“There’s a lot of talk about the importance of a company being ‘founder-led.’ Ultimately I believe that’s severely limiting and a single point of failure…I believe it’s critical a company can stand on its own, free of its founder’s influence or direction.”

– Jack Dorsey, Founder and Former CEO of Twitter

Jack Dorsey’s sudden resignation from Twitter last month created a major stir, in Silicon Valley and around the world. Especially after his long-fought victory over an activist investor’s attempt to oust him back in 2020, Dorsey’s decision to hand the reigns over to CTO Parag Agrawal came as a shock to many. The move also bucked the recent trend of “founder-friendly” venture capitalists encouraging founder-CEOs to stick around for as long as possible. Dorsey’s resignation demonstrates how — and why — a founder might voluntarily step aside once their organization has reached a certain level of maturity, and invites the question: Should others follow his lead?