Sears: Denial and the Slow Decline

Sears was once so dominant it sold entire houses through its catalog — a retailer that doubled as a platform, owning Allstate, Coldwell Banker, and the Discover card. By 2018 it was in bankruptcy. The striking part isn't the collapse; it's how long it took. Walmart, Kmart, Home Depot, Best Buy, then Amazon picked the company apart category by category over decades, and at almost no single point did any one quarter look like a catastrophe. That, it turns out, is the trap, not the reprieve.

For founders and operators, this is the case on slow-moving threats — the kind where denial stays rational for years because you can always name a reason the trend will reverse. Early action feels expensive and unnecessary; late action is impossible. It sharpens the uncomfortable exercise of writing the honest bear case for your own company — and noticing how fast you reach to dismiss it.