When I launched The Water Coolest in 2017, there was no plan, let alone a reader persona doc.
Like Picasso (except a beat-up laptop was my brush and MailChimp was the canvas), The Water Coolest had its persona “periods”…
Early days: Writing for myself (think: mid-twenties consultant interested in investing)
2018-2020: Wall Street-types, because that’s where most of our early growth came from
2021-now: Hard pivot to retail investors thanks to 2020 (see: GameStop, crypto, etc.) & the Barstool acquisition
Catering to two (arguably three) very different groups of readers killed momentum more quickly than the Gmail gods banishing us to the promotions tab.
I think a lot about what we should have done differently in those early days. Spoiler: not defining our audience was just the tip of the iceberg…
With the benefit of hindsight and the opportunity to work with countless clients early in their newsletter journey, it’s become pretty obvious that one of the biggest factors that separates the newsletter haves from the have-nots is knowing exactly who you’re writing to.
And I mean really knowing them.
An audience of one
One of the biggest lies newsletter operators tell themselves is that they know their audience.
Go ahead, ask one. It’s either “founders.” Or “marketers.” Or “anyone interested in AI.” It’s usually vague enough to keep the door open, but specific enough to sound like a strategy.
But the newsletters that actually break through are written to one person. One real-life human being (who just so happens to be totally made up) that you can picture reading your newsletter. They’ve got a name, age, LinkedIn profile, and, most importantly, things that keep them up at night.
Sounds simple. But almost no one does it. And even fewer operators actually bake it into their content.
Let’s build your audience of one, shall we?
Exec summary
You might not have time for 930 words about newsletter strategy, which is exactly why I summarized the entire email below in just 70…
Most operators think they know their audience. "Founders" isn't an audience. "Marketers" isn't an audience. The newsletters that break through are written to one person.
Build a real, specific (totally made-up) human. Name. Age. Sex. Location. Title and company stage. Comp package. Education. What keeps them up at night? Career goals with a time frame.
Now write an email (not to be confused with a newsletter) to this person.
Think of this exercise like NBA 2k “Create a Player” (or maybe you’re more of a fan of The Sims?). You’re building the exact person you want reading your newsletter. Every detail matters.
There are dozens of attributes you can adjust, but you’ll need these ten at a minimum…
Legal name: Pick one. We use Jordan at The Water Coolest. You’re going to be saying/typing/thinking about this a lot, so make sure it’s something you like. And don’t let me hear you getting cute like the marketing department: “Whimsical Wendy.” Give them a real government name, dammit.
This will resonate with the AOL Instant Messenger crowd (see A/S/L)…
Age: Not “30s.” 37. A 30-year-old and a 35-year-old could be in very different parts of their lives and careers.
Sex: Let’s play a game: what sort of reader do you think about when I say “Arnold’s Pump Club?” Ok, how about “theSkimm?”
Location: City is important, but so is the arrangement. Living with their buddies in a walk-up in Midtown Manhattan or three kids in the Midwest?
Build their LinkedIn profile…
Title and company stage/size: Senior PM at a Series B SaaS company. Head of Content at a 200-person agency. Be precise.
Comp package: Salary, bonus, and equity can tell you a lot about what makes a person tick
Education and career path: How did they get here? The trust fund Harvard grad and the kid from the school of hard knocks do not look at life the same way.
Hopes and dreams…
What’s keeping them up at night (job): The stuff that causes the Sunday scaries. I’d argue you can split this one into 1) stuff their boss knows about, and 2) things that are better left unsaid
What’s keeping them up at night (personal): Relationships, money (see: comp packages), family stuff. You know the drill.
Their goals (both job and career): Not “grow professionally.” Get the CMO title before Jeffrey retires in late 2026. Time frame matters here.
There are countless rabbit holes you’ll want to explore here. And you probably should.
I cannot stress this enough: when you think you’ve gone deep enough, go deeper. If it doesn’t feel like you know this person better than your spouse, you’re probably doing it wrong.
Let’s make it real…
Last week, Alex Lieberman (great minds…) shared “the audience of one” that the Morning Brew (perhaps you’ve heard of it?) was writing to in the early days…
“Stephen, 30 years old, equity trader at a mid-tier bank in NYC. East Village apartment, midtown commute. Planet Money on the train.
His biggest pain point = not looking like a schmuck in front of his boss on Monday morning.”
Probably not a coincidence that MB’s landing page headline is “Become smarter in just 5 minutes.” They are literally speaking to Stephen.
Stephen is a guy the Brew’s writers know. When they drop a pop culture reference, they already know whether it’s going to resonate. If they use an acronym, they know whether they need to drop an explainer. Spoiler: Stephen knows what EBITDA stands for (and what Warren Buffett thinks of it).
Oh, and bonus…
The Brew’s sales team understands what Steph likes to drink after work, and the type of financial services products fit his lifestyle
The growth team knows where to find more Stephens
Now, test it
Before you hit send, answer this…
(Back to Jordan… no hard feelings, Steve.)
Would Jordan give a damn about this email when he opens it on the 10-minute subway ride after his 7:30 AM workout class?
Not "would someone like Jordan." Jordan. The 37-year-old Big 4 accountant who's sick of his bosses' bullsh*t and considering leaving money on the table for a VP of Finance role at a fast-growing startup.
Weak answer: "Yeah, I think he'd like it."
Strong answer: "J-Dogg (that's what his high school friends still call him) is going to forward it to his mentor before he gets off the train. The masterclass on plotting your next move hits him exactly where he's been stuck for six months."
What happens when you find your audience of one?
You can write an email (not to be confused with a newsletter blasted out to a bunch of anons) to Jordan. Emails are personal. They’re 1:1. You can get to the same level of specificity as a friend or family member.
Putting in the work here will reframe how you look at each newsletter email…
Subject lines: Written for him
Voice: Peer-to-peer
Examples: Companies, people, and references he'll recognize
Value: You’re solving his problem
Put his name on the whiteboard. Hell, print out a picture and put it in a frame next to your kids. It is that important to get this right.
By the way
Next Friday, I’ll be MCing the Newsletter Conference in NYC.
The lineup is stacked with newsletter legends who are going to be deep diving into all the things that keep you (and me) up at night: AI, monetization, growth…
Jesse and Ryan gave me a 15% discount code to share with CNO readers: use “TYLERMORIN” at checkout. There aren’t many tickets left (don’t say I didn’t warn you).
Look forward to seeing you all in NYC. Reply if you’re going to be there. Would love to catch up IRL.
Before you go, I’d love to know what you think about CNO. After all, would I really be a newsletter operator if I didn’t ask how likely you are to recommend it?