The Ability to Fail Is a Hard Thing

Amy Errett might be a natural leader, and an expert team-builder–but she wasn’t always a founder. She spent her early career in banking and investment companies, before turning to venture capital. But once she was at the table with startup founders, making decisions on who deserved funding infusions…she realized she wanted to be not in her seat…but rather, the CEO’s seat. She founded Madison Reed in 2013 out of San Francisco as a hair-color subscription brand. She’s grown it–even as the pandemic shut down 12 beauty bars she’d opened across the country–to a company that has raised more than $220 million, in part from Jay-Z’s Marcy Ventures. Now, she has her sights set on opening 20 more stores in 2022, and hiring up to 800 people. Amy spoke to host Christine Lagorio-Chafkin about her rich career and her thoughts on leading growing organizations through big changes–including navigating the unknown, seeing around corners, and helping large teams make dramatic shifts.