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 built its first computer in 1966 just to run its own instruments. Its first desktop PC flopped. The lesson: HP's adjacency moves won when they followed the installed base - and its $25B Compaq bet, chasing scale instead, won a shareholder vote by 45 million shares and destroyed value doing it.

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.

After its founders, HP burned through five 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.

Three CEOs forced out in under a decade, a fourth departure that the filing called voluntary, more than $83M in severance, an $8.8B write-down. The revolving door wasn't a run of bad leaders. It was the same dysfunctional board making the same hire, then firing it, then doing it again.