Here Are the Finalists for the Inaugural Inbox Awards

These stories are presented by Optimism, an email-first media company that publishes History Facts, Nice News, Word Smarts, and 15 other brands. They believe in the importance of bringing positive and informative content to the inbox. They’re also the proud sponsor of the Inbox Awards, which honor newsletter operators who are delivering exceptional experiences through email. Readers like you are voting to pick the winners. Cast your vote here.

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Earlier this month, I announced the first-ever Inbox Awards, presented by Optimism, and asked readers to submit newsletters for one of six categories:

• Innovation in Content
• Innovation in Design
• Innovation in Engagement
• Innovation in Growth
• Innovation in Revenue
• Innovation in Technology

I’ve been thrilled to go through the submissions for this year’s awards. Over the past week, I’ve reviewed applications from all parts of the newsletter ecosystem, from internationally-recognized newsrooms to indie operators, from start-ups to non-profits. Newsletter operators in 14 different countries applied for the awards. (If you’re curious: Applicants came from Australia, Bangladesh, Canada, France, Germany, India, Israel, Nepal, Nigeria, Portugal, South Africa, Spain, the United States, and the United Kingdom.) A huge thank you to each and every newsletter that applied for this year’s awards.

I left the definition of “innovation” intentionally vague — I wanted to see what newsletter operators defined as innovative. Some readers told me they didn’t apply because they felt their work didn’t clear their own bar for innovation. (“I’m very proud of the work we’ve done, but it clearly takes inspiration from others,” one reader told me.)

So how did I define it? I looked for applicants who were trying things that others weren’t, or experimenting with newsletters in exciting new ways. I’ve been working in the email space for more than a dozen years, and I wanted to find newsletters that were trying things I’d never seen before. 

My goal was to pare the submission list down to three finalists in each category. One category, Innovation in Content, had so many wonderful submissions that I couldn’t decide which to cut. (I decided to name four finalists.) Another, Innovation in Revenue, only had two submissions that I felt truly met the standard for innovation. 

The result is a group of finalists unlike any I’ve ever seen for a digital award. Take the Innovation in Content finalists, which include:

• A museum in New York City.
• A software company for customer service professionals.
• A Pulitzer Prize-winning newsroom.
• A newsletter by two French-Canadian researchers who’ve written extensively about cults.

Below, I’ve listed each of the 18 finalists, with a form for voting at the end of each category. You, the readers, will choose the winners of the Inbox Awards. I’ll also note that your definition of innovation may vary from mine, and that’s fine! When you go to vote, keep whatever definition you like in mind. Voting will close on Sunday, March 16, so get your vote in now!

Winners will be announced later this month, and I’ll be telling more of their stories here on Inbox Collective.

Cast your vote below. And to our finalists: Congratulations, and good luck!

-Dan

Innovation in Content

Brooklyn Museum: “Ms. Lonely Arts”

Ms. Lonely Arts is something entirely unexpected from an art museum: It’s an advice column, published via newsletter. A few times per month, the advice columnist — known by the pseudonym “Ms. Lonely Arts” — responds to questions on a wide range of topics. One recent edition featured questions about pacing oneself in a museum, the impact of AI on the arts, and tips for dating someone new. (Ms. Lonely Arts’ dating advice even had a museum twist — she tied things back to the Korean moon jar, and reminded the reader how imperfect halves of a jar can come together to form something wonderful.)

“Why did we start an advice column for art lovers?” said Katie Yee, the senior digital content manager at the museum. “We want to meet people where they are. We want to create new entryways into art. We want to make a painting or a sculpture or a photograph feel accessible to everyone. So even if you’re intimidated by the Museum, even if you don’t have an art degree, even if you don’t know a single thing about art, you can feel like there’s a story here for you to connect to.” 

Forget-Me-Not Journal

Forget-Me-Not Journal comes from Dr. Lorraine Derocher and Elizabeth Boileau, who’ve extensively researched and written about children who grew up in cults, and in this newsletter, they’re writing specifically for what Derocher has described as these “forgotten children.” Issues of the newsletter often discuss themes from novels, poetry, or fables — usually something tied to overcoming obstacles — and then close with lessons from their research or action steps. The newsletters are short but hopeful; as the writers are based in Quebec, each edition is published in both French and English. (The newsletter is written first in French, and then translated below in English.)

Theirs is a niche audience, but one with the potential to have a powerful impact as they reach their intended audience. “By attempting to popularize the little research that has been done on the subject of children who have lived in a sectarian environment,” Derocher said, “we hope that this letter can change things a little.”

Help Scout: The Supportive Weekly

I’ve subscribed to a lot of newsletters from tech companies, and most send a monthly update with their latest features or blog posts. But that’s what makes the newsletter from Help Scout so unexpectedly different — and great.

“I write a newsletter for a software company (sounds dull) that makes customer support software (sounds even duller),” said Help Scout’s Mathew Patterson. “Our competitors send newsletters about ‘Developing your AI Support Strategy’ and being ‘an AI-powered CX Trendsetter.’ We’re much smaller than them, with less money to spend. We have to stand out.”

So how do they do that? By sharing stories from outside the world of customer service — and then offering specific lessons for their audience. Recent editions discussed topics ranging from Billy Joel to artificial intelligence to Charles Dickens, but each closed with a surprisingly useful lesson for someone in the customer service space. Each newsletter comes from Patterson, too — a nice reminder for customer service teams to add their own personal touch whenever they talk to their customers.

The Wall Street Journal | From the WSJ Archives: 8 Epic Start-up Failures

I’ve seen plenty of teams that have built courses — those short-run newsletter products that teach readers a new skill or lesson. I’ve seen plenty of teams that have tried to utilize their archives. But the Wall Street Journal did a clever thing by combining the two into a nine-week-long email course all about the biggest start-up failures in Silicon Valley history.

Each edition features the story of one company — like Pets.com or Theranos — and leans on the Journal archives to explain what went so wrong. “Diving into the Journal’s archives allowed us to offer readers distinctive and authoritative stories with the kinds of quirky details we know they love,” said Liz Webber, a newsletter producer at the Journal. “It resurfaced exclusive reporting and scoops from decades past. And it provided a historical perspective on well-known startups and a few that readers might know less about.” Webber said the series has been a hit, with open and click rates well above Journal averages, and since it’s an evergreen course, they’ll be able to promote it to readers for years to come.

Innovation in Design

Email Love

So often, we think about design in terms of the art or layout within a newsletter. But great design starts with smart copy choices.
Case-in-point: The experiment Andrew King ran with his newsletter, Email Love. He noticed that 8% of users had filled out their profile to share personal details, like first or last name. So for the other 92%, he started including silly first names in the newsletter — ”Dear No-Name Nigel”, or my personal favorite, “Hello First Name” — and linked the names back to the preferences center. Curious readers saw those links and clicked through. Thanks to that small design tweak, the percentage of readers who filled out their profile rose from 8% to 28%.

There was an additional benefit, too: “I also started getting replies,” King said. “Real responses from subscribers telling me how much they enjoyed the nicknames and how it made them want to engage more with my emails.”

The Republic: This Week

So many magazines try to replicate the design from print in their newsletters, but it doesn’t always work. The inbox tends to reward simple-but-bold design, and that’s what Nigeria’s The Republic has done with their newsletter. “We think that good design can better capture Africa’s complicated, multi-dimensional realities,” founder Wale Lawal said. “We’ve attracted readers by presenting African stories as cool and stylish.” They’ve created a distinctive and vibrant illustration style to showcase the people featured in their stories. 

What I like most about their design, though, is that it’s connected back to a larger revenue strategy. “Our best-performing art is then sold as merchandise (wall art, stickers, etc.) which helps us further monetize our newsletter,” Lawal said.

Strategy Breakdowns

There are plenty of newsletters that explain the secrets behind successful start-ups. There’s only one, to my knowledge, that also has a mascot inspired by Microsoft’s ‘90s icon, Clippy.

The mascot — a manilla folder with glasses named Filo — was the inspiration for the total redesign of the Strategy Breakdowns newsletter. Each edition dives into the strategy behind one successful company, with different sections broken into blocks with that same manilla background. There’s an emphasis on scannability, with bolding, bullets, and numbering to move the reader through the content. And each edition features the same format: A quick explanation of the tactic, three takeaways, and three bonus things to read.

“The best companies are artworks. I genuinely believe that,” said Tom Alder, the creator behind the newsletter. “Not saying Strategy Breakdowns is there yet, but that’s the (aspirational) goal.”

Innovation in Engagement

Dense Discovery

Many newsletters build a community on Discord or Slack to create conversations around newsletter topics, but Dense Discovery’s Kai Brach felt like those communities could “feel a bit tired.” Instead, he decided to custom build his own community for paying members of his community. Those members (“Friends of DD,” he calls them) can join the DD Lounge to discuss issues, share links, and connect. Each newsletter includes a link that takes you directly into the lounge where readers can join the discussion or recommend websites, apps, books, or other things to the community.

“The Lounge is deeply integrated into the newsletter: Friends of DD do not need to log-in to access it,” Brach said. “They find a unique log-in link in each issue that takes them straight to their Lounge account. They also see little ‘+’ signs inside the newsletter to save items they like in their Lounge bookmark list.” It’s not just a community — it’s a community directly connected to the inbox.

Try & Reply

Danielle Cambio launched Try & Reply with an interesting theory: What if there was a newsletter that tested out different newsletter tactics — from A/B testing in subject lines to in-newsletter interactive elements — and then reported back to its audience about what it learned from those live experiments?

The resulting product is surprisingly meta: A newsletter about newsletter experiments that is itself an experiment. “Instead of relying on case studies or best practices from others, this newsletter runs live experiments, capturing real engagement data to reveal what works and what doesn’t,” Cambio said. “Subscribers don’t just read insights; they take part in A/B tests, engagement challenges, and are encouraged to try tactics and reply with results, questions, or ideas for future tests.” By incorporating reader feedback and ideas into the newsletter, Cambio’s going to have new tests to run for years to come.

Wired: AI Unlocked

In 2023, Wired launched a five-day email course, called AI Unlocked, all about ideas for using artificial intelligence. When Wired decided to bring the course back for a second season in 2024, they turned to the audience to figure out what to focus on. They conducted a big audience survey, and used those responses to shape the content strategy for the new newsletter. Each edition in season 2 of AI Unlocked also features a mailbag section, where Wired’s Reece Rogers answered questions from the audience and encouraged readers to write back with their own questions about that day’s topic.

But Wired took engagement a step further: They also held three subscriber-only webinars, called “AI Unlocked Live,” where paying subscribers could talk directly with Rogers. They’ve been so successful that Wired’s looking to do even more with webinars in 2025. “What we started as an experimental supplement to the AI Unlocked newsletter has now also become a wider initiative at Wired,” Laura Fillbach, the audience development manager at Wired, said. “We have started conducting webinars with other journalists on other topics we’re reporting on as a subscriber perk.”

Innovation in Growth

Apartment Therapy and The Kitchn

Sites like Apartment Therapy and The Kitchn have a deep archive of content. The question is: How do you take advantage of that to grow your list?

For Hollis Miller, senior manager of email and acquisition, that meant turning some of the top-performing content into a series of downloadable .pdfs, like a list of the best recipes ever published on Kitchn’s website. These lead magnets were curated by editors, designed by their in-house art team, and promoted widely across their site. “We were able to create nine .pdfs and add 61,000 new subscribers to our lists,” Miller said — all by repromoting old content from their site.

Financial Times: White House Watch

The FT launched a newsletter in February 2024, called U.S. Election Countdown, to cover the presidential campaign. It became their fastest-growing newsletter ever, and they rebranded it in 2025 as White House Watch. Most FT newsletter content is exclusive to paying subscribers, but White House Watch is free. The FT has promoted the new newsletter aggressively, through a specialized registration wall on site, on politics stories, and even through a major investment in paid ads. The investment’s paid off — the FT’s U.S. newsletter editor, Emily Goldberg, said two out of three readers on the list are new to the FT.

But the FT also looked to expand the newsletter reach to other platforms. They created a White House Watch newsletter on LinkedIn, where they now have more than 940,000 subscribers. “We post a portion of the newsletter on LinkedIn and prompt readers to register (and share their email with the FT) to receive the full newsletter in their inbox,” Goldberg said. “Essential to this process was a new journey we created for seamless registration through LinkedIn.” All of these new email addresses represent a major revenue opportunity — with a yearly subscription price north of $300 per year, these newsletter subscribers could be worth seven figures annually to the FT.

The New Republic

The New Republic has their own newsletter and paid subscription strategy. So why launch a second newsletter on Substack?

For Daniel Pritchett, TNR’s director of engagement, it was all about leaning into a growth channel that few legacy media companies were using. They created a mini-version of their newsletter, which they called “TNR-lite.” It highlighted one main story in the inbox and then drove readers back to their site for additional stories. Then they partnered with writers on Substack to test intra-newsletter recommendations. “Collaboration tapped into an audience keen on authoritative, left-leaning political content,” Pritchett said. TNR content now averages more than a million views per month across Substack’s platforms.

The growth has also led to another unexpected outcome: They’ve added a paid product via Substack, separate from TNR’s core subscription, which Pritchett said “has turned Substack into a substantial, unforeseen revenue generator for TNR.”

Innovation in Revenue

The Assist

For newsletters that spend money to grow, there are a few metrics that matter: Customer acquisition cost, which is the cost to acquire one email address, and customer lifetime value, which is what that reader is worth to that newsletter in the long run. But one metric is particularly important: Payback period, which measures the length of time it’ll take you to make back your money from that new reader.

The Assist’s Andy Mackensen has optimized his welcome journey to an unusual extent: “I designed an acquisition funnel that takes new subscribers and immediately monetizes them on the thank you page and in the welcome sequence so that we get all of our paid media subscribers more than paid for in the first seven days.”

As soon as someone signs up for The Assist, they ask readers to take a quiz, and the results direct readers to one of three landing pages, each with different offers. Readers might see offers from affiliates, for paid courses, or even for a paid membership. The ensuing welcome series features additional customized offers, which gives The Assist even more opportunities to monetize those readers in that first week.

TextHacks

Berlin-based consultant Anne-Kathrin Gerstlauer writes a German-language newsletter with writing tips. She has a list of more than 15,000 subscribers, and she monetizes in two ways you’d expect: A paid subscription and advertising. But she’s also experimented with a brand-new revenue stream: Licensing her content to German businesses. Many companies are buying old issues of her newsletter — or in some cases, paying Gerstlauer to personalize an issue specifically for their company — and redistributing them to their employees, often through their internal newsletters.

“I’ve already made 4 and 5-figure-deals with this,” she said, and she’s made a point to pursue additional deals to license content — much of which she originally published for free in her newsletter — to other businesses.

Innovation in Technology

Mailmodo: Idealetter

AMP for Email is one of those email technologies that’s yet to reach widespread adoption in the email community. It promises to allow any newsletter to create interactive elements within the inbox — but many email platforms and inboxes do not support it.

Still, the brands that have experimented with AMP for Email are able to create interesting experiences for readers. I love this example from Mailmodo that asked readers if they wanted to refer a friend to their newsletter. Using an AMP for Email element, they can enter that friend’s email address within the body of the newsletter. After they do, the friend receives an email with an opportunity to opt in to the newsletter — this time powered through an AMP-powered button. “If the person selects ‘Yes’ and opts in to receive our newsletter, we have set up an automation to add them to our newsletter list and send them a welcome email,” said Jyothiikaa Moorthy, a product marketing manager at Mailmodo. It’s a simple-but-smart experience like this that gives me hope for AMP for Email moving forward.

Only In Your State

Only In Your State produces 51 different daily newsletters, each with personalized content based on a reader’s interest and location — and they’ve automated the entire process.

I’ll let Kali Acerra, retention manager at Only In Your State explain: “Data feeds pull in content to our email templates based on editorial tagging. Our strategy accounts for the type of content we include, the recency and personalization at a user-specific level. This means that each subscriber is getting a newsletter tailored to their specific interests, whether that be the best hiking trails, restaurants, places to stay, and more throughout their states of interest.” There’s still plenty of editorial work to be done to create the original content, but the automations make sure all 51 editions go out the door every day. 

Kara’s Three Things

For years, I told anyone who asked that publishing via a Google Doc was a bad idea — and then Kara Brown went and proved me wrong. She writes a weekly newsletter, on a custom tech stack, all of which starts with a Google Doc.

She drafts her weekly newsletter in Google Docs, adding the copy and images there. Then she downloads it as a .zip file and uploads it to a custom app she built. From there, the app uploads the images to the web, converts the content into HTML, and allows her to schedule the newsletter. 

“Owning the infrastructure and code that drive my business operations allows me to customize solutions to meet my needs, rather than adapt my project to fit in the mold of an existing platform,” she said. If she wants to move to a different email platform or add additional functionality to her emails, the custom app gives her the ability to make those changes in the future.

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