The 80 Best Single-Operator Newsletters on the Internet - InsideHook

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In 1971, MIT grad and computer engineer Ray Tomlinson sent the world’s first official email.

Tomlinson, who passed away in 2016, remarked in interviews before his death that the actual text contained in the body of that message — a test sent between two machines in the same room — has been lost to time. “Most likely [it] was QWERTYUIOP or something,” he once wrote on his website.

Over the decades since, new forms of communication have come and gone: pagers, chatrooms, message boards, blogs, internet relay chats, AIM, SMS, Myspace, BBM. And yet, here we are, the majority of those technologies disappearing in the rearview as the humble email remains king. Sure, the format has undergone some renovations (Outlook and Gmail were both game changers), but the gist as well as the utility are largely intact.

Which isn’t to say that email is still a simple tool for communicating with friends and colleagues, as Tomlinson intended. Brands, as they are wont to do, have co-opted the technology for sales and advertising purposes, relying on email service providers (or ESPs) like Mailchimp and SailThru to blast out communiqués to thousands of customers — or potential ones — in one fell swoop.

For a long time, these were email’s two primary functions: direct peer-to-peer messaging (your friend emails you a funny link or life update) or business transactions (a brand solicits your patronage; a publisher sends you something to read). But in recent years, a third cohort of email sender has cropped up: the individually authored, mass-distributed email. Or, as we’re calling it for our purposes here, the single-operator newsletter. These are entrepreneurial folks going at it alone, independent of media organizations.

This rise of the single-operator newsletter owes to a few factors. First and probably most importantly, there is now technology available that will allow anyone, no matter their technical background, to distribute their own mass emails. This trend started with the likes of Mailchimp (who acquired the Tiny Letter platform — aimed at individual publishers — in 2011), but has flourished more recently thanks to the success of a platform called Substack, which launched in 2018 with Bill Bishop’s Sinocism newsletter about China.

Substack makes sending an email blast as simple as writing a blog post, and more importantly includes a subscription component that allows publishers to collect fees directly through the same platform. Their value proposition is an interesting one: publishers don’t have to pay to use the platform, with Substack simply collecting a small percentage of the dues that subscribers pay.

Dan Oshinsky, founder of email consultancy Inbox Collective, says that “five years ago, before there was an easy way [to distribute newsletters], there was really only one person doing it: Ben Thompson of Stratechery. Now we’re seeing a rise in newsletters because of the rise in technology.”

It’s not just about the new platforms, though. As Oshinsky also points out, success begets imitators: for every writer or influencer who strikes out on their own and makes a living at it, five more will follow, hoping to build something great themselves. (I’ve even started my own weekly newsletter, The Breads, which comments on longform articles and internet trends that exist outside of or tangential to the mainstream news cycle.)

A second reason for the rise of the single-operator newsletter is the volatility of larger media properties. Laying off entire newsrooms at a moment’s notice has become commonplace as traditional revenue streams have dried up, and veteran journalists are increasingly looking to unmoor themselves from the system in favor of self-sufficiency. As Oshinsky says, “so many people are launching these because of insecurity in the industry.”

With email newsletters, the journalist is no longer beholden to the whims of a sales department for revenue, or a social-media platform for traffic. “You can be totally in the driver’s seat,” says Fiona Monga, head of writer partnerships at Substack. “The writing is yours, the payment is yours and the content is all yours.”

Charging readers for subscriptions — rather than advertisers for pageviews — is also in line with a more general shift in digital content. After the mid-aughts clickbait boom that incentivized publishers to prize the volume of their traffic above all, people are realizing that thoughtful content and careful research are qualities worth paying for. Monga points out that “a writer is really only going to do well if their readers feel served.” In the single-operator email space, this ethos has translated to properties that focus on niche topics like the English Premier League, the music industry or climate change rather than broader interest sets like politics, the economy or technology.

The greatest benefit of email to publishers may well be what made it great in the first place: direct contact. Inbox placement doesn’t rely on upvotes or shares or some inscrutable third-party algorithm; all that matters is how recently a message arrived and whether the recipient trusts the sender.

Nick Martell and Jack Kramer, co-founders of MarketSnacks, a daily finance newsletter that was acquired by investment platform Robinhood to become Robinhood Snacks in 2019, explain that newsletters are so valuable because they “allow you to build a routine with your reader, which ideally evolves into a ritual. That’s the power, stickiness and habit-forming uniqueness of the newsletter game.”

With thousands of talented writers and creators now trying their hand at the newsletter, the medium is set for a boom. Oshinsky only wonders how many newsletters will pop up before a bubble is inevitably breached: “Is this something for a large number of people to fully support themselves? Or just a select few, and for most others it’s a side hustle much like the blog and podcast industry?”

Only time will tell, but in the meantime, you should start to familiarize yourself with the offerings that are currently available. Below, we’ve rounded our 80 favorite newsletters run by individual curators and creators. They run the gamut from business to tech, politics to sports, and everything in between. Most are free (though some of them have a paid component) and will hopefully give you plenty of goodies to read while you’re stuck in the house being a responsible and socially distanced adult.

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