Archive - Michael’s Substack

AI Has No Playbook—Here's Ours

Hype is everywhere. Best practice isn’t. We’re writing ours in the open and sharing as we go.

Aug 19 •

July 2025

How We Prove Our Tech Transformation Works (with 6 Years of Evidence + AI)

Disciplined data collection turned boardroom confrontations into predictive intelligence

Jul 27 •

The AI Productivity Trap

Why Your Peculiar Obsessions Are Now Your Strategic Advantage

Jul 12 •

April 2025

The Technology Scaling Trap: What Got You Here Won't Get You There

From travel website to a benchmark for Google's AI: How shifting technology mindset transformed loveholidays

Apr 23 •

I'm Stealing From Creators Every Day With AI (And So Are You)

AI theft isn't just about visual art—it's extracting value from every creative domain. And we're all complicit.

Apr 13 •

March 2025

How We Transformed a Failed Business into a £2.2B Exit with This 3-Stage Data Framework

The data maturity roadmap that turned a £5M acquisition into a billion-pound delisting—and the sequence most businesses get wrong

Mar 27 •

5 AI Techniques That Expand Your Thinking (Instead of Replacing It)

In a world of increasing AI automation, those who use AI to replace their thinking will themselves be replaced—those who use it to enhance their…

Mar 4 •

February 2025

Stop Writing Documents Nobody Reads

I learned this lesson the hard way.

Feb 3 •

December 2024

How I Stay Organised: My iPad Note-Taking System

Keeping on top of the constant deluge of information, tasks, and meetings you experience as a CTO requires adopting and maintaining a…

Dec 16, 2024 •

August 2024

Transforming Technology: Guiding Principles for Navigating Digital Evolution in Business

At loveholidays, when our customers contact us for help with their booking, they are now greeted by Sandy, our AI-powered virtual…

Aug 20, 2024 •

December 2023

Grappling with Growth: The Unlikely Parallels Between BJJ and Scaling a Business

The arm around my neck gets tighter, making my vision blur and little stars of light appear. My laughable attempt to overpower the much…

Dec 15, 2023 •

July 2023

Scaling technology teams: the three essential things I learned

Over the last two decades (man, I am old), a recurring challenge has been providing a view of the capability of a technology organisation…

Jul 25, 2023 •

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