Idea Ripper // ArchiveCards: 1555 [Live] | Updated: 2026-10-14
Card #c1365IR // #c1365Synthesis

"At the time, Barstool was losing close to $12 million a year. I would buy the entire company back for one dollar, taking us off Penn’s books and inheriting all the expenses."

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

[Use when]

The owner of something you want is under pressure to get rid of it.

[Why it matters]

Penn needed a money-losing asset gone to pursue its ESPN deal. Portnoy offered to take on the losses in exchange for ownership, plus a ten-year promise not to disparage ESPN Bet. A buyer's need to unload can be worth more than the price.

Filed under situations:When the other side has more leverageWhen it’s day one and nothing exists yet

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

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