Welcome to the May 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 the next edition goes live!
This month, I’ve got a brand-new feature for you in the Google Doc: Ask a Deliverability Expert, where Yanna-Torry Aspraki will answer your biggest deliverability questions! Plus, you’ll find:
- Tips and tools for driving more ad revenue from newsletters.
- Several fantastic reader revenue success stories from newsrooms.
- Thoughts on Spotify’s and Apple’s big announcements in the podcast space.
..and more!
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 the full archive at this link.
-Dan
This Month in Email Headlines
- ActiveCampaign raises $240M at a $3B valuation as marketing and sales automation come into focus for SMBs (TechCrunch)
- Klaviyo Raises $320 Million, Doubling Its Valuation To $9.5 Billion In Seven Months (Forbes)
- SparkPost Acquired By Communications Platform MessageBird For $600 Million (MediaPost)
- Taxi for Email is joining the SparkPost family (Taxi for Email blog)
- For those who might think there’s a typo above: Yes, Taxi for Email was recently acquired by Sparkpost, which was recently acquired by MessageBird…
- Piano raises $88M for analytics, subscription and personalization tools for publishers (TechCrunch)
- Mailchimp moves into e-commerce (TechCrunch)
- Native in Email: Blueprinting the Future for Publishers (AdMonsters)
- Verizon sells AOL and Yahoo for about half of what it paid (Verge)
- As Al Iverson points out, we’re still waiting to see what effect this might have on the second-largest B2c email provider in the U.S.
- HelpSystems expands email, cloud security portfolio with acquisition of Agari, Beyond Security (ZDNet)
- For Mother’s Day, More Brands Are Letting People Opt Out This Year (NPR)
- And on a related note: Mother’s Day Opt outs may have unintended side effects (Email Snarketing)
- Changes to the Spam Act in Australia (Dotdigital)
- LSD, Cargo Shorts and the Fall of Justin Zhu, the High-Flying Tech CEO of Iterable (Bloomberg)
- As subscriber growth slows, The New York Times reveals 100 million registered users (CNN Business)
- The real people of Substack: 12 newsletter writers detail how much money they’re making on the platform (Insider)
- Why Is Everyone Talking About Newsletters? (WAMU’s 1A)
- What Substack Is Really Doing to the Media (Slate)
- On Substack, You Can Never Go Too Far (The Atlantic)
- Creators are making money selling Google spreadsheets (Mashable)
- Mighty Networks raises $50M to build a creator economy for the masses (TechCrunch)
- To Ratchet Up Retention, the Financial Times Restructures Its Consumer Revenue Team (Adweek)
- Fifty new outlets, 250 journalists: Canadian startup unveils plan to revive local news (The Guardian)
- Flipboard shifts from programmatic display ads to selling newsletter sponsorships (Digiday)
- Telegram adds new features for payments and Voice Chats in latest update (Windows Central)
- Microsoft: Office 365 is blocking emails from Google, LinkedIn domains (Bleeping Computer)
- Google Tests Ad Relevance Survey In Gmail Desktop (MediaPost)
Introducing… Ask a Deliverability Expert
I get a lot of questions about deliverability, and I don’t always have the right answers. But I know someone who does: Yanna-Torry Aspraki, a true deliverability expert. She’s been working in the email space since 2014 in all sorts of roles — at ESPs, with brands, and as a consultant. She really knows her stuff!
So let’s get to this month’s question:
💌 💌 💌
I’ve heard that if an email has too many images in it, it’s probably going to end up in a reader’s spam folder. Is that true?
Are your image-heavy emails affecting your deliverability? Let’s find out together.
For Your Reading / To-Do List
- There’s been a real boom in tools to help sell newsletter advertising — especially for individuals or smaller teams. On BuiltIn, Hal Koss interviewed some of the companies working to drive revenue for newsletters. As noted here, the three biggest challenges when it comes to email advertising: Simplifying the workflow (so someone can book an ad in as few steps as possible), helping creators set the right pricing, and helping advertisers understand how an ad performed (and even what the metrics mean — many advertisers don’t fully understand if an ad performed well or not!).
- A few general rules of thumb, if you’re an individual or a small team selling email ads:
- Most newsletters are starting to shift to a CPM rate based on opens — how much it costs for every thousand readers who open the email. So let’s say you have 10,000 readers, and a 30% open rate. A few years ago, you would’ve seen most newsletters selling based on list size. Now, advertisers are looking more for engagement: How many readers actually open that newsletter and see the ad?
- These CPMs vary wildly — I’ve seen numbers anywhere from $5 to $50 per thousand opens.
- Here’s how you’d calculate the price for the ad:
- So for the example above, that’d leave you with this: 3 times whatever your CPM is.
- In that example, if you’re on the low end for CPMs, that ad might only be worth $15 per newsletter. On the high end, it might be worth $150.
- Again, these are general rules of thumb. Many newsletters charge flat rates for advertising that are much higher than this, and some feature ad products, like classifieds, that are far less expensive. If you’ve got questions about how to price ads, my inbox is always open: dan@inboxcollective.com.
- Sue Cross, executive director of the Institute for Nonprofit News, wrote an open letter to Substack asking them to consider offering a donation option for non-profits — not just a subscription option.
- ConvertKit’s Kayla Voigt interviewed Bonnie Christine, a fabric designer who’s built a successful business thanks to her email list. I especially love what Bonnie’s done with her lead magnets: She’s used a combination of downloadable guides, Courses, and paid acquisition to grow her list — and then deepens engagement through a welcome series. And you better believe I loved this:
While Bonnie uses plenty of automations for her campaigns, this wasn’t one of them. Sometimes, the things that don’t scale really can pay off. “We were sending over 500 emails a day because we personally responded to every single email that came in. We were drowning in emails, but it was worth it,” she says. “Several people have been surprised that we responded.”
- And on a related note: For MarTechToday, Ryan Phelan explained why it’s so important to make time to reply to customers. As Ryan points out — and as I’ve mentioned here before! — if you’re not making time to talk with your audience, you’re missing out on an opportunity to learn (and potentially to make a sale!).
- Fascinating case study here: In January, Aha Media Group, a content marketing agency for the healthcare space, announced that they were ungating all of their content on their site — you wouldn’t need to enter an email address to get access to their content. Three months later, they shared the results with Ann Handley: Not only did they see a 143 percent lift in pageviews compared to Q1 2020, but they also saw a 55 percent increase in email signups.
- And this is where I’ll make my plea, again: What works for one newsletter may not work for you! Some sites see amazing results via registration walls and lead magnets; others do far better with pop-ups, events, referral programs, contests, or any number of other sign-up tools. Don’t assume that what works for another newsletter will work for you — test, test, and test some more, and see which strategies actually make sense for your newsletter!
- I just loved this blog post, from Deborah Augustin of The New Naratif, a newsroom that covers Southeast Asia. In a story on Splice, she detailed how she surveyed her audience to better understand what made them likely to convert and support her newsroom. And better yet: Her research included actual calls with readers! This is something I’ve encouraged several clients to do — yes, it takes more time, but the lessons you learn from these 1-to-1 calls might change the way you market your product.
- Simon Owens talked with the team at Crikey — an Australian newsroom — about how they’ve built a subscription business thanks to their smart investments in email. I’m more than a little biased here — I’ve worked with Crikey through Inbox Collective on their email strategy — but I think Crikey does an outstanding job of using registration walls and newsletters to grow their paying audience, and I was really happy to see them detail that strategy here.
- And if you want to learn more from the Crikey team, Jane Mahoney, their head of reader revenue, is doing a series of podcasts with Splice about building out a reader revenue strategy. You can listen to the first one here.
- Speaking of reader revenue: I loved this story, from the recent INMA Master Class on Digital Subscriber Retention, about the South China Morning Post. In less than a year, they’ve built out a series of email automations to target readers at every part of the funnel. (I do mean *every* part of the funnel — just look at the slide below.)
- Here’s an absolutely lovely story from Mia Sato of MIT Technology Review about Epicenter-NYC, a newsletter that’s not just been reporting about vaccinations in New York, but also helping its readers schedule vaccine appointments. As S. Mitra Kalita, founder of Epicenter-NYC, explained:
“Inevitably, the question I get is ‘Is this the role of a journalism organization?’ The essence of what we are describing is [a method] for these people to prove that they are human. In some ways, there is no greater purpose of our journalism.”
- As we see more newsletters pop up to serve specific communities, it’s worth asking: What’s the role that we can play right now to serve our readers? As Epicenter-NYC has shown, it may go well beyond what organizations like yours have done in the past.
- Thinking of launching a referral program for your newsletter? Sparkloop’s Louis Nicholls walked through a few rewards that aren’t physical products (t-shirts, coffee mugs, tote bags, etc.). From shout-outs to Courses, there are a few ideas here worth exploring.
- Here’s a quick behind-the-scenes look at The GIST, which uses segmentation in two interesting ways: To customize an onboarding journey based on a reader’s location, and to dynamically customize the content of a newsletter based on their interests.
- Oracle’s Peter Briggs explained how to build a really great preferences center. I know, this doesn’t sound like the most exciting topic — but if you’re a big publisher or in the eCommerce space and you haven’t optimized your preferences center, you’re missing a chance to win back readers who might otherwise leave! Peter’s got a few examples here to help.
- The next time someone emails to ask, “How do I get out of the Promotions tab and into the Primary Inbox,” I’m just going to send them this blog post by Andrew Barrett, the Director of Deliverability for Braze. Here’s the crucial part:
To get into the Primary tab, marketers must send mail that is at least as important to the recipients as any other message already in their Primary Tab.
That might not be the advice senders are hoping to hear, but it’s really the only meaningful way to think about Primary tab placement. There is no “one weird trick” that senders can use for instant results.
- Big shoutout to the teams at ActionRocket and Beyond the Envelope™, who are putting together resources about email accessibility through a new project, called Email for All. If you have a few minutes to take their survey, do so here, and if you want to read accessibility best practices from Paul Airy of Beyond the Envelope™, that link’s here.
- If you’re sending a ton of email to readers with AOL, Outlook, or Verizon emails — and if you’ve got a list of 100k or more, you probably are! — make sure you check out Verizon’s new developer portal for email. They detail opportunities for AMP, BIMI, and even tactics for making sure that messages around sales, deals, or receipts get read.
- Long-time readers of the Google Doc know that I absolutely love a good email Course. GQ’s Stephanie Talmadge shared the story behind their 17-day How to Do More Push-Ups course. Two fun notes here: Half of all subscribers were brand-new to GQ’s emails, and they found that this course was very effective at converting readers on social media over to their newsletters.
- On the Active Campaign blog, the team at Bonjoro — an Australian company in the video space — shared a few lessons about deliverability. From driving email replies to running reactivation campaigns, there’s a lot here that’s worth learning from.
- Good stuff here from David Bauer, of The Weekly Filet newsletter, about lessons from 10 years of writing a newsletter. If you’re a beginner in the email space, make sure you note David’s lessons.
- Ali Abouelatta, who runs a newsletter called First 1000 — about how companies got their first 1,000 customers — detailed the road to his first 2,000 subscribers (and then the road from 2,000 to 10k here). I’ve said this many, many times before, but for a new newsletter, creating original content and sharing it (and making sure there’s a clear call to action to subscribe to your newsletter!) is almost always the first strategy to start with.
- For those who work in eCommerce, make time for this comparison of Mailchimp vs. Klaviyo, from Kelsey Donk of Marketer Hire.
- Great stuff here from Laura Bosco of The Good about how to create delightful emails after someone purchases something from you. Those post-purchase emails get super high open rates — don’t miss out on your chance to engage with a subscriber while you have their attention!
- At The Next Scoop, Uplers’s Kevin George detailed a few strategies for great email copywriting. This recommendation is particularly spot on: To convert readers, focus on the benefits of your product, rather than features you offer.
- And on a related note: As Carolyn Nye of Practical eCommerce wrote, when you’re building your funnel, don’t forget about targeting readers who drop out along the way. Those include readers who stop opening emails, readers who open but don’t click, and readers who make it to the purchase page but don’t complete the transaction. There are opportunities here to build emails — both one-offs and automations — to convert each type of reader.
- It’s never too early to start thinking about planning your email campaigns for the holiday season. (Seriously, now’s the time to start making plans. Don’t wait until November to plan!) The team at InboxArmy detailed the email strategy they used to help one eCommerce company increase holiday sales by 120 percent last year.
- A few links from the creator space:
- Mario Gabriele of The Generalist put together some slides detailing his growth in Q1 of this year. If you want an under-the-hood look at the stats of a successful subscription product, give this a read.
- Shoutout to Charlie Warzel, who left the New York Times to start a subscription newsletter, and is already having to answer the age-old question: Why didn’t my newsletter become a million-dollar business in its first month? (Charlie has merely generated tens of thousands of dollars of annual recurring revenue in his first few weeks as an independent writer.)
- The news that made headlines for most was: “Facebook plans to go after Clubhouse — and podcasts — with a suite of new audio products.” The news that made headlines for me was: Mark Zuckerberg announced it live on Sidechannel, a Discord community started by several newsletter creators.
- On the Digiday podcast, Emily Atkin of Heated shared lessons in year two of running her newsletter, which was (and continues to be!) one of the early success stories from the subscription newsletter world.
- Newsletter Crew’s Ali Montag interviewed The Half Marathoner’s Terrell Johnson about how he built his newsletter audience. I particularly appreciated his advice about avoiding burnout. And Alicia Kennedy, who also has a subscription newsletter, wrote about the struggle to come up with new ideas.
- Good stuff here from Victor Ijidola on the GetResponse blog, who laid out 10 product landing page templates that actually convert people to your email list.
- Really enjoyed this, from Matt Taylor, who looked back on his work on the product team at the Times (the London one) — specifically, on five years of publishing a daily edition there. To be honest: Until I started working with international news clients, I didn’t think much of these daily edition products. In the U.S., these are often .pdf replicas of the print version, and they’re difficult to use. But in Europe, particularly, they’re a completely different experience, and one with lots of similarities to newsletters. In this piece, Matt talked about how they built habit with the Times’s editions.
- There were a few big announcements in the podcast space that tie back to the larger subscription economy, and they’ve got implications for the world of email:
- Let’s say I decide to launch a new news product for my neighborhood, and call it The Midtown Times. I’m building a subscription business, and I decide to launch a podcast just for my paying subscribers. Right now, trying to distribute that subscribers-only feed is a pain — often, it involves sharing a private RSS feed to my readers, and spending a lot of time educating them about how to access the podcast. Not great!
- But Spotify recently announced a big change, as Ben Thompson of Stratechery reported: It’s going to build a new workflow to support subscription products using oAuth, a tool you’re probably already familiar with, even if you might not know the name. (If you’ve ever logged into a website using your Google or Facebook credentials, you’ve used oAuth.)
- Here’s how it might work for my readers at The (hypothetical) Midtown Times: When a reader goes to access subscriber-only content on Spotify, they’ll be prompted to log in with their Midtown Times username and password. With a click, oAuth will let Spotify know that this person is a paying supporter of mine, and they’ll get access to the premium audio feed. No more private RSS feeds — all it’ll take is a click!
- And the really, really interesting part: Per Stratechery, Spotify says they’ll host this content for you, but will take no cut of revenue. (The key quote from Spotify’s Gustav Söderström: “Having all of audio on Spotify means meeting independent creators on their terms, not ours.”) You can create that podcast for subscribers, host it on Spotify, let subscribers access it with a single click — and not give up any revenue in the process.
- So this really opens up some interesting possibilities for creators or newsrooms! Trying to figure out new, exclusive benefits to offer subscribers, members, or donors? A supporters-only podcast might suddenly be one of them. Nathan Baschez of Every wrote a bit more about the opportunities here.
- There’s still significant work to do here. The ESPs and CRM systems that power these subscription products (Substack, Ghost, Mailchimp, ConvertKit, Pico, and so on) need to set up the oAuth integration with Spotify to allow you to publish private audio feeds just for your supporters. But Spotify’s laying the groundwork to make that possible.
- But that’s not all! Spotify also announced that if you don’t have a paid product elsewhere, you could launch a subscriber-only product through Spotify — they won’t take any fees until 2023, and then 5 percent of subscription revenue after that. Apple also announced a push into the subscription podcast space — though they plan on taking a larger cut, 30 percent to start, later dropping down to 15 percent, somewhat like they do with the paid apps in their app store. Nieman Lab’s Joshua Benton had a good explainer about what this means, and the potential upside for publishers.
Stuff I Loved This Month
- Jessie Willms of The Globe and Mail and Shelby Blackley of Indiegraf launched WTF is SEO, a newsletter with SEO tips for journalists. I’m writing something about this for later this spring, but with all the growth of Not a Newsletter, I’ve been surprised that other publications haven’t popped up to serve reporters around search, social, and other key topics. Kudos to Jessie and Shelby for creating this — and if you’re looking for a starting place, their guide to headline writing is particularly good!
- Writer Will Oremus shared a clever hack for anyone who subscribes to a lot of newsletters: He turned the “Forums” tab in Gmail into a newsletter-only folder.
- If you’re curious how I manage my inbox: I’ve been using a tool called SaneBox for nearly a decade. It allows me to set up custom folders in Gmail — in fact, one of the secrets of Not a Newsletter is that I have a folder set up just for newsletters that I use to discover links for this Doc! And it does a remarkably good job of keeping the emails you want in your inbox, and putting everything else in other folders for you to check later. If you want to give it a try, here’s a referral link you’ll use to get $25 off. (It costs $99 for a two-year subscription.)
- Looking for a Zoom background that shows off your love of email? Designer Najmah Salam has you covered. (The spam devil is my personal favorite.)
- I don’t quote internal memos all that often, but I loved this line in the New York Times’s announcement that Choire Sicha was joining their newsletter team: “Newsletters are the internet’s oldest and newest format.”
- I think this might be an internet first: Elan Kiderman, who runs the product team for The Marshall Project, launched a newsletter designed to go straight to your spam folder. (It’s about odd corners of the internet, and he told me he’s taken real steps to make sure it goes to spam — which is actually harder than you’d expect!)
- The Wall Street Journal’s website turned 25 last month, and I loved this look back at the evolution of their homepage through the years.
- I’d heard the story of The Black List, a yearly roundup of the best screenplays in Hollywood. What I didn’t know until I watched this TEDx Talk, from Franklin Leonard, creator of the project, is that it all started with an email.
- Chuck Geschke, the man who invented the .pdf, died last month. Do read his obit — his was a fascinating life.
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:
- From the mid-1600s through the 1800s, beavers in North America were hunted for their fur, nearly to the point of extinction. Canada’s Hudson Bay Company even had their own currency, “Made Beaver,” that valued goods against the standard of a single beaver pelt. In 1733, for instance, one Made Beaver would buy you one hat, two ice chisels, or eight hawk bells.
- But in the early 1900s, new environmental protections helped the beaver population start to grow again. Today, their numbers are back to levels that precede the arrival of European settlers in North America.
- A family of beavers is called a colony, typically consisting of a handful of beavers. These colonies, as you’re surely aware, live in homes that they construct, called dams — the largest of which is about a half-mile long. (You can even find it on Google Maps. Naturally, it’s in Canada.)
- Beavers secrete a substance called castoreum, which smells a little like vanilla. Naturally, that’s led to some internet rumors about companies using castoreum in household products. For more on the topic, I recommend this very real Snopes headline, “Does Vanilla Flavoring Come from Beaver Anal Secretions?”, and this equally real Vice headline, “A History of Flavoring Food With Beaver Butt Juice.”
- The CBC reported last month that nearly a thousand customers in British Columbia, Canada, lost internet access when beavers accidentally chewed through a cable carrying internet to a local community. A spokesperson for the internet company, Telus, called it a “very bizarre and uniquely Canadian turn of events.”
Anyway, the Beaver! That’s your Google Docs Anonymous Animal of the Month.
That’s all for this edition! Want to be notified when next month’s edition of Not a Newsletter is live? Sign up here: