This week we’re talking with Alex MacCaw — he’s well known for his work as founder and CEO of Clearbit. In May of 2021, Alex shared a personal update with the world on his blog. After much reflection, he decided to step down as CEO of Clearbit to go back to his roots. In his words, “I love the early stages of company building. Hacking together code, setting up the Stripe account, getting the first customer. That’s my jam.”

We talk with Alex about this portion of his journey at Clearbit, the Catamaran he bought in South Africa and then sailed across the Atlantic Ocean, and the new thing he’s building called Reflect that let’s you keep track of your notes, books, and meetings.

This path might not be for everyone, but what’s important to think about while reading Alex MacCaw’s story is…IT IS POSSIBLE.

I started working on open-source libraries and publishing them on a blog. This quickly gained a bit of a following resulting in offers of paid consultancy. They say that on the internet nobody knows you’re a dog. Well, in this case, nobody knew I was a 15-year-old schoolboy working on consulting gigs between French classes.

My grades were getting lower and lower, and I realized there was no way I was going get into a computer science course with my poor math scores. When I discovered I was making more than my teachers’ salaries, I came to a sudden realization: why do I need to go to college? I could just drop out!

Wynn caught up with Alex MacCaw to talk about Spine, CoffeeScript, writing books, and working at Twitter.