“Was there a palpable time when you felt like…you had to have a new kind of thought as you got bigger?” asks Mike Maples Jr., host of the Starting Greatness podcast in an April conversation with Automattic founder and CEO Matt Mullenweg.

Matt shares several such pivotal moments in an episode full of stories and insight from the growth of Automattic, and of his own journey and leadership evolution.

“For better or worse, you become close personal friends with everyone because you’re kind of in the trenches,” Matt said, sharing a story about when the company almost accepted an acquisition offer at a time of friction among the small, but growing, Automattic team. “So when you fight, it kind of feels like you’re fighting with your partner, your significant other.”

Matt reflects on a journey from his Palm Pilot user group to first meeting Jeffrey Zeldman of A List Apart (and now a Principal Designer at Automattic), and later his first visit to San Francisco, all before committing full-time to WordPress and Automattic. Mike and Matt also touch on the difference between a learn-it-all and a know-it-all, and even some books that have been influential along the way.

Maples, partner in venture capital firm Floodgate, has also hosted Annie Duke, Mark Cuban, Tim Ferriss and David Sacks in the second season of Starting Greatness, a podcast dedicated to startup founders who want to go from “nothing to awesome, super fast.” You can listen to the full Starting Greatness episode, and all others, right here.