In today’s episode, I join Michael Chernow, founder and host of Kreatures of Habit, to share what I look for before investing in an entrepreneur or a business. I explain why my first priority is always the person—not the product—and how I qualify desire, teachability, and alignment with what’s working now and in the future. I also share the “thousand-step” rule that determines whether someone has the persistence to succeed and why culture, not company, is the true investment. Along the way, I reflect on the lessons learned from losing $100 million and how that experience shaped my approach to evaluating risk and leadership.