Sears: Denial and the Slow Decline
Featuring Eddie Lampert
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.
Frequently asked questions
What happened to Sears?
Sears was once so dominant it sold entire houses through its catalog and owned Allstate, Coldwell Banker, and the Discover card, but it filed for bankruptcy in 2018. The striking part is how long the decline took. Competitors picked the company apart category by category over decades.
Which competitors dismantled Sears over the decades?
Walmart, Kmart, Home Depot, Best Buy, and then Amazon picked Sears apart category by category over decades. At almost no single point did any one quarter look like a catastrophe, which made the threat easy to dismiss. Eddie Lampert later ran the company through its long final decline into 2018 bankruptcy.
Why is Sears a case study in denial and slow-moving threats?
Sears is a study in slow-moving threats because denial stayed rational for years; leaders could always name a reason the trend would reverse, and no single quarter looked like a disaster. Early action felt expensive and unnecessary, while late action became impossible. The gradual pace was the trap, not a reprieve.
What can founders learn from the decline of Sears?
The lesson is to write the honest bear case for your own company and notice how fast you reach to dismiss it, because slow-moving threats stay easy to rationalize until action is too late. Early moves feel expensive and unnecessary precisely when they are still possible. CaseBook turns this into a move you apply to your own company, with an AI coach that reads your answer.