS's approach to this thinking. They raised their pricing to start at $49 a month. At that price point, anyone who was going to complain about your pricing isn't even going to bother, and their open-source version satisfies that need anyway since they can go host it themselves. But, if you can afford $49, it's a no-brainer to just pay them to solve the problem for you. Less support for them, and better quality service for customers.
This model is interesting because the constant push to raise prices in this space does worry me quite a bit, and I'm aware that pushing higher prices means cutting off access to people who are less fortunate and might actually need access to the thing you're making. I think somewhere in the middle is a better approach, so what I've done is instead offer a 60% discount to students, no questions asked, and 60% off to anyone who identifies as a minority. You don't have to tell me which minority, or even justify it, but you do have to email me and say "I want that discount," which seems to be working. The community has gotten more diverse, and the barrier of actually emailing a human seems to have reduced the people using that just to get a discount code. I'd rather get a few people who are cheating me for a few bucks but have a more diverse set of users.
Want to learn to code? The absolute best resource I've ever, ever read is the free Ruby on Rails book. I don't even write my applications in Rails, but it taught me how to think while most coding platforms or books just tell you about the tools. This book tells you the dumb stuff you have to care about before you can even start, like how to use the terminal and what Git is, so you don't feel completely overwhelmed before writing any code.
Other than that? Just...launch your thing. Stop worrying about it being perfect. Don't bother with that fancy onboarding. Just get it out there into the world and see if people want to use it. If they do, then ask them what they like (or don't) and work your way from there.
Never shipping means never knowing or finding any sort of market. Ship sooner, and you'll know if you're wasting your time. But the caveat to all of this? Build your audience, as I mentioned already. Having no audience makes all of this an uphill battle.
If you want to try the briefing, it's right over here, or you can check out the Charged website here.
You can find me on Twitter at my ultra-short username, @ow, or my personal website right here. I also happen to have a fancy new column on Medium's OneZero, if you want to read my words.
If you made it this far and have questions, let me know in the comments! I'm more than happy to answer them, on any topic.
@ow Great interview - I just became a subscriber! Wishing you the best of luck with both the newsletter and Mailcircle.
Great interview. Great perspective. I really like the creative way you're managing your discount program.
Thank you so much!
Very cool. Have you considered Substack (https://substack.com/) to manage the operations? The price might not be all to different from your current individual pieces added up.
Hey! Yeah I know the Substack folks, they're great! It doesn't really glue together anything beyond the email part unfortunately, but I love that they've lowered the barrier for those who want to monetize newsletters.
Nice interview. You did a great work! Chapeau 🎩 Pivoting away from the daily newsletter sounds like a good idea to me, especially if you want to create a product that on the long term can sustain itself and generate revenue without asking you 24/7 work.
Thanks so much Dave! Yeah I struggle with it because it's really hard to find the time, but it seems to work as well, so I just have to do a bit at a time.
This is a great interview! I especially like the bullet points on "the couple of things learned along the way", especially the lower pricing for whoever asks for it. We need more trust in the world, it's inspiring.
Thanks, Markus! I figure the majority of people won't ask if they can afford it, but those who wanted a cheap pass probably wouldn't have ever been customers otherwise.
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