The problem with email

Newsletters have a lot of looming disadvantages

The summer is in full swing, which in Miami means constant rain that breaks up the stifling heat and humidity. I’m off to Europe for a couple weeks this weekend, so next week’s edition will come from Belgrade. This week, I’m working out something that’s been nagging at me for a long time: Email. The pivot to email newsletters is both exciting and baffling, since most people dislike email. Also a quick note: If you’re interested in reaching people building sustainable media businesses, check out the sponsorship sales kit. Also, if you’re not already subscribed, please do.

The problem with email

Digital media has pivoted so many times it eventually ends up where it started. Back in April, I wrote about how it’s not yet time to retire the website as the home of publishers, even those that began as email newsletters. Email continues to be the rage lately with publishers, offering an antidote to the recent travails of digital media. The advantages:

  • Email is ubiquitous. Everyone has an email account and checks it regularly.
  • Email is a push technology. Why wait for people to come to your content when you can bring it to them?
  • Email is personal. The shift from institutions to individuals is happening across many sectors, notably in media. Getting an email delivered to you is different than ending up on a website because you clicked a Facebook link with a curiosity-gap headline.
  • Email is a direct connection. Email is an entree into knowing more about your audience, then using that information for other purposes, including ads, upsells, etc. At Digiday, sending an email about an event meant lots of revenue. Couldn’t say the same about running a banner ad for the same event. Email simply works -- sometimes too well. (See: Spam.)
  • Email is finite. At least in theory. An email newsletter offers a chance at the type of tight curation that made magazines. Site-based digital media was usually a grab bag, with some stories doing work to catch SEO, others for Facebook clicks, etc.
  • Email is “ownable.” For the most part, email hasn’t been subject to the whims of tech platforms that have given publishers PTSD. Publishers were screwed over so many times by platforms that we kept running the gif of Charlie Brown getting the football pulled from in front of him by Lucy.

And yet email has its many shortcomings, and these are likely to become more apparent in the near future. Much of the fervor for email is, ironically, from people who bemoan email still existing as a communication mainstay. I can remember feeling excitement at that “You’ve got mail!” announcement. That was a long time ago. In a digital context, email is fairly old. Early forms of it were in use all the way back in 1988. I can remember my oldest sister getting her first job in the 1980s and telling us she had something called electronic mail that could send messages between computers. Seemed crazy. I was still amazed fax machines existed. And yet email has persisted, even as people and businesses tried their best to kill it.

Many don’t recall but email had a near-death experience in the early 2000s. In the aftermath of the dot-com collapse, the internet media and marketing business was in survival mode. Email was beloved by direct marketer, who immediately understood that it had the same dynamics as direct mail -- targeting, optimization, quantifiable results -- but without one key factor: It was nearly free to send. That meant sending one email or one million wasn’t an enormous investment. Guess which way people went? Email became nearly unusable, filled with all kinds of spam offers for hidden cameras, penis pills, Xanax and who knows what else. My favorite story of that time was about IronPort, a maker of high powered email sending software that was used by many spammers. Naturally, IronPort went into the anti-spam software space too.

But email survived, thanks to legislation like the Can-Spam Act, litigation against spammers by the FTC and state attorneys general, and tech advances by email providers to block a lot of spam before it got to people’s in-boxes. Many people have tried to kill email only to be proven wrong. RSS didn’t. Apps didn’t. Facebook didn’t. Slack didn’t. So I wouldn’t follow that lead and declare the end of email. I would caution that there are many factors working against email that argue for a distributed media strategy that doesn’t overly rely on email as a distribution mechanism.

  • Gen Z hates it. Take it with a grain of salt, since everyone says they hate email. But generationally, email is a strange communication technology for young people. The old rule of thumb was that would change when they got to college and then got a job. Could be, but it’s easy to see email becoming less critical as a communication method.
  • Platforms are cracking down. There’s a reason that whenever you sign up for an email newsletter you’re immediately met with a desperate plea to engage in a complicated process to make sure the newsletter isn’t shunted off to the Promoted tab/graveyard. No distribution method is free of platform meddling. What’s more, Apple is planning to reset the market by taking away key data from senders, such as how many people open their email. (I’m sympathetic to part of this, since I think most people would be weirded out at a meeting when I asked why they didn’t open the past three issues.)
  • Fatigue. Email is a chore. It used to be a source of connection, now it’s something that has to get done. What’s more, there are a lot of email newsletters out there. And the business model of email always demands more, whether that’s sending frequency or getting cute with spamming people with unrelated newsletters -- I signed up for a specific publication, not something else -- promotions for other publisher products or, the worst, “partner emails.”
  • Growth hacks wane. It’s harder to build an email list to scale now, and it’s getting harder by the day. Paid distribution is hard to master when competing with companies that put a far higher lifetime value on a customer. Copying Morning Brew’s referral program isn’t going to be as effective the 500th time around.

The answer is the same as for many issues in digital publishing: diversify. Email is a great base for starting out, especially to test new ideas as a true minimally viable product, but if there’s one lesson in the last two decades of digital publishing it’s to have several sources of distribution and several sources of revenue.

Sustainable is the new scalable

The pandemic has taught the world many valuable lessons. One is that growth can’t come at the expense of resilience. When the times are good, we often don’t stop to concern ourselves about protecting against downside risks, also known as “bad shit happening.” The rolling chip shortages that are making cars both scarce and expensive is an abject lesson in this.

In publishing, the sustainability gospel has now replaced the growth gospel. BuzzFeed was synonymous with the era of digital publishing where publishers could grow abnormally quickly on the back of the massive audiences assembled by Facebook and Google, along with a few other smaller platforms. The downside risks were brushed aside. Times change. WIth BuzzFeed going public, CEO Jonah Peretti used a variation of “sustainable” a half dozen times in an interview with the Financial Times. The next generation of digital publishing companies being built will not need to pivot to sustainability since they’ll have it in their DNA.

Final thought: On writing

The Economist has done some great subscriber-only Zooms on a disparate array of topics. This week, it had a session featuring Lane Greene, The Economist’s language columnist. He made some great points worth repeating for anyone who writes, which is everyone.

  • Compression gives writing more energy. I got a note on  LinkedIn complaining my newsletter on brevity was too long. Very true, although I replied that brevity is a virtue we should aspire to while realizing we’ll frequently come up short. The process is still worthwhile. Greene’s rule of thumb: Cut a minimum of 10% of what you write. Good writing, like diamonds, shines brighter when cut.
  • Write prose, not poetry. Good writing is simple and clear. Technical terms and unfamiliar words don’t make you sound smart. Write how normal people talk. If you wouldn’t invite a friend to a “cohort” heading to the bar later, don’t write it. Greene noted the serious part of this with the reminder that writing like a bureaucrat, academic or technician takes the humanity from writing. Write for humans.
  • Follow a style. Just pick one. Every publication has a style guide. We used AP Style as a basis, then complemented it with our own choices. Style is a lot like cooking; much comes down to personal taste. But the key, as always, is consistency. That tells your audience you give a shit.

Thanks for reading. I always like to hear from people with feedback, even just tell me to make them shorter (I know). You can reply to this email or send me a note at