Most people take a few days to catch their breath if they lose their job, tidy up their LinkedIn bio, maybe read some alarming Medium posts about reinvention. Craig Calcaterra, went a different route, he’d opened a Substack account before the ink had even dried on the layoff email and began building what would become a single-person media business now bringing in nearly $280,000 a year.
His newsletter, Cup of Coffee, isn’t some niche baseball stat feed. It’s a daily email that covers everything you need to know about Major League Baseball, with a healthy dose of culture, politics, and Craig’s own perspective informed by decades of experience covering the sport, and with in a writing style that treats readers as sports fans rather than SEO traffic.
With over 10,500 total subscribers and more than 3,300 paying either $7/month or $70/year, the newsletter now earns more than $20,000 per month, without ads, a team, or any real infrastructure beyond Substack and a lot of coffee.
Speed mattered when ad sales paid the bills and SEO was everything, but a subscription model was something different.
Craig Calcaterra
From Law to Baseball to Substack
After graduating from law school in 1998, he practiced for more than a decade before growing increasingly disillusioned with the legal profession. By 2007 he began writing a blog in his spare time, mostly about baseball, sometimes about its legal and ethical entanglements, with no grand ambitions beyond having a place to think out loud.
The blog, known back then as Shysterball, gained traction partly due to Craig’s coverage of the legal fallout surrounding performance-enhancing drugs in MLB. By 2009, NBC Sports invited him to join their newly revamped digital platform and what started as a part-time side project quickly escalated; within months, Craig had pitched a broader editorial vision for NBC’s baseball coverage and was asked to come onboard full time. He left the law behind and became the lead voice of HardballTalk, covering everything from World Series games to labor disputes.
For the next 11 years, he built a reputation as one of the more thoughtful and skeptical voices in baseball media, someone who could analyze a box score and an antitrust lawsuit in equal measure. That streak came to an end in August 2020, when NBC eliminated the site during a wave of pandemic-related layoffs.
Instead of scrambling for a new job or falling into a mid-career identity crisis, Craig launched Cup of Coffee and the idea came quickly. He already had the writing habit, the audience, and the credibility so Substack provided a clean platform and a payment system. Within days, the newsletter was live and within a week, over a thousand readers had subscribed.
What the Newsletter Covers and Why People Stick Around
Rather than try to replicate his NBC work which involved chasing news stories as they broke (which is always harder on a smaller budget), Craig opted for something more focused Cup of Coffee is published each weekday morning by 7AM Eastern. Each edition basically forms three parts:
- A daily roundup of the previous night’s games, with short recaps and occasional dry commentary (especially if a team played poorly).
- A news briefing, summarising 5 to 10 stories that matter in baseball and beyond.
- A catch-all section for whatever else he wants to talk about, culture, politics, tech, or media, always in his own voice, and never just for the sake of clicks.
He believed people didn’t need instant news alerts or breathless speculation about every trade rumor, hey needed something more consistent. A calm, authoritative voice telling them what happened, why it mattered, and what else was worth paying attention to, the kind of thing he’d always wanted as a busy reader himself, a dependable daily digest to read with coffee and move on.
The model worked and evenue surpassed his former NBC salary in just seven months, since launch, he’s grown from a loyal base of early subscribers to a far broader audience.
Growth Strategies
It’s tempting to think that success on Substack comes from clever tactics or viral content, but Craig’s approach has been more traditional and probably more sustainable and last year the newsletter actually moved from Substack to Beehiiv. Obviously his built-in audience was an advantage and he doesn’t claim otherwise, but the newsletter now has over 3,300 paying subscribers, and most of them arrived through one of three simple things:
- Twitter promotion. Craig tweets links and commentary about each newsletter, sometimes multiple times a day, creating a steady stream of clicks and signups.
- Free Thursday editions. Each Thursday, the newsletter is free for anyone and many people start here before later buying paid plans.
- Seasonal sales. Around events like Opening Day or the World Series, Craig offers 20% off for new subscribers e.g. a $7 monthly subscription drops to $5.80, or an annual plan goes from $70 to $62. It’s not a massive discount, but baseball fans like a bargain, and the conversion rate is consistently strong.
There have been a couple of experiments with paid ads, mostly on Facebook, but nothing meaningful came from them, Word of mouth and habit-forming content have proven far more effective. People forward the newsletter and they gift subscriptions or they reference his writing in online baseball conversations. Not super fast growth (though 7 months is pretty incredible), but solid momentum.
Both Substack and Beehiiv’s own tools for discoverability have played a minor role, but most of the growth seems to have come from readers who already knew Craig’s work or found him through recommendations.
Running a Solo Business With Minimal Overhead
As solo operations go, this one is about as lean as it gets, Craig writes, edits, publishes, promotes, and manages the newsletter entirely on his own. Beehiiv handles delivery and payments via Stripe. Other than paying for subscriptions to major news outlets like The New York Times, The Athletic, and The Washington Post, there are no recurring costs. While there are occasional thoughts about expanding, perhaps adding weekend editions or experimenting with a podcast, Craig isn’t in a hurry to complicate something that’s already profitable and manageable.
Lessons Learned
One of the main reasons the newsletter found early traction, Craig believes, is that it launched just before the subscription fatigue fully set in. Back in 2020, Substack newsletters were still novel but now, inboxes are flooded. People are more cautious about where they spend their money and time. But because Cup of Coffee established itself early, and has been a great read throughout, it has largely avoided the churn that newer newsletters struggle with.
He’s also made a conscious choice to avoid the increasing push toward gambling content that’s taken over much of sports media. ESPN, The Athletic, and other major outlets now run extensive betting partnerships, with articles, odds, and affiliate links everywhere. Craig saw that trend coming and decided not to participate and for many readers, that choice is a reason to subscribe and they want news and analysis, not sportsbook banners between every paragraph.
More broadly, Craig says the key to any creative business is knowing who you’re serving and resisting the temptation to chase people who aren’t listening. It’s better to write something smart and thoughtful for 3,000 people who value it than to water it down for the vague hope of hitting 100,000 clicks. If you have paying readers, they’re your business, not an audience to impress in passing.
And while writing about baseball every day might sound like a dream job, he’s quick to note that it only works if you genuinely enjoy the process. You can’t fake curiosity or force consistency, if you’re not interested in the subject, it will show. And readers are quick to notice.
If you’re going to make a go of writing, the most important thing is to make it a habit and to work at it, every day, as opposed to waiting for some sort of overwhelming inspiration, because that rarely happens. Write on a regular schedule.
Craig Calcaterra
Advice For Others
For anyone thinking about launching a newsletter or turning any creative habit into a business Craig’s advice is simple. Don’t wait for inspiration, build a routine. and publish regularly. Respect your audience’s intelligence, and don’t waste their time, but most importantly, choose a subject you can imagine working on every day for years.
He says the biggest thing he learned is that you don’t need to go viral or build a massive audience to make a living you just need enough people who genuinely care what you have to say.
The barriers to entry are low, but the work itself still matters, Beehiiv or Substack won’t save bad writing and Twitter won’t carry content that doesn’t deliver, but if you can show up, say something useful, and mean it, people will pay attention.
