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Randy Cassingham’s coworkers didn’t believe anyone could make a living on the internet, much less from sending out emails.
One could hardly blame them. This was in 1994, back when most people barely even understood what the internet was. At the time, Cassingham was a technical publisher at NASA’s Jet Propulsion Laboratory in Pasadena, California, and one morning he showed up to work excited about a new business idea that had sprung into his mind the night before: a free email newsletter. “They’re looking at me like I’m an idiot,” he told me. “They asked, ‘How can you make money by giving away this stuff for free?’”
Cassingham was undeterred, and he promised to return in a few days with a more formal business plan. “So I printed up several copies of my business plan and gave it to these people who were doubtful,” he said. “After they read it, they said this isn’t going to work, you’re not going to make any money. They assumed that because I gave it away for free, there was no income potential, even though I said in the business plan that I could publish books, I could syndicate this to newspapers, I could sell advertising. They just didn’t see it.” The document even projected how long it would take for him to generate a full-time income: two years.
Soon afterward, he launched This is True, a weekly email roundup of weird and quirky news stories. And two years later, almost to the day, Cassingham quit his job and moved to Colorado. By that point, This is True had tens of thousands of readers, had sold thousands of books, and was syndicated to newspapers all across the globe. Cassingham had been featured in outlets like The New York Times, LA Times, and Newsweek, all of which wanted to explain to their readers what the internet was and what people could do on it.
Flash forward almost 30 years, and it’s no longer considered crazy to think a creative person could generate a living on the internet. Hundreds of thousands of people who work in what is often referred to as the Creator Economy collectively take home billions of dollars every year. And though it’s impossible to definitively pinpoint the first creator to crawl out of the internet’s primordial ooze, Cassingham is certainly a contender.
Why did Cassingham think he could build such a business, especially when many of the basic tools of internet commerce didn’t even exist yet? He had to figure it all out himself, and in the process he helped influence innovations in modern email marketing. He walked me through his journey in a recent conversation.
Let’s jump into my findings…
It all started with a corkboard
Today if you want to launch a newsletter, you use one of the hundreds of email service providers that range from Mailchimp to Substack. But in the early 90s, there were no ESPs; in fact, it was still difficult to send messages outside of your own organization.
Working at NASA, Cassingham had access to cutting edge email products, but his interest went well beyond his dayjob. He recalled walking into a book store in 1993 and buying The Whole Internet User's Guide and Catalog, by Ed Krol; it was the only book in the entire store about the internet. “Literally the first thing I did when I got a network connection on the job — and I already had this book in hand — was that I asked myself, ‘what is the farthest thing I could connect to?’” It ended up being a server in Australia. “I followed the directions. I typed the command, and a second and a half later, I got the prompt, ‘yes, how can I help you?’ And I was like, woah.”
The idea for This is True came not from reading other email newsletters — Cassingham maintains he wasn’t subscribed to any at the time — but from a corkboard he kept outside his office. “I would clip out news articles, highlight parts of them, hand write little comments on them, and stick it on the bulletin board,” he said. “And anytime I put up new news clips, people would gather at my bulletin board in the hallways, and they just loved this stuff.” A clipping from 1991, for instance, is about a woman who kept both her asthma inhaler and gun under her pillow, an unfortunate pairing that put her in the hospital with a bullet to the jaw. Cassingham’s commentary is written underneath it: “There she goes, shooting her mouth off again…”
Cassingham had been posting to this board since 1987, but it would take seven years or so before it would collide with his newfound obsession with email. In June 1994, LA was hit by a particularly bad heatwave, and one night his inadequate air conditioning left him awake and struggling to fall asleep. “My mind kind of churned, and then suddenly this idea dropped into my consciousness, fully formed.” At the time, most people who had email addresses used them to forward jokes, and what were his bulletin posts other than topical, news-driven jokes? His idea that night was relatively simple: he would take the basic structure of his corkboard clippings and convert it into a newsletter.
By the time Cassingham fell asleep that night, he had not only settled on a format for the newsletter, but also the business model. And despite the skepticism he received from his coworkers the next day, he immediately set about launching it.
He still had to navigate the technical hurdles, however. Remember, there was no Mailchimp back then. Cassingham needed a way to compile a large list of email addresses and distribute to them all at once. Luckily, the Ed Krol book he’d bought mentioned a service called Majordomo, an early mailing list manager that would provide most of the functionality he needed.
A few days later, Cassingham sent an email to all of his personal contacts. “It said, ‘hey, I’m starting this newsletter. Here’s the first issue. If this is something you like, here are the instructions on how to subscribe.’” There was no landing page where people could sign up; instead, you had to send an esoteric command prompt to a Majordomo address. “Immediately, I started getting subscriptions. The first one was my best friend from high school.”
The newsletter version was slightly different from what Cassingham posted to the office corkboard. After all, those articles were protected by copyright, so he couldn’t simply reprint them in full. Instead, he rewrote the stories in his own words, which made it much easier to quickly get to the point and set up a punchline. Each item ended with his pithy commentary, which often involved some sort of pun-based joke. The email was a couple hundred words, all painstakingly composed by Cassingham, but perhaps the most important line appeared at the very bottom. “When I sent out the first issue, I said that if you know anybody you think would like this, go ahead and forward it. It did have a copyright notice on it, but it said you’re welcome to forward it as long as you do it in its entirety.”
Back in 1994, the term “going viral” hadn’t been invented yet, at least in terms of spreading internet content, but that’s the phrase we would use today to describe what happened with This is True. Within days, the newsletter had spread well beyond his own circle of friends. “I remember getting a subscription from someone in Singapore and thinking, ‘I don’t know anybody in Singapore,’” he said.
Cassingham’s list grew so quickly that it soon threw up logistical hurdles. For example, Majordomo only allowed for lists of 10,000 email addresses; anything larger than that and it started to suffer from delivery issues. Cassingham was forced to begin creating separate lists and then sending the newsletter out in batches. And because he stored the lists offline, that meant he had to manually remove addresses that unsubscribed or bounced back; this quickly became a logistical nightmare that ate up more and more of his time.
While This is True initially relied on word-of-mouth, it soon got a boost from the legacy media. “Journalists had to cover this new thing called the internet,” Cassingham said. “And the obvious question for them to answer was: what can you do there?” The primary use case for the internet at the time was email, and given that Cassingham was running one of the first newsletters, he was a natural interview subject. “Because my newsletter was journalism based, journalists loved it. They would use it as an example for their lay audience of what you can do online.”
Cassingham still remembers the day he received a call from a fact-checker at Newsweek; the magazine was running a several-page spread of items that could be found on the internet. He was also the subject of longer profiles in The New York Times and LA Times. “How did he get so popular so fast?” wrote the NYT tech columnist. “Well, for one thing, he writes funny stuff.” Every time such an outlet featured him, he’d see a wave of new signups. It was a testament to the reach these publications had that they could drive so much attention even though a very small portion of their audiences even had access to the internet.
One thing nagged at me as I spoke to Cassingham: where did he source his news stories? This was before newspapers had websites, remember, meaning that they were mostly limited to regional distribution. Even when you allow for the fact that Los Angeles probably had a healthier newspaper industry back then, surely there wasn’t much space in the print broadsheets for the kind of oddball stories the newsletter featured. “I figured out how I could subscribe to and quickly skim through the AP, UPI, and Reuters newswires,” he explained. “It was a dial up thing I could do that wasn’t available on the internet proper.” Cassingham paid for these services by the minute, so he learned to quickly log in, scan the feeds for interesting headlines, download them, and then log out.
Paywall incoming…
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