Episode 0007: Craig Calcaterra

Read the transcript

In this episode, Kendall talks with Craig Calcaterra, author of Cup of Coffee, a daily newsletter about baseball and everything else that’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’t recognize until it was already over.

Craig talks about how he started blogging under a pseudonym in 2006 because he was afraid of getting fired, how a cold email to an NBC executive after a few bourbons led to a job offer, and what it felt like to get laid off during COVID and discover that five years of newsletter-writing had built an audience willing to pay for his work. He’s honest about the parts that didn’t add up to a tidy success story—the clients he didn’t respect, the career he undermined before he knew he was doing it—and the strange peace that comes from finally doing the thing you actually want to do.

They also get into the evolution of sabermetrics: how advanced baseball analytics gave Craig permission to have real knowledge about the game without having played it, and how that same community eventually became the thing he resented—gatekeeping, elitist, joyless. His book Rethinking Fandom makes the case that you don’t owe sports teams anything. Fandom is entertainment, not obligation, and you’re allowed to walk away.

The conversation ends somewhere unexpected: Craig admits he’s struggling. The world right now is making it hard to focus, hard to write, hard to care about baseball when larger things are happening. He asks for help. It’s the kind of honest, unresolved ending that makes conversations worth having.

Question of the week:

Anyone has any ideas of how you tune out what’s going on in the world and focus on what’s going on?