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.

Thanks. For a while there, it wasn't clear to me which side of the line I was walking.

Something that stuck with me from Poor Charlie’s Almanack is that low expectations are a cornerstone of a happy life. I built this for myself first, so when people actually signed up and paid, it was incredibly motivating. I was thrilled to spend my free time treating those early customers like royalty and building more of what they wanted.

If I had instead come into this with the expectation of quick success, I doubt I would have made it through those early years.

And cheers from one bootstrapper to another. It's not easy, but I can't imagine a more rewarding way to build.

Another lesson here: you built for a specific community who is passionate, money-motivated, and concentrates in specific social spaces (forums, reddit, etc.) where you can promote your business. This isn't always a recipe for success, but it's a damn good starting point. You need to adjust to the sensitivities of the community to avoid overly self-promotional content, but you always have a clear channel to promote your very specific product that meets their needs.

+1 from someone who also bootstrapped a side project into a 7 figure business, and just happens to be absorbing some lessons from Poor Charlie’s Almanac on Audible recently.

ha I listened on Audible too. great audiobook for a walk after dinner. Charlie's advice really holds up. which part have you gotten the most out of so far?

also, congrats!

> 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.

As much as I like to agree with this message ... isn't there a big portion of luck involved here that makes the difference between the two sides of this line? In other words, aren't we seeing huge survivorship bias at play here?

That's what makes the line so hard to walk. Surely skill helps, but more than most like to admit it's the unpredictability of outside forces that makes the line really hard to walk.

> isn't there a big portion of luck involved here that makes the difference between the two sides of this line? In other words, aren't we seeing huge survivorship bias at play here?

Luck and survivorship bias may not be the same thing.

Sure, but when you can’t clearly attribute the survivor’s survival, there’s still no meaningful conclusion to draw. And given how many different ways there are for businesses to succeed or fail, that are never ever repeatable due to the passing of time in the market, then I think attribution is impossible, so having the humility to somewhat attribute luck is admirable.

Persistence and Stubbornness are just different words for the same personality trait. The former is used when looked at a positive light while the latter is used in the negative.

You're persistent if your project succeeded but you're stubborn if you keep at it despite unfavourable outcomes.

So the difference between the two is just luck?

I apply to a thousand job offers, get rejected every time => I'm stubborn.

I apply for job #1001, I get the job => I'm persistent.

I would say that you are persistent if you keep getting rejected but keep improving but using feedback and you would be stubborn if you don't change a thing while keeping being rejected.

There is a fallacy in over application of the survivorship bias concept.

Literal survival for early cultures was often a matter of luck. Agriculture was an innovation that improved the odds. Early cultures that practiced agriculture outperformed those that did not, and were more likely to survive black swan events. All major cultures in existence are now based in agriculture.

Should we assume then that because we only see agrarian cultures that that is not useful information, because of survivorship bias in the resulting sample?

On the contrary, survival itself is the signal that is useful… it’s really a matter of what behavior the signal can be attributed to- was it the agriculture, or was it the human sacrifices? Was it the red ochre face paint? The storing of grain in pots instead of skins?

Failure bias is just as large of a red herring. It’s easy to imagine that it retrospect, we understand why failures happen, and sometimes the reasons are very clear. That’s why there is often more to be learned from failures than from successes. But still, it’s easy to look at the things they did right that successful example B also did, and then conclude those things weren’t critical to success because they sometimes end in failure.

The point is that we shouldn’t judge the value of information based on ideas like “survivor bias” but instead look for more methodical and logical connections between causes and outcomes, and not fall victim to cargo-culting nor casual, hand wavey dismissal of potential lessons.

Survivorship bias mitigation is a matter of determining which survivor signals are instrumental , and those which are coincidental.

Many things are fraught with risk and low probabilities of success. That does not make them primarily a matter of luck.

Aviation is a great example of an environment that is nearly 100 percent risk, where without knowledge and the correct tools the very small chance of not dying would be purely a matter of luck.

Yes.

You were stubborn for applying for jobs beyond you.

Your persistence led you to finding that amazing job.

The way I see it, persistent founders keep looking for evidence and adapt / adjust course based on what they learn. Stubborn ones just keep going, even when there are clear signals that it's time to step back and refocus.

If he wouldn't he wouldn't have make it.

You have to take the risk in your life or you're gonna be stuck where you are.

Was he lucky? Perhaps.

Would he make it if he wouldn't risk it and put in all the work that he need with nothing to show if he would fail?

He would not.

Even carefully thought out comments like the above are only hints and ideas relating to making sense of the world. They don’t talk about building quantitative predictive or causal models to disentangle the many factors driving success, failure, and everything in between.

I recommend The Book of Why by Judea Pearl as a starting point for digging into the lesser-known techniques of assessing causality. The causality work over the last couple of decades is still under-appreciated and not used often enough.

One is unlikely to find anything close to rigor when it comes to business or entrepreneurial books. They can be a starting point for analysis, but their bias to tell an interesting story and sell copies often work at odds with truth seeking.

At the risk of oversimplification, one decent model for acting comes from decision theory. (1) Look at the data probabilistically and act accordingly. (2) If you don’t have enough data, assess the cost/benefit of acquiring more.

But we don’t have the time or the discipline to make all important decisions this way, do we? Probably not. So, (3): if you act on intuition, be honest with yourself about that. Be curious about yourself and your decisions and how you can do better. Focus on areas where improvement is likely to make an outsized impact. (This leads back to #2, except it is about seeking better knowledge and self-awareness instead of just data.)

I try not to exaggerate, but these three principles might be sufficient to subsume all other business advice.

Embrace the uncertainty and move forward anyway.

Thanks for the book recommendation! I’ll look at that.

>> Embrace the uncertainty and move forward anyway.

This. This is the key factor that prevents attempts at success, or leads to failure by a thousand cuts.

There is no gain without risk. Significant gain usually comes through significant risk. Position yourself in life to be sufficiently resilient to take 10:1 bets with 100:1 odds until you can weather the 100:1 bets with 100000:1 odds. Avoid the 1:50 bets that pay at 1:50 odds like the plague… they are a comfortable quagmire of rotting aspirations.

> 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.)

Strange analogy. I'd say stay away from that line and run into the direction of persistence.