Is your newsletter a path to reader revenue success, or a dead end?

birds on a wire

We must do a better job of selling journalism. Your livelihood depends on it. Our communities depend on it.

“But Cory, you say, I’m a [your title here]. I’m not a sales & marketing person.”

I know! That’s why I want to help guide you to an easier road to reach your goals.

Being a journalist in 2019 is hard. Getting people to pay for journalism in 2019 is damn hard. That’s why it’s important to be good at selling your work. Journalism isn’t going to sell itself.

For a lot of people — paying for journalism isn’t self-evident. They have read all this free content for a while.

Where did readers get the idea that news should be free?

Last fall, I signed up for 99 totally free newsletters. Didn’t pay one silver dime. I’ve read some interesting stories from all over the country. It’s pretty great.

Additionally, 96 of those 99 newsletters said I should follow on Facebook, Twitter or Instagram. Those platforms are all free to catch up on news.

To be clear: I’m not saying you shouldn’t use social media. But for many publications, a reader can get enough free information to feel satisfied — from the publication itself!

That’s a lot of news and information. All for free. All from original publishers.

People didn’t dream up the idea that news is cheap. They’ve experienced an all-you-can-eat buffet of free news for two decades now.

But we know the real story. Journalism isn’t cheap. It’s an expensive enterprise, and it’s getting harder as a business every year.

The importance of selling your journalism

I love seeing more newsrooms moving toward reader revenue. The hard part is that you can’t flip a switch to make the change. Building loyal audiences takes a different strategy than getting more clicks. You have to change your strategy to connect with people in a different way.

You have to sell the work.

Think of it this way. If a new friend asked you why they should pay for a subscription, would you tell them some good reasons?

Or, have you ever posted a link on Twitter or Facebook asking people to subscribe?

That’s selling your work! The difference is that I don’t want you to ask people to pay for your work. I want you to give them a compelling reason to pay for your work.

A lot of journalists see business functions as outside of their responsibility. I’m not saying remove the wall between editorial and business. I’m saying your newsletter can be a great place to sell your work. The Seattle Times found that readers referred by a newsletter are 25x more likely to subscribe than a Facebook referral.


Set ’em up and knock ’em down

Here’s a great email to get inspired by. It’s so good at guiding the reader to where you need them to go. I’ll even give InsideClimate News a pass for violating an important newsletter rule: Don’t use the “Dear Reader” intro.

One thing that makes this so great is it follows an old copywriting rule: What’s the job of the first sentence? To make you read the second sentence. What’s the job of the second sentence? To make you read the third sentence. Check this out:

InsideClimate News fundraising email
  1. Chances are ICN readers are more inclined to buy a smaller, more efficient car. This subject line “Remember when we were all going to drive small cars again?” introduces tension between what was supposed to happen — and what is actually happening. Open!
  2. A bold vision a year ago. You can feel the “but…” coming. This opening sentence gets you to read the next sentence.
  3. General Motors isn’t keeping their promise, and it’s making things worse? How bad is it?
  4. Here, ICN does two important things: (1) bold the outrage-inducing number and (2) link to their coverage to give more details about what this means. The bold and the link are visual cues.
  5. Boom. ICN is telling you that they have your back. Strong and sharp: “No news outlet is bringing clarity about the climate crisis, and those responsible for it, like InsideClimate News.” That’s powerful. It makes me want to stand up and pump my fist when I read it. They are not asking you if you value journalism. They are not asking you if you have thought about supporting their journalism. They are telling you to give them money so they can kick a polluter’s ass.
  6. “We need you to be our 1 in ten!”. That seems pretty achievable. They don’t need 50,000 people, they need one.
  7. Big easy to spot button dying to be clicked on.

What purpose does your newsletter serve?

Take a minute to think about that. It’s not a trick question, but it’s a question that trips a lot of smart people up. It’s really two questions in one.

  1. What purpose does your newsletter serve for your newsroom?
    This will depend on your business model and newsletter strategy.

A few common answers:

  • A tool to develop a deeper relationship with your readers.
  • Part of a strategy to convert more readers to paying subscribers, members or donors.
  • Increase reach and distribute your stories to a wider audience.

Got your answer to the first question? Good! Here’s the second question:

2. What purpose does your newsletter serve for your readers?

The answer to these two questions may be different, but they need to be facing in the same direction. For example, what if your purpose is to convert more readers to paying members, but your readers see a free way to catch up on the stories of the day? Sounds like you have a problem. Do your metrics show you are converting readers?

No need to get fancy: Short and to the point examples

Make it clear as day and super obvious like The Colorado Sun: “Three Ways to Help The Sun”.

The formatting is helpful, too. Each item is numbered, bold and includes a link. Tells you exactly what they want you to do. Disclosure: I supported the Colorado Sun’s Kickstarter campaign, although I am not a current member.


Julia O’Malley writes Anchorage Eats, the food newsletter for Anchorage Daily News. Each week, she signs off and includes a link to subscribe.

Alaska Eats closing subscription ask

Alaska Eats gift subscxription ask.

Alaska Eats subscription ask

What I love is that each week, it shows some personality while tying back to the great work going into the newsletter. The Tang comment is a bit of an inside joke, referring to Julia trying to remember a Tang drink from her childhood.


The Texas Tribune does a solid job of connecting the dots.If you love the newsletter — you will know who you are — then show them with a donation.

Here’s the flipside: Texas Tribune launched a much-ballyhooed membership push last year, yet they haven’t asked me to join a handful of times: in the first email, one month after signing up, and twice at the end of the calendar year for those last minute deductions. Not a peep about their membership program in 3 months since.


Show your readers what you want them to do

You need a plan for what you want people to do. Then you need to show them what you want them to do.

  • If you want people to buy your product, sell it to them.
  • If you want them to join your membership program, show them the benefits.
  • If you want your newsletter subscribers to attend an event, invite them.

If that sounds like oversimplification, think about how many notifications you get every day. Plus emails. Plus text messages. It’s a lot of information. People don’t know everything you think they know. Guidance helps.

The reader’s next step may be different for different newsletters. In most cases it should be. The key is to be as clear as possible with the goals of your newsletter in the planning process. Be deliberate and specific about what outcomes you want from your newsletter.

The clearer you are, the easier it is to visualize the path from stranger to customer.


Don’t give bad email.

This is bad email. There are no notes on it, because it lacks any useful information. It also doesn’t tell me what it wants me to do, or where to go.

Marshall Project fundraising email.

The worst part is this email is a waste of my time. Emails this bad are telling me I can ignore emails from Bill Keller. They provide no content and no value.

Not to be outdone apparently, Marshall Project founder Neil Barsky send me this email almost two weeks later (there were some better ones in between).

Second Marshall Project fundraising email

Again, what do you want me to do? This email points out The Marshall Project is “entirely donor-funded”, but it doesn’t ask me for money.

This close-the-deal paragraph is especially odd. How do I “participate further” in your mission? I haven’t participated at all. Do you need money? Do I need to share something? Call my Governor? I have no idea.

This last sentence is a doozy. No one wants to “engage” with another person, much less an organization. Talk like a human, not a conference panelist. People may want to talk to journalists, or ask them questions. Use familiar words.

The important thing to remember is that I’m not a normal reader. I read these and break them down to analyze how they work (or don’t). Normal readers won’t give this a half second of extra thought. They will delete and forget you ever emailed.


Visualize the path from reader to customer

The most common visualization for how a stranger becomes a loyal customer is the purchasing funnel. If you’ve been to a conference lately or a webinar, you’ve heard of the funnel. Some people use a pipeline or a ladder.

No matter the shape, it’s all the same idea. In 1898, E. St. Elmo Lewis created the AIDA model. The letters in AIDA stand for Awareness, Interest, Desire and Action. In each stage, the number of people decreases, so the Funnel is narrower at the bottom than the top.

The Purchase Funnel

Funnels are useful for planning your strategy to get new readers and convert them to paying customers.

There’s one problem with funnels that fools even experienced marketers. Liquid moves through a funnel because of gravity. You don’t have to do anything, it just happens.

Customers don’t work that way.

Customers need to be persuaded to move to the next step. They aren’t whisked away by gravity. You have to guide them.

Give your potential customers a friendly nudge

Have you ever lined up a bunch of dominoes to trigger a chain reaction? If you spaced them too far apart, it didn’t work. And if you bumped your domino masterpiece too early, well…


Instead of a funnel, let’s try another visualization. Think of each step a person takes from total stranger to happy paying customer. Imagine each step as a standing domino. We have a series of steps as dominos standing next to one another.

The first domino needs a nudge to knock it over. If we set them up right, each domino falls forward. This creates a nudge for the next domino, which knocks it over. Like this:


People need a nudge to get from Awareness to Interest, another nudge to get from Interest to Decision, and so on. You have to provide the nudge, otherwise people don’t know where you want them to go.

If you don’t nudge people, they are likely to stay right where they are. A few people will take the initiative to figure out how to give you money for your work, but most won’t.

There’s been a lot of ink spilled about subscription fatigue. I’m less concerned about that. You aren’t competing with the New York Times, and you aren’t competing with Netflix.

You’re competing against inertia.

Leverage your newsletter relationship to encourage reader revenue

24 of the 99 Newsletters didn’t mention how to support their work in the after I signed up. Never brought up how to give them money. Not through a paid subscription, not through a donation for nonprofits. Nothing.

19 of the 99 Newsletters included a button or ad, but no sales pitch.

5 of the 99 Newsletters mentioned how to support their work in the Welcome Email, but didn’t bring it up again.

That’s 48% of the 99 Newsletters who didn’t try to convert me from a free newsletter subscriber to a paying customer.

I’m shocked.

It’s damn hard to avoid intrusive subscription pop-ups and paywall reminders on news websites. But there is virtually no attempt to drive more readers to subscribe in the newsletters.

Longform newsletters are getting more popular. They spend 500-1000 words — or more — each edition. Yet how many take a few sentences to nudge people to pay for the main product once a month?

A “subscribe” button ain’t gonna cut it. Mailchimp says Media & Publishing averages a 4.55% click rate. How many of those are on a Subscribe button rather than a story link?

If I’m dead wrong and you have numbers to prove it — shoot me an email. I’m happy to share your story.


Be excellent to each other

ProPublica Illinois and Block Club Chicago partnered on a fantastic project analyzing parking ticket disparities around Chicago. Both newsrooms are nonprofits. Block Club is reader supported with a paywall, but ProPublica Illinois has no paywall. Look at how ProPublica shared the spotlight with their partners:

Not only did a Block Club reporter write the intro, but ProPublica gave space to sell Block Club’s work! We need more collaboration and sharing like this. The more people pay for great journalism, the easier it gets to sell. Disclosure: I am a Block Club Chicago member. I worked at ProPublica in 2017.


Scolding people isn’t a strategy.

One last important point. Scolding people who don’t pay isn’t selling. Scolding people who question why they should pay isn’t a strategy.

It might make you feel better for a fleeting moment. But it’s going to hurt you in the long run.

Do Costco servers with free samples scold customers who don’t buy the product they are promoting? Of course not. They are there to promote and educate people on the product. It’s an introduction. The first step in a potential new relationship.

If people handing out meatballs on toothpicks aren’t scolding people who don’t buy a box, then why are we scolding people who don’t pay for articles we share?

Should we scold a person who had to work and missed a zoning meeting, so they rely on our coverage?

Should we scold people who go to the library and read the articles there — for free?

Should we scold the obnoxious daily Facebook commenter who complains about the paywall? Absolutely not.

Maybe he’s an asshole. But maybe he’s broke. Or poor.

Even if he really is an asshole, don’t scold. There are too many people reading that don’t know he does this every week he annoys you. It’s likely they will see you as out of touch or rude.

This is an opportunity to sell your work. Nudge the lurkers and the frequent friendly commenters. And share where your work can be read for free — like the library. There are probably people who don’t know and are afraid to ask.

You may not get a new subscriber every time. But you’ll get more in the long run than if you scold people who complain.


Featured Photo by Slava Bowman on Unsplash

Keep your newsletter strategy simple, or you risk feeding the beast

A puppy stand-in for the beast

There’s a lot to consider when you think about launching a new newsletter, or revamping an existing one.

A lot of advice I’ve seen out there starts with something like “what type of newsletter do you want to create?” and goes on to describe several different formats. Long form. Short form. Hybrid. Pop-up.

Some advice puts the cart-before-the-horse with topics like who’s going to produce the newsletter or how to monetize.

This is 100% backwards.

Form follows function

You can’t decide your newsletter format, writing style or even content until you decide what outcomes you want. You can’t pick the right metrics or key performance indicators (KPIs) either.

The biggest challenges aren’t technical. They need simplifying.

I’ve seen plenty of smart people stumble on this first part. It’s easy to get excited about a new idea and failure is scary. That’s why I help newsrooms develop processes to reduce that risk.

Strategy only works when you define the outcomes and measure what happens. If you don’t define success before you start, you’ll never know if you were successful.

Far too often, I see people say, “let’s launch this new thing” without specifying what the goal is. Then they cherry pick the metrics that look great while ignoring the less impressive results.

Don’t create a beast you have to feed!

That may make you feel good, but it’s not actionable or sustainable. Without clear goals and outcomes, you are very likely to end up feeding the beast.

The beast has one job: it eats resources. It doesn’t care what’s good and what’s not, so you keep shoveling resources its way. Know what’s gonna come out the other end when you’re feeding the beast? A big pile of shit that one day will be someone’s job to clean up.

You don’t want to feed the beast. I don’t want you to feed the beast. I want to help you learn some new practices to reach your goals.

This week, let’s look at how to simplify and focus on the most important problems first. I’ve detailed the three main types of newsletters. Take your newsletter, and decide which of these three is the most important. From there, you can work your way down the ladder: outcomes, metrics, design, workflow, etc.

Let’s dig into each one!

1. Positioning Newsletters

When you think of Volvo cars, what is the first thing that pops into your mind? Safety, right? Now do Disneyland. The happiest place on earth! That’s positioning.

Positioning is the space you occupy in people’s minds. It’s a term introduced in 1969 by Jack Trout and Al Ries in their book Positioning: The Battle for your Mind.

Quick — think of Axe body spray. What’s the first thing that pops in your head? This one is trickier. The answer depends on how you perceive yourself, what you aspire to, and what you value.

For too long, newsrooms have found ways to squeeze their coverage into people’s lives. That doesn’t work as well as it used to. The problem is people aren’t looking for all the news that fits.

In the era of 24-hour news cycles and content everywhere, they are looking to belong to something.

Journalism is a unique opportunity to give people something to belong to. Positioning is one way to welcome people to a larger cause and community. Interest based newsletters must keep Positioning top of mind in order to be seen as experts in their field.

If this seems new or maybe hard to understand right now, don’t sweat it. Positioning isn’t a concept I’ve encountered a lot in newsrooms. It takes some change in thinking, because you don’t control positioning. It lives in the minds of the people in your market.


Show your members you belong together

Contrary to popular belief, TheSkimm is not an email company. It’s an “audience routine obsessed company”. Those are the exact words VP of Product Dheerja Kaur used to describe theSkimm at ONA 2018.

theSkimm is a membership business. They started with a newsletter, because that’s where their target users were. The Daily Skimm is fantastic at showing people what theSkimm is about: membership and belonging. Here are few examples from a recent email:

  1. theSkimm does a great job of curating and distilling big stories. With “Skimm More”, they are showing readers that they have additional resources to learn more. A reader can, uh, skim – or they can do a deeper dive.
  2. Great example of showing readers you understand them. It diffuses what we know as an awkward moment and turns it into a lead-in to a news story. Shock isn’t the only attention grabbing technique.
  3. I love these spotlights. Real Skimm members sharing success with the larger group. Skimm’rs belong to a larger community.

From theSkimm.com: “We make it easier to live a smarter life by integrating in the routines of our target audience — female millennials.”

That’s a great vision. But a vision or tagline isn’t positioning. theSkimm uses that vision to drive strategy, and they measure outcomes against that vision.

When they are successful, members describe theSkimm in words that align with that vision. A few words I’ve heard my friends use to describe theSkimm are: Smart. Confidence. Morning routine. Notice those the first two words describe how theSkimm makes them feel.

Each new product – the app, the calendar, the podcast – builds on that positioning.

(Note: The email above is excerpted, because it’s long. You can see the complete image of the email on his page.)


Lead with your strengths

The “Show, don’t tell” rule is crucial to positioning. Positioning is what your readers think of when they think of your newsletter, not what you tell them to think.

If you can’t commit to backing up your claims, you’re going to struggle. People aren’t dumb, and if you turn them off with poor value or service, they leave. Probably forever.

What’s the one thing you want your newsroom to be known for? Be ultra-specific. It has to be something you can stake out and own. Your Positioning message can’t be a commodity. This isn’t the time for the Voice from Nowhere. Boasting about “facts” won’t work.

I have a zillion options to be “informed”. But I only have one for “informed about my neighborhood”.

There are a dozen options for “casual clothes”. I have one for “hoodie”.

You have useful, valuable content. All you need is the right Positioning strategy to strengthen the connection.

2. Engagement Newsletters

Engagement is the practice of encouraging readers to take part in your reporting. This includes crowdsourcing, collaboration and sharing knowledge. In this study, engagement is not clicks or shares or video plays.

I’ll tell you straight up: if you aren’t having conversations with your readers, you are leaving all your important revenue decisions to chance. I love how many newsroom are adopting more engagement practices. Getting out of the building and listening to readers has tremendous benefits.

Engagement reporters incorporate community expertise into their work. It makes the reporting better.

There are only a handful of the 99 Newsletters that appear to focus on Engagement over the other two types. More common was an Engagement + Positioning combination, which is great. There’s more on that below.

For example, take The Tyler Loop. In the last three months, they asked for questions on recycling, traffic, and affordable housing.


Show readers how their contributions are used

Take a look at this recent email from The Tyler Loop. Notice how each paragraph in this email encourages readers to reach out and share:

  1. Big button at the top makes it clear: The Tyler Loop wants your questions and input. Here’s how to share.
  2. Sharing the process of recording reader input shows that input isn’t tossed into a “Suggestion Box” no one reads. It’s treated with respect, and the newsroom thinks about other concerns that people may be facing.
  3. This email shows how a reader’s question or insight brings new issues to light. New questions to answer and problems to investigate. This encourages more people to come forward.
  4. There’s another call-to-action button. Make it super easy for people. They are helping you out.

3. Broadcast Newsletters

Broadcast is the most common format for newsletters across all types of media. Most consumers think of a headlines digest and links when they think of a newsletter.

Broadcast newsletters are distribution tools. They use email to deliver new content to readers with little or no added commentary. This format can be designed to drive traffic back to the primary website or self-contained products.

49 of the 99 Newsletters are Broadcast newsletters.

Below are some samples of Broadcast newsletters from the 99 Newsletters. They should look pretty familiar: a digest of links, maybe some images. That’s about it. From left to right: Midday News Update from Arkansas Democrat-Gazette, Long Beach Post daily newsletter, and Madison365 Week in Review.


You still have to determine your outcomes for a Broadcast newsletter. If you want people to click-through to the site, be clear about that with your team. Otherwise, there’s a decent chance it won’t be designed or formatted to drive clicks.

Broadcast newsletters are limited. It’s one-way communication. The newsroom blasts out what they think is important, and that’s about it. Readers learn to be passive consumers, not participants.

Just because they’re one-way communication doesn’t mean they’re bad. Some users are just looking for the headlines. Broadcast newsletters need less hands-on work than other newsletters. They are often automated.

Broadcast newsletter subscribers include a segment of reliable paying subscribers or donors. Don’t sleep on these readers. More revenue for less work is a good problem to have.

Combining two newsletter types

As long as you are clear on what your #1 goal is, you can combine approaches. Remember that the goal is to simplify:

  1. Decide which goal is the most important for each newsletter. Decide before you start designing or writing. Stick with it. Don’t change it until the evaluation period is complete.
  2. Stick to Positioning + Broadcasting or Positioning + Engagement. Don’t do all three.
  3. Seriously, combining all three types is a lot harder than it sounds. You risk trying to do too much and blurring all three strategies.

For the 99 Newsletters, 35.4% were a combination of Positioning and Broadcasting. The most common format is commentary for the intro, links to current stories, and links from other news outlets.

The reader benefits from getting your latest stories. Additionally, they see that your newsroom is on their side. You share relevant information from other sources, and you take time to add context to the story. This feels like bonus content when it’s done well.

The tradeoff is it takes more work.

If your newsroom invests in Engagement and crowdsourced reporting, a Positioning and Engagement newsletter is a boss move. You have the opportunity to create a virtuous feedback loop.

You ask for help. Readers chip in. You share the result back to the community. This encourages more people to get involved — which makes them feel like they belong to something bigger than a newsletter.

How to put your strategy into practice

If you’ve been following the 99 Newsletter Project so far, you’ve read about my love of Welcome Emails. Perhaps you’ve even written or revised your own.

That Welcome Email represents what readers need to know about your newsletter, right?

  • If your Welcome Email primes readers to share their stories, to contribute content, or how they can get involved with your reporting, it’s Engagement.
  • If your Welcome Email’s most important information is the morning headlines arrive every day at 6 am, rain or shine — that’s Broadcast.
  • If your Welcome Email’s biggest promises are insider local information, shares the recent top stories or promotes your mission, it’s Positioning.

How does your Welcome Email align with your newsletter goals? If your Engagement newsletter feels like a Broadcast email, success will be hard to find.

On the other hand, when your Welcome Email is aligned with your strategic goals, then it’s more than a Welcome Email. It’s a vision to guide you as you define your outcomes, design and metrics.

My former publisher had a saying: “It’s better to be the big fish in a small pond than a little fish in a big pond; you’ll get invited into big pond anyway.”

What does that mean for your newsletter strategy? It means focus and specificity are your biggest advantages. You can’t be all things to all people. It’s scary at first, but it’s the best long-term plan.

Look for small ponds you can takeover that align with your newsroom goals. You’ll have better opportunities to learn and grow than if you keep things too general.