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Cacioppo: The median startup downside is a multi-year slog, not sudden collapse

Christina Cacioppo · The early-stage lessons of a $2.45 billion company (Vanta's Christina Cacioppo) | Masters of Scale · Mar 17, 2025 · at 9:15

Christina Cacioppo, founder and CEO of Vanta and former analyst at Union Square Ventures, reflects on the risks of starting a company without deep conviction.

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“And I think again at USV I'd seen that actually starting the company isn't the hard part. That's, you know, shockingly easy. The hard part is like in year four when it's not really working, but you've raised this money and you have employees and you're still doing it. And like, maybe you don't want to, but you're not really saying that out loud yet. And like, That. And that's actually kind of the median case. And I think the downside isn't the thing, you know, becomes a crater in the earth and just ends. Like, then it ends and you can move on. It's sort of that slog.”

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Assertion Not checkable as stated
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