About the Company

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Craig Calcaterra is the founder, writer, and editor of the daily Substack newsletter "Cup of Coffee." Published five days a week, each newsletter is sent to subscribers by 7 AM Eastern time. The newsletter offers a comprehensive digest of significant news in Major League Baseball, designed to keep baseball fans informed about everything they need to know by the time they have their first cup of coffee.

In addition to baseball news, the newsletter includes a substantial amount of analysis and commentary on various topics such as pop culture, media criticism, technology, politics, and other current events. This blend of content provides readers with a rich and engaging reading experience beyond just sports updates.

The subscription model for "Cup of Coffee" includes both paid and unpaid tiers. One free newsletter is published each week, and the total subscriber count is just under 10,500, with over 3,300 paying for monthly or annual subscriptions. The average monthly revenue for the newsletter is around $18,400 and continues to grow.

Idea Behind Company

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Cup of Coffee is the latest milestone in Craig Calcaterra's distinguished career. Graduating from law school in 1998, Calcaterra practiced law for 11 years before feeling burnt out and disillusioned. Seeking a positive outlet, he turned to blogging about baseball, a sport he had loved since childhood. In 2007, he launched the blog Shysterball, which gained a significant following due to its unique coverage of the legal aspects of Major League Baseball's performance-enhancing drugs scandal.

In early 2009, NBC Sports, reimagining its web presence and seeking bloggy, editorial-style sports writing, invited Calcaterra to contribute part-time while he maintained his legal job. By the summer of 2009, his ideas for enhancing NBC's baseball coverage led to an offer to join NBC full-time, leading their baseball coverage and shaping the editorial voice. He left his legal career in November 2009 and became the lead voice for NBC Sports’ MLB vertical, HardballTalk, for 11 years. During this time, he covered multiple World Series, All-Star Games, Spring Training, and Winter Meetings, becoming a notable authority on the intersection of baseball, business, labor, and law.

On August 3, 2020, NBC/Comcast announced a 10% across-the-board layoff, resulting in the elimination of HardballTalk and Calcaterra's departure. Within hours of being notified, he launched Cup of Coffee on Substack, convinced that his loyal readership would follow him. Announced on August 10, 2020, and starting daily newsletters on August 12, Calcaterra aimed to match his NBC salary within a year—a goal he exceeded in seven months. Reflecting on his journey, he realized that he could have made the move earlier, even if it took getting laid off to recognize the opportunity.

Creating the Company

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In designing Cup of Coffee, Craig Calcaterra decided to diverge from the rapid news cycle approach he followed at NBC. Instead of producing multiple stories as news broke, he opted for a subscription model that valued thoughtful, well-curated content over speed and search engine optimization. Calcaterra believed his subscribers would appreciate and pay for his editorial judgment, preferring to wait for his considered take on events rather than immediate, fast-paced updates.

Inspired by his reading habits from a decade earlier, Calcaterra aimed to create a daily briefing that busy professionals could rely on. He envisioned a newsletter that would provide comprehensive updates each morning, allowing readers to catch up on the previous day's events without constantly refreshing various websites. The goal was to offer a mix of timely recaps and engaging commentary, making the morning read both informative and enjoyable.

Calcaterra settled on a three-part format for the newsletter: daily recaps of baseball games with added insights or humor, a "Daily Briefing" covering the top 5-10 news stories, and a section titled "Other Stuff" discussing non-baseball topics like politics, movies, and pop culture. This structure, fine-tuned with reader feedback, proved successful, offering subscribers a complete and engaging overview of the previous day's news. For most fans who want a thorough yet concise update, Cup of Coffee delivers an excellent product that stands out in the crowded field of sports media.

Launching the Business

The layoffs at NBC in August 2020 garnered significant media attention, with Craig Calcaterra being one of the first to publicly announce his layoff on social media. This unexpected exposure created a buzz about his next move, as people speculated on his future endeavors. Although the anticipation was unplanned—Calcaterra tweeted about his layoff shortly after being informed and before deciding on his next steps—it ultimately worked to his advantage. The launch of his new venture, Cup of Coffee, was straightforward: he shared a link to the Substack page where the newsletter would be hosted. With minimal overhead, including a logo designed by a friend in exchange for dinner, and the setup of a bank account linked to Substack and Stripe, Calcaterra was ready to start writing.

Attracting and retaining subscribers has been crucial for the success of Cup of Coffee. Within a week of launching, about a third of his current subscriber base had signed up, consisting of his most loyal readers and social media followers from his NBC days. This initial support was pivotal, as growing a readership from scratch on Substack can be challenging without a core audience at the outset. Since then, Calcaterra has tripled his subscriber base through various strategies. His active Twitter presence plays a significant role, where he regularly tweets links to his newsletters, converting a steady stream of new subscribers. Additionally, he offers a free newsletter every Thursday, encouraging people to subscribe with their email addresses, and runs periodic sales aligned with key baseball events, attracting many new subscribers with discounted rates.

Word of mouth has proven to be the most effective tool for growing the newsletter. Readers often recommend and share Calcaterra's work, purchase gift subscriptions, and engage with his writing on social media. Whether they agree or disagree with his opinions, they help integrate his work into broader online conversations. To ensure the newsletter's success, Calcaterra focuses on writing compelling, regular content that balances serious analysis with lighthearted commentary. By maintaining an authentic voice and building a connection with his readers, he fosters a loyal and engaged community.

Earnings

Cup of Coffee has exceeded all expectations. As a one-person operation with minimal overhead costs, the primary goal was simply to replace the salary Craig Calcaterra earned at NBC, enabling him to continue writing for a living. This goal was achieved within a few months, and the newsletter's success has since surpassed those initial aspirations.

Looking ahead, Calcaterra does not have immediate plans for expansion but is considering several possibilities. One potential avenue is launching a podcast, which could broaden the newsletter's reach and engage a wider audience. Another consideration is hiring a part-time writer to extend the newsletter's publication to seven days a week, providing readers with continuous updates and insights.

Overall, the future of Cup of Coffee appears promising. With a solid subscriber base and steady growth, Calcaterra is well-positioned to explore new opportunities and continue delivering valuable content to his readers. The success of the newsletter demonstrates the viability of a subscription-based model and the strong demand for high-quality, independent sports journalism.