Digital Transformation

Digital Transformation, Executive Coaching, Innovation

The Richest Mathematician in History

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Jim Simons died as the richest mathematician in history. He made his fortune by hiring scientists and refusing to hire anyone from Wall Street. The Medallion Fund delivered ~39% net annual returns for thirty years — beating Buffett, Soros, Lynch, Cohen, and Dalio combined. The six principles that produced those returns are now the foundational operating principles of every AI-native organization. Most enterprises still haven’t adopted them. Here’s what they’re getting wrong.

AI, Digital Transformation, Executive Coaching

Jeff Bezos Decision Framework in the Age of AI.

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Jeff Bezos’s two-way doors policy says it’s cheaper to try a reversible idea than to argue about it. It’s the framework behind AWS, behind the two-pizza team, and behind Amazon’s invention rate. In 2026, with AI collapsing the cost of experimentation, it’s also the single most important decision framework for any enterprise serious about AI transformation.

AI, Digital Transformation

Steve Wozniak Called the Macintosh a Failure

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Steve Wozniak called the Macintosh a failure. He was right. The Apple III melted. The Lisa was priced out of reach. The original Macintosh nearly bankrupted the company and got Steve Jobs fired. The real history of Apple is a string of near-fatal failures — and it’s the most important lesson available to anyone leading an AI transformation today.

AI, Digital Transformation

EY Canada Just Quantified the Single Most Painful Paradox in AI Transformation

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EY Canada just published research showing the most successful AI training programs are also the ones causing the most employee turnover. Employees with fewer than 4 hours of AI training express 21% intent to quit. Employees with 81+ hours express 45%. The retention problem isn’t an AI problem. It’s a career architecture problem most enterprises haven’t updated since the 1990s. Here’s what’s actually going on — and what to do about it.

AI, Digital Transformation, Innovation

A Tufts Neuroscientist Used Machine Learning to Solve a 100-Year Mystery

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In 2021, a Tufts neuroscientist named Erik Hoel proposed that dreams exist to keep the brain from overfitting to everyday life — exactly the way dropout prevents overfitting in AI. The hypothesis explains why senior leaders, calibrated against decades of same-industry inputs, gradually lose the ability to lead through change. The fix — what I call “executive dropout” — is the most important leadership discipline of the next decade.

AI, Digital Transformation, Executive Coaching

A Viral Reel Says Microsoft “Banned” AI

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A clickbait Reel is going viral claiming Microsoft banned engineers from using AI because AI costs more than humans. Almost every part of that framing is wrong. The actual story — about token-based pricing creating a new enterprise cost class that finance teams aren’t prepared for — is harder, more important, and the most useful lesson available to any leader running an AI program in 2026.

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