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.
Congrats. A word of warning: I scaled my SaaS site to $1M in AAR in a few years, but then a lot of competition appeared and a decade later it's still at only $1.5M. I have a good time running it and I can live comfortably while feeding my team, but with my initial success I had hoped it would go up further faster. So keep those expectation low, the next million may not come as easily as the first.
> 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.
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.
It's hugely about luck. We can look back on any success story and identify what made it successful (sometimes) but it only has a little predictive power. Success in startupping ultimately comes from either trying a lot of things (amplifying your luck until it approaches 100%) or survivorship bias when you get lucky on your first try and then write about how smart you are.
It helps to have an idea of what might succeed, by studying things that succeeded before and the present business environment, but that increases each attempt's success chance to, like, 2% rather than 0.2%.
(There's nothing wrong with getting lucky, we just probably shouldn't plan around it being the normal case. It has extreme variance by definition.)
> 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.
> 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.)
“Courage is knowing it might hurt and doing it anyway. Stupidity is the same thing.
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.
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.
> 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.
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.
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).
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.
It’s also entirely possible to make something that just gives you a little extra cash, which can be a huge difference. I imagine an extra $2,000 a month of fun, self-made income feels pretty incredible.
"But without trying, you are guaranteed failure"
>> But without trying you are limited to a relatively safe and certain affluent paycheck from your day job.
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.
There are probably tones of ideas that would be viable businesses if executed. One problem though is between "scratching my own itch" and "payroll bigger than my old day job" is working "4-6 hours every night after work, entire weekends, holidays". And even that is no guarantee of getting to a big payroll (another thread is discussing persistence vs stubborn).
Not many people are even in a position to do this (family, health etc), or have the mental and physical energy to do this for years. This is one of the potential benefits of something like UBI. It allows people to pursue these ideas without having to work another 9-5.
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.
This is my plan now, launch a free product and use it to promote myself as a contractor or consultant. Commit to some time spent on maintenance weekly and consider it as part of the marketing time. Maybe I will be able to monetize it in the long term, but in the short term, I need it to escape the bottom of the barrel I am currently at. You don't get to have a good resume when you are tinkering with products on your own... and I realized that especially in this job market, I can only make decent money on my own. It helps that the product is quite technically complex, gives me ideas for blog posts and the idea itself is already validated (as a free product), but the existing implementations are poor. And I absolutely love developing it.
The big lesson for me is know what you are getting into. Look at the OP - he spent every spare hour he had. This is no joke. I have done something similar in the past for a time and I ended up constantly running into conflicts of priorities between that and personal life. I ended up wasting a few years, in both personal life and professional life, although the former hurts much more. This is how I ended up in a scenario where I have nothing to show and nothing to lose. I just hope I can do it all at some 50 hours per week total, where the product is just a part of the day job (promotes the consulting offering) and lower the volume of paid work as I need, if I want to have more time to make a big move with the product.
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!
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.
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.
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:
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.
Congrats on 350k downloads, sounds like you had a good year! You mentioned SEO finally kicking in. Do you attribute that to anything in particular? Any strategic changes you made? Also curious how you incorporate AI tools into your workflow, if at all.
It's an impressive accomplishment. I've always struggled to get through the valley of despair in a new project. I've decided that I can only build and sell things that I regularly use. Otherwise the signal is just too weak, and I eventually get burned out. But if I'm always a user of one, then at least it's validated for me.
Caring is kind of a superpower. And not just in terms of signal, but also the quality of work. I don't think this would have gone anywhere if I hadn't cared deeply about solving the problem in an elegant way.
Earlier in my career, I worked on some things as a corporate engineer that were hard to care about, and there's just no comparison.
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.
> I will put a few more extra hours today in my project thinking about you.
And that's the recipe for failure right there. Your passion side project needs to be fueled by passion, not thinking about somebody else's success that you are trying to replicate.
I find this such a strange comment, to be able to reach such a conclusion so quickly without any idea what my side project is, how much passion I have put into it, and how much still have in me, with no idea how many people I've helped already with it.
Like Kyle writes keep showing up to make it a little better every day. Today again I will show up, but today I'll think of him and it will help me.
What's your passion project? How do _you_ keep the motivation every day? How long has it been?
> Your passion side project needs to be fueled by passion
Maybe he's in that valley of despair right now that the article shows occurs many times. Passion is fleeting and at times you just need a little inspirational jolt to get back into it and regain some of that passion.
Also, to share a personal experience, passion is not sufficient. You need favorable conditions as well (or the ability to create them). For example, the article talks about working nights and weekends. I'm not sure if the author has kids or what the arrangement is in his family, but personally, as much as I wanted to work whole weekends on my passion project, I would feel like a shitty father if I ignored my kids over the weekend for months, so the project gets put on the back burner a lot while I'm biking with my kids outside and having fun.
How do you differentiate between persistence or stuborness. I have been developing a SaaS product since 2020 which currently is at 3K ARR with a very slow growth (20%). It's a B2B and are we are still missing a bunch of features to make us on par with competitors. We did survive a couple of competitors that came and go as we still have our day jobs and running it costs peanuts ($$$).
It often feels I should give up but having had customers who used us for years makes me think we have something that one day will make serious money.
Are your existing customers vocal about what they love or wish you'd add? Do you know how they found you and what made them choose you over competitors? Is there a niche/segment within your larger TAM with a specific pain point you're solving really well? And how big is that segment?
Either way, if your existing customers don't all come from paid channels, and they're loyal, and you've outlasted multiple competitors, that already sounds like a real achievement to me. My progress was slow for years before things started to really pick up, so don't discount signs of traction if there are some meaningful ones.
Very vocal, we do have a very solid TODO list for another 12 months. They are also quite loyal and number of them are with us for 3+ years and they use software daily (its just a very small customer list overall). I do wonder sometimes why they stay with us given other competitors are much better. We mostly grew through word of mouth and cold emails. I believe we are already solving a fairly niche use case (TAM is few thousand customers in USA) and my idea is to grow revenue enough to go after larger TAM (several milion).
What I'd really appreciate is a demo/sandbox version where I can try out the functionality without having to enter anything personal.
I appreciate that you have a (generous looking) free tier and various screenshots - but it just seems like something I'd want to play around with before taking the time to create an account and start entering personal data into.
As someone that has tried and failed at many attempts over a decade, I just wanted to take a moment to congratulate you. This is so wonderful, and I couldn’t be happier for you. Thank you for sharing your journey, and lessons learned .
I’m now a single working mom supporting 2 young kiddos on my own, so my time has become limited; but I’ll be back :)
Thanks so much, that means a lot. It's challenging when time and life pull you in so many directions. Wishing you and your kids all the best. When you jump back in, I'll be rooting for you.
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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.
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.
> 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.
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.
It helps to have an idea of what might succeed, by studying things that succeeded before and the present business environment, but that increases each attempt's success chance to, like, 2% rather than 0.2%.
(There's nothing wrong with getting lucky, we just probably shouldn't plan around it being the normal case. It has extreme variance by definition.)
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.
Luck and survivorship bias may not be the same thing.
“Courage is knowing it might hurt and doing it anyway. Stupidity is the same thing.
And that’s why life is hard.”
You're persistent if your project succeeded but you're stubborn if you keep at it despite unfavourable outcomes.
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.
Strange analogy. I'd say stay away from that line and run into the direction of persistence.
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.
Not many people are even in a position to do this (family, health etc), or have the mental and physical energy to do this for years. This is one of the potential benefits of something like UBI. It allows people to pursue these ideas without having to work another 9-5.
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.
The big lesson for me is know what you are getting into. Look at the OP - he spent every spare hour he had. This is no joke. I have done something similar in the past for a time and I ended up constantly running into conflicts of priorities between that and personal life. I ended up wasting a few years, in both personal life and professional life, although the former hurts much more. This is how I ended up in a scenario where I have nothing to show and nothing to lose. I just hope I can do it all at some 50 hours per week total, where the product is just a part of the day job (promotes the consulting offering) and lower the volume of paid work as I need, if I want to have more time to make a big move with the product.
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!
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.
Thanks for the reminder.
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...
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.
I attribute the search traffic growth to:
1. A critical mass of content, after a number of years of writing - without a lot of search traffic for the first few years
2. Re-wrote and polished some of my earlier articles so that they were improved
3. Wrote more guides related to my app which were helpful to users; such as:
Safari Extensions Guide - https://www.magiclasso.co/insights/safari-extensions-guide/
Best Web Browser - https://www.magiclasso.co/insights/best-web-browser-2025/
> Also curious how you incorporate AI tools into your workflow, if at all.
Not a lot myself, except for sometimes helping with polishing and checking of writing and sometimes coming up with options etc.
In my experience AI tools are like having a junior assistant – they can be helpful but you always need to check and polish everything they do.
Earlier in my career, I worked on some things as a corporate engineer that were hard to care about, and there's just no comparison.
>Caring is kind of a superpower.
>the quality of work.
>I was thrilled to spend my free time treating those early customers like royalty
Well, the secret's out, thanks for that, now anybody can do it ;)
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.
And that's the recipe for failure right there. Your passion side project needs to be fueled by passion, not thinking about somebody else's success that you are trying to replicate.
Like Kyle writes keep showing up to make it a little better every day. Today again I will show up, but today I'll think of him and it will help me.
What's your passion project? How do _you_ keep the motivation every day? How long has it been?
Maybe he's in that valley of despair right now that the article shows occurs many times. Passion is fleeting and at times you just need a little inspirational jolt to get back into it and regain some of that passion.
Also, to share a personal experience, passion is not sufficient. You need favorable conditions as well (or the ability to create them). For example, the article talks about working nights and weekends. I'm not sure if the author has kids or what the arrangement is in his family, but personally, as much as I wanted to work whole weekends on my passion project, I would feel like a shitty father if I ignored my kids over the weekend for months, so the project gets put on the back burner a lot while I'm biking with my kids outside and having fun.
It often feels I should give up but having had customers who used us for years makes me think we have something that one day will make serious money.
Either way, if your existing customers don't all come from paid channels, and they're loyal, and you've outlasted multiple competitors, that already sounds like a real achievement to me. My progress was slow for years before things started to really pick up, so don't discount signs of traction if there are some meaningful ones.
I appreciate that you have a (generous looking) free tier and various screenshots - but it just seems like something I'd want to play around with before taking the time to create an account and start entering personal data into.
I’m now a single working mom supporting 2 young kiddos on my own, so my time has become limited; but I’ll be back :)