Vanta

Christina Cacioppo had a cushy job at Union Square Ventures (USV) in 2012, but something gnawed at her. She wanted to build things, not just invest in them. When a senior partner suggested she specialize in crypto to differentiate herself, she pushed back: "I don't know if I want to be an investor. Everyone else wants to be a VC, but I want to go make things." She quit with a plan to teach herself to code, living off her prior year's bonus. The decision baffled her former colleagues—why give up the powerful USV.com email domain to bet on "Christina"?

For two years, she operated from a friend's office space across the street from USV, creating structure by showing up at 9 AM as if she had a real job. She built 35 projects: a Goodreads competitor (book website), a voice assistant for biologists, animations, and more. Almost none were businesses. But she internalized a lesson from the book "The Art of Fear": "The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars." Like the pottery class assignment where quantity beats perfection, she understood that iteration—not genius—was the path forward.

After her self-taught years, Christina joined Dropbox to work on Paper (a collaboration tool). There, she hit a wall: the product couldn't launch because they needed SOC 2 compliance certification. She had to run screaming from the room—the compliance process seemed impossibly burdensome for a startup. But the security team was great, and she spent 18 months learning the space. The insight crystallized: security was a massive, competitive market, but no one focused on startups. Startups didn't have dedicated security teams like Dropbox did.

She returned to the idea later with a validation sprint: instead of coding, she created an Excel spreadsheet and asked one or two startups, "If I did this for you, would it be valuable?" They said yes. The key rule she established: anything less than "Can you do this for me now? Tomorrow, next week?" is a no. People are kind and say "maybe," but that means no.

Vanta's early growth came from multiple channels. Christina sent cold outbound emails to YC founders, framing them as feedback requests—which were partly genuine, but clearly also customer acquisition. "I didn't know the word outbound at the time," she admits. More importantly, word-of-mouth exploded through founder and VC Slack channels where people would say "talk to Vanta." She also tried hard to build brand association in these communities.

Podcast advertising became unexpectedly powerful. Eric (her co-founder/team member) pitched spending $20K on Twitter/startup podcast ads. Christina rolled her eyes but said yes. "She was totally right," Christina recalls. The team also put up a billboard with the tagline "Compliance that doesn't suck," which still stands. "We make software, but we also make a billboard. We're equally known for both."

The early strategy was intentional: "Just do and try everything and then see what works."

Vanta reached a $2.45 billion valuation. Christina credits high standards, care, and a culture of progress as core to Vanta's success. She holds founders and early employees to quotas and expectations "way off industry" for go-to-market roles—initially scary for new hires, but infectious once they join a team of people obsessed with getting better every day. She philosophizes that "progress equals happiness," meaning the slope of improvement matters more than the current state. Moving goalposts isn't failure; it's choosing to keep progressing. The through-line of her entire journey: not counting herself out, even when the evidence said "you suck."