Prefer to listen to this story?
This was year three of The Newsletter Conference, and with every year, it feels more and more like a family reunion: Catching up with old friends, meeting new ones, and having lots of big conversations about where the newsletter space is going.
This year felt a little different, though: So many of the conversations centered around building something a bit bigger than newsletters, and finding ways to continue to build loyalty and drive revenue. Email still matters — but the people I spoke to and heard from on stage are starting to think about email as one of many touchpoints in their relationship with readers.
Here’s what I took away from this year’s conference.
1.) There’s a growing tension between scale and quality
Until a few years ago, some of the fastest-growing newsletters were sometimes spending cents, not dollars, to acquire a new newsletter subscriber via paid ads. At big publishers, social and search were still driving lots of traffic to websites, and the sites that optimized their pages to convert readers into subscribers saw consistent growth.
Things have certainly changed. I lost track of the number of times someone came up to me in the hall between sessions to ask: “Is it just me, or is it getting a lot harder and a lot more expensive to acquire new subscribers?”
But list growth may not be the name of the game anymore.
Adam Ryan, founder & CEO of Workweek, nicely framed the key question: “Am I in a ‘how many’ business or a ‘who’ business?”
A “how many” business is one where revenue is tied primarily to ad sales. The bigger the list, the more you can charge for ads in your newsletter. (Though I heard some great ideas for ways to shift your ad sales strategy. More on that in a moment.)
A “who” business, on the other hand, is built around list quality, not size. Monetization can come through ads, but also through other channels: Reader revenue (subscriptions, memberships, donations), consulting, products, workshops, or events. It’s not so much about getting as many people in the room as it is getting the right people in the room.
As Jacquelyn Cameron, chief revenue officer at Axios, said: “There is more power in the number 535 than in 535,000.” Sure, she said, Axios wants to reach as many readers as possible, but if they’re putting on an event with a sponsor, that sponsor wants to know: Are you getting us in front of key decision makers? A room packed with 1,000 college students majoring in political science isn’t all that valuable to an advertiser, but a private meetup of 10 chiefs of staff on Capitol Hill could be a goldmine.
So much of this requires a shift in understanding what’s most important for your bottom line — and that of your sponsors or partners, too. Tony Napoleone, a vice president at Omeda, said a lot of publishers are still stuck in “a programmatic mindset,” one built around a 2010s strategy for selling website ads at scale. An anonymous reader isn’t all that valuable anymore, he said. Focus instead on bringing in high-quality readers and then learning more about them. Survey data, click behavior, enriching a reader’s profile through third-party tools like Clay — all of this helps you prove that you’ve got the right readers on your list.
Making the pivot from scale to quality is absolutely doable. “A ‘how many’ business can quickly turn into a ‘who’ business,” said Kristine Wyatt, VP of audience and ad operations at Morning Brew, which played the scale game for years. Now they’re investing more into B2B products and events as a way to monetize.
2.) Newsletter-first orgs are moving beyond the inbox
Even at a conference focused on newsletters, just about everyone on stage talked about building something a bit bigger than their newsletter. Eric Newcomer, founder of a newsletter about technology and venture capital called Newcomer, put it nicely: “You want to have more than one way to reach people.” Leaning into multiple 1-1 channels — email, SMS, and events — gives him lots of ways to get in front of his core audience.
Events were a major theme of the day. Some teams are hosting big conferences; others are putting together small, private dinners. Events of any size present opportunities to build relationships, sell tickets, and bring sponsors into the fold.
Anna Palmer, CEO and founder of Punchbowl News, said her team hosts 50+ events per year. Some are as small as 25 people, and most are just 70-100 people. They’re selling their audience — and their advertisers — on exclusivity, not scale. Some events aren’t what you’d expect from a newsroom that covers D.C. politics, like the cornhole tournament they host. “We’re all about people becoming fans,” she said, and events like that can build loyalty with the brand.
Lachlan Cartwright, founder of Breaker Media, which covers media and power in Manhattan, said that he tries to bring something unique to every event — something that makes people want to show up again to see what he’ll try next. One happy hour featured a pair of tarot card readers. At another, he built a confessional booth.
All of this emphasis on events matches up with data I’ve seen elsewhere. A recent Omeda report found that 71% of orgs surveyed met or exceeded their event revenue goals for the past year. Events are definitely a bright spot in the media world.
Other newsletter operators looked to new channels. Punchbowl’s made an investment in YouTube. Guy Short, founder of the Flyover, said they’re investing money from their recent crowdfunding round into a few new platforms, including SMS. Algorithmic channels (like YouTube or social media platforms) can bring in new readers, while owned channels (like SMS or Discord) can deepen relationships with existing readers.
Partnerships also represent an opportunity, especially for independent newsletter. Joanna Stern, the former tech writer for the Wall Street Journal, shared her journey to going independent with her newsletter, called New Things. She wanted full ownership of her newsletter, but also wanted to find a way to get in front of new audiences. The compromise: A partnership with NBC. She can tap into their much larger audience, creating written and video content for NBC platforms, like the “Today” show, while still having her own newsletter, YouTube channel, and membership program.
It’s all part of this larger shift, as Omeda’s Napoleone put it, where “newsletter businesses are scaling up to become media businesses.” Email is a part of a larger ecosystem — not the entire business anymore.
3.) Everyone’s finding new metrics to measure success
The newsletters I heard from at the conference have moved past traditional metrics — list size, open rates, click rates — and are looking deeper to understand what’s really happening with their audience.
Ryan, now at Workweek but formerly of the Hustle, spoke about the idea of “three-hour virality” — the idea that if a newsletter hits a certain open rate within three hours, that’s a sign that the story is going to overperform with their audience.
The Flyover looks closely at something they call “cost per ad clicker,” which measures how much it costs to acquire one reader who’ll click on their ads.
Andy Mackensen, co-founder and chief growth officer of the Assist, went into detail about a core metric for his team: Lifetime value to customer acquisition cost ratio (or LTV to CAC ratio). He said most newsletters focus on trying to reduce the cost per new email address — say, spending $1 to bring in a new reader instead of $2. But instead, his team is focused on trying to find new ways to monetize those readers. It’s often easier to increase that LTV instead of reducing CAC, and it’s OK to spend $5 to bring in a new reader if you’re able to make $10 or even $25 from them.
One more unusual metric: Cartwright, of Breaker Media, said he keeps a close eye on which users are showing a higher-than-expected number of total opens. If a single reader appears to have opened an email dozens of times, it might be a signal that they’ve forwarded that day’s newsletter — which includes paywalled content — around to their colleagues. When that happens, he or a member of his team might reach out to that reader to inform them about his group subscription offer, and he said that’s been an effective paid conversion tactic.
4.) Success in advertising is about identifying outcomes
Advertising isn’t going away, but how teams sell ads is changing. So much of it starts by understanding what the advertiser really needs — and what they hope to get out of working with your newsletter.
Stacy Bradshaw, vice president for data and technology at Canada’s Annex Business Media, said for her publications, advertisers are consistently asking for a few things. “Advertisers want exclusivity, they want top placement, and they want to reach the right audience,” she said. She pointed to one example: They run some truly niche publications, including one about pulp and paper in Canada. If an advertiser wants to reach, say, 10 pulp executives in the Toronto area, her team might be able to get all of those people in a room for dinner. That sort of thing is worth so much more than just selling a few ads in a newsletter.
Newcomer said it’s so important to really dive into the data and understand more about your audience. When he hosts events, he said he’s able to promise his sponsors that 45-50% of people in attendance are going to be the founders of startups — a core group many of his sponsors are trying to reach. “Know exactly who is in your room,” he said, and it’ll make it that much easier to bring on the right partners.
The Assist’s Mackensen said his team has done away entirely with the typical rate card, showing how much the typical newsletter ad costs. Instead, they’re focusing on what they call “activations,” which are ad packages custom-built for each advertiser. Their process: First, they start with a call with the advertiser to understand what their goals are. Are they trying to build awareness? Drive leads for their business? Grow their newsletter list?
Then they put together a package with dozens of different sponsorship opportunities, including:
- Newsletter ads
- Dedicated emails
- Case studies
- Lead magnets
- Webinars
- Live events
- Onboarding offers
Mackensen said that because these packages are fully customized around the sponsor’s outcomes, they’re able to close a lot more deals. Plus: The lack of a public rate kit means they can adjust pricing for each sponsor instead of having one-size-fits-all rates.
5.) The right tests often take months, not hours or days
A/B testing isn’t going away — it’s just shifting towards tests that have much higher impact.
Tim Huelskamp, co-founder & CEO of 1440, walked through how his team ran tests on their in-newsletter ads. He said that they spent a period of months testing out different versions of ads: Some with just one or two links, versus some with four or five; some with a few extra sentences of copy; some with straightforward headlines versus more curiosity-focused ones; some with different colors for links. Through all of those individual tests, they were able to significantly increase the number of clicks on their advertisements.
“We essentially tripled our revenue by improving the efficacy of our ads,” he said.
Mackensen tried a similar approach with his newsletter’s landing page. They started with a version of a page that converted 35% of readers into subscribers. That number’s pretty good, but they wanted to see if they could improve things. Over six months, they tried a number of tests to add social proof, adjust copy, try new calls to action, and remove unnecessary elements. By testing one thing at a time, they boosted their conversion rates to 46%, then to 53%, and then to 62% — and finally, to a winning version of the page that converts 70% of readers into subscribers.
Jacquelyn Cameron, chief revenue officer at Axios, talked about the idea of the “two-way door.” After Axios runs a test, they take a closer look at the data to decide what happens next. If things are working, they invest heavily in the idea. If not, they pull out a few learnings and apply it to the next test. They don’t double down on things that aren’t working. “Otherwise, it’ll be a drain on the business,” she said.
One such example: An early foray into audio didn’t work out. They decided to sunset the product, and they’re working on a brand new approach to audio.
“Every day, we’re experimenting,” she said. “Otherwise, we’re dead in the water.”
