Do You Earn Your Gifts?

Why is Sukkos in Tishrei? The Clouds of Glory first surrounded us in Nissan, when we walked out of Mitzrayim, so the festival that commemorates them should really fall in the spring. The Tur asks it, and the Vilna Gaon answers it in a way that quietly rewrites what the whole Yom Tov is about: the Clouds we sit under are not the first Clouds at all.To bring it to life, I share the story of a young man who drove to his warehouse at two in the morning, in his pajamas, and watched every dollar he had ever earned dissolve in front of him. That night he nearly gave up entirely. What he did the next morning made his own workers think he had lost his mind, and it is the reason a certain kind of jeans exists in the world today.How it all ties together is in this week's episode.