Indie Hacker Diaries #13: Thinking Iteratively About Success + Failure

The first “hit” I ever had was The Meteor Chef.

If you’re not familiar, that was a site where I wrote long-form tutorials on the Meteor JavaScript framework and later, offered mentorship sessions to help developers build their Meteor apps.

It peaked at ~80K monthly views in 2015 and then slowly died.

From that, I learned a ton about full-stack development and spotted an opportunity. Most of the people I was mentoring were consistently doing two things:

1. Using the Meteor boilerplate I had built.
2. Building a product using that boilerplate.

Iterating on this, the next business I built was Clever Beagle. This was a more formalized version of the TMC mentorship sessions, offering an improved version of the boilerplate I was offering, backed by a soft-methodology for planning and organizing feature development, and focused on helping you build your (typically, first) product from scratch.

After a few years of running that, I noticed a problem. The JavaScript ecosystem had become bloated. Most of the people I was teaching were scrambling to keep up with the new tech and fluctuating opinions, all the while trying to ship a product that worked well-enough to earn customers (and not require constant refactors to keep up with the bleeding edge).

In 2021, as a result of burnout from teaching and itching to fix the ever-shifting tech problem, I started CheatCode. I had built up enough knowledge of how Meteor worked under-the-hood and decided it was worth attempting to create a new, Meteor-style framework that was simple, easy for beginners to pick up, and most importantly, rarely—if ever—changed the developer-facing APIs so they could build their app once without having to constantly rewrite it.

I share this brief story to make a point. Notice that each business I built was an iteration on the previous. Even though they weren’t directly connected (I wasn’t pivoting those businesses), they were compounding on the lessons I was learning.

Whether I found success or failure with each one didn’t matter. What mattered was developing an awareness for the “next logical step.” They weren’t million dollar grand slams, but they did put enough gas in the tank to help me get to the next one.

I learned this idea from a veteran indie hacker, Amy Hoy. She refers to this concept as “stacking the bricks.” Instead of darting from idea to idea or chasing random trends, I made a point to consciously stack the lessons from each business on to the next one. This meant that—at least in theory—each new business got me closer to the “one” that just worked.

Along the way, too, I was learning not just what worked in business, but also related areas like the technology, marketing, sales, customer service, etc.

Was it all sunshine and rainbows? Hell no. I almost quit multiple times.

But by not quitting and continuing to stack, I’ve now gotten to a point where I’m able to build products quickly that are more likely to work than not.

Applying this as an indie hacker

So. How do you do this? Well, frustrating as it may be, there’s one word you have to get comfortable with: patience. I’ve been running my own businesses for ~13 years now and I’m still trying to find the one that really takes off.

Do I see that as a failure? No. Despite not quite knocking it out of the park, I’ve been able to keep going. There have been ups and downs, happy moments and scary moments. Ever had a negative bank account balance and have to bite your nails while you wait for customer payments to flow in? I have!

The half-full perspective is that, by inching forward, I’ve managed to develop a deep awareness for what works and what doesn’t.

Sure, I’d loved to have been one of those 20-something unicorn wünderkinds who stumbled upon success. Well, maybe.

Fast, massive success can also be toxic

Recently I’ve been reading Never Enough: From Barista to Billionaire, written by one of my long-time inspirations/heroes/email acquaintances, Andrew Wilkinson. He was one of those 20-something wünderkinds, and if you read his book, you’ll find that early success ain’t it’s all cracked up to be. In fact, the majority of the book finds him in one version or another of misery.

Damaged relationships, confused desires, and the type of stress you’d think was reserved for a tight rope walker.

A billionaire.

Reading that made me grateful for the path I shared above, and I think it’s worth your time to contemplate it yourself. Despite the struggles to get to here, the emotions that Andrew described didn’t resonate. Quite the opposite. Because of the approach I shared above, every day, I get to wake up on my own terms and do work I’m proud to ship. My phone isn’t blowing up. I don’t have thousands of employees to worry about. I’m unbothered, moisturized, happy, in my lane, focused, flourishing.

I realized that how we think about “success” as a society is so out of whack that you can trick yourself into thinking you’re a dismal failure when you’ve actually been killing it all along.

And as an indie hacker, the importance of identifying what success means to you—even if everybody else thinks you’re a total loser—is absolutely key.

Putting this into practice

So how do you apply this sort of iterative thinking to your own indie hacker adventure?

1. Identify the topic(s) that really grip your attention. The stuff you go to bed thinking about, waking up to write notes on your phone about, or getting distracted by while you’re in conversation with someone else.

2. Don’t think of the current project/product/iteration as having to be “it.” Instead, focus on the joy and opportunity of building something and learning what works and what doesn’t.

3. Take copious notes. Notes should be raw. Schizophrenic ramblings about product ideas. Random journal entries. Scraps of paper with throw-away sketches. Quotes you’ve saved that inspire you. Screenshots of products you’d love to be able to build. Anything. One of my favorite quotes by Tony Robbins is “success leaves clues.” Think of your notes as leaving yourself clues that will help you become successful.

4. Define a vision that you’re moving towards (please, please, please, take the time to read this and listen to Ari). Get really clear about what you want and what you don’t want (your via negativa) so your efforts aren’t scattered or wasted. Make time to reflect as you move forward and develop an awareness for how your life and work are moving in the direction of the vision you defined.

5. Avoid getting sucked into the pop culture definition of success. As an indie hacker, the overwhelming majority of that stuff will just result in making you feel like shit and getting distracted from working toward your vision. My own trick for getting around this: read books and watch interviews with people who are successful but haven’t really captured the attention of the masses.

The journey is NOT the reward

Before I let you go, I want to kill a sacred cow.

The above should not be read as “the journey is the reward.” The journey is the journey. What really matters is moving toward your ultimate goal or vision.

The last piece of advice I have: avoid the hand-wavy platitudes about how “money is the root of all evil” or “the journey is the reward.” You and I, if we’re honest, both know that’s a complete and total lie.

If you’re serious about getting somewhere, define where that somewhere is and then reverse engineer the map to get there. It’s okay—arguably, preferred—if your map and destination look completely different from mine or anyone else’s.

THAT’S THE POINT.

Just. Stay. On. The. Road. If you need to pull over and scream into the night sky, I’ll be there with you in spirit.

Till next week,
Ryan

P.S. Have something to get off your chest? Want to share an idea you’re excited about? Hit reply. I’m all ears.