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I'm Mike Jones, CTO at loveholidays 👋
Over the last two decades, I've been helping scale and exit technology companies. I've had the privilege of staying with companies through multiple stages of growth, which has given me insight into what's important. It's also built "scar tissue" from the things that have gone wrong. Along the way, I've received
lots of help from generous people and unexpectedly learned too much about myself.
My first significant experience was uSwitch. When I joined, it was worth £5 million (down from £300 million a few years earlier). The platform "would never scale," consultants told us. Most people saw a failed business. We saw an opportunity to rebuild from the ground up. Fast forward a decade, and that "failed" business became part of a £2.2 billion transaction.
My most recent challenge has been scaling loveholidays from a "travel company using tech" to a "tech company in travel". We had to rebuild the plane while flying it, transforming systems already struggling with growth. Now, we handle 4.5 million visitors monthly with systems that process over 10 trillion holiday packages daily.
I write about these experiences because there isn't much information out there, meaning most of us in technology leadership have to learn the hard way. My learning accelerated dramatically when I received help and mentoring from generous people like Phil Male. He told me, "It doesn't count unless you do it twice," I now see why. You learn much more when you've done something in different contexts.
So, I use writing to think deeply about and understand these experiences. I also share them, hoping others find them useful. Whether that's insight into approaches that have worked or just realising you're not alone in facing these challenges.
What You'll Find Here
🏗️ Technology Transformation Stories
The detailed accounts of what I learned it takes to scale systems and teams:
How we went from daily deployment freezes to 250,000 system changes annually
Why reverse engineering Conway's Law became our secret weapon for organisational design
The 3Ps framework that actually worked when scaling loveholidays
🤖 AI and the Future of Work
I'm fascinated by how AI changes how we think, create, and lead. But I'm also uncomfortable with how we're collectively stealing from creators every day (myself included):
5 techniques to enhance (not replace) your thinking with AI
The uncomfortable truth about our complicity in intellectual property theft
How AI changes leadership and what that means for the rest of us
🧠 Leadership Lessons from Unexpected Places
Sometimes, the best insights come from the strangest places:
Why Brazilian Jiu-Jitsu taught me more about scaling businesses than most management books
How taking a mental health retreat changed my approach to performance
The art of writing documents people actually read (learned the hard way)
📊 Data-Driven Business Transformation
Numbers tell stories, and those stories can transform companies:
The 3 stages of data maturity every business goes through
How we went from operating blind to influencing entire industries
Practical steps and mindset shifts that actually work (not theory)
Start With These Posts
If you're new here, these three give you a sense of my approach:
The Technology Scaling Trap: What Got You Here Won't Get You There
The story of how loveholidays shifted from nearly breaking under its own success to being held up as Google's AI benchmark. It's about the three distinct phases of growth and why each requires fundamentally different thinking.
Stop Writing Documents Nobody Reads
Describing the time I wrote a dissertation-length proposal that no one read past the first page. It taught me the difference between writing to think and writing to influence. Plus, there's an AI-enhanced workflow that might save you similar embarrassment.
I'm Stealing From Creators Every Day With AI (And So Are You)
The uncomfortable truth about how we're all complicit in history's largest intellectual property heist. And what we might do about it.
Who This Is Probably For
CTOs and VPs of Engineering dealing with scaling challenges
Technology leaders wrestling with technical debt vs feature delivery
Anyone trying to build data-driven cultures
Those interested in navigating AI adoption in their organisation
People who like long-form thinking about complex problems
Who This Probably Isn't For
People looking for quick productivity hacks or 2-minute solutions
Those wanting coding tutorials
Anyone seeking pure theory or not interested in honest accounts of failures and mistakes
A Few Things to Know
I often write long pieces because complex problems deserve nuanced thinking. Most posts are 10-15 minutes, not quick tips.
Everything I share comes from specific experiences, including failures that became learning opportunities. I'm not interested in theories that haven't been tested in the real world.
I do use AI to help with my writing, but only after I've done the thinking. I believe there's a difference between enhancement and replacement, and I try to stay on the right side of that line.
My style is "contemporary abstract" (a polite way of saying chaotic), but note-taking saves me. Brazilian Jiu-Jitsu keeps me humble. And yes, I talk about both more than I should.
Recent Popular Posts
How We Transformed a Failed Business into a £2.2B Exit with Data seems to resonate with people wrestling with data maturity. It's the complete journey, including the bits where we had no idea what we were doing.
The 5 Principles That Helped Scale loveholidays gets shared a lot by engineering leaders. These aren't generic principles—they're the specific ideas that took us from a startup to handling exponential growth.
How Autonomy Is Transforming loveholidays explores what happens when you allow people to "leave a footprint." Turns out, they build amazing things.
Get Connected
I publish here regularly, usually monthly with longer pieces and more frequently with shorter observations. If you find this helpful, I'd love to have you along for the journey.
You can find me on LinkedIn for professional connections, or reach out directly at hi@michaeljon.es if you want to discuss technology transformation, scaling challenges, or why everyone should try Brazilian Jiu-Jitsu at least once 🤙
Thanks for reading. I hope something here helps you avoid a mistake or two.
Mike
