Zach Sims at Startup School NY 2014

At 13, Sims emailed manufacturers to develop a waterproof case for his iPod, learning that the internet let him pursue an idea despite his age and lack of experience. Later, books on PHP and MySQL did not help him build anything, which shaped his view that practical projects are a better way to learn.

At Columbia, Sims struggled to find peers interested in startups, then persuaded Drop.io founder Sam Lessin to let him work for free. He joined GroupMe after seeing how its founders built a group messaging tool to solve a problem they had at a music festival. The company grew quickly and was acquired by Skype less than a year after it started.

Sims and Ryan began by trying to connect students with jobs, but both startup mentors and Columbia students dismissed their first idea. During their Y Combinator interview trip, they pivoted toward programming challenges, then struggled to find a product users wanted. With only a few weeks before Demo Day, they returned to teaching programming, drawing on Sims’s own experience as a beginner.

Sims and Ryan built Codecademy around learning by doing, with coding exercises and immediate feedback instead of videos or books. They expected fewer than 50 people to use it at once, but saw 1,000 visitors simultaneously after launch. Sims said that designing for himself helped the founders understand what beginners needed, even when experienced programmers did not see the appeal.

After raising a $2.5 million Series A, Sims found that launch attention did not guarantee continued traffic, and the team interviewed 100 candidates before hiring its first employee. He said startups bring sharp swings in confidence, and that caring about the problem makes those periods easier to handle. He closed with advice to start without excuses, prioritize learning, persist, and work on something meaningful.