Idea Ripper // ArchiveCards: 1555 [Live] | Updated: 2026-10-14
Card #c1355IR // #c1355Synthesis

"If you ever have to beg for an investment, if you feel like a used car salesman during the process, if you aren’t 100 percent comfortable saying yes to a deal, then don’t do it. Investment should never be a last resort or come out of desperation."

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

[Use when]

You're raising money and the process feels like pleading.

[Why it matters]

Portnoy wasn't looking for money when the Chernin Group approached. He gave them access to his analytics and nothing else. Being able to walk away is what let the price rise.

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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