There's intentionality in everything we do. I approach leading Shopify with my team with the same intentionality Lindsay uses when cooking dinner, or even when I consider the wine we'll drink tonight. This intentionality makes life fun and interesting. After 16 years at Shopify, I've realized my greatest value comes from being a great storyteller. I want to be world-class at that.

When we started Clear 15 years ago, our vision was to evolve from a travel-centric company into the de facto secure identity platform for leisure access and commerce. We didn't initially envision healthcare. This bold vision stemmed from my Wall Street experience, observing products transform into platforms. The core idea behind Clear was using identity to make physical and digital experiences safer and easier. It's about enrolling once and using it everywhere. As a woman, I constantly dig through bags for plastic cards to prove my identity and access. This is ridiculous because no one truly checks, and it's clunky, expensive, inefficient, and insecure. That's the foundation of Clear.

At that time, the major VCs seemed overwhelmingly invincible. They were giant, long-lasting businesses; the industry had existed for 50 years. Some of these firms, like Sequoia, had invested in an impressive array of successful companies. We were trying to challenge this status quo. One idea was to make numerous angel investments in addition to venture investments, which was unheard of then. We'd start complementarily, building enough reputation to eventually do venture deals ourselves. That's how we pitched it, and we actually took it around.