Today in Tedium: Some might say that peak newsletter came and went already, but in some ways, it just means the newsletter space is starting to right-size itself again. A recent piece on Vox’s Recode makes the case that newsletters are not the gold mine a lot of people once thought. “The scaled-down, sobered-up reality of newsletters is also sinking into media and tech companies that became newly interested in them over the last couple years,” the site’s Peter Kafka wrote. If that’s the case, well, it wouldn’t be the first time the newsletter emerged and receded into view. This is a cycle that has happened repeatedly over the last 100 years or so, even before newsletters became purely digital endeavors. And with all of that in mind and a new book on my shelf, I’d like to spend today’s Tedium looking back at some pre-digital newsletter efforts, and the parallels they might carry. Maybe it might offer a good refresher for my fellow newsletter authors out there. — Ernie @ Tedium
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The year that The Boston News-Letter, the first continuously published newspaper in the United States, sent out its first issue. (It, like other publications of its time, required approval by the Royal governor before release.) The single-sheet publication, which stayed active for about 72 years under a variety of titles, ceased being published in February of 1776, a date that implies why it was shut down. The publication was intended to share British news to the mainland—and the final publisher of the newspaper, Margaret Green Draper, was a British loyalist. Draper (along with other loyalists) left for Britain in March of that year, amid a broader evacuation of the city during the Siege of Boston. Hey, it could have been worse: Publick Occurrences, a predecessor, only published a single issue before the British government shut it down.
The mercantile family that accidentally set the basic template for newsletters
You ever notice how a lot of newsletters appear to be about finance and various niche trades? While there are lots of other newsletters, like this one, those seem to be the most traditional types.
As you may be aware, one of the biggest newsletters on the block, Morning Brew, makes business and financial news its bread and butter. But it’s far from alone—newsletters are often great ways to deliver information in a periodic format, something that business and financial news tend to dominate.
While the newsletter concept started in personal letters in the days of the Roman Empire, which I’m sure was fun in an era long before modern or even last-gen copying techniques were used, the early days of the printing press in the 15th and 16th centuries were still an in-earnest time for publishers, who finally had a way to mass-produce information for large audiences.
And it turned out, strangely enough, that some of the early efforts to publish periodicals utilizing printing technology had many of the same goals as something like Morning Brew or my apparent nemesis, Axios. The concept of trade, whether on land or sea, allowed for the spread of information across borders and settings, made it a great vessel to deliver information broadly and consistently.
And that meant that there was a thriving newsletter trade long before everyone had an inbox. The most famous of this early generation of newsletters came from Renaissance Europe in the form of correspondence sent by the Fugger family, a family of mercantile bankers from Germany who also were early to another thing we often think of as highly modern—venture capital.
To give you an idea of the legacy of the Fuggers, I submit a 2015 lead from a Reuters story: “Warren Buffett and Bill Gates have nothing on Jacob Fugger, a German financier during the Renaissance who monopolized the silver business, became the banker of kings, convinced the papacy to legalize moneylending and paved the way for today’s bond market.”
The Fuggers were a big enough deal that they had a network of correspondents around the world, and these correspondents would send letters in that mostly offered information on recent financial data and trades, but also dipped into political commentary. The commentary, collected by brothers Octavian Secundus and Philipp Eduard Fugger, is kind of like a newsletter but might also be compared to a telegram.
In the 1950s, Columbia University historian George Tennyson Matthews gathered up a number of these newsletters, which spoke to world events of the era, and published them in a book, titled News and Rumor in Renaissance Europe; the Fugger Newsletters.
Emphasizing that the recovered documents “are not what historians would call primary sources of evidence for the establishment of fact,” Matthews made it clear in a lengthy introduction that we were essentially reading gossip and commentary, rather than news:
The Fugger correspondents, whoever they may have been, display a certain consistency of attitude toward the great questions of politics, war and religion. Hawkins and Drake are not depicted as heroes, but as wild pirates preying upon the peaceful trade of Spain. The Huguenots of France are heretics and rebels, while the Sea-Beggars of Holland are outlaws. This is only natural, for the Fuggers were Catholic. They were loyal subjects of the Hapsburgs in Spain and in the Empire. They were bankers committed to the finance of states and the trade of regions, threatened by the eruption of the new powers of En land and the Dutch into an established commercial world which they had for decades dominated. The Fugger Newsletters were not objective pieces of reporting, and their writers frankly disclose their biases and interests, their joy or despair over every turn of events.
In many ways, we are essentially reading the equivalent of blog posts or newsletter commentary in the book, and not particularly objective commentary. The commentaries vary in length, some taking up multiple pages but others just a single paragraph. Here’s just one:
Unrest among the Miners in Schwaz
From Augsburg, the 20th day of December 1569.
In Schwaz it is rumoured that the miners are about to rise on account of the Religion which the Archduke in-tends to observe in his domain according to his own pleasure. That doth not please the overseers of the mines and they needs must incite the other poor simpletons to rebel. This can, however, soon be prevented by removing the foremen or bidding them follow the customs of the land in matters of religious observance and to keep their mouths tight shut. The others are to work or pray, whether they wish it or not, and therefore may well be kept within bounds.
In some ways, the Fuggers were prominent enough that they had their own network of quote-unquote “reporters” who were sharing information relevant to the family’s business but refracted through their own point of view—an approach not dissimilar to what we see from commentary blogs on the modern internet.
Separated from its original goals, it has taken on new historical context. It is a way for us to better understand how this prominent mercantile family and its associates saw the world, yes, but in many ways it shows that they were just as committed to relaying random crap without confirmation as we are now.
The year that Kiplinger, a publisher focused on financial topics (particularly in the field of personal finance), was founded by Willard Monroe Kiplinger, a former Associated Press journalist. The company helped to popularize the newsletter in the 20th century through the Kiplinger Letter, a monthly forecasting tool that was designed to help investors make decisions about their future. The Kiplinger company was family-owned all the way through 2019, when Dennis Publishing acquired the brand. (It now is a subsidiary of Future plc, which acquired it and numerous other brands in 2021.)
What a book about newsletters from 1982 can tell you about running a newsletter today
You may not know the name Howard Penn Hudson, even if you create newsletters today, but Hudson’s name carries a long shadow over what we call a newsletter.
A man whose lineage set him up for success in the way that anyone you might assume with the surnames “Penn” and “Hudson” might (he was reportedly related to William Penn and Henry Hudson, along with Ralph Waldo Emerson), he was seen as an icon of newsletter publishing, so much so that when he died in 2005, The Washington Post wrote this about him:
Mr. Hudson did not invent the modern newsletter—that honor goes to Willard M. Kiplinger, who started his first newsletter in the 1920s. But because of his timing and organizational ability, Mr. Hudson became the embodiment of the booming field.
Hudson was basically at the center of a broad cultural movement of niche newsletters that only got broader and more niche over time, even after its disruption by email in the 1990s and 2000s. He ran a newsletter about newsletters called The Newsletter on Newsletters (which he didn’t start himself, but purchased), and he was an educator focused on teaching others how to run newsletters themselves. On top of all that, he helped to found an association dedicated to niche newsletters in the 1970s, becoming one of the leading lights in the space of newsletters.
And recently, I got a hold of his book about creating a successful newsletter business, titled Publishing Newsletters. (It’s on the Internet Archive in two separate editions, though through a controlled digital lending setup. If you’d like to read it, you’ll have to wait your turn.) The first edition, the one I have, came out in 1982, and it’s weird how much some of the things he talks about remain totally relevant 40 years later, despite completely being written before the revolution of the internet. From the book’s intro:
Newsletter writing requires precision and discipline, two factors missing from much student writing. It has a purpose: the communication of information in an understandable form to others. Students preparing their own newsletters would have the fun of seeing their words in print, and would learn both writing and the role of computers in information processing. They would also acquire a pleasant hobby and, if they sought a career in journalism, they would have had several years of practical experience before their first job interviews.
In his book, Hudson cites the Fugger newsletter as the first true newsletter, with Kiplinger setting off a broader trend in the 20th century. By the time Hudson was on board, the newsletter space was well-established, with the era of muckrakers such as George Seldes and Claud Cockburn already past. If I had to describe Hudson’s role in this sector, it might be as a mainstreamer and educator—he made the case for this market as a tool for building a business, rather than aggressive muckraking or the presentation of political information.
A Wired piece from 2020 described the time period in which Hudson had worked as such: “Newsletters had gone corporate. Trade associations cranked them out, as did big publishers like McGraw Hill.” In this 1982 book, Hudson, already a seasoned hand at this point, was clearly writing for the estimated one-third of newsletter publishers who failed each year.
I’m going to go into some more specific elements from the book in a list below, but broadly, this book is surprisingly relevant to running a newsletter in 2022. It talks a lot about tactics to help stretch your dollar, how to write more effectively for a given audience, how to decide on a niche, and who to target with your messaging.
If you were starting an email newsletter and this was your only resource, you might get a lot further than you think.
Nine interesting facts about newsletters from Howard Penn Hudson’s book on newsletters
- Subscriptions were the rule, not the exception. Because the model was print, advertising was a no-no in publishing, according to Hudson. “The reason newsletters do not take advertising is because if you are charging a hefty price for a four- or eight-page newsletter, you are defrauding your subscribers if you devote even an inch to someone else’s ad.”
- Washington D.C. was seen as “the cradle of newsletters.” Hudson noted that the large amount of information available from the federal government, mixed with the high concentration of journalists, made the Nation’s Capitol a particularly prime area for newsletters at the time his book published. As one publisher told Hudson, “Our position is secure until the government learns to write in English. But that will not happen in our lifetime, if ever.”
- The niche was everything. In his book, Hudson includes a graph called Hudson’s pyramid, which makes it clear that if you want to make money, at least with a printed newsletter, you have to aim narrow. This is highlighted by naming conventions. “Magazine-type names like Life and Look don’t belong in newsletters. You want your prospects to know what field you are covering. In the field of energy newsletters, it is becoming increasingly difficult to choose an original name because it’s essential that the word ‘energy’ be prominent,” Hudson wrote. In the book, Hudson quotes Gershon Fishbein of Environews, who says regarding reporting, “you must go on the assumption that your readers also have access to the papers,” meaning that the newsletter should focus more on perspective.
- Brevity was the name of the game. When every page means having to spend more money on paper, limiting the amount of space your content takes up was especially important, according to Hudson. “The objective of newsletter writing is to make this limitation an asset,” Hudson wrote. “However, it’s not enough just to condense—the end result should be better readability.” That meant very tight writing and rewriting to get thoughts down in a minimal amount of words.
- As with email, costs must be managed. While cheaper than printing a daily newspaper, if you print a newsletter, you are likely on the hook for working with a printer, who will have to manage different kinds of paper for you. Your publishing schedule and time frame will determine the overall costs. There are ways to trim here and there—it can save money over time to buy envelopes in bulk, for example—but the physical nature of mailing created real concerns, like envelopers sticking together by being in place over long periods. In regards to printing in house, Hudson had this to say: “Some publishers do and they swear by it. Others do and they swear at it.” (This book was published just before the age of laser printers and desktop publishing, which may have changed this equation.)
- Advertising was a real pain. Getting new subscribers often meant using tactics that would be considered controversial today, including telephone cold-calling and sending advertising notes through direct mail, particularly if you get access to a solid mailing list. “While direct mail irritates some people, the irritation is not so immediate and personal as is the telephone,” Hudson wrote. “All they have to do is throw away your mailing.” A large portion of the book focuses on direct mailing techniques that could be used to obtain subscribers that is basically not relevant in an email-driven world—though basically everything surrounding it is still relevant. (One section of the book focuses on the idea of “renting” mailing lists, at a cost of around $45 per thousand people, to get access to new potential subscriber bases. If people did that today, they’d be labeled spammers.)
- The potential of newsletter burnout was real then, too. Hudson, in his piece, noted that time was the number one challenge for newsletter production, and in many cases, the large amount of time often discouraged many publishers from continuing on. For solo creators, Hudson described a challenging situation: “If you start a one-person newsletter, as so many have, you will have to report, research, and write. You produce the letter, take it to the printer, pick it up, run off stencils, collate, stuff, and mail. The faster you can dispose of the purely mechanical functions, the more time you will have for writing and editing.”
- The Xerox machine was a real risk for newsletters. Here’s a concern I think most people have gotten past—the idea that, if you send an issue, they might share it with their coworkers. Hudson makes clear that his association, the Newsletter Association of America, had actually lobbied Congress around this risk, leading in changes to copyright law. Hudson suggested that efforts to prevent copying had their limitations. “There has been a lot of tilting at windmills in trying to find a paper that doesn’t photocopy or an ink that foils the copier,” he explained. “Certain color combinations will be uncopyable on some machines but not on all. The technology of the copying industry is such that it will always overcome such devices.” Oh, these people would have been mad about the internet.
- Then, as now, supplemental services helped to fund the newsletter. Do you offer white papers with your newsletter, or put on in-person seminars? Does your newsletter have classifieds? Then you are part of a long tradition of newsletter senders trying to make extra money from additional offerings, something this book goes deep on. “Once your newsletter is established, your subscribers should be viewed as satisfied customers who trust you and who will give consideration to other products you have for sale.”
“An article in the June, 29, 1981 issue of Business Week predicts that videotext receivers will be in 8 million U.S. homes by 1990. That’s a lot of receivers, but still a long way from saturation. So all we can do in the eighties is to keep informed of developments, get acquainted with the new medium, and be ready when the time seems right for us.”
— Hudson, discussing the potential impact that technology might have on the newsletter space. As you can tell by this 1982 description, which I’m presuming was written before the IBM PC came out, Hudson was unaware of what was actually going to disrupt newsletters. Putting your money on videotext as the great disruptor in 1981 might have seemed like a good bet (after all, Ceefax was big in the U.K. around this time), but it obviously looks quite a bit off in retrospect. It’s OK—he wrote a pretty good book.
To me, reading books about how things we do today were done decades prior has a flattening effect. It makes me realize that, hey, in a lot of ways, some of the challenges we face today aren’t quite so bad.
Newsletter publishing is a tough gig full of burnout and competition, and there is pressure to make business decisions you may be unsure about. For example: Should you advertise? That’s a question I’ve debated on my end for years, and ultimately have avoided in favor of word of mouth, though I think the case could be made that maybe inertia shouldn’t be the modus operandi long term.
Howard Penn Hudson was an important figure in the evolution of the newsletter, and in many ways, the group that he founded, while not active under its current name, serves a similar mission, even if the focus is no longer newsletters. I did a little research on this, and the organization evolved into the Specialized Information Publishers Association, or SIPA. (Hudson’s role in the growth of the industry is noted on the SIPA website.)
Eventually, SIPA was acquired by the Software & Information Industry Association (SIIA), which has a niche publishing arm under the Associations, Media & Publishing (AM&P) Network. AM&P is active today, although it seems that the publishing space actually evolved somewhat away from the printed newsletters Hudson emphasized so strongly.
(The Newsletter on Newsletters, which hasn’t seen a new post since 2015, nonetheless maintains a digital presence in 2022, managed by longtime newsletter publisher Joel Whitaker.)
Eventually, the world of B2B publishing found its way back to newsletters in a digital form, but something interesting happened along the way: The newsletter, once the domain of companies trying to reach executives or niche audiences, became a point of interest for the regular person again, and recovered a tone not unlike that of the mercantile Fugger era, or maybe even the era of George Seldes.
The digital era opened newsletters back up to the common person once again—if they’re into that sort of thing, of course.
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