The latest for the Flops File — Zillow Offers

Rita McGrath
9 min readNov 19, 2021
Photo by Breno Assis on Unsplash

It takes a special combination of ingredients to land in my “flops” file. You have to lose your parent company at least $50 million. You probably started out with big ambitious goals, all-at-once funding, leaders personally committed to a given approach and most of all, a boatload of assumptions relative to facts. It’s a recipe for totally unnecessary disaster.

Big corporate flops have been a fascination of mine for ages. And they are a puzzle — why do otherwise smart, sensible, executives who know their business so often get into big trouble when they tackle a challenge that has even a touch of uncertainty to it?

One big reason is that people in “thoughtland” underestimate how many assumptions they are making, especially if they are used to a long track record of success. Take Quibi, the short-form movie company that promised to fundamentally alter how young people consume content. When it still had the working name of “NewTV” in 2018, even veteran entrepreneur Steve Blank wondered whether the fact that the Katzenberg — Whitman venture had successfully raised over $2 billion meant they didn’t have to test their assumptions as they launched the business. In other words, was “lean startup” or what I would call “discovery driven”thinking not necessary if you had all that cash?

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Rita McGrath

Columbia Business School Professor. Thinkers50 top 10 & #1 in strategy. Bestselling author of The End of Competitive Advantage & Seeing Around Corners.