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Email Newsletter · How to / How not to

How to Write an Email Newsletter (and How Not To)

Most newsletters are a founder talking to themselves in public and charging you the unsubscribe fee in guilt.

By Cynical SallyIssue Nº 1

A newsletter is the one channel you actually own. No algorithm, no ad auction, no platform deciding who sees you. Which makes it remarkable how many people treat that direct line to a human's inbox like a place to dump a changelog and a motivational quote they found on a slide.

This is what you getA real Full Truth, in full
Cynical SallyEmail Newsletter

The Full Truth

on A founder's weekly 'Building in Public' email newsletter

4.2
out of ten
The subject line was 'Big week!!' and the big thing was that you redesigned a button nobody clicks.
The Investigation
  1. 01

    The subject line is a mood, not a reason to open

    Critical

    'Big week!!' promises excitement and delivers a button redesign. Subject lines are a contract. Name the actual payoff, like 'We cut signup from 6 fields to 2 (here is what broke)', so the open is rewarded instead of punished.

  2. 02

    Everything is 'we', nothing is a story

    Notable

    Eleven sentences start with 'We're excited to' or 'We've been working on'. Readers do not feel your excitement, they feel told to. Lead with what changed for them, or with the messy decision behind the change, not your internal sprint board.

  3. 03

    The real news is buried under housekeeping

    Critical

    The one genuinely interesting line (you churned a big customer and learned why) sits in paragraph five under a fold of metrics. Open with the scar. Lead with the thing you would actually tell a friend at a bar.

The Copy Clinic

Hope you're all having a great week! We're super excited to share some big updates on what we've been building. It's been a busy few weeks at the company and we can't wait to tell you all about it!

We lost our biggest customer on Tuesday. Here is the exact email they sent, and the three things it taught us about onboarding that I wish someone had told me a year ago.

Stay tuned for more exciting updates coming soon. As always, thanks for being part of the journey!

Next week: the pricing change we are scared to ship, and why we are doing it anyway. Reply and tell me the dumbest reason you ever cancelled a subscription. I am collecting them.

The Action Plan
  1. 1Rewrite every subject line as a specific promise with a concrete payoff, then delete any that contain 'update', 'news', or an issue number.
  2. 2Find the one sentence in your last issue you would actually say out loud to a friend, and make it the new first line.
  3. 3Enforce one idea per send. If you have three, you have three newsletters, not one crowded one.
  4. 4Add a real reply prompt at the end of each issue and answer everyone who responds, so the list becomes a conversation instead of a broadcast.
Yours for the price of a coffee.Printed with disdain
Your turn

That was a stranger's email newsletter. Drop yours, I will go just as hard.

One coffee, from €2,99. No mercy.

Good ones feel like a smart friend forwarding you something they could not keep to themselves. Bad ones feel like homework. The difference is rarely the writing talent. It is whether you respected the reader's time before you asked for theirs. Think you can tell which one you send?

How to do it right
  • 01Open with the single most interesting sentence you have, not a greeting. The first line is the whole battle, because it is what shows in the preview.
  • 02Pick one idea per send and develop it properly. One sharp thought beats five shallow links every time.
  • 03Write to one specific person you actually know, by name, in your head. It kills the committee voice instantly.
  • 04Earn the call-to-action by being useful first. Give three times before you ask once.
  • 05Cut the last paragraph. It is almost always you reluctant to stop talking, and the reader noticed two paragraphs ago.
How not to
  • Opening every issue with 'Hope you're having a great week!' which tells the reader nothing and burns your most valuable line.
  • A subject line like 'Newsletter #47' as if the reader has been counting, or cares, or remembers issue #46.
  • The 'quick update' that is 1,400 words of features nobody asked about and one buried link to the thing that actually matters.
  • Reusing your blog post as the email, so the email is just a guilt-trip with a 'Read more' button stapled to the top.
  • Signing off with 'Stay tuned for more exciting updates!' as a load-bearing promise you have no plan to keep.
How to Write an Email Newsletter (and How Not To) - Cynical Sally