What's Keeping You Up at Night? Great Founders Ask Great Questions

What's Keeping You Up at Night? Great founders ask great questions. Every startup begins with a question. But the most important questions often come later-when you're in the thick of it, when things break, when you're stuck. That's where 9others comes in. Since 2011, 9others has hosted over 500 private founder dinners in 45+ cities worldwide. At every meal, ten entrepreneurs gather and are asked just one question: What's keeping you up at night? Over 5,000 founders have shared real, raw, and sometimes painful challenges at these tables. What emerged wasn't just advice-it was a pattern of thinking, a set of questions and behaviours that helped the most successful founders push through. In this second edition of their bestselling book, 9others co-founders Matthew Stafford and Katie Lewis reveal the core questions that have helped thousands of entrepreneurs navigate uncertainty, break through roadblocks, and build better businesses. Whether you're just getting started or scaling your startup, this book will help you: Ask the questions that matter most. Reflect on your mindset, relationships, and blind spots. Learn from the real stories of founders around the world. Build resilience by thinking better-not just working harder. This isn't a guidebook full of hacks or blueprints. It's a conversation-one that invites you to stop pretending, start reflecting, and become the kind of founder others want to build with.