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Creator of popular baseball newsletter Cup of Coffee tells us how he starts his day online

The litigation attorney of 11 years switched careers and created a baseball newsletter with thousands of subscribers.

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Grace Stanley

Craig Calcaterra inside of a cup of coffee
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This story was originally published on Passionfruit.

We’re reaching out to some popular creators to get their best tips and tricks for success and better understand the ups and downs of life as a trailblazer on the internet.

This week, we caught up with Craig Calcaterra via email. Calcaterra is the creator, writer, and editor behind Cup of Coffee, a daily baseball, news, and culture newsletter. He has over 12,000 newsletter subscribers and over 55,000 followers on Twitter. Calcaterra was a litigation attorney for 11 years but changed paths when he became the lead national baseball writer for NBC Sports. He’s been featured in National Public Radio, Bloomberg News, MSNBC, Yahoo, Bleacher Report, Baseball Prospectus, and more. 

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