Idea Ripper // ArchiveCards: 1555 [Live] | Updated: 2026-10-14
Card #c1358IR // #c1358Synthesis

"The opening bid from Peter Chernin and Mike Kerns was $7.5 million for 51 percent of the company, and I would retain all creative control over the content. It wasn’t just low; it was embarrassingly low." "The timing was right and the number seemed right. It wasn’t even close to what the company was actually worth, but it all worked out in the end."

— In our words · Source: Cancel Me If You Can (Dave Portnoy)

[Use when]

An offer undervalues you but solves your real constraints and comes from a partner you trust.

[Why it matters]

Portnoy expected the talks to end at $7.5 million. Chernin came back at $12.5 million. He took it for $5 million of personal security, an end to his personal liability, equity his partners could cash in and an investor he trusted. Five years later the company sold at a $650 million valuation.

Filed under situations:When the other side has more leverageWhen you must decide and the facts aren’t in

More from Cancel Me If You Can

#c1344"At this point the business model was pretty simple: if I could sell $3,400 worth of ads in the newspaper, I would break even."You're running a new venture on thin cash and the finances feel vague. #c1345"How do you sell ads for a newspaper that doesn’t exist? On promises."You need paying customers before you have a finished product. #c1346"I’d sift through all my competitors’ publications in Boston and call every single one of their advertisers every single week to poach them…You're looking for your first customers and your competitors publish who theirs are.

Same situation, different book

#c1293Don't let adverse selection paralyze youYou're worried that anyone willing to deal with you must know something you don't.From Trade Outside the Box #c1292Weight their view by how wide they quoteThe other side's number differs from yours and you have to decide how much to move.From Trade Outside the Box #c1273Moving the goalposts, best versus goodEach time a deal gets close, someone declares it not good enough.From The Oxford Handbook of Modern Diplomacy #c1267Test motives instead of pleadingYou're chasing a reluctant party to the table and wondering why each round goes nowhere.From The Oxford Handbook of Modern Diplomacy