What If Not as Decision Filter

"One lesson I learned from Monty that would save me time and again in the future, even to this day, was to ask on every big deal, a simple three-word question: What if not? What if this doesn’t work? What if this venture or idea falls apart completely?"

"I started seeing risk through a different lens: When you focus on the opportunity and genuinely deconstruct the hazards ahead, the fear of taking a leap begins to fade. Knowing with certainty that the risk won’t kill you is what liberates you to take it."

"People like Monty Shapiro, my first business mentor, when I was in my twenties, who told me, “Son, always ask, ‘What if not?’ What if things do *not* go as planned?” He taught me to assess the worst that could happen and ensure that we could live to fight another day, advice that I hear in my head thinking over every big deal."