https://somanyquestions.show/media/Recent content in Media on So Many QuestionsHugoen-usWed, 04 Mar 2026 19:00:00 -0700https://somanyquestions.show/episodes/ep0007-craig-calcaterra/Wed, 04 Mar 2026 19:00:00 -0700https://somanyquestions.show/episodes/ep0007-craig-calcaterra/<p>In this episode, Kendall talks with <strong>Craig Calcaterra</strong>, author of <a href="https://www.cupofcoffeenews.com/" target="_blank">Cup of Coffee</a>, a daily newsletter about baseball and everything else that&rsquo;s been running for more than five years. Craig came to newsletter writing after eleven years at NBC Sports and ten years before that as a litigation attorney—a career path he describes as less a plan and more a series of lucky breaks, bad fits, and quiet self-sabotage he didn&rsquo;t recognize until it was already over.</p>