I had the opportunity to know Christina Cacioppo early in her time at Union Square Ventures. Always whip-smart and ever curious, we found ourselves drawn to similar founders and edges of emerging markets. When her time at USV ended, we lost touch. She moved from NYC to San Francisco, took a job at Dropbox, and carried on with her post-VC life.

Fast forward a few more years, and she’s leading one of the fastest-growing SaaS businesses as the co-founder and CEO of Vanta. A few weeks back, we got to reconnect for a long overdue catch up at Vanta’s office in San Francisco. Initially scheduled for 30 minutes, our conversation expanded into nearly two hours of lessons learned, hilarious anecdotes, and a genuine reconnection between two old friends.

Although Vanta is not an indie portfolio company, you’ll quickly notice Christina’s indie-aligned approach to starting and scaling Vanta. From her quick product iteration, to early paying customers that led to early profitability, and intentional decisions around how and when to best capitalize the business. We cover it all. I’ve watched a bunch of Christina’s past interviews and feel like this one gets closest to the intensely whip-smart and soulful person she is.