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Not a Newsletter

Not a Newsletter: July 2020

Welcome to the July edition of Not a Newsletter, a monthly, semi-comprehensive, Google Doc-based guide to sending better emails! I’m Dan, the founder of Inbox Collective, an email consultancy, and the former Director of Newsletters at The New Yorker and BuzzFeed. Every month, I update this doc with email news, tips, and ideas. Sign up here to be notified when a new edition goes live!

This month’s doc is presented by Revue, a newsletter tool built specifically for writers and publishers! This month, in the Revue newsletter spotlight, I talked with the Chicago Sun-Times about how they’ve designed their newsletters to build relationships with readers. They also shared an amazing tip about how to ask great questions to your readers — read on for more!

Also inside this edition: Gmail announces big news about BIMI; lots of great advice about improving email deliverability, a look at the best political email I’ve seen in 2020; and some newsletter monetization experiments worth keeping an eye on.

One of the advantages of a Google Doc is that it makes it easy to read and search through older editions of Not a Newsletter. You can find them all at this link.

-Dan 

(Email / Twitter / LinkedIn)

a highly-distracted man struggles to understand why he can't get any work done
Joe Dator / The New Yorker

This Month in Email Headlines

**SPONSORED** Newsletter Spotlight, presented by Revue

Email isn’t just a way to broadcast information to readers — it’s also a way to start a real conversation with your subscribers. You can ask them questions and encourage them to reply. You can showcase personalities that readers are excited to invite into their inbox. You can establish trust and use that to turn casual readers into loyal subscribers.

What would it look like for a newsroom to truly embrace the conversational side of email? For a great example, look to the Windy City, where the Chicago Sun-Times has rebuilt their suite of newsletters around starting a true “two-way conversation between our audience and our journalists.”

That’s how Lizzie Schiffman Tufano, Director of Audience Engagement and Special Projects at the Sun-Times, explained it to me when we spoke recently about the organization’s newsletter strategy. But the Sun-Times didn’t always do things that way.

Last fall, when the Sun-Times shifted all of their editorial newsletters to Revue, Schiffman Tufano said the team decided to look critically at their current suite of newsletters to see what was working and what wasn’t. Were they driving the engagement the newsroom wanted? What metrics mattered most? And were there any newsletters they needed to launch to better serve their readers?

Here are a few examples of the Sun-Times's newsletters, including emails in both English and Spanish

A small team from the newsroom — Schiffman Tufano, alongside leaders on editorial, product, and data teams — dug into the data, and also looked broadly at what was working at other news organizations. They signed up for more than a hundred local and national newsletters to see what else was out there. What they saw was an opportunity to bring unique voices into the inbox and to do more to actually talk directly with readers.

“It forced us to get creative with the workflows that we designed and also with some of our content and strategy choices,” she said.

Here’s what that looks like today: The Sun-Times still has a morning newsletter, a curated list of top stories that’s designed to drive traffic to the site. That’s an intentional choice: It’s what their team has the resources to produce and send early in the morning. The Morning Edition is one of their longest-running newsletters, with more than 19,000 readers and a unique open rate of about 26%.

But they also have a second daily newsletter — the Afternoon Edition — and that has an entirely different feel. It’s a destination product, one where the reading experience takes place in the inbox. It’s built around a specific voice — Alice Bazerghi, the Assistant Audience Engagement Editor at the Sun-Times — and features original reporting that a reader can get without having to click out. The goal with this product, Schiffman Tufano explained, is to build trust with the reader right there in the inbox.

“It delivers on a promise and offers value without really asking for anything in return, and I think that establishes a really positive foundation for a relationship with our readers,” she said. Winning over readers — and ultimately becoming a primary source of news for Chicagoans — starts with the trust being built through these newsletters.

Measuring success for these destination products hasn’t always been easy. The Afternoon Edition’s recently passed a thousand subscribers, with an average open rate above 50%. But without many clicks out to the Sun-Times’s site, it’s often been tough to measure the true impact of an email like this. The good news: This month, Revue rolled out a new audience engagement dashboard that shows how often certain readers actually open and engage with newsletters. (Next on Revue’s roadmap: Allowing publishers to target readers in each of these buckets with specific emails encouraging an action, which could be used to drive a paying subscription, sign up for another newsletter, or re-engage with the brand.) It’s data like this that will help newsrooms like the Sun-Times really understand the value of their newsletters.

Here's a sample dashboard from Revue that helps a newsroom understand which percentage of their newsletter is highly engaged

But success for the Sun-Times goes beyond open rates and list size. They’re also focused on starting actual conversations with their readers.

“We don’t have comments on our website, but we respond to people on Twitter, we respond to people on Facebook, we respond to all the messages we receive on our accounts,” Schiffman Tufano said. “We do Facebook Live with our reporters, where people have the opportunity to speak to them directly. And it’s a huge part of what makes us who we are — we listen to them.”

That strategy’s carried over to the new newsletters, too. Every day in the Afternoon Edition, the Sun-Times asks readers a question about that day’s news, and asks them to reply. The next day, they’ll share the answers they received from readers via email and on social media. Revue makes it easy to embed tweets in a newsletter, which helps them bring the conversation from social over to their newsletter.

And some of the most popular questions even turn into articles on their site. On a recent visit to the Sun-Times’s site, you might find stories like “We asked parents and teachers if they’re OK with in-class instruction returning. Here’s what they said” and “How do you plan to spend your (coronavirus) summer vacation?”, both of which were crowdsourced from reader replies.

Launching on Revue’s also allowed the Sun-Times team to launch new products quickly. Earlier this year, as COVID-19 spread across the U.S., the newsroom decided that they needed to launch an “exhaustive” product to keep readers informed about the latest coronavirus news.

“I think it satisfies two different types of readers,” Schiffman Tufano says. “Those who are hungry for as much information as possible and seeking out all these stories and appreciate having them all gathered up in one place, and people who have the opposite impulse: ‘I don’t want to have to be checking the news every day. I don’t want to have to keep refreshing this website. I just want to know that tonight before I go to bed, I can open my inbox, skim through this, click on anything I need, and feel that I have caught up, and I’m not missing anything important.’” Today, more than 5,000 readers get the Sun-Times’s coronavirus briefing seven days a week, with open rates above 30%.

That willingness to experiment has even extended to something rarely seen in American newsrooms: A daily newsletter briefing delivered in a second language. It started earlier this year when AARP Chicago partnered with the Sun-Times on an initiative to deliver public health information to the Spanish-speaking community.

“We have a Facebook account, a Twitter account for that channel, and newsletters have become such a huge part of what we do and how we do it that it was a no-brainer to us that that would be part of our initial launch strategy,” Schiffman Tufano said. The new newsletter, La Voz a Las Dos, utilizes the personality-first approach that the team first tried in the afternoon briefing. (This one’s written by the Sun-Times’s Jackie Serrato and Ismael Pérez.) It’s a smart way to tackle newsletters — test different formats, and then take what’s working and apply it across your email program.

Five Newsletter Lessons from the Sun-Times

1.) Define the audience + add a personality — Most newsrooms still build around their verticals: You’ve got a business section, so you launch a business newsletter. But the best newsrooms actually build around unique audiences, looking closely at who their readers are and what they need. The Sun-Times does that well, but also adds a twist: They bring a unique personality into the mix. Schiffman Tufano told me that this is a big change they’ve made to their product development process. Previously, the voice would’ve been the last step in the process: “Here’s what we want the newsletter to be like, here’s how we think it’ll work, oh, and who’s going to do it?” Now, finding the voice for a newsletter is one of the first steps they take when launching a new product.

2.) Engagement comes first — Finding the right questions to ask readers can be tricky, but Schiffman Tufano suggests a great framework for this: “Our general approach is, if you were just chatting casually with a friend, what would you be talking to them about today?” Those types of questions tend to be the ones readers actually want to answer.

One more thing to note: The more readers reply to your newsletters and engage with you directly, the more it will benefit your email deliverability. Asking questions is a great way to make sure your emails stay out of spam and land in the right parts of the inbox.

3.) Have a clear structure — The Sun-Times’s “Halas Intrigue” newsletter, which covers the Chicago Bears, is a great example of a heavily structured newsletter. Every newsletter opens with a “the good, the bad, and the ugly” section before diving into the latest news and behind-the-scenes notes. That structure helps subscribers find the things they want to read, even in the offseason when newsletters aren’t going out as regularly. “Our content is unpredictable and varied,” Schiffman Tufano said. “So we’ll balance that with an extremely structured newsletter.”

4.) Find partners to work with — La Voz regularly features stories from Chicago’s Univision station, which allows the Sun-Times to produce a newsletter that offers comprehensive coverage of local stories. “We want this to be a consistent, reliable destination for you where you can get the news you need, and if there’s an important story that we haven’t covered, we will find it elsewhere and serve it to you,” Schiffman Tufano said. But good partners don’t have to be other news organizations. Back in 2017, the Chicago History Museum discovered millions of lost photos from the Sun-Times. This month, the Museum’s reopening with a new exhibit featuring more than a hundred of those photos and launching an online archive of 45,000 digital images. The Sun-Times is currently experimenting with new newsletter products that’ll highlight photos from the archive. It’s a great example of an untraditional partnership that can benefit multiple stakeholders in a community.

5.) You don’t have to use one tool for everything — Revue’s strength is in its simplicity — it’s an incredibly easy tool to build and send editorial emails with. But it doesn’t offer the ability to send, say, the transactional messages tied to a subscription. So the Sun-Times is using Revue in a really interesting way. They’ve made it their tool for all things editorial, but are using another ESP to handle transactional messages or marketing emails. Everything’s synced up through a central CRM, so there’s a single hub for all of their data. I think more newsrooms could learn from their example. You don’t have to have a single tool that does everything — you may be better suited by using specific ESPs for specific purposes.

This month’s Not a Newsletter is presented by Revue, an editorial newsletter tool for writers and publishers. Revue’s used by both individual writers and news organizations, like the Chicago Sun-Times, to send newsletters. If you’d like to give Revue a try, sign up for an account here.

For Your Reading List

  • This is a pretty big deal: Gmail’s starting to roll out BIMI, a tool that will allow anyone to display their logo alongside their brand’s “sent-from” name in the inbox. The BIMI rollout is in the pilot phase, and there are still some unanswered questions about how it’ll work. (For one: Gmail’s requiring companies to obtain a BIMI certificate, called a Verified Mark Certificate, but the two companies that will be granting these haven’t yet announced details about the cost of or process through which one can obtain such a certificate.) Still, BIMI’s going to be a big step forward for all of us, and I’ll try to get some answers about BIMI certification in time for the next Not a Newsletter.
    • I’ve also added some links in the Resources section at the bottom of the doc to help you make sure you set up the authentication tools (SPF, DKIM, and DMARC) that you’ll need to eventually deploy BIMI.
  • I wrote about this in my “25 Things” doc, but quizzes are a great way to engage an audience and then capture an email address. (As I look back on my time at BuzzFeed, one of the biggest mistakes we made was not using quizzes to drive email signups. We really missed the boat on that one.) Zapier’s Maite Mugica explained how to drive email sign-ups using quizzes.
  • So many of you have been asking about best practices around email deliverability. Take a look at this great set of rules for deliverability, from setting up an onboarding series to segmenting your lists — there’s a lot of great advice.
    • Tamara Bond of Dot Digital wrote about deliverability and Gmail. Many of these best practices shouldn’t surprise regular Not a Newsletter readers: Send only to your engaged readers, work to win back inactive subscribers, and let the ones who don’t engage go. The companies that do deliverability well are the ones that are careful and thoughtful about the emails they send. Do that, and you’ll do fine in the long run.
    • The team at Oracle held a webinar recently on key factors affecting deliverability, including some KPIs to monitor. The Oracle team is incredibly smart, so if you’re interested in deliverability, make an hour for this one.
    • And if you want to go even deeper down the deliverability rabbit hole, here’s a set of tips from Kickbox of some of the trickier issues that might cause deliverability problems
  • Switching gears: It’s encouraging to see more publishers experimenting with text messages as a channel for building relationships. The data from text isn’t quite what you get with email, but I think there’s an opportunity for many organizations to test and learn on this platform.
  • InsideHook’s Eli London put together a list of the 80 best single-operator newsletters today. (It’s a heck of a list — I even discovered a few new newsletters from it!) I talked with Eli for the piece, and one thing I did want to expand upon briefly here: Overall, I’m very bullish on the future of newsletters run by a single person. We’re only scratching the surface of what can be done with these products. Will everyone who starts one build a successful business from it? No, certainly not. But we’re already seeing plenty of success stories, and there will be even more to come in the years ahead.
  • Lenfest’s Joseph Lichterman and Ralstin Agency’s Carrie Porter gave an ONA talk about using your newsletters to learn about your audience. Lots of good advice in here!
    • Speaking of which: The European Journalism Centre’s Tara Kelly wrote about The Local Europe, a digital publication that used reader surveys to help build a paid subscription base of more than 11,000 readers.
    • And I loved this Splice story from Meghna Rao about a news site in India called Lokal that used user research to figure out how to best serve their audience. This sounds so simple, but so many news organizations forget to actually listen to their readers!
  • The Wall Street Journal announced a new newsletter, Elevate the Conversation, that’s being built on Substack. (The rest of the Journal’s newsletters are on Campaign Monitor, and they’re not suddenly switching all of their newsletters over to Substack. Substack doesn’t yet offer the integrations, APIs, or data that most newsrooms would need to make it their primary ESP.) It’s great to see a newsroom try something like this. The Journal’s just experimenting here, using a different platform to try out a more conversational style of newsletter. It reminds me of the experiment The New York Times did a few months ago with Google Docs. Sometimes, trying new tools or platforms leads to ideas that you can implement across the rest of your products, and I applaud these newsrooms for being willing to test and learn.
  • Also on the note of Substack: They’ve been rolling out a new pilot program, called the Substack Defender program, offering legal support for writers who might be under legal pressure due to the topics they cover in their newsletter. Huge kudos are due to Substack for stepping up to support their users — I think this is fantastic.
  • A few personal stories worth sharing:
  • The Nielsen Norman Group did some research into whether readers were more likely to respond positively or negatively to emojis in subject lines. Their research found that emojis hurt more than they helped. (Although, I should note, the research was done with a small sample size of 100 readers, and the readers didn’t necessarily have a relationship with the brands they were reacting to.) One finding I do agree with, though: Be judicious about your use of emojis. Don’t just throw one in to be ~fun~. Make sure that when you use them, you’re using them for a specific purpose.
  • Taxi for Email’s Bettina Specht walked through the simple code you’ll need to add background colors to your text. It’s a great way to add a little pop to any email.
  • Something just for readers who use Pardot: Here’s how to automate the process of removing spammy signups from Pardot.
  • My friend Grzegorz Piechota of INMA once gave me a great piece of advice: Sign up for emails from politicians. “You’ll learn a lot from them about how to convert readers and what messages convert best,” he said. Greg was right. I’ve read through many political emails this year — but the one I’m about to share is the best I’ve seen yet in 2020.
  • (I know I’m wading into murky waters by even sharing something about politics. I’m not endorsing a candidate — just this email strategy.)
  • It’s an email from Joe Biden. There’s a few things I loved about it:

1.) It’s a great piece of writing. You don’t often see opening lines like this: “The story I’m about to share with you about Joe Biden is special — in fact, I’m fairly certain I’m the only living person left who actually witnessed it firsthand.”

2.) Trust always comes before money. This email focuses on building a relationship, and only once they’ve done that do they ask you to donate.

3.) It includes a personal photo, the kind of photo that the writer’s had on their fridge for years, and that matters. This isn’t an endorsement from a celebrity — it’s from someone like you or me.

4.) The story prominently features the number 18 — chai, in Hebrew — so the first two donation asks are in increments of $18.

  • 2PM’s Web Smith wrote about a new collaborative effort among several prominent newsletter creators. It’s great to see a group of independent newsletter operators banding together to share ideas and stories — love this!
  • I’m not going to go too in-depth on this story from Digiday’s Kayleigh Barber about referral programs, other than to say, 1) I agree that there’s a big opportunity here for a lot of newsletters to use these for growth, and 2) Stay tuned to this doc for more on referral programs later this summer. 👀
  • This story from NPR about the collapse of NPR’s radio ratings is worth reading. (Full disclosure: I work with one NPR station through Inbox Collective, and more importantly, I’m a huge fan of NPR. I’m rooting hard for them to succeed.) Due to the pandemic, many NPR listeners aren’t commuting to work — and the commute is when these listeners used to listen to NPR. Here’s the key quote: 

“We’re experiencing a sea change,” said Lori Kaplan, the network’s senior director of audience insights. “We’re not going back to the same levels of listening that we’ve experienced in the past on broadcast.”

  • Whatever comes next, remember those words: We’re not going back. It’s not just the terrestrial radio world that’s saying that — all of us are facing a brand-new future.
  • And that may seem scary to you. Frankly, it is! But it’s also an invitation. The window is open for you to try new things: New formats, new ideas, new business models. The organizations that will thrive 3-5 years from now are going to be the ones that, right now, don’t get complacent and try something new. I can’t tell you which experiments are going to work, but I feel absolutely confident that the ground is shifting underneath our feet. You can try to hang on to what used to be, or you can work to build whatever needs to come next. It’s up to you.
  • Speaking of newsletter experimentation, I did want to mention a few promising new monetization opportunities I’ve seen recently. There’s so much excitement right now around paid newsletters, but there are plenty of other ways to get paid for your newsletter.
    • Dan Runcie, who writes Trapital, a newsletter about hip-hop, announced that he was ending his paid membership program. Instead, he’s pivoting towards consulting. We’re in very different lanes (at least when it comes to content), but what Dan is doing is so similar to what I’m doing here with Not a Newsletter, which is still the no. 1 driver of new client work for Inbox Collective. I really like this move for Dan.
    • Girls’ Night In announced a new membership program, called The Lounge. Again, this is super smart: At a time when it’s so hard to network, the GNI team is building a way for their members to connect. Add a membership on top of their existing revenue streams — advertising and affiliate links — and you’ve got a really strong business.  
    • Lastly, take a look at what The Juggernaut is doing in Asia. They don’t do advertising in newsletters, but are pushing in the direction of partnerships. Experiments like these are going to open opportunities for a lot more of us in 2021 and beyond.

Stuff I Loved This Month

  • If you’re thinking about launching a digital news startup in the not-too-distant future, check out the Google News Initiative’s Startups Lab. It’s for anyone in the U.S. or Canada, and the team here — led by Phillip Smith — is fantastic. It’s a pretty incredible opportunity, and you can apply here.
  • Wondering if that copy you grabbed from a Google Doc might have some unwanted code hidden inside? Check out Taxi for Email’s “What does it paste?” tool. It’ll show you the extra code you don’t want to drop into your email.
  • An internet trend to keep an eye out: There are now a bunch of different sites trying to become the discovery engine for newsletters. 
  • The new Quartz homepage is… well, basically a newsletter! I do like the idea of a homepage you can actually finish — one that’s not just an endless scroll of stories. It’s a pretty unique concept, and I love that they’re using the learnings from their (very good) newsletters to inform the web experience.
  • This New Yorker Daily Shouts piece from Margalit Cutler is called “Sending Tony an E-mail,” and it’s perfect.
  • Over the course of the past year, I’ve gotten the chance to talk with a few hundred Not a Newsletter readers, and it’s always so exciting to see what comes from these conversations. Here’s one I wanted to share with you: Mansi Gupta runs Unconform Studio, a design shop trying to create more equitable workplaces for women. When we talked about the Unconform newsletter, I had a suggestion: Create a lead magnet — some sort of downloadable guide — that readers would be excited to read, and trade an email address for a free download. What I didn’t expect is that a few weeks later, Mansi would put together such an incredibly detailed, actionable guide to helping organizations improve gender equity. It’s great, and worth signing up for!
  • A great example of a pop-up newsletter out in the world, from an unexpected source: The YWCA of Utah put together a 21-day challenge to understanding the deeper issues behind racism in our modern world. It’s excellent — but I wish they’d built it as a Course (in which you could sign up today, tomorrow, or next year and get the full series) instead of as a pop-up!

The Google Docs Anonymous Animal of the Month

One of the quirks of publishing in a Google Doc is that when readers like you visit, Google identifies you as an animal in the top right corner of the doc. So to close out this edition of Not a Newsletter, I want to spotlight one of the Google Doc animals in a feature I call… the Google Docs Anonymous Animal of the Month! This month:

the anonymous walrus

I’m not going to hide my love of walruses. (Side note: Big shoutout to whoever on Quora asked if the plural should be “walri.” I wish that was a thing.) They’re gigantic, they have huge tusks, and were into mustaches long before Tom Selleck came around. A few things you might not know about the walrus:

  • A group of walruses is actually called a herd.
  • The word walrus comes from the Dutch words meaning “whale horse.” In Latin, their name is Odobenus rosmarus, which is Latin for “tooth-walking seahorse.” Point is: In just about any language, walruses are being oddly compared to horses.
  • The size of a walrus’s tusks can determine social status — and tusks can sometimes be more than 3 feet long. But those tusks are also what walruses use to help lift themselves out the water and onto land. (Hence the “tooth-walking” name in Latin.)
  • Most importantly: There are many, many excellent versions of The Beatles classic “I Am The Walrus,” but nothing quite compares to the version that Jim Carrey recorded with Beatles producer George Martin. (“I have defiled a timeless piece of art,” Carrey sings at the end, although I rather enjoyed it ¯\_(ツ)_/¯.)

Anyway, the walrus! That’s your Google Docs Anonymous Animal of the Month. 

Here's a decorative image of three animals: An owl, a flamingo, and a seahorse

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By Dan Oshinsky

Dan runs Inbox Collective, a consultancy that helps news organizations, non-profits, and independent operators get the most out of email. He specializes in helping others build loyal audiences via email and then converting that audience into subscribers, members, or donors.

He previously created Not a Newsletter, a monthly briefing with news, tips, and ideas about how to send better email, and worked as the Director of Newsletters at both The New Yorker and BuzzFeed.

He’s been a featured speaker at events like Litmus Live in Boston, Email Summit DK in Odense, and the Email Marketing Summit in Brisbane. He’s also been widely quoted on email strategies, including in publications like The Washington Post, Fortune, and Digiday.