Bootstrapping a side project into a profitable seven-figure business

I love how these stories always start with “I just wanted to scratch my own itch” and end with “...and now I’m running a company with a payroll bigger than my old day job.” It’s inspiring, but also a little bit intimidating. Makes you wonder how many potential seven-figure ideas are just sitting in people’s “maybe someday” folders. The real lesson here? Ship something, even if it’s ugly. You can’t optimize what doesn’t exist.

For me the lesson is: ship the thing that makes you feel like you are playing Golf doing it (assuming someone who plays Golf enjoys it alot).

The golfer won't regret their day on the course. And if you fail on the passion project it won't feel like a fail.

I have another idea too. It's the win anyway system. Pick something that if you fail you use those skills at work and get ahead. E.g. the side project is also the training for the gap in your career.

To me, a lesson is: If you keep chugging along on your idea then you might get lucky and be the one out of 10,000 for whom this single-entrepreneur-bootstrap project works out, you get to be your own boss, have a big payroll and it ends up as a success story on HN. Without that luck, you are among the other 9,999 where it just died. But without trying, you are guaranteed failure (though with less frustration perhaps).

See to me the "running my own company with a payroll bigger than my old day job" isn't something I'd want - it actually sounds like a total nightmare to me.

The whole point to me is getting to a stage where you can work when and where you want and only if you want to. Having it set up in such a way where its small enough to manage but big enough to self sustain if you wanted to go off on vacation for a few weeks at the drop of a hat.

I don’t really like golf but I’d imagine that if I did, I might stop liking it once I had to do it professionally every day even when I didn’t feel like it.

Well, you are at least guaranteed to not get this kind of success.

Exactly! If you can get some exposure as a « specialist », build a network or just learn a ton of new skills (marketing, accounting, PR, devops) it tends to be a win/win. That’s what I’m currently doing and by no mean would I have better myself as much in any other way.

If you enjoy Charlie’s, you will definitely enjoy Kahneman’s Thinking Fast and Slow, especially the part about being an « expert »: a few talks in empty classrooms in a famous Uni, a radio show nobody knows and voila, you get some cred!

True but if you are building it for yourself then you will still have something useful in the end. Chances are that you also probably enjoyed or took satisfaction in the process of building it. Also, if it is truly a passion project and not just attempt to make money, it’s probably more interesting than most of the stuff shared.

Yeah, this resonates with me. My side project for 6 years was generating very, very little. Enough for a few pints a month.

Fun fact: The project survived a total destruction of the datacenter where it was hosted (remember the ovh incident?) which took it offline for maybe 4 months (no backups at the time). Luckily the server it was on didn't get melted.

Also at some point I started questioning why was I still working on it for so little. My wife convinced me to keep going and to be honest I still enjoyed working on it.

Then on year 7 things started to change, and on year 8 I was able to quit my daily job! I'm on year 10 now. It's not a 7 figure business, but I enjoy every single day. Also the flexibility it gives me is excellent.

Choose not to pursue CS because of that. I like coding a lot and can spend lots of brainpower and time coding things I am interested in. Once you start working as a programmer, coding becomes something else. Therefore I rather take a different career path and can keep enjoying my little projects.

That's an impressive number of years to stick with a product you questioned. Probably 2x longer than Google would have maintained it lol

(who says products by indie devs always have higher long-term support risk?!)

I'm really happy to hear it turned around for you. The 4 months of down time sound terrifying. Can you share more about how you navigated that, how it impacted customers, and what you were able to restore vs what you couldn't, and what processes you changed in the aftermath?

What career path did you pursue instead, and how does that fit into the framework of your life and goals? Do you ever wonder if you could have bounced around enough to find a CS role that might enhance rather than corrupt your passion? Or do the odds of that just seem too low in your experience?

My business is transactional where email is still king for all after sales support. I guess that makes it way easier to handle than a SaaS one.

The biggest impact for the business was not making any sale during this period and my SEO rankings going down. Actually the site disappeared from search. I guess the biggest impact for me - personally - was psychological. All production data was gone and I was seeing it as a sign I should just let it go. I had all the source code, so in theory I could do it, but not sure I would have the motivation to.

Then in the end my thingy was hosted in a section that was salvaged from the fire. I saw it as a sign that actually I SHOULD keep going, lol. I don't remember exactly how long it was off but yeah, 4-6 months. Everything was restored though.

The only thing I did was to implement automatic backups and to a different datacenter. I remember from the incident, one issue for many was their servers were hosted in Strasbourg with backups also hosted there.

I've touched on this in my last comment, but my wife is by far my biggest motivator. It's tough life for us working solo, with our minds playing tricks on us all the time. It always sounds so much easier to go and work for someone else again or to just start a new side project from scratch. Not sure if there's any Alex Hormozi fan here, but one thing he's always repeating is to not give up, not start anything new over and over and just keep pushing that one project.

Ah so with this business model there was minimal impact to existing customers? That's fortunate.

Out of curiosity, what kind of transactional product has a substantial production database that would be daunting to re-build in a 4-6 mo window given you still had the source code during that time?

And I hope you've taken your wife out for some nice dinners (or whatever she likes). Totally agree that having a supportive and encouraging partner can make all the difference in challenging times.

The business is a car rental platform for niche destinations https://bonjourpaco.com/

At the time I was working with maybe 30 providers and it would be doable to rebuild the server and reconfigure all providers, cars, insurance, etc. Content would probably take longer, but also doable. But at the time I took it as a sign to shift to something else.

Glad I didn't and that the project came back from the ashes, literally.

Neat, someday I'd like to see the Azores. I've heard good things.

FYI if you click on a destination name, it's currently throwing a 500 error.