Cup of Coffee by Craig Calcaterra: A $200K/year Success Story!

Cup of Coffee, founded by Craig Calcaterra, is a daily newsletter that covers baseball, sports, politics, and culture. Launched in 2020 after Calcaterra was laid off from his position at NBC Sports, Cup of Coffee was created as an independent media venture. Through insightful commentary and witty reflections, Calcaterra’s newsletter has grown into a successful paid subscription service on Substack, bringing in over $200,000 per year. This is the story of how a laid-off sportswriter turned his passion into a thriving business, driven by loyal followers and a deep love for baseball and beyond.

Craig Calcaterra

Founder, Writer and Editor, Cup of Coffee

Founder(s)
1
Year Founded
2020
Customers (B2B / B2C)
B2C
Industry
Media, Email Marketing
Revenue
$200K
Funding
Self-funded

The Idea

Craig Calcaterra, a former NBC Sports writer, founded Cup of Coffee in 2020 as a daily newsletter focused on baseball news, commentary, and culture. The idea emerged as Calcaterra sought a direct way to engage with his dedicated following while bypassing traditional sports media, which he felt had become saturated with gambling-related content. If you’re a true baseball fan, subscribing to Cup of Coffee will provide you with in-depth insights and thoughtful commentary that you won’t find in conventional sports coverage.

Challenges

While the initial traction was strong—a third of his early subscribers signed up within the first week—Calcaterra had to contend with subscription fatigue in a crowded market. Competing with other paid newsletters and free content available online, maintaining and growing his subscriber base required constant effort. He faced challenges in keeping the content fresh and engaging while staying true to his style of writing, which mixes insightful sports analysis with political and cultural reflections.

Another key challenge was ensuring steady growth without resorting to heavy paid advertising. Calcaterra largely relied on Twitter, word-of-mouth referrals, and his Free Thursday newsletter strategy to convert readers into paying subscribers.

Industry Context

Calcaterra launched Cup of Coffee at a time when the sports media landscape was rapidly changing. Mainstream outlets were increasingly filled with gambling ads and commercial partnerships, turning off many traditional fans. Additionally, paid subscription models, particularly newsletters, were booming during the pandemic, with platforms like Substack empowering writers to monetize directly.

Founders

Craig Calcaterra is a seasoned baseball journalist who spent over a decade at NBC Sports as the lead writer for its baseball blog, HardballTalk. Before his sports media career, Calcaterra was a litigation attorney. His decision to launch Cup of Coffee was motivated by a desire to write independently and reconnect with readers on a more personal level(Craig Calcaterra).

Product

Cup of Coffee is a daily newsletter that offers a blend of baseball analysis, cultural commentary, and personal anecdotes. Subscribers get a mix of humor, analysis, and personal stories from Calcaterra, delivered by 7 AM ET, five days a week. Each newsletter is published early in the morning, making it a go-to read for sports fans before getting their first cup of coffee. Subscribers receive five issues per week, focusing on everything from game highlights to broader social issues in baseball.

The website also features a Leaderboard, allowing readers to show their support by sharing the newsletter and earning rewards for their referrals. Current rewards include a one-month subscription for three referrals, a three-month subscription for five referrals, and a six-month subscription for 25 referrals.

USP

Cup of Coffee’s primary selling point is its independence and integrity. While major sports outlets have leaned heavily into gambling-related content, Calcaterra’s newsletter remains free of such influence. Additionally, his distinct voice—balancing wit, deep analysis, and personal engagement—sets it apart from more formal, impersonal sports journalism.

Competitors

Cup of Coffee competes with other sports newsletters, such as The Athletic and smaller independent newsletters on Substack. However, its unique value proposition lies in Calcaterra’s style and the avoidance of commercial ties to sports betting, which many fans have grown tired of(Craig Calcaterra). Craig has recently shifted Cup of Coffee to Beehiiv.

Build

Building Cup of Coffee involved minimal initial investment. Calcaterra designed the logo himself with the help of a friend and hosted the newsletter on Substack, which handles payments and distribution. He promoted the newsletter heavily through his existing Twitter following (over 58k) and word-of-mouth marketing.

Implementation

Calcaterra leveraged his social media following and long-standing reputation in baseball journalism to grow his subscriber base. He also implemented strategic promotions, like Free Thursdays, to convert free readers into paying subscribers. Occasionally, he runs discounts tied to baseball events, like Opening Day, which have successfully driven subscription growth.

Growth

Within a few months of launching, Cup of Coffee exceeded Calcaterra’s original goal of replacing his NBC salary. Today, it generates around $200,000 annually, a remarkable feat for a one-person operation. The newsletter has experienced steady growth, tripling its subscriber base since its launch. This growth is primarily attributed to Calcaterra’s active engagement on Twitter, the introduction of free issues, and occasional sales.

Pricing

Cup of Coffee follows a subscription model, with monthly and annual subscriptions available. Subscribers can also take advantage of occasional discounts, such as a 20% off sale during key events.

Key Takeaways

  • Niche focus: Cup of Coffee’s mix of sports, culture, and politics allows it to stand out in a crowded subscription market.
  • Loyal audience: Calcaterra’s long-standing reputation in baseball journalism has helped build a dedicated readership.
  • Organic growth: With minimal paid advertising, Cup of Coffee relies on word of mouth, social media engagement, and Free Thursday promotions to attract subscribers.

Cup of Coffee has proven that independent media, when done right, can be both financially successful and sustainable. Craig Calcaterra’s journey from a mainstream sportswriter to a successful independent newsletter creator showcases the power of niche, authentic content in today’s digital economy.

Our guide on “Email Marketing for Startups: Best Strategies for Building and Nurturing Your Subscribers” will be helpful if you’re looking for more strategies!