Welcome to The Pragmatic CTO
Welcome to The Pragmatic CTO
Some of the best engineers I've ever worked with will quit over a meeting, or a poor choice of words from the CEO. Not over a layoff, not a bad performance review, not even a compensation issue—but due to principle and values.
It was an all-hands meeting with the entire company present—a gathering that should celebrate everyone's wins and hard work; a time to build excitement and momentum. Instead, it turned into a nightmare. Rather than focusing on our company, the CEO decided to go on a 20-minute ego trip talking about his other company. Then he landed the killing blow when he referred to our existing 160-person company as his "toy"—something for him to have fun and experiment with.
Needless to say, that messaging and tone was about as well received as you can imagine. It marked the beginning of that company's downfall.
That's the moment I realized the things that kill great teams, great startups, and great products aren't the obvious disasters. They're not the failed deployments or missed deadlines. They're the death by a thousand small cuts. The processes that protect mediocrity. Leadership getting comfortable and losing focus and humility. The meetings that value attendance over contribution. The subtle signals that say we don't trust you to do the job we hired you for.
Most leadership advice focuses on the big, dramatic failures. I'm more interested in the quiet ones—the small decisions that compound into great people walking away.
That's why I'm starting The Pragmatic CTO.
Why me?
I often pitch myself not as the best developer or tech leader or the most experienced executive, but as the guy who already watched the horror movie and knows when the killer with the knife is jumping from the closet. Simply put, there's value in my past mistakes.
I'm not here to sell you the next big framework, management methodology, or productivity hack. I'm here because I've already made the mistakes you're about to make, and maybe I can save you some pain.
For example:
I've hired the wrong senior engineers and learned what actually matters in interviews
I've built processes that sounded great in theory and fell apart in practice
I've navigated acquisitions from both sides and seen what actually matters in due diligence
I've scaled teams from 5 to 50+ and learned where the real breaking points are
Over 18 years, I've been an IC, Principal Developer, Director, VP, and CTO twice. I've worked across ecommerce, travel, HR/payroll, and even soil remediation. I've had two successful exits and learned from plenty of failures along the way. All the content you'll read in this publication is driven by these real experiences—not theory, not trends, but what actually happened when the rubber met the road.
What Makes This Different
I don't want to be another influencer talking in platitudes. You won't find listicles about "10 Revolutionary Leadership Hacks" here. You won't find breathless coverage of the latest trend that's going to "transform everything." You definitely won't find humble brags disguised as advice.
What you will find:
Battle-tested frameworks that actually work in practice
Honest assessments of what failed and why
Cross-industry insights from sectors that don't get much tech press
People-first leadership approaches that scale
Pragmatic takes on technology decisions
What to Expect
Every Tuesday morning, you'll get one essay. No fluff, no filler. Just practical insights you can use.
Here's what I'm committing to:
70% Practical Leadership Wisdom: Team building, hiring, scaling, decision-making frameworks
20% Industry Commentary: My take on trends, acquisitions, and what's actually worth your attention
10% Personal Stories: The failures, mistakes, and lessons that shaped how I think about technology leadership
I won't waste your time with obvious advice or theoretical frameworks that sound great in MBA classes but fall apart in practice. If you want inspiration, there are better places to find it. If you want practical wisdom from someone who's made the mistakes, you're in the right place.
The Promise
If this resonates with you, subscribe. If you know other tech leaders who might benefit from practical, no-BS advice, share it with them.
I can't promise I'll always be right. I can promise I'll always be honest about what worked, what didn't, and what I learned in the process. Most importantly, I promise to share the kind of advice I wish I'd had when I was figuring this out myself.
Welcome to The Pragmatic CTO. Let's figure this out together.