Christina Cacioppo

From VC to Building a $2.5 Billion Company

December 26, 2024

Happy Holidays and Merry Christmas!

This is the third issue of Web Worth Reading - we're just getting started as the year ends.

Christina Cacioppo is a great entrepreneur. Through Vanta, she has defined a new category in compliance technology.

While many interviews cover her journey building Vanta, we're sharing some of her lesser-known early writings that we believe are gems for aspiring entrepreneurs.

BIO
Why Christina Cacioppo?

We discovered Christina reading her curated list of fiction and non-fiction books.

After starting her career at Union Square Ventures, she left a secure job and promising trajectory to teach herself programming and "build on and for the internet."

While she launched several products along the way, it wasn't until identified an opportunity in the compliance space that Christina founded Vanta, now the leading certification automation platform valued at over $2.45 billion.

Though she's no longer actively blogging (but posts frequently on X), her early writings documenting her journey into programming and building products remain some of the most insightful content about entrepreneurship and non-linear career paths.

Topics: Programming, Books, Entrepreneurship

3 ESSAYS TO GET YOU STARTED
1 - Learning to Make

We strongly believe that focusing solely on learning programming is misguided. Instead, learn to create things, figure out where to start and work through the process of turning a blank page, screen, or board into something real.

While coding may seem outdated in the AI era (though I'd argue it remains crucial), the key isn't the code itself but the creative process. Christina shows how learning to shape ideas into reality remains the most powerful way to direct your life's journey and career toward your chosen path.

“I also wanted to learn to write software out of stubbornness. It felt that you're not really supposed to do that after school, and such low expectations amazed me. When did we decide our time's most important form of creation is off-limits? How many people haven't learned to write software because they didn't attend schools that offered those classes, or the classes were too intimidating, and then they were "too late"? How much better would the world be if those people had been able to build their ideas?”

This article covers some similar themes and is particularly compelling as it was written right before Vanta's founding in 2016.

Seeing someone's thought process before building a successful venture, finding product-market fit, and scaling to millions in revenue demonstrates how entrepreneurship is rarely linear—it's an iterative process filled with failures and course corrections.

Here are two takeaways that are still very relevant today:

  • Learning to program is about persistence rather than innate talent. It's a process filled with constant cycles of success and failure, where practical hands-on building is more valuable than theoretical knowledge.

  • Creating products is fundamentally about making things you want, accepting initial failure, and improving rapidly. The focus should be on building "living products" with real users rather than perfect launches.

“If you’ve graduated from college, most people – including those who work with startups – will tell you that you shouldn’t do what you’re doing: you’ll never be as good at making things as those who’ve done it longer, and you should specialize in whatever you’ve been specializing in. How correct they are is up to you.”

Customer discovery and interviewing users, or simply gathering feedback, is often easy to conceptualize but very hard to execute effectively.

This guide is a great summary of the book Interviewing Users by Steve Portigal.

We just admire her love for reading: it shows you can be a great tech leader while cherishing literature.

It's not surprising that, as CEO of a billion-dollar company, she has a list of over 800 books. The drawbacks of not reading outweigh reading less or not at all.

This list stands out for its simplicity: a collection of fiction and non-fiction books with straightforward YES/NO recommendations. While not an essay, we found some hidden gems and great recommendations in her list.

WHAT IS WORTH CHECKING THIS WEEK?

Some of our favourite things we found on the internet this week:

SUGGESTION BOX

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Enjoy Christina Cacioppo’s writing, happy Christmas & see you next week! 🙂