Hello! Who are you and what business did you start?
I’m Craig Calcaterra, the founder, writer, and editor of the daily baseball and culture Substack newsletter Cup of Coffee. I publish five days a week, with each newsletter going out to subscribers no later than 7 AM Eastern time.
The newsletter contains a full digest of every bit of significant news in Major League Baseball, aimed at bringing baseball fans up to date on everything they need to know in the sport by the time they’ve had their first cup of coffee. In addition to baseball, the newsletter contains a hefty dose of analysis and commentary on pop culture, media criticism, technology, some politics and other current events, and other things.
I have a paid and unpaid tier of subscribers, with one free newsletter published each week. There are just under 10,500 total subscribers, over 3,300 of who pay for either monthly ($6) or annual ($65) subscriptions. The average monthly revenue is around $18,400 and growing.
What's your backstory and how did you come up with the idea?
Cup of Coffee is just the latest stop on a wonderful career journey.
I graduated from law school in 1998 and practiced law for 11 years. Toward the end of that time I, like a lot of lawyers, was getting pretty burnt out and disillusioned. I was looking for a positive outlet and decided that blogging about baseball, a sport I’d loved since I was a child, was the way to go. I had no commercial ambitions whatsoever. I just wanted to write about something that brought me joy in my spare time.
I began the blog, then named it Shysterball, in 2007. Over the next two years, the blog gained a considerable following by a few influential people discovered it and shared it with their audiences and my unique coverage of the legal context of Major League Baseball’s performance-enhancing drugs scandal.
In early 2009, NBC Sports, which was reimagining its web presence and looking to focus on bloggy, editorial-style sports writing, asked me if I’d like to contribute to the site on a part-time basis. I agreed to do so, keeping my legal job as my primary employment.
In the summer of 2009, while still a part-timer, I sent an email to the head of NBC Sports Digital and told them that I thought we could do more, better things with NBC’s baseball coverage than we were doing and offered some ideas.
In response he asked me if I’d be willing to quit my legal job and work for NBC full time, leading the site’s baseball coverage and shaping the site’s editorial voice. I left the practice of law in November 2009 and never looked back.
I was the lead voice for NBC Sports’ baseball coverage at its MLB vertical, HardballTalk, for 11 years. While there I had the opportunity to cover the multiple World Series, All-Star Games, Spring Training, and the Winter Meetings. I also became known as one of the top authorities regarding the intersection of baseball, business, labor, and the law and became one of the sharpest and most notable critics of Major League Baseball’s leadership.
On August 3, 2020, NBC/Comcast announced a 10% across-the-board layoff. As baseball was not the network’s top sports priority, HardballTalk was eliminated and I was let go.
Within a few hours of receiving the call notifying me of my layoff, I set up a Cup of Coffee on Substack. I did so because I was convinced that, while NBC did not have room for me any longer, there were still a considerable number of readers who were interested in reading what I had to say.
I announced Cup of Coffee to the world on August 10, 2020, and began writing daily newsletters on August 12. I set a goal of realizing average monthly revenues which matched my NBC salary in one year. I met and exceeded that goal in seven months. In hindsight, I should’ve, and could’ve, made the move years before, even if it took getting laid off for me to realize that it was possible.
Take us through the process of designing, prototyping, and manufacturing your newsletter.
In deciding what I wanted Cup of Coffee to be, I decided that, contrary to what I did at NBC, I did not want to be in the business of trying to produce news stories multiple times a day, moments after news broke. Speed mattered when ad sales paid the bills and SEO was everything, but a subscription model was something different.
People weren’t going to stumble upon my writing, thereby incentivizing fast, search engine-friendly articles. Rather, they already had faith in my writing and editorial judgment – they were willing to pay for it, in fact – and thus, I assumed, they’d be willing to wait to hear what I had to say on any given matter.
That’s what inspired me to launch a daily newsletter, published each morning, as opposed to a different sort of website with a more variable publication model. I remembered back 11 years to the sort of reading about sports I did when I worked in an office all day.
Back then I had other responsibilities so, rather than constantly refresh websites, I always thought it would be better to get a daily briefing, as it were. Something I could check at the same time each day and then move on, knowing that I was fully up to speed. If it was fun and funny too, all the better.
In the end, I settled on a three-part format:
(1) daily recaps of the previous night’s baseball games, with a few short sentences summarizing each game and adding some insight or humor in the process;
(2) “The Daily Briefing,” where I talked about the top 5-10 news stories of the day; and (3) “Other Stuff” in which I talked about non-baseball topics such as politics, movies, pop culture, and whatever else was on my mind.
That formula, which I figured would require some tweaking as time went on and readers provided feedback, proved to be quite successful, and, to this day, I approach each newsletter the same way. In the end, I believe that, in one newsletter each morning, I’m providing readers with everything they could’ve reasonably learned by spending the entire previous day reading multiple websites and news outlets.
Sure, if one is a genuinely obsessive fan, you may still want to do that. But for most people who simply want to know what’s going on in the sport and then get on with their day, I think I make a pretty darn good product.
Describe the process of launching the business.
NBC’s layoffs in August 2020 got a lot of press attention. Because I was one of the first front-facing NBC figures to announce that I was being laid off on social media, a few news stories named me as one of those losing their jobs. This, in addition to my social media following knowing about it, created a bit of a buzz, with people wondering what I might do next. All of that was unintentional – when I tweeted about my layoff I had just gotten off the phone with my old boss and had yet to decide what I would do next – but it did create some anticipation about my next gig that worked to my benefit.
The launch was merely me sharing the stub link to the Substack page where Cup of Coffee would begin. The only overhead was creating a logo for the site. A friend of mine who is a graphic designer accepted a dinner out in exchange for creating one. After that, I set up a bank account, linking it to Substack and Stripe account, and writing.
Since launch, what has worked to attract and retain customers?
About a third of my current subscriber base signed up within a week of my launch. These were people who were my most loyal readers or social media followers while I was at NBC and who were willing to give me a chance and support me before they’d even seen much of the newsletter product.
While Substack will suggest that writers can grow a readership from scratch I am having a hard time imagining being able to make a full-time go of it on the platform without having some core support at the outset.
That said, I have tripled my customer base since launch. I’ve done this in several ways:
- Twitter: I have an active Twitter presence with a decent following in the baseball/baseball fan community, and I’ve made a point to tweet out links to newsletters multiple times a day, every day, teasing what can be found inside. This converts a small but steady number of new subscribers each day.
- Free Thursdays: I make every Thursday newsletter free for the public. A lot of people are willing to give their email addresses to receive the free one each week. Over time I’ve seen a healthy conversion rate of free subscribers to paying subscribers.
- Sales: Three or four times a year, I’ll run a 20% off sale, usually tied in with something notable on the baseball calendar such as Opening Day or the start of the World Series. On either a monthly or annual subscription, the sale pricing lasts for a full year for those who take advantage. It’s not a big discount – a monthly goes from $6 to $4.80, an annual from $65 to $52 – but a LOT of people take advantage of sale pricing because, I guess, people love bargains. I was worried at first that full-freight subscribers would resent others getting the product cheaper, but that hasn’t seemed to be a problem and I get very little subscriber churn during sale periods.
- I have only used paid advertising – Facebook ads and promoted posts – on a couple of occasions. They were small buys, under $100, but I don’t think they really moved the needle at all and I likely will not be doing it again.
In the end, though, word of mouth is, by far, the most important thing for the growth of the newsletter. People recommend things I wrote or share them with their friends. People buy gift subscriptions for friends and family.
People discuss my writing on social media, whether they agree or disagree with it, and place my work in the greater online conversation. For this, all of the usual things that help make a digital media career successful apply – write regularly, write compellingly, balance the serious stuff with more lighthearted content, and, above all else, write in your voice and in such a way that allows readers to connect with you and feel like they know where you’re coming from honestly.
How are you doing today and what does the future look like?
Cup of Coffee has been far more successful than I could have ever imagined. As a one-person operation in which the only real costs involved are my time, the end game was merely to replace my salary from NBC so I could continue to write for a living. As mentioned above, that goal was reached in a matter of months and we’re far beyond that now.
I do not have any specific expansion plans now. However, possibilities in that regard involve launching a podcast and, possibly, hiring a part-time writer to allow the newsletter to publish seven days a week.
Through starting the business, have you learned anything particularly helpful or advantageous?
I think I got a little lucky in that I launched my newsletter just before the trend pieces about Substack and other subscription model services began, and the market for paid newsletters became a little saturated. Once someone has subscribed they tend to hang around as long as the content is good but getting them to make that first payment can be a challenge.
I think there’s something of subscription fatigue that has set in in the last year – there are so many newsletters and streaming services and whatnot now – but Cup of Coffee got in under the wire on that and is an established enough brand to where people don’t think of it as just one of the many, many latest things for which they don’t have time or money.
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.
Another timing thing that has benefitted me considerably involves the current state of sports media. Given the proliferation of sports gambling in the past couple of years, nearly every commercial sports media outlet has heavily pushed gambling via ads, affiliate links, and gambling-oriented content.
There’s a lot of money to be made in that, for sure, but it also turns off a great many readers and there has been a big backlash to how ESPN, The Athletic, Yahoo, and all of the other major sports outlets are pushing gambling. I have made a point to not get involved in that and a number of my readers cite the fact that they can avoid that and get simple, straightforward sports news and commentary from me as a reason they’ve signed up.
Finally, I’ve learned that it’s way, way better to have a loyal, niche readership than it is to try and chase massive traffic by attempting to appeal to all people. My readers hang around because they want to hear what I, particularly, have to say on a given subject. After all, it will be unique and will often push back against conventional wisdom.
I’m way better off serving those people, and growing that reader base, than trying to chase readers with attempts at viral content, trend-surfing, or what have you. If the choice is between pleasing the three thousand people who have already paid for your product vs. potentially alienating them by trying to appeal to the undifferentiated millions who do not read your work, go with the former every time. They’re the ones who pay your salary.
What platform/tools do you use for your business?
Like written content, it’s nothing more than Substack’s CMS and the Stripe payment platform.
I’m on Twitter all day, as it’s the best place to learn about breaking news and to grasp what’s going on in the national baseball conversation.
What have been the most influential books, podcasts, or other resources?
I mostly just go with my gut and I don’t read many if any, business books or things like that. People laugh when I say this but the most influential bit of writing on my work was probably Raymond Chandler’s 1944 essay in Atlantic Monthly, entitled “The Simple Art of Murder.”
It’s primarily an essay in which the detective fiction writer, Chandler, critiques the work of conventional murder mysteries that were popular at the time, but it contains a great deal of insight about the importance of writing, directing, and in an unadorned fashion. It has a lot in there about trusting your readers and respecting their intelligence and not condescending to them.
Advice for other entrepreneurs who want to get started or are just starting out?
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. Make sure your readers know when to expect new content and don’t leave them guessing. Also – and perhaps most importantly – make sure whatever you write or write about is something that interests you, because if it interests you it will interest your readers.
If you find yourself writing about something out of obligation or because you think it’s something someone else wants, your heart won’t be in it and your writing will suffer for it.
I suppose that sort of advice, broadly speaking, applies to all businesses and pursuits beyond writing. Regular work, predictable schedules and processes, managing customer expectations, and making sure you love what you do and are committed to what you do is important in everything.
Where can we go to learn more?
- Cup of Coffee Newsletter
- My Twitter Account
- My personal blog, where I have a lot of archival writing and sometimes write new, longform pieces
- My Instagram
- My LinkedIn
- Email me
If you have any questions or comments, drop a comment below!
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