Don’t miss Part II of this series: How to pick your newsletter tech stack
It’s really hard to repeat any activity for 25 consecutive weeks. No, I don’t mean watching Game of Thrones re-runs or smoking a joint – I’m referring to an activity with just a pinch of struggle. Like going for a long run, reading Infinite Jest or sending an email to a bunch of friends. Each week acts like a tiny little deposit into the “bank account of you” – a gift to your future self. And once you cross the 25 week threshold, the activity becomes internalized. A habit, requiring minimal effort. And a gateway of untapped possibility.
You should start an email newsletter. This week. And if you make it past week 25, your life will be transformed. Yes, 25 is the magic number. We’re talking half a year. (That’s a long time.) But once you cross the threshold, the doors of serendipity will open: event invitations, access to some of your personal heroes, stealthy job postings, and offers to trade your time for money (via consulting, speaking or coaching). But you gotta make it past week 25.
When it comes to email newsletters, I’ve got a bit of experience. I’ve sent a weekly email since January 2015 pretty much every week. Today, marks my 241st issue, spanning the birth of two kids, a career change, and cross country move. I’ve worked with hundreds of creators looking to start their own, fervently cheering them on, while seeing where they get stuck.
A group email changed by life.
But everyone, I mean everyone has to start somewhere. And for me, I was on vacation (still employed on Wall Street) with a surfeit of free time and the creative confidence that comes from frozen Daiquiris.
I sent this email out to 36 friends:
Yup. Gmail. No flowery prose. No graphics. No email marketing software. Now it’s your turn to try. I’ve heard your apprehension. I’m not a good writer. I have no interesting ideas. I don’t know what technology to use. I can’t find a name. I don’t want to be one of “those people.”
I get it, and if you don’t feel a calling to put yourself out there, that’s fine. But if that tiniest little spark exits in you… you owe it to yourself to yank it out.
The myth of “not interesting enough”
“I’ve got nothing interesting to say.” This is by far the most common rebuttal against starting an email newsletter.
Oh my friend. Srlsy? Do you talk to people? Are you curious? Do you watch TV? Read? Have opinions about the world?
The newsletters that make it out of Week 25 originate from the curiosity of their creators. They run the gamut of topics, ranging from product reviews, interesting Tweets, book summaries, Spotify playlists, productivity and life advice. Here are a few examples:
- Unreadit’s Self-Improvement Newsletter (Francesco Di Lorenzo) is a collection of sub-reddits
- Recomendo (Kevin Kelly) reviews cool gadgets, gear and apps
- CoFounder Weekly (Greg Kubin) cover startup trends and Internet culture through a collection of tweets.
The myth of “I’m not a good writer”
I’m going to blow your mind. Starting a newsletter doesn’t require a lot of writing. Here’s the main section from of my favs the Ann Friedman letter:
Yup, it’s mostly just the headlines with a few connector words.
And if that’s too much writing, here’s Albert Chu’s dope newsletter “Links”. Yes, there’s no intro, no title, no graphics, no social media promotion. Albert literally just copies a paragraph directly from the article. He does add one (important) piece of value, a “star rating” system. And his newsletter is AWESOME:
How to start: Grab what interests you
Think about the information you consume and the rabbit holes you find yourself in. Your rabbit hole is someone else’s treasure. Go through your favorite Tweets, your Instapaper/Pocket, podcasts, and yes, even the other newsletters you subscribe to. Start collecting these links and adding 1-2 sentences of commentary to inject your voice into the process.
If you’re still looking for a topic, here are some newsletters I’d love to see:
- Curated podcast episodes organized by themes
- Sports-related stories that aren’t about sports themselves
- A guide to navigating shows on streaming
- More how-tos on becoming a No-coder (a la Makerpad)
- Reviews of beautiful websites
Pick a format
Now armed with your topic and minimal writing skills, it’s time to pick a format. What makes crappy Dunkin Donuts coffee so desirable? It’s consistent in its sugary-water taste. Using a consistent format has two benefits: it lessens the cognitive load on your readers, while building up a habit expectation in their own minds.
The most common format comes from the venerable Tim Ferris and his Five-Bullet Friday email newsletter. He’s got the core section of:
- What I’m reading
- What I’m watching
- What I’m listening to
- Quote I’m pondering
And then mixes it up with:
- Device/App/Tool I’m trying
- Artist I’m studying
- Challenge I’m undertaking
It’s that simple. If you leave this post with one takeaway, just copy Tim Ferriss’ format. It can cover any range of topics and you can mix-and-match the components yourself. If you want to see a bomb-ass version of this format with great design AND copy writing, check out Kai Brach’s stunning newsletter Dense Discovery:
In the video below (queued) the talented and prolific creator Tiago Forte recommends a few other “proven formats:” the personal update, the book review, the article summary and even spreadsheet templates.
Scope your topic
Now while it’s possible to just send a kitchen sink newsletter, you’ll definitely benefit from slightly narrowing the scope of your topics.
My own newsletter RadReads covers a range of topics around productivity, personal finance, careers and self-discovery. But all these topics could be lumped into the master category of self-improvement.
Each Thursday, Anne-Laure Le Cunff’s Maker Mind newsletter delivers “science-based tips to maximise your productivity.” On Twitter, we debated the tension about “content consistency,” particularly in the early days.
Individuality is a feature, not a bug
A RadReader recently gave me some feedback that my email greeting (“Sup – “) was too bro-y and it was tempting him to unsubscribe. He also felt that since I cater to a professional crowd, others might feel the same. I always consider and honor feedback, but here was my response:
My newsletter oozes my personality. It’s an extension of my brain, my soul. Which is why you’ll find random hip-hop references, memes about 40 year olds, and dad jokes. And that’s ok.
We all have that friend who follows around a Soul Cycle instructor as if they were the Second Coming. That’s because they bring all aspects of their personality to their workouts.
And as an individual creator, you should lean into your personality and showcase your quirks and the niche-y things that make you come to life. Your audience will feel it! The Andreessen Horowitz’s post The Passion Economy and the Future of Work, summarized this effect well, declaring that in this new regime “individuality is a feature, not a bug.”
In my own newsletter, I sign off with a random funny link, like a Bitcoin Rap Battle or Travis Scott getting hyped (below). Believe it or not, this is often top clicked links.
I think a light hearted tone is important. Humor is a great tool for delivery that is under utilized. The writer who is also able to distill complex topics down into a simple and authentic manner will go far.
Using a “fake voice” might work for a few weeks, but eventually you’ll flame out.
What platform should I use?
I promise to answer the question, but first I wanted to start with an example involving Post Malone and Childish Gambino. Do you know how these two Grammy-winners came up with their rap names?
A rap name generator. (My rap name? Big Corky)
The search for the perfect platform is purely a distraction from the key action. Starting. So I’ll present two options for you.
Option 1: Cheap and fast
Use a free service. Substack is incredible, but MailerLite, Mailchimp, and TinyLetter all have free plans. It’s that simple. And it’s free. Heck, if you really want to go cheap and fast, just use your Gmail like I did.
Option 2: Customized and with potential to scale
If you want to preserve the option of making your newsletter more scaleable, you might want to consider the following:
- Getting a custom domain (via Namecheap or Google Domains)
- The paid versions of the providers above (personally, I use a more advanced service called ConvertKit ← affiliate link)
- Potentially a home page for your newsletter (Carrd.co is incredible for this)
If there’s any hesitation for the more complex set up, you’re doing it wrong and should just pick Substack. Because unlike social media, you’ll always control your audience, changing services isn’t too difficult.
Writing good subject lines
So now you’re armed with a format and a tech stack and it’s time to start writing your first issue. I’m here to save you a classic mistake — a bad subject line. My first 100 issues suffered from this deficiency. I’d use something along the lines of: RadReads #56: A great productivity app, tips from VCs and Sam Altman profile
This is uninspiring. Nobody wants to read this. Instead, try engaging the reader with some curiosity, mystery, intrigue, or tension. It’s gotta be loosely related to the content of your newsletter, but play around with it.
One of my favorite newsletters, Ozan Varol’s Weekly Contrarian has some of the best headlines I’ve ever seen. His advice:
Generate curiosity and build tension. The subject line should challenge something that people take for granted. My post popular article of all time (with 400K+ views) is titled “Facts Don’t Change People’s Minds. Here’s What Does.” The first sentence challenges conventional wisdom. The second sentence generates curiosity.
But this does NOT give you permission for click-baity nonsense. Varol continues:
Most important: You must deliver on what you promise. Clickbait is a terrible long-term strategy. If you don’t deliver on what you promise, people will be fooled once–but not again.
Ann Handley who writes Annarchy a fantastic newsletter on copy writing and marketing suggests writing 20 headlines for every post. For the interested’s Josh Spector recommends teasing out subject lines on Twitter to get feedback and build anticipation. I tried this for this post, it’s intense:
Other good headline techniques include:
- Alliterations (“Double-down” or “peak productivity”)
- Pegging to the zeitgeist (“OK Boomer” or “Millennial Burnout”)
- Curiosity gap (What’s your Gazingus Pin or The Dubious Promise of Financial Independence)
And finally, subject line writing is a learned skill. Courseboss Insider creator Billy Bross recommends learning from the copy writing masters (like Dan Kennedy or David Ogilvy) and then keeping a swipe file of great headlines. Billy, BTW, is the holder of my favorite headline of all time: The time I partied with Snoop Dogg in Bel Air.
But I don’t have an audience
Newsflash. No one starts with an audience. NO. BODY.
And I’m going to teach you how to guerrilla market the crap out of your proud new creation.
The good news is that everyone has parents. And most of us have friends. Right there, you’re good for 15-20 subscribers. But pay attention to this important rule first. Repeat after me:
I will never, ever, add someone to my mailing list without their permission.
This includes your mom. Newsletters operate in the private walled garden of an inbox. They enter people’s personal space. They’re intimate. Therefore they’re based on trust. If you violate that trust, you will be brutally penalized. Ann-Laur reminds us that newsletters are a contract:
Someone giving you their email is like a contract. Don’t break it by sending stuff people never asked for / emailing more often than you said you would.
So how do you grow your audience from zero? Here are a few tactics:
- Put sign-up forms in all your social profiles (including non-obvious ones YouTube, Instagram, Reddit)
- Link to your newsletter in your email signature
- Use a poll on Instagram inviting people to join (then manually pasting the addresses)
- Encourage your subscribers to forward it to 1-2 people (in this instance, specificity matters)
- Add a link in your newsletter that says “Did someone awesome forward it to you?”
- Every time you meet someone new, in your follow-up email invite them to join
- Create pages for your newsletter on Facebook and LinkedIn
- Share each issue of your newsletter across all social media profiles (including the ones you hate, like LinkedIn)
It’s going to feel like you’re spamming your feeds. You’re not (in fact, feeds are designed for this). And if you do this for 25 straight weeks, I guarantee your audience will cross into the hundreds.
It’s all about consistency
Here’s the brass tacks. It ties back to the rule of 25. You just need to show up. And then luck will take over. As Seneca said, “Luck is what happens when preparation meets opportunity.”
Paul Jarvis (Sunday Dispatches) told me that you “build trust through consistency” and Dave Perell (Monday Musings) shared that “better to be consistently good than inconsistently great.” My friend Josh Spector has an entire playbook on how to become a better writer.
I couldn’t agree more with both of them. A big mistake I see with new creators is that they try to hit home runs (i.e. be consistently heroic) when they should instead focus on heroic consistency.
But there’s more; not only do you need consistency, but you need to dismiss any expectations of rapid growth. Here’s Ozan Varol on the futility of shortcutting the process:
I would advise dropping all expectations of rapid growth. It takes a very long time to build an audience, notwithstanding the numerous articles and courses you find online promising strategies to generate 10,000 subscribers in 6 months. It won’t happen. I would commit to doing a newsletter only if you enjoy the process. Otherwise, you won’t last.
And Matt Clifford the co-founder of Entrepreneur First and creator of Matt’s Thoughts in Between (covering the intersection of technology, society, and politics) adds that you need to be intrinsically motivated and recognize the internal benefits of writing:
But if you you show up, luck will find you. Here’s a chart of my own newsletter’s growth, from 36 subscribers to 17,000:
Each point corresponded to the following milestone:
With the exception of point D (which changed the long-term slope of the growth rate) none of the other spikes could have been predicted. Luck found me. But I had put myself out there to be found.
25 emails until transformation?
Twenty five is empirical. I’ve seen hundred creators make the attempt. It’s a lot of work. It requires discipline. But if you can tap into your own creativity and curiosity, it will start to feel effortless. And dare I say, fun.
And the result? An opportunity to clarify your thinking. A canvas for new ideas. An invitation for conversations. New relationships. New perspectives. New sources of income.
Writing a weekly newsletter has been one of my life’s greatest gifts. And I thank you for being a part of the journey.