I'm Allan MacGregor, CTO with multiple exits and team-building experience across e-commerce, HR, fintech, travel, and soil remediation. I've learned the hard way that the biggest technology failures aren't dramatic disasters—they're the thousand small decisions that quietly kill teams and waste millions.
This newsletter shares the hard-won lessons from building and scaling technology organizations. Not the stuff they teach you in computer science, but the pragmatic wisdom you desperately need as a tech leader: how small management decisions compound into people leaving, why your best engineers quit without warning, and how cross-industry patterns reveal blind spots in software leadership.
What you'll get:
Real failure stories from someone who's already made expensive mistakes
Cross-industry insights that pure-tech CTOs miss
Practical frameworks tested in production, not business school
People-first approaches that actually scale with teams
No hype, no flavor-of-the-week trends, no humble bragging disguised as advice. Just honest conversations between experienced tech leaders about what actually works and what quietly destroys teams.
Why subscribe?
If you're a CTO, VP of Engineering, or tech leader who suspects that your biggest challenges aren't technical—you're right. The hardest part of our job is the human part. I write for leaders who want to learn from someone else's mistakes instead of making all the same expensive ones themselves.
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Full access to all articles and archives
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Community discussions with fellow tech leaders
Frameworks you can implement immediately
Join the conversation
This isn't a one-way broadcast. The best insights come from the community of experienced leaders sharing their own battle scars. Every article includes space for your experiences, corrections, and additional insights.
We're building a community of pragmatic tech leaders who believe in learning from each other's failures, not pretending we have all the answers.
This publication is powered by Substack's platform, but the hard-won wisdom comes from real experience in the trenches of technology leadership.
