Steve Jobs’s most famous line — “good artists copy, great artists steal” — was stolen from T.S. Eliot, simplified in the stealing, and has been quoted in defaced form ever since. The original 1920 Eliot version contains a clause that the popular version drops, and that clause is the single most useful framework for AI transformation in 2026.
Edward de Bono coined the term “lateral thinking” in 1967 and compressed the entire framework into one sentence: “You cannot dig a hole in a different place by digging the same hole deeper.” Most senior executives in 2026 are digging a deep hole in the wrong location — with all the wrong instincts, all the right credentials, and a culture that rewards intensification over reorientation. This is what to do instead.
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.
In 1994, anthropologist Eugenie Scott coined the term “Gish gallop” to describe a debate technique where a speaker overwhelms an opponent with so many false claims that no rebuttal is possible in the time available. The technique has now migrated from creationist debates into the default information environment of senior decision-making — and AI has industrialized it. Here’s how to recognize it and how to defeat it.
A waterfall would never sound melodious if there weren’t rocks in its way. The very thing we love about waterfalls is created entirely by the obstacles we’d remove if we could. Most executives spend their careers trying to smooth the path. That’s exactly why their careers are silent — and why AI is the biggest rock the executive class has encountered in a generation.
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.
70% of major transformations fail. Cloud, digital, platforms, agile, now AI. The technology changes. The failure rate doesn’t. Here’s what the 2025-2026 McKinsey and BCG data actually says — and what the 5% who succeed are doing differently.
Jeff Bezos almost destroyed Amazon — not with a bad bet, but with too many ideas. Here’s the release-rate lesson every leader running an AI transformation needs to hear.
There’s a short quote often shared in leadership circles: “It’s impossible,” said pride.“It’s risky,” said experience.“It’s pointless,” said reason.“Give it a try,” said the heart. While its exact origin is
In 2007, the iPhone shipped with no screenshot feature. The gesture you use every day exists because one journalist made the workaround more expensive than the fix. Your organization is full of the same workarounds — here’s how to find them.
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