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> Anyway, if I had my shot again, I'm not saying I'd renounce funding. Bootstrapping for a short period to figure things out is great, but funding also creates opportunities where an immediate business model is not clear. Opportunities exist for different approaches.

Absolutely! There are some problems that can only be tackled with some serious funding. There are people who enjoy the go-go-go attitude of VC-based startups so much. I'm not against VC funding per se. It's just important to recognize that it's not the only path and that there's nothing wrong if that route isn't for you, for any reason. You can be successful in other ways.


Totally agree! Can't tell if I'm the go-go-go person anymore. So much stress...


E andiamo! :)


Ouch, I'm a Firefox user myself, but this one slipped! Thanks!


In general, we try to keep things extremely simple. And then we simplify some more. If you're very strict on this basic rule and apply it at every level, from the start, you can go a long way with a small but stable team.

Regarding k8s: EKS is a very different beast compared to managing your own cluster in terms of complexity. We invested months into understanding a lot, yes, but then the day-to-day operations are not that heavy. At least, that's our opinion after 6 months; we'll see!


ahaha, true. on the other hand, wordpress is more 20 than 15 now :)


`Yet you rely on ${new Date().getFullYear() - 2005}-years-old solutions like Wordpress`


Sorry to hear. Why exactly?


Well, for a start, you guys brag about having great margins, which is not a problem in itself, but as a potential customer, it gives me the impression that the product could be cheaper.

Then it's all self-congratulatory, with overemphasis that I find lacking taste. Just my personal opinion...


Businesses have no issue with their suppliers making reasonable margins as long as the value offered is acceptable or better.

I'd rather know a supplier is healthy than scraping by. I just got an email from one of mine saying that they aren't doing great, so please buy as much as possible before the holidays? I'm now making sure I'm not overly dependent on them for anything, which I'd rather not spend time doing if I didn't need to.


I would say after somebody spends years not tooting their own horn, when a bit finally comes out I wouldn't let it bother me even if it's more exuberant than others who do it all the time.

I understand that most people who do it as a habit are often mostly exaggerating, and that's what doesn't really inspire me.

In Texas there's a common saying, "No brag, just fact."


Some (more niche) industries/products/etc require larger margins to be able to exist. Without scale, they need to sometimes charge more.

It's the classic single gas station in the middle of nowhere argument. Without volume, they can't reasonably survive without charging more per unit - if competition shows up, one of them will inevitably go out of business due to the reduced margins.


As an actual customer, I have the opposite reaction. They are doing well and that gives me peace of mind.


Also a customer here, DatoCMS is fantastic product. We run hundreds of sites on their platform. Their team also works with you on pricing as you scale.


Not in my experience at all. Very solid product but incredibly frustrating trying to negotiate / get a bit of wiggle room in regards to pricing.

My plan auto-renewed for 2026 but it's become a priority to move everything off of Dato to another CMS for 2027.


Totally agree, that's exactly what we did. As a web agency, we tried every CMS out there and struggled with all of them for different reasons (quality, maintenance, pricing, scalability, development speed), so we built our own. The key thing is you need to genuinely identify with the people you're selling to. Without that connection, every doubt (and there will be tons) becomes nearly impossible to overcome.


I'd wager that most agency devs have wanted to do this too. CMS's never work the way you want them to as an dev.

Thankfully, the work you have done (along with your competitors) in making headless CMS's viable not just for devs but also for content maintainers has made CMS work far more enjoyable.

It's awesome that you not only built out the dream most agency devs have, but made a successful business out of it at the same time.


That is a really nice comment, thank you a lot


To be fair, 10 years ago was still a reasonable time to do this (build your own CMS). In the early/mid 2010s the commercial CMS market was dominated by some pretty terrible large enterprise incumbents still stuck in the early 00s.

Would you agree (bias aside, being a CMS provider now) that in 2025 it's probably _less_ advisable to try to build your own bespoke commercial CMS product?

It feels like the CMS market is pretty crowded now, with lots of modern, high-quality open source and commercial products.


> It feels like the CMS market is pretty crowded now, with lots of modern, high-quality open source and commercial products.

I don't know, I feel like it's crowded with options but no options are high-quality and ready to be used commercially. Things like Strapi gets somewhat close, but then fucks up the operational parts by being complex to handle with multiple environments, bad history tracking and much else. So the space of "high quality production-ready open-source CMS" is less crowded than you think, particularly if you aim for a specific niche.


That was one of our early fears. Wanting to continue to remain small, will we be swallowed up by larger competitors, who will devour the entire market? Turns out, it didn't happen. The websites space is really huge, I think there is still an endless number of niches you can attack and optimize for and get a pretty interesting revenue from.


Totally, I think people miss the trees for the forest because VC-fueled startups always have the "all-or-nothing" and "eat the world" attitudes, so people grow up thinking those are the available alternatives. While in reality, getting enough profits to support a team and their "modest" dreams (in comparison) is often more than enough.


I did say both open source and commercial, in the context of "starting a business around a new CMS", so you may be correct about the open source side of the market but that wasn't really what I was asking about.

The commercial/SaaS side specifically is quite crowded now, with lots of good options for businesses of all sizes.


Thank you! It was never an all-in bet for us, so we never struggled too much tbh. It slowly grew inside our web agency as a part-time side-quest, and only when we reached an OK level of revenues that could feed our families it became a full-time job and an actual funded company.


Ah, a spin out, ok, that makes good sense, and that helped you avoid a lot of the dangers that would have killed an entity all-in from day #1. More often than not that kind of pressure leads to sub-optimal decision making and you budded off in a nice and controlled way. Web agencies are pretty good as the basis for this kind of thing, I've seen it happen multiple times now. I think the reason is that you know exactly where the pain points of your customers are and that sets you up for productization. And in lean times you can't fall far because the agency customers will need to be served anyway.


That's a really neat and natural approach to build sustainable businesses, thank you for that and extra thanks for publishing something public others can point to as successful examples of that process being implemented in real life.


Did you keep a blog during the early days? Wouldn’t mind reading it if so.


infortunately not.. too low self-esteem at the time to think that would have been interesting for anyone :)


I think it may well be still worth it to look back and note it down as much as possible and I'm sure that it will be interesting to many people.


Noted, thanks! :)


I know https://tinyteams.xyz/ but it's not specific to bootstrapped companies!


Yeah and a lot of these are small only temporarily. Many of these startups are following the grow-at-all-costs VC philosophy that doesn't optimize for small team size. So I'm trying to find those alternate stories. Much harder to find, so when I see the post like this of OP's, I get excited. Hard to find stories of teams that are small by intent, but looking to scale big.


Something feels suspicious about those top three revenue numbers.


This is literally an anti-list of bootstrapped

Unicorn-level sounds extremely stressful, happy to pass the burden to someone else. I seriously can't imagine a sane lifestyle that requires more money than what we already have.


Not only that, the vast bulk of unicorn wanna-be's end up failing (sometimes failing upwards though) and then it is all for nothing.

Aiming for the middle ground: reasonable growth, good financial strategies based on unit cost profitability and a very tight hand on the purse will get you a solid business that can serve as the jump off point for many other things on top of giving the founders a much better shot at financial independence. This is all a variation on the risk/reward theme.


To be fair, it's rarely all for nothing for what I hear. Secondary stock sales [1] are very common and allow founders to take some big chips off the table. To me, it is more a matter of keeping things simple, manageable, safe and more fun for how I like to work :)

https://www.startuphacks.vc/blog/founders-guide-to-secondary...


Sure, but your personal preferences have an outsized effect on your chances for success because they are very much aligned.

I know plenty of founders that gave it all and then some (including their health, their family relationships and in some cases their lives) and that ended up worse than the shape they were in when they started. So yes, you hear a lot of stories about secondary stock sales and so on but those are the exceptions and very much not the norm. That's just survivorship bias.


Fellow small business owner here. Just as a reminder, discussing any successful (where successful is defined as not failed) business is a lesson in survivorship bias.

Most businesses of all sizes, shapes, and forms fail within 10 years.


> Most businesses of all sizes, shapes, and forms fail within 10 years.

I hear this all the time with variations to the number of years, which makes me suspect it isn’t true.


What part do you suspect isn’t true?


That a majority of businesses fail over a given duration of time. It’s probably true on a long-enough timescale, but the idea that the majority of businesses fail within one year or ten just seems completely dubious. How is a business defined? How is failure defined?


You don’t need to wonder, that information is readily verifiable. Most businesses fail. https://www.bls.gov/bdm/bdmage.htm


Ignoring the available data indicating that it is the case, I'm curious about why this seems dubious to you in the first place?

Starting and maintaining a functioning business is difficult; the default outcome is failure (the end of the business as an operating entity) and you have to work to prevent that from happening every day that you want to remain open.

And I've never seen a claim that the majority of businesses fail in a year. Most anecdotes say a majority fail within 5 years, which seems to be approximately correct based on US data.


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