Bootstrapping a side project into a profitable seven-figure business

It's so, so , so hard to walk the line between persistence (which leads to glory) and stubbornness (which leads to more time following already wasted time.)

Congratulations for walking this line correctly.

I agree that some sort of market validation is necessary to at least pretend you are on the former not the latter. Those early usage spikes are helpful reminders that there is a business here somewhere.

I'll also make a note that you spent time on marketing from the early days. Writing blog posts, promoting said posts, having a Discord server, committing to answer emails, all of this is marketing and its likely lead to success more than the code.

I notice whenever there was a dip in revenue, marketing (in the form of more blog posts) was the response. I suspect that was intentional, and definitely a better approach than "let me go away and silently code more features."

So there are valuable lessons to others here. Congratulations not just on the current success but also on sharing the path that leads to success. Ultimately you can show the way, but you can't make people learn from it.

Oh, and I like the bootstrapping approach. I did the same, and I'm not sorry. It's longer and harder but also skips an enormous amount of extra work.

Thank you so much Kyle for sharing all this. This is very inspiring. I will put a few more extra hours today in my project thinking about you.

I'd love to have some info about the hiring of Jon, anything you may feel like sharing, while I realize a lot of it is very confidential. For example:

- I am wondering how the working relationship got started since you write that he "spent a year contributing real value", and he was not asking for equity upfront. Did you hire him as contractor initially, did he volunteer his time?

- the structure of the deal with him, and of course the equity part, especially _if/while_ you are not planning to sell the business. Maybe you have some pointers on "possible deal structures" that you looked into without spilling the beans on the actual deal?

I know I am asking a lot, I hope it does not hurt to ask, so realistically I don't expect any answer, but any breadcrumbs would be so valuable/helpful! In any case, thank you so much already.

Great post and congratulations.

Similar approach and story to myself, in that I started a side project for my own use and interest, and then released it to great feedback as a side hustle, went part-time and over the last 2.5 years managed to go full time.

I've yet to reach your $1M ARR though.. but hopefully getting there one day!

Recently wrote up a Year in Review which touches on similar learnings as you've written over the last year:

https://www.magiclasso.co/insights/ad-blocker-year-in-review-2025/

Have also had a keen interest in FIRE over the years and hadn't heard of your product... personally I've just kept my own spreadsheet which runs through scenarios, progress etc.

Congratulations! But I’m disappointed with no mention of profit level in this post or another one linked. My last business I scaled to 500K ARR in less than two years, with $20K in total annual profit including the $0 my cofounder and I paid ourselves for many hours of work. I shut it down a year later and strongly regret the amount of work I put into it.

There’s an ARR metric trap in the founder community where people focus on revenue rather than on reaching a level of take-home income comparable to what they could make at a normal job. The former is a lot easier than the latter (especially in the US for people who can take home $250K fairly easily working in tech) - as the saying goes, you can make infinite revenue by selling dollars for 99 cents.

During the first few years, I was approached by dozens of potential “partners.” Several wanted an outsize equity stake to essentially just make suggestions.

A warning to others starting new ventures: once you get a whiff of traction, and sometimes even before then, the parasites will ooze out of various nooks and crannies, attempting to latch onto a fresh new host.

HN loves to pound on MBAs weaseling their way into startups, but opportunists may come from unexpected quarters.

I experienced a classmate sidling up to offer "translation services" for 2% of outstanding shares. Then there was a startup that proposed a "merger" which would basically allow them to walk away from failure in exchange for equity.