Cacioppo: Lived off VC bonus for two years teaching herself to code
Christina Cacioppo · The early-stage lessons of a $2.45 billion company (Vanta's Christina Cacioppo) | Masters of Scale · Mar 17, 2025 · at 7:35
Christina Cacioppo, founder and CEO of Vanta, explains why and how she left her early career investing role at Union Square Ventures to become a technical product builder.
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“What I did was I took my bonus basically lived off of it for two years. So that was kind of my grad student living and taught myself to code.”
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More from Christina Cacioppo
Cacioppo: USV invests in markets and ideas over founder personalities
“USV, I think they're good at a lot of things. They are very, very, like, market and idea driven. And, you know, like all investment theses, sometimes it works, sometimes it doesn't, but I think their, like, fundamental world view to me was if you pick, or if a…”
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“If you are growing and you feel like your product market fit, start at 20, such that you don't You don't have to start later when everything is kind of even more chaotic.”
Cacioppo: Union Square Ventures hires off the internet, not personal networks
“They, like, they build their firm off the internet. They hire off the internet. They do not hire off of, kind of, personal networks or anything.”
Cacioppo: The median startup downside is a multi-year slog, not sudden collapse
“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 d…”
Cacioppo: How Vanta automated compliance despite intentionally ambiguous industry regulations
“These regulations are complex and nuanced, and there's, they're actually Full of gray and the gray is kind of purposeful so companies can figure out what's best for themselves. But I think that ambiguity led lots of folks to look at it and say, oh, you can't a…”
Cacioppo: Big tech engineers were the wrong profile for early Vanta
“Asking someone, hey, you're, you have this career path at the Silicon Valley company, you have this mortgage, you have this annual bonus, like, do you want to make one third of that amount and like sit in a room with us and see if this will work? It was like a…”