Eight Years of Building: From Side Projects to a Product Studio

Eight years ago, I built my first web product. I'd already been building iOS apps since 2008 — sixteen years of software overall — but 2016 was when I made the leap to web development. That transition from iOS to web unlocked everything that followed.

Looking back across eight years of web products (and sixteen years of building software), the journey from "person who made a side project" to "solo founder running a product studio" was not a straight line. It was a series of experiments, failures, accidental successes, and slowly compounding lessons. Here is the honest arc.

Phase 1: The Side Project Years (2016-2018)

The first few products were built for the joy of building. I was learning web development, learning what was possible, and scratching my own itches. Each project taught me something specific:

My first projects taught me the fundamentals: how to ship something, how to put it in front of users, how to handle the gap between "it works on my machine" and "it works for other people." They also taught me that finishing is harder than starting. I've lost count of how many projects I started during this period that never shipped. The ones that did ship were not the most technically impressive. They were the ones where I was disciplined enough to define a scope and stick to it.

The biggest lesson from this phase was about scope. My early projects were either too ambitious (I would work for months and never ship) or too trivial (I would ship in a week and nobody cared). Finding the middle ground (substantial enough to be useful, constrained enough to actually finish) was the skill that unlocked everything else.

Phase 2: Aviation Takes Off (2015-2016)

AvioSharing and New Pilot Shop were the products that changed everything. After launching Aviation Infinity on the App Store in 2014, I went deeper into the aviation vertical. And the response was different. People used it. People came back. People told other people about it.

The aviation vertical pulled me in deeper than I expected. Pilots had adjacent needs that Aviation Infinity could not serve, and each of those needs became a new product. AvioSharing (cost-sharing for flights), New Pilot Shop (aviation uniforms and gear), Want To Be a Pilot (mentoring for aspiring pilots): each one emerged from a real gap identified through the community I'd built.

This phase taught me the power of going vertical. Instead of building unrelated products for unrelated audiences, I was building a portfolio of complementary products for interconnected audiences. The shared context, shared infrastructure, and shared user base created compounding returns that isolated products never could.

It also taught me that one good product in a vertical leads to the next one naturally. You don't have to brainstorm ideas when you are deeply embedded in a community. The ideas come to you through user conversations, support requests, and observed behavior.

Phase 3: The Scale Challenge (2020-2022)

By 2020, I'd enough products that managing them started to become the primary challenge. The early days of each product were exciting: building, launching, getting first users. But the ongoing maintenance, the accumulating technical debt, the compounding complexity, that was a different game entirely.

This was the period where I nearly burned out. I was working long hours, context-switching constantly, and feeling like every product needed more attention than I could give. The quality of my work degraded because I was spread too thin.

The turnaround came from two realizations:

First, not every product needs active development. Some products are done enough. They serve their users, they are stable, and they don't need new features. Giving myself permission to let products coast was psychologically difficult but operationally essential.

Second, systems beat heroics. Instead of relying on my memory and energy to keep everything running, I invested in systems: shared infrastructure, automated monitoring, template-based development, structured time allocation. These systems made maintaining a large portfolio sustainable rather than heroic.

Phase 4: AI Changes Everything (2023-2024)

The AI era didn't just add new products to the portfolio. It changed how I build and maintain everything.

In 2023, I started experimenting with AI integration across my products. By 2024, AI was embedded in my entire workflow: coding, writing, research, product management, system administration. The vertical AI thesis emerged as the natural next step: building AI-native products that go deep into specific verticals.

My AI-powered products represent the convergence of everything I've learned over eight years of web development and 16 years of building software total. The vertical focus from aviation. The product discipline from the scale challenge. The technical patterns from building 9 products. The AI expertise from two years of intensive Claude integration.

What Changed Over Eight Years

Technical skills matured. My first products were built with whatever tutorial I'd watched most recently. Now I've strong opinions backed by experience about architecture, tooling, and patterns. The stack has evolved (from vanilla JavaScript to React to Next.js App Router with TypeScript), but the principle of choosing boring technology for infrastructure and interesting technology for differentiation has been consistent.

Product intuition developed. I can now evaluate a product idea in hours instead of weeks. Not because I am smarter, but because I've seen enough products succeed and fail to recognize patterns. The user research still matters, but I know what questions to ask and which signals to watch for.

Ambition scaled. My first product was a simple tool. Now I am building AI-powered products that could serve entire industries. The ambition grew because the capabilities grew, both my technical capabilities and the capabilities of the tools I build with.

Patience increased. I used to want every product to take off immediately. Now I understand that products need time to find their audience, time to iterate, and time to compound. Several of my products finding their market by accident taught me that patience and observation are as important as speed and execution.

What Stayed the Same

Building is still the best part. Eight years in, the moment a new feature works for the first time still gives me the same rush it did on day one. The scale is different, the stakes are higher, but the fundamental joy of creating something from nothing has not diminished.

Users are still the best teachers. No amount of research, analysis, or planning replaces watching a real person use your product. The surprises, the frustrations, the unexpected use cases: these still come from user observation, not from spreadsheets.

Shipping beats planning. I've never regretted shipping something imperfect. I've often regretted waiting too long to ship. The best feedback comes from real users using real products, and you only get that feedback by shipping.

What I Wish I Had Known

Start shared infrastructure earlier. My first five products should have shared code from the beginning. The migration pain of consolidating independent repos into monorepos was significant and avoidable.

Build monitoring before you need it. I added monitoring after I'd outages. I should have added it before the first user signed up.

Write more. I started blogging seriously in 2024. I wish I'd started in 2016. Writing clarifies thinking, builds an audience, and creates a record of decisions and reasoning that is invaluable for future reference.

Protect your energy. Burnout isn't a badge of honor. The periods where I built the best work were the periods where I was rested, exercised, and mentally fresh. The periods where I worked the most hours were often the periods where I produced the least value.

The Next Eight Years

If the first eight years took me from zero to 9 products and a deep expertise in building vertical software, I think the next eight will be defined by AI.

Not AI as a feature, but AI as a fundamental capability that reshapes what a solo founder can build. The vertical AI products I am planning represent a new kind of product, one that combines deep domain expertise with AI capability to serve people who were previously unserved.

Eight years ago, I was a person who made a side project. Today, I run a product studio with 9 products across aviation, AI, and travel. In eight more years, I hope to look back and see that the products I built actually changed something: that vertical AI products helped people who were previously unserved, that going deep into specific industries proved to be the right strategy, and that the journey from side projects to meaningful impact was worth every late night, every failed experiment, and every hard lesson along the way.

It has been eight years. I am just getting started.