Why Big-Company Executives Often Fail in Start-Ups

And Why Your Next CEO Shouldn’t Be a Fortune 500 Star

There’s a persistent fantasy in the start-up world: the belief that bringing in a “seasoned” executive from a major corporation will instantly transform a fledgling business into a well-oiled machine. After all, they’ve run billion-dollar divisions, sat in polished boardrooms, and managed global teams. What could possibly go wrong?

Plenty.

While there are exceptions—executives who truly get it—more often than not, this move leads to friction, disappointment, and premature exits. Here’s why:

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The Tipping Point of Generosity: What Human Nature Reveals When the Stakes Rise

There’s a curious paradox in human behaviour that surfaces time and again—in boardrooms, villages, families, and even start-up ventures. Yep, I’ve personally bore witness to this a couple of times.

When resources are scarce, people often band together. They share, compromise, and look out for each other. But when the prospect of abundance looms—when the pile starts to look like it might become substantial—something changes.

Cooperation turns to competition. Altruism gives way to ambition. The same people who were content to share a crust suddenly start elbowing each other over the banquet.

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Start-up Founders: The Good, the Bad and the Ugly

Much of the venture capital discourse centres around the usual suspects: product–market fit, TAM, defensibility, and traction. But rarely do investors address a far more insidious risk — the psychology of the Founder.

Let’s look at the good, the bad and the ugly of Founders…

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