HP

When HP CEO Leo Apotheker paid $11.1 billion for Autonomy in 2011, he was trying to transform HP from a hardware manufacturer into a software powerhouse. Instead, the deal produced an $8.8 billion write-down, allegations of massive fraud, criminal charges, and a case study in due diligence failure that continues to haunt corporate boardrooms — one where, more than a decade on, a U.S. jury ultimately rejected the fraud allegation at the center of HP's own account.

HP's CEO said the quiet part out loud: the company loses money on the printer and makes it back on the ink. That single sentence explains the cheap hardware, the firmware that bricks third-party cartridges, and the lawsuits - the whole architecture of a loss leader defended to the death.

HP started with a $538 audio oscillator and ended up two companies. From test gear to PCs, PCs to services via Compaq, services to software via Autonomy — each leap destroyed value, and 2015 wasn't a masterstroke. It was a confession.

In 2015 HP became two companies, and the tidy story says each one then splintered further. It didn't. Only the enterprise twin kept separating — spinning off two businesses in 2017 and exiting China by 2023 — while HP Inc., legally the original firm renamed, never split again.

From 1999, HP burned through four outside CEOs in sixteen years - two forced out, one in eleven months - chasing a single transformational thesis. The 2015 split wasn't a triumph. It was the board admitting no one person could carry both halves of the legacy.

HP spent $1.2 billion on Palm to fight Apple, then priced its tablet at $499 — the same as the iPad — and killed it 49 days after launch via an earnings-call afterthought. The product wasn't the problem. The decisions around it were.