Defeat can always be snatched from the jaws of victory.
In business (and private equity especially), the danger isn’t always in the obvious losses. It’s in the near-wins. The times when you think you’ve got it wrapped up, only to watch it slip away through complacency, ego, or poor execution.
I’ve seen deals where the thesis was spot on, the growth levers were identified, and the market tailwinds were there… but the team got sloppy after the close. Or worse, they overestimated their own brilliance and underestimated the grind.
Some famous cautionary tales:
• Blackberry: Market leader with 50%+ share in smartphones. They laughed off the iPhone. Defeat from victory.
• Yahoo: Rejected a $44B offer from Microsoft in 2008. By 2016, they sold to Verizon for $4.8B.
• Kodak: They literally invented digital photography. Then buried it to protect film.
Private equity flameouts weren’t any prettier:
• TXU Energy (2007): A record-setting $45B buyout by KKR/TPG. Natural gas prices cratered, leverage suffocated, and the “can’t miss” deal became the largest LBO bankruptcy in history.
• Quiksilver (Bain Capital): Global surf icon. But management doubled down on wholesale when consumer spend was shifting online. They were left with collapsing retail and stale inventory.
• Linens ’n Things (Apollo): Classic turnaround play, until execution stalled, Bed Bath & Beyond kept gaining share, and the “second bankruptcy” sealed the fate.
And at the operator level, I’ve seen plenty of “own goals”:
• Management refusing to integrate bolt-ons because they “liked their own systems better.” Synergy never showed up.
• Pricing initiatives launched without proper salesforce buy-in. Growth flatlined as reps quietly kept discounting.
• Companies chasing international expansion before nailing domestic unit economics. A shiny distraction that drained capital.
Winning positions are fragile. Momentum is perishable. “We’ve got this” is often the most dangerous phrase in business.
The real skill isn’t seizing victory. It’s protecting it.