The Lawyer Mistake That Nearly Killed a Deal: CEO Mike Grossman

To save a few thousand dollars in legal fees, six-time Silicon Valley CEO Mike Grossman decided to act as his own lawyer on a routine distribution contract. Years later, when Dun & Bradstreet moved to acquire his company, he reread that contract and realized a single ambiguous sentence could be read to block any sale without his competitor's permission. His board told him not to worry. His mentor, Bill Campbell -- the "trillion-dollar coach" -- told him the board was wrong and that he had to fix it fast. Episode page with video, links, and more  That story is Mike's favorite mistake, and it opens a candid conversation about what running a startup actually feels like when the cameras are off. Mike is the author of the new book Failure Is an Option: Reflections of a Silicon Valley CEO, and he doesn't filter out the hard parts. We get into why the most common layoff mistake is cutting too little rather than too much, how staged cuts become a "death by a thousand cuts" that erodes a leader's credibility, and why luck and timing often matter more than the Silicon Valley meritocracy myth admits. Mike also makes a practical case for radical transparency -- about finances, lost deals, and failures -- as the way leaders earn the trust they'll need when things get hard. If you lead a team and want an honest look at decision-making, psychological safety, and learning from mistakes, this one's for you.