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Expensive Lessons
Famous business mistakes, and what they cost.
Smart people running big companies made these calls. We name the mistake, show what it cost, and tie it to something happening right now, so you can check your own business before your next meeting.
Latest · Lesson 11 · Money
WeWork Signed 15-Year Leases to Rent Desks to Members Who Could Leave in Months. The Math Was in Its Own IPO Filing.
The quick take
Read the lesson- Why it matters now: flexible office space is booming again. In India, flex operators now account for 27% of new commercial space, and WeWork India calls itself the country's biggest flex operator, while WeWork's U.S. parent is still rebuilding after bankruptcy.
- WeWork signed office leases that averaged about 15 years in the U.S. and rented the space to members who could commit for as little as a month. Its own 2019 IPO filing showed $47.2 billion in lease obligations against $4 billion in committed revenue.
- The lesson: match how long you're on the hook with how long your customers are. When those two numbers are far apart, one bad year can sink you.
Every lesson
Lesson 10 · MoneyThe Company That Tells You What Your House Is Worth Bought Thousands of Homes on Its Own Estimates. It Guessed Wrong.The lesson: a model that's good at estimating is not the same as a model you can bet your cash on. Find out how wrong it can be before you...Nov 11, 2026
Lesson 09 · MoneyHertz Said It Would Buy 100,000 Teslas. Two Years Later, It Was Selling 20,000 EVs and Taking a $245 Million Hit.The lesson: the sticker price is the smallest number in a big equipment decision. Repairs and resale value decide whether it pays off.Nov 10, 2026
Lesson 08 · AI & TechJuicero’s $400 Juicer Lost a Race to a Pair of Human Hands. Investors Had Already Put In $120 Million.The lesson: find the most expensive part of what you sell and ask whether customers actually need it. If you don't test that, a customer, a competitor or a reporter...Nov 9, 2026
Lesson 07 · MoneyPopeyes’ 136-Restaurant Franchisee Had Profitable Stores. Its Debt Sank It Anyway.Popeyes says most of Sailormen's restaurants were making money. The company still lost every one. Too much debt, a sale that fell through, and...Nov 8, 2026
Lesson 06 · GrowthBlockbuster Collected $800 Million in Late Fees. The Same Year, It Passed on Buying Netflix for $50 Million.The lesson: if a big piece of your profit comes from something customers resent, you've written your competitor's sales pitch for them.Nov 6, 2026
Lesson 05 · PeopleWells Fargo Got Caught Again and Again for a Decade. Here’s Why It Kept Happening, and Why It’s Still Standing.The lesson: a bad incentive doesn't stay in one department. Wells Fargo's own board found the root problem was sales pressure and unrealistic goals, and it took the bank a...Nov 4, 2026
Lesson 04 · GrowthQuibi Paid Hollywood Up to $6 Million an Hour to Make Shows for Your Phone. Then It Let the Creators Keep Them.The lesson: don't pay premium prices to make something your customers are used to getting free. And if you're carrying all the risk, make sure you own what you're paying...Nov 3, 2026
Lesson 03 · PeopleCircuit City Fired Its Best-Paid Salespeople to Save Money. Two Years Later, Every Store Was Closed.The lesson: in a business that sells on advice, your most experienced people are the product. Cutting them shows up in sales before it shows up in savings.Nov 2, 2026
Lesson 02 · MoneyGetty Images Just Filed for Bankruptcy. AI Was Only Part of It.Getty Images filed for Chapter 11 on Oct. 21 and public shareholders are set to get nothing. AI squeezed its core business, but a...Nov 1, 2026
Lesson 01 · MoneyThe Giant-Cookie Boom Is Over. Crumbl’s Sales Are Down 70%, and a Chain Backed by Shake Shack’s Founder Just Shut Down.Crumbl's August sales were 70% below two years earlier and Chip City closed all its stores overnight. Why the gourmet cookie craze is fading,...Oct 27, 2026More case studies
MoviePass Lost Money Every Time a Customer Used It. Then 3 Million People Signed Up.
Nike’s Founder Owns the Studio That Spent 16 Years Making One Movie. Here’s the Math.
A 13-Year-Old Video Game Has Made More Money Than Any Movie in History. That’s Why Its Sequel Gets to Be Late.
Nearly Half the Shark Tank Deals You Watched Never Closed. The Show’s Biggest Winner Got Rejected.Get in the room with the people who make these calls.
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