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The Case For 249 No's episode artwork

Oct 1, 2026 24 min

The Case For 249 No's

from The Case For... (with Matthew Campobasso) Hosted by matthew.r.campobasso

At twenty-nine, Matt Campobasso had a good job. Steady, secure, nothing wrong with it. He also had two hundred and fifty cover letters, a printer that ran for a month, and a question he was afraid to find the answer to. In this episode, Matt makes the case that the question you're afraid to ask is already a no by default, and the only thing that ever changes it is being willing to risk something good for a shot at something better. Drawing on his own 0.4% hit rate alongside research on dating, salary negotiation, publishing, and startup funding, Matt builds the case exhibit by exhibit, takes on the strongest objection to his own argument, and leaves you with two tools for deciding, in advance, how many no's you're willing to sit through to get to a yes. A companion essay, "The Case for 249 No's," is live on Substack. Subscribe so the next case comes straight to you.

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The Case For 249 No's

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This episode was published on October 1, 2026.

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