This is a no-fuss summarization of what I’ve learned from running my own startup and failing hard at it. The good, the bad, and the brutally honest. It’s a series of short essays where I dissect every mistake, every win, and every “what the hell was I thinking?” moment.
If you’re thinking about a side project, already knee-deep in one, or just enjoy watching someone learn expensive lessons so you don’t have to - then this series of essays is for you.
Introduction
What is it? A SaaS platform for dental offices. Patient management, staff scheduling, appointment booking, billing, compliance — the whole nine yards. Think modern practice management software that’s not stuck in 2003 with a UI that makes Windows XP look cutting-edge. => smayl.io
Why dental? Started in a dentist chair (literally) listening to complaints about terrible software. Seemed like a golden opportunity.
Why build it at all? The product itself wasn’t the sole reason I started. I was at that dangerous intersection of:
a) competent enough to think I could build anything
b) naive enough to think that's all that matters
c) hungry to level up my technical skills in areas I'd been itching to explore
From June 2024 to September 2025, I poured every weekend, vacation day, and non-work hour into this thing. I was obsessed. My wife handled solo parenting on weekends. My kids learned to associate Daddy’s working with the office door being closed. Friends stopped inviting me places because the answer was always some variation of can’t, working on the startup.
Looking back? Worth it. But not in the way I expected.
I thought I’d build a successful company. Instead, I built a comprehensive education in what not to do, learned a ton of new tech, and came out the other side with battle scars and a much clearer understanding of how startups actually work.
In my opinion, most individual contributors can benefit massively from a learning side-gig. The key word being learning. Not building a unicorn. Not disrupting an industry. Just shipping something real, facing real problems, and learning from them.
This series documents those lessons. And trust me, I’m laughing while writing and proof-reading.
ℹ Both segments will be updated as I write the accompanying pieces.
The Bad & Terrible
The mistakes that cost me 18 months and nearly broke me. If you’re building something on the side, these are the traps waiting for you.
- Not Validating the Idea Early Enough - Talked to users. Got excited. Confused compliments with commitment. Continue reading ➡️
- Huge MVP - Built 80% of the product before a single paying customer. Continue reading ➡️
- Time Strain - 1,500+ hours. $3.33/hour ROI, and even that’s stretching it.
- Sunken Cost Fallacy - Six months in, knew it wasn’t working. Kept building anyway. The trap that keeps you digging.
- Continue reading ➡️
- AI Making Me a Dumdum - Let Copilot and Mr. Claude do the thinking. Atrophied my problem-solving muscles. Had to relearn how to ponder.
The Good
Not everything was a disaster. Some expensive lessons actually paid off.
- K8s, Bazel, Kustomize - Production infrastructure skills that directly leveled up my day job
- iOS Development - Built a genuinely good mobile app. Still not sure if I regret it. 😂
- IaC & Rebranding - Could rebuild the entire stack in 20 minutes. Saved my ass multiple times.
- NextJS Mastery - React Server Components, streaming SSR, the whole modern frontend stack
- gRPC & Streaming - Real-time features, bidirectional streams, backpressure handling
- Stripe Integration - Payment processing, subscriptions, webhooks. It’s less scary than you think.
- The AI Awakening - Learned when to use AI and when to think for myself.
Bottom line: I failed to build a successful startup. But I succeeded in building a comprehensive, expensive, and incredibly effective education in software engineering, startup mechanics, and self-awareness.
Would I do it again? Ask me in a year.