Here Are the Winners of the 2025 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.

When I look around the inbox today, I see a lot of copycats. It’s always been this way, of course. I’ll give you an example: When Morning Brew launched a referral program, other newsletters started launching their own referral programs. When Morning Brew invested in paid ads for growth, others did the same. When Morning Brew introduced rounded corners to each section of their newsletter, rounded corners suddenly popped up in lots of other newsletters.

Occasionally, newsletters even copied ones that weren’t Morning Brew.

So when I launched the Inbox Awards, presented by Optimism, I wanted to shine a spotlight on newsletters that were trying to find a unique path forward. I hoped that these awards would help surface outstanding newsletters in the worlds of content, design, engagement, growth, revenue, and technology.

In the end, after a final round of voting from Inbox Collective readers, I’m thrilled to announce the winners of this year’s awards. These six newsletters are doing innovative new things with their newsletter strategy — and these are their stories.

Innovation in Content: Help Scout’s The Supportive Weekly

No category received more applications than Innovation in Content, but The Supportive Weekly — a newsletter from Help Scout, and the 2025 winner in the category — truly stood out. Their newsletter was entirely unexpected: A weekly email, aimed at people who work in customer service, published by a company that makes software for customer service, with stories that — at first glance — have absolutely nothing to do with customer service.

“The ideal story for me is something that helps readers see familiar things in new ways: Their work, their companies, their customers,” Mat Patterson, who leads the newsletter strategy at Help Scout, told me. “Something to help them rethink things from a new perspective.”

It helps that success for such an unconventional newsletter is tied back to an unconventional metric. “One of Help Scout’s values is ‘Happy to help,’ and that’s my guiding principle,” Mat said. “Is this email helpful? Is it worth reading? Is it adding value to their lives in some way?”

That approach makes for a compelling newsletter in a space where you wouldn’t expect such a product. It also means that Mat consistently pulls ideas from outside the world of tech or the web. He’ll write about Attila the Hun or the history of Auto-Tune and use that as a way to discuss customer service ideas. For instance, here was the closing section of one recent newsletter:

Shifting market expectations mean support teams and their customers have to deal with a lot of change. New product features, new approaches to business, new policies and practices. 

Change is hard for everyone:

• Fear of losing time and money dealing with an unknown system
• Having to learn new ways to work
• Breaking hard-earned habits and muscle memories
• No obvious benefits to trade off against the costs of change

The biggest challenge for support teams is going through all those same issues while trying to help customers down the same path. If you’re a support leader, and you want your team to engage positively with customers through big changes, then you need to help your team first.

What was the lead in to those takeaways? A story all about Billy Joel’s recording career.

It was absolutely unexpected — and a newsletter that continues to surprise and delight its readers is always going to stand out in the inbox.

You can sign up for The Supportive Weekly here.

Innovation in Design: The Republic’s This Week

I asked Wale Lawal — founder of Nigerian magazine the Republic, which was this year’s winner for Innovation in Design — why design mattered to his publication, and he had a great answer.

“We tell important stories, but in this age, that’s not enough,” he said. “Audiences want to be engaged, and they gravitate towards experiences. Good design helps us create experiences out of appreciating the nuances of African realities.”

In the inbox, design can help separate an average newsletter from a great one. But what I especially love about the Republic’s weekly newsletter is that they don’t overdo it with design elements. They’ve picked striking fonts and art to make the newsletter stand out, but otherwise, they’ve kept things fairly simple.

“Our design process is collaborative,” Wale told me. “We make sure to involve perspectives across various teams — editorial, design, comms, even sales! — enabling us to follow an approach that is not only aesthetically pleasing but also effective at helping us meet our shared goal of telling compelling African stories to a global audience.”

And they continue to test new design ideas and review them, as a team, every quarter. Is the newsletter too long? Are there too many links? And can they collect audience feedback to improve the product? “The idea is to make incremental, not drastic, updates,” Wale said. Oftentimes, being willing to iterate in small ways is what builds a smart strategy in the long run.

You can sign up for The Republic’s This Week newsletter here. Want to read more about The Republic’s strategy? We profiled them in this 2024 story.

Diversify, Monetize, Share: The Republic’s Strategy to Build a Mission-Led Newsletter

Innovation in Engagement: Dense Discovery

There’s so much competition in the inbox, and many of the newsletter operators I meet are making decisions out of a sense of competition. But I got a different vibe when I talked with Kai Brach, who publishes the newsletter Dense Discovery, and whose members-only community, the DD Lounge, was the winner of the award for Innovation in Engagement.

“I didn’t develop the DD Lounge to gain a competitive advantage over other newsletters,” he said, “but as a way for the most dedicated readers to be able to come together and feel a stronger sense of connection. Especially at this moment when the societal impact of large social media platforms is becoming more apparent, some people find comfort in smaller, more thoughtful online communities that defy the algorithmic popularity contest.”

What you’ll find when you move through the DD Lounge feels like something out of a different era of the internet. Many internet communities are full of fighting or one-upmanship, but the DD Lounge is more like a small group of friends, eager to share ideas or recommendations.

And a different type of community requires a different way to measure success. Kai said the big metric isn’t revenue or comments, though those still matter. His metric: “Readers writing in to say ‘I found this link or I met this person on your platform that helped me a lot.’” You can’t put a dollar amount on that sort of thing, but Kai said “it validates my own desire to create a space that people enjoy but also find useful.”

You can sign up for Dense Discovery here or become a member in the DD Lounge here.

Innovation in Growth: Financial Times’ White House Watch

Innovation comes from a realization born out of necessity. As Emily Goldberg, the U.S. newsletter editor at the Financial Times, told me: “Across the business, there’s an understanding that we need to continue to reach new audiences, especially in the U.S., where readers might not be as familiar with the FT as they are in the U.K.” That led to the strategies behind the FT]s White House Watch newsletter, which was this year’s winner for Innovation in Growth.

White House Watch actually started as an election newsletter in 2024, and it became their fastest-growing newsletter ever. But Emily said their team knew there was an opportunity to keep building and growing. That meant:

• Making White House Watch free to all readers, even though most FT newsletters are just for paying subscribers.
• Creating a special registration wall on site to convert readers to the newsletter.
• Running paid ads on channels like Facebook to grow the newsletter list.
• Republishing part of the newsletter as a LinkedIn newsletter — which now reaches more than 940,000 subscribers — and creating a custom landing page to convert readers from LinkedIn to the inbox version of the newsletter.

Was it hard to convince the team to try new strategies? Emily told me the FT quickly got behind the idea: “Our strategy for White House Watch is in line with the FT’s goal of building our base of registrants, which we see as potential subscribers to the FT, while continuing to engage existing subscribers.” It’s certainly easier to convince your colleagues when there’s such a large revenue opportunity at stake. With a yearly subscription price north of $300 per year, the White House Watch list could be worth seven figures annually to the FT.

You can sign up for White House Watch here.

Innovation in Revenue: TextHacks

There are a handful of tried-and-true monetization tactics that most newsletters use. Even I’m guilty of pre-sorting newsletters into specific buckets — I’ve published pieces like “The Five Types of Indie Newsletter Business Models” that encourage newsletters to lean into the revenue strategies that work for similar types of products.

That’s what was so exciting about this year’s Innovation in Revenue winner, TextHacks, from Germany-based writer Anne-Kathrin Gerstlauer. Instead of sticking with just the usual revenue streams for a consultant — ads, subscriptions, and, of course, consulting — she tried something new: Licensing her content to other businesses for a fee. They pay to take her existing content and republish it in their internal newsletters, and Anne-Kathrin can charge four or five figures as a licensing fee.

“This opportunity was the solution to a problem that I already had,” she told me. “I’m doing a lot of workshops but it’s hard to keep the knowledge after a workshop. So why not sell them a workshop plus an internal newsletter?” The best part: You can sell licensing and workshops in either order. “It’s a perfect full circle moment: The newsletter sells workshops, the workshops sell the newsletter.”  

I also wanted to know: How did she set the price for licensing when there weren’t other examples to compare it to? Anne-Kathrin said she had lots of conversations, including with colleagues or friends who worked at business that might want to license her content, and she looked for comparable offerings in other industries. “For example, photographers also have license models,” she said. “For a text, it is unusual, but in other industries, it’s common.” All of those data points helped her set the price and turn licensing into a five-figure — and growing — revenue stream for her newsletter.

You can sign up for TextHacks here. Want to read more about Anne-Kathrin’s newsletter strategy? We profiled TextHacks in this 2025 story.

How Anne-Kathrin Gerstlauer Built More Than a Consulting Business Around Her Newsletter, TextHacks

Innovation in Technology: Only In Your State

What I love about the winner of the Innovation in Technology award, Only In Your State, is that they had a strategy that worked — but that they knew they needed to improve upon it in order to scale.

“Initially, our 51 local newsletter campaigns were created manually, requiring significant investment to fund a team that could execute them at scale each week,” said Kali Acerra, who oversees newsletters for Only In Your State. In order to unlock bigger opportunities, they needed something that allowed them to work smarter with a smaller staff.

The answer: A series of newsletters that were both automated and personalized. Kali got their brand and product teams, as well as their email platform, or ESP, in the room and communicated the big idea: “By completing this work, they would set countless other teams up for success.”

Building out the tech for this took time, but the end result is impressive. I’ll let Kali explain what’s happening behind the scenes:

“We have content data feeds for each of the 50 states that pull in content based on editorial tags. The personalization piece comes in when determining which articles to include each day. Our ESP collects data on every user profile based on articles they’ve clicked on in the past. For example, if a user tends to click on articles tagged with ‘hiking’ or ‘nature,’ they’ll see more articles related to these tags in their newsletter each day.”

But the really exciting thing: They didn’t just set up these feeds and then call it a day. “This is far from a set-it-and-forget-it process,” Kali said, “as we’re constantly updating the filtering in the feeds based on seasonality, content relevance, and more. We have room for creativity in our sends, as we can add or remove manual content blocks if we want to promote something specific on a certain day.” Is it a lot of work? Absolutely, but the ability to scale a personalized newsletter — and then layer on new content or monetization opportunities — made the project worth the investment.

What makes for an innovative newsletter?

To close out the 2025 Inbox Awards, I asked each of our winners the same question: What advice would you give to someone trying new or innovative ideas with their newsletter? Here’s what they told me:

Mat Patterson, Help Scout

We’re in an age of distrust, and great email newsletters can connect with people on a much more personal level. Most newsletters are forgettable at best. 

Don’t be dull. Be intentional, authentic, consistent, trustworthy, and offer genuine value to your readers. Be human. Newsletters are for readers, not just subscribers — focus on creating something worth reading rather than merely growing your list.

Wale Lawal, The Republic

I’d say first, treat your newsletter like a distinct product. Set clear goals you want to achieve with it, take its branding and design seriously. Develop and manage it with the right people/skills. When we first started, we made the mistake of treating our newsletters as distribution channels for our website and not as unique publishing platforms. The big lesson here is to prioritize your newsletter as soon as you can and to take it very seriously. 

Second, innovation does not have to be grand or highly technical. Innovation is just a smarter way of carrying something out — so don’t wait for the grand ideas. Think of the smaller changes you can adopt to make your newsletter a more enriching experience. This spans from how you design your newsletter to how you send it (e.g. in batches) to what even happens after it’s been sent. The opportunities to innovate are everywhere! 

Third, don’t be afraid to experiment, and do so as often as you can. 

Fourth, listen closely to your audience; communicate regularly with them and carry them along. One misconception media companies have is that (because we are in the business of content) simply pushing out content counts as communicating with your audience. It doesn’t. Communication is intentional. Ask them questions: What do you think about this update we’ve just made? Rate our layout change on a scale of 1-5. Dedicate time and resources to processing and implementing their feedback. Communicating with your audience could save you a lot of mistakes (and money!). 

Kai Brach, Dense Discovery

Some practical advice: if you know a little bit about HTML/CSS, try to create a more unique newsletter template. The limited format options of, say, Substack make all of their emails extremely predictable and a bit boring. I appreciate people experimenting with creative ways of presenting content in emails. Look at how much the newsletter by Today.Design pops compared to the standard templates used everywhere.  

Emily Goldberg, Financial Times

Make sure you can track the results. Ideally you’ll decide what your metrics for success are before the project starts, but by tracking various data points (open rate, newsletter growth, traffic back to your website, etc.) you will no doubt come away with actionable takeaways — whether they show something worked, or if it’s not the right approach for next time. 

Anne-Kathrin Gerstlauer, TextHacks

It sounds cliché, but there is no one-size-fits-all for newsletters. Paid subscriptions work great for others, not for me. People have repeatedly told me they don’t believe in my new revenue stream — why would someone pay for a license? But I knew from instinct that this was the right way for me.

An easy way to start out new ideas: Build a small landing page and link to it in your footer. You don’t need a big announcement for every small test. 

Kali Acerra, Only In Your State

My advice for someone trying new or innovative ideas is to collect data before going to leadership with a new idea. Whether your idea aims to increase opens, clicks, page views, save money, or even just build trust with your audience, there needs to be a reason you want to try something new — making data-driven proposals and decisions is vital. And then, testing, testing, and more testing! We’ve been refining our process for several months, making small tweaks here and there to get things just right. 

Here are all the winners and finalists for the 2025 Inbox Awards

Out of 94 entries to the Inbox Awards, presented by Optimism, 18 finalists were selected by Inbox Collective’s Dan Oshinsky. (You can read more about each of the winners here.) In the final round of public voting, more than 2,000 votes were cast for the winners.

Here are all the winners and finalists for each category:

Innovation in Content

Winner: Help Scout: The Supportive Weekly
Runners-up: Brooklyn Museum’s Ms. Lonely Arts; The Wall Street Journal’s From the WSJ Archives: 8 Epic Startup Failures; Forget-Me-Not Journal

Innovation in Design

Winner: The Republic: This Week
Runners-up: Email Love; Strategy Breakdowns

Innovation in Engagement

Winner: Dense Discovery
Runners-up: Try & Reply; Wired’s AI Unlocked

Innovation in Growth

Winner: Financial Times’ White House Watch
Runners-up: Apartment Therapy / The Kitchn; The New Republic

Innovation in Revenue

Winner: TextHacks
Runner-up: The Assist

Innovation in Technology

Winner: Only In Your State
Runners-up: Kara’s Three Things; Mailmodo’s Idealetter

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