Alex MacCaw taught himself to code and built his career around a craftsman's eye for design, something he traces back to his time at Stripe and later applied to ideas like giving away Clearbit's logo API for free to grow its reach. He later chose to step back from running Clearbit as it scaled because he knew his strength was building new things rather than managing a large company, a preference that shows up again in how he runs Reflect with just a few people, writes about privacy-focused AI and encryption, and has lived and worked from a sailing boat while writing about travel and lifestyle design.