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Five years of indie hacking

This February marks five years since quitting my corporate 9-5 job and jumping into indie hacking full time.

Five years always felt like an important benchmark for my journey. Therefore, I wanted to take time to share the three biggest things I’ve learned so far, as well as reflect on my progress.

Lessons Learned

Passion is a Double-Edged Sword

My original foray into indie hacking was the result of my passion project, Fantasy Congress. Without my strong love for this idea, I would have never taken the jump to pursue entrepreneurship.

Alas, in many ways, I feel my passion for this project also prevented it from being more successful.

Passion is an internal experience. But building a successful business relies heavily on external stimuli, like customer feedback. If you’re consumed by passion, you will inoculate yourself to the feedback and needs of the outside world.

Like a mad scientist, I was committed to my vision for Fantasy Congress in the beginning. I had a one track mind, and this prevented me from course correcting or honestly reflecting on my circumstances.

I spent a whole year building the wrong product. Eventually I realized if I wanted to see this idea succeed, my vision and desires had to be set aside.

This changed some things. Most of all my motivation. I lost some of my gusto for the project, and eventually burned out.

This isn’t to say passion is bad. On the contrary, you need some amount of passion or delusion to motivate you to start a business. It’s fucking hard! Especially without funding or co-founders.

But passion alone won’t sustain you.

Moreover, intense passion is probably more of a hindrance than an asset.

In my opinion, the indie projects most likely to succeed are the ones where founders aren’t wildly passionate about the product or its subject matter (aka, “boring businesses”). It helps them maintain objectivity and flexibility as their problem, product, and market evolve.

You Can’t Get Away From People

Many are drawn to bootstrapping as a way to “maximize” their freedom. In my particular case, I was looking to free myself from others.

After a few years working in the corporate world, I longed for hyper-independence.

The illusion of meritocracy had faded. I realized water-cooler politics had a bigger effect on my day-to-day tasks and overall career than I expected. There was so much more to work than just doing the work. And I hated it.

I thought the fix would be working by myself, for myself. And this is where my interest in bootstrapping came from.

Using my skills, if I had enough time and money to support myself, couldn’t I just build a successful product all on my own? I imagined solitary days happily chipping away at features and bugs, free from the pressure and politics of corporate culture.

But I soon realized that building a business harbors its own form of social pressures. In many ways, you become more involved with people when you work for yourself.

Much of this comes in the form of relationships. Relationships with customers, vendors, contractors, industry influencers, competitors, and if you’re lucky, eventually employees.

Starting out, I thought bootstrapping meant freedom from the messy complications of building and maintaining relationships. Turns out, it’s just the opposite.

One of the biggest struggles I faced on my journey was “you don’t know what you don’t know.” That is to say, you might know you’re missing a piece to the puzzle, but you don’t know what that piece looks like yet.

As a true beginner, I didn’t know where or how to gather information on building a business. I had Google, but I didn’t know what to search, or which information was trustworthy.

There’s an iconic scene from HBO’s Silicon Valley where the main character is trying to learn how to write a business plan, and the camera pans to him staring blankly at the Wikipedia page for “Business Plan.” I snickered at that scene initially. Then, I lived it. 💀

The turning point occurred when I stumbled upon some Twitter users who were also trying to build self-funded businesses (or “bootstrapping” as they called it).

Following these people introduced me to relevant podcasts, influential books, and a host of other credible creators to follow. Finally, I started to learn the lingo and concepts of business building. But most importantly, I learned why many of my initial choices were mistakes.

Surrounding myself with people doing the thing I wanted to do, helped me learn even when I wasn’t trying.

Just listening to someone’s story or general banter about their project, might expose me to a new marketing tactic, or a better on-boarding strategy, or a tool to help speed up my development workflow. It also gave me a wider breadth of experience to draw on when I faced new problems.

For a long time, I thought the benefits of “community” were purely social. The past five years taught me that a community is actually a valuable learning resource. Sometimes, your peers are the best teachers.

Was it worth it?

Though I’ve spent five years working on my own businesses, they still don’t make a substantial income.

With the launch of my second business last July (a programmatic SEO tool called PageFactory), I finally started generating enough consistent revenue to pay myself a meager salary. After five long years, I now make $1k/month.

And this realization is…disappointing.

My brain knows that starting a business is not a linear journey. That 99% percent of people are not overnight successes. And that most people take many years, and many failed ventures, to eventually build a sustainable, profitable business.

But my heart is…a little crushed. Five years is a long time! I gave up a lot in my life to keep pursuing the indie hacker dream, and so far the monetary results have not been worth it! 😆

And yet, am I ready to give up?


There’s definitely a lot of things I wish I’d done differently. For instance, I wouldn’t encourage anyone to quit their job until they’ve made at least one dollar selling a product or service online. Alas, hindsight is 20/20 right?

More than anything though, I’m so thankful I had the courage, and privilege, to take a swing at this.

I don’t know if I’ll stay on this path forever, but I can’t imagine doing anything else. Maybe I’m not where I thought I’d be in five years, but I’m content with where I landed.

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