To save a few thousand dollars in legal fees, six-time Silicon Valley CEO Mike Grossman acted as his own lawyer on a routine contract — and nearly torpedoed the acquisition that would later save his company. He shares how a single ambiguous sentence...
Kate Lowry — CEO coach, venture capitalist, and author of Unbreakable: How to Thrive Under Fear-Based Leaders — joins to share why reporting misconduct early in her career backfired, and what it taught her about the gap between good intentions and ef...
Eric Ries's favorite mistake wasn't a failed product, it was not knowing what “strategy” meant until a panel of Boston consultants told him so. We trace that lesson from The Lean Startup to his new book, Incorruptible, and the structural reasons good...
Joe Hennes built a career around what he loves most — first as editor-in-chief of the Muppet fan site Tough Pigs, then as an employee at Sesame Workshop itself. In this episode he opens up about what it actually costs to get that close to your fandom...
Deborah Coviello, known as The Drop-In CEO, shares the leadership presentation that fell flat with her boss but resonated with her peers – and the deeper lesson about change management when introducing new ideas. We also dig into her three Cs framewo...
Jesse Jackson, contact center leader and host of Set Lusting Bruce, on the mistake of going gun-shy as a new leader when veterans push back with “we tried that, it didn't work.” He explains why deferring to that resistance costs you your best ideas –...
Dr. Melisa Buie spent years trying to avoid failure — until she realized the bigger mistake was disappearing after a win and treating rest as the finish line instead of part of the cycle. The author of Faceplant: FREE Yourself from Failure's Funk sha...
Joel Steele built a healthy fast food chain in his early 20s and watched it collapse into roughly $800,000 of debt – the result, he now says, of confusing growth with success. In this conversation, he unpacks the warning signs he refused to see, the...
Irna Hutabarat Athans is an innovation strategist, MIT Sloan grad, author, poet, and former Tango World Championship competitor. Her favorite mistake was walking away from technology entirely because she felt it was soulless and couldn't accommodate...
Andy Freed has spent 30 years helping leaders communicate with clarity — but one cross-cultural marketing blunder taught him that clever means nothing if you haven't considered your audience. The CEO of Virtual Inc. and author of “Lead Like the Boss”...