In July, a few hundred newsletter operators gathered on a livestream for the first Newsletter Awards, organized by Breaker (newsletters.club). You can watch the full ceremony on YouTube (watch here).
The timing was almost funny. Google is dropping AI summaries into the inbox. Spam filters shift faster than anyone can track. Every few months a headline announces that email is dead, or dying, or broken.
And yet here was a room full of some of the sharpest people in media, treating the inbox as the most valuable real estate they own. Because it is.
The person behind the awards
The awards were created by Ben Billups, founder and CEO of Breaker (joinbreaker.ai), after he noticed a gap. Every other digital craft has its trophy. Video has the Webbies. Film has the Oscars. Newsletters had nothing.
“It just occurred to me that there isn't really any type of awards for newsletters. What if we just invested in digging up the best newsletter operators? You don't have to have the biggest list or the biggest brand, but just finding the best newsletter operators and giving them awards each year.”
More than a hundred newsletters entered. Judges scored craft, consistency, and impact across three categories, with $500 for each winner. Readers then voted a People's Choice winner.
The winners
Dense Discovery, by Kai Brach (Creator)
A weekly digest at the intersection of design, tech, and culture, published every Tuesday since 2018 without missing a week.
Judge Dylan Redcott gave it the Creator award for sheer craft:
“Kai's newsletter is phenomenal. He's been publishing it since 2018... if you look at the effort that goes into every edition, it's kind of mind-blowing.”
Ben Billups became a subscriber the moment Kai entered. “I've never seen an email that looks like this. The design is really awesome.”
Growth Unhinged, by Kyle Poyar (B2B)
Weekly playbooks on pricing, product-led growth, and go-to-market, read by more than 85,000 operators. Kyle (LinkedIn) built it as an owned channel after growing an audience on other people's platforms first.
Judge Lewis Schulman on why it took B2B:
“They're accessible without being too beginner, without being too basic. The takes are truly unique... it's genuinely useful material.”
Semafor, by Ben Smith and Justin Smith (Publisher & Media)
Global news built around email briefings, now past a million subscribers. The whole operation is email-first by design.
Judge Ryan Carr gave it the Publisher award:
“For the breadth and depth of their coverage, the maturity and the execution of the newsletter ecosystem that they've put together across around a dozen categories.”
Tangle, by Isaac Saul (People's Choice)
Tangle takes one big political debate a day and lays out the facts, then the best arguments from the left, right, and center, then its own take. Readers cast more than ten thousand votes to hand it the People's Choice award.
In Isaac's (LinkedIn) words:
“We tackle one big debate happening in US politics every day. And we cover the debate by giving you a neutral breakdown of the facts of the story. We're trying to bring conservatives and independents and liberals under one roof for a shared set of facts, reality, and arguments, and understand the world a little bit better together. We are not a short form summary newsletter. We're doing it in a way that's designed to be sat down with for 10 or 15 minutes.”
Isaac runs Tangle on subscriptions, not ads, with about 90% of revenue coming straight from readers. That is a deliberate bet on the owned inbox, and he thinks it gets more valuable as the channel gets noisier:
“As more people enter the space and everybody's inbox gets a lot more crowded, we're gonna need judgment, human judgment to sort of suss out what's great and what's not.”
The finalists
Six more made the shortlist, all worth subscribing to. We caught up with two of them.
Lifecycle Leaders, by Luke Kline (B2B)
Luke (LinkedIn) reverse-engineers how big brands actually run their email and loyalty programs, from Starbucks rewards to Netflix win-back flows.
“Lifecycle leaders is just kind of pulling back the curtain on that whole world. For lifecycle marketers, one of the main channels they use is email. So we started in email, and it's been a pretty good fit. Every email we send averages about a 60% open rate, which is pretty crazy for newsletters.”
404 Media, by Joseph Cox and team (Publisher & Media)
A subscriber-powered investigative outlet the four co-founders built after leaving Vice, covering surveillance, privacy, hacking, and AI. Email is how the journalism reaches people, and Joseph (LinkedIn) is clear about why:
“The social media networks are constantly changing with their algorithms and recommendation engines. And that's part of the reason we emphasize email, because it's something we can control.”
When they started asking readers for an email address to keep reading, and explained exactly why, the response was immediate. “It was like the graph went like a hockey stick.” But he does not take the channel for granted:
“I'm still nervous about deliverability, whether that's going to be a Google or a Gmail change, whether that's going to be landing in someone's spam filter or something like that. And frankly, it can be hard to get visibility into this.”
The rest of the shortlist
What to Cook When You Don't Feel Like Cooking, by Caroline Chambers. One complete, fast weeknight dinner delivered every Saturday, from a New York Times bestselling author who built a whole brand on not feeling like cooking.
Experimental History, by Adam Mastroianni. Funny, deep essays on psychology, science, and culture from a working researcher, every other Tuesday.
MKT1, by Emily Kramer and Kathleen Estreich. Frameworks and tactical guides for building B2B startup marketing, from two former startup marketing leaders.
Front Office Sports, by Adam White. The business of sports, grown from a college class project into a media company with a newsletter audience in the hundreds of thousands.
Why email keeps winning
Across creators, B2B operators, and publishers, the reasons rhyme. They own the relationship. They control distribution. A direct line to the inbox outlasts any algorithm.
Joseph frames it as control. Isaac bets that human judgment matters more as AI crowds the inbox. And Ben Billups, who watches every kind of sender from the platform side, puts the case simply:
“Email is still the most consistent, reliable thing that you can do. And that's been the case basically forever.”
A note from SendX
There is one catch. Owning the channel only matters if the email actually arrives.
For anyone funding their work through sponsorships, the math is short:
Inbox placement drives opens.
Opens drive clicks.
Clicks are what sponsors pay for.
When a send slips into spam, the sponsor gets a fraction of the audience they bought, and from where they sit it just looks like the list went cold.
SendX sponsored this year's awards because that is the problem we work on. SendX runs on its own sending infrastructure rather than renting it, so you can test your inbox placement at every major provider, watch your sender reputation, and catch trouble before it costs you a renewal.
The operators honored this year have the hard part handled: making something worth opening. Keeping it in the inbox is the part we can help with.
Book a demo with SendX to see exactly where your newsletter lands across every major provider, and protect the opens and clicks your sponsors are paying for.
