Depending on who you ask, it’s either the best time ever to launch a newsletter… or “eMaiL iS dEaD.”

Last week, Google held its I/O conference and it’s become abundantly clear that Alphabet CEO Sundar Pichai and the rest of Google have a fever… and the only prescription is more AI.

Well, in addition to killing search as we know it, Gmail is rolling out its AI Inbox product to Plus and Pro users (previously, it was only available to Ultra users), which means it’s only a matter of time until it hits the gen pop.

It’s not entirely clear how this will all shake out (and anyone who says they know is probably full of sh*t) because Gmail doesn’t exactly put its playbook on a silver platter.

But between this latest announcement and previous rollouts, we know enough to understand what some of the biggest threats to newsletter operators are…

1) Your email could be a line item in some sort of AI Daily Brief (if you’re lucky)…

2) These AI overviews become a permanent fixture in the inbox and in threads (note: these already exist in some capacity)

3) Gmail goes full AI-powered algorithm mode. Think: a world where nothing is chronological. Your entire inbox is prioritized based on what Alphabet thinks you want/need to see. This is already happening in the Promotions tab.

Yes.

In fact, if your newsletter’s business model is one or both of the following, this is existential…

1) You get paid to run ads in your newsletter. In a world where subscribers don’t need to open your email to get the gist of it, your ads don’t get seen, thus making them worthless

2) You sell a product or service in your newsletter. Pretty much the same as above. No eyeballs = no sales.

So, yeah, it’s kind of a big deal.

Well, for starters, don’t freak out.

Unless, of course, you don’t have a newsletter yet. Or you haven’t begun collecting email addresses on your website. In that case, run (don’t walk) to set up a way to capture email addresses (and phone numbers… trust me).

For everyone else… let’s talk strategies for prepping your content for the end times.

(Yes, there are a boatload of other considerations when it comes to the impending AI apocalypse, like list hygiene tactics, diversifying your biz, and thinking outside the inbox. But today, let’s talk content).

Time to start optimizing your newsletter for AI summaries. This, of course, is easier said than done. There’s no way to know exactly how Gemini is summarizing or prioritizing emails.

But, here’s what we know based on what we can see in our inboxes…

For inbox summaries:

On the thread level summary front (once you open an email), here’s what we know:

It appears that Gemini is a lot like most of your readers: they only read the first few sentences. That means you’ve got to make those first 200 characters count.

Those first few lines need to be treated like hooks. Preferably, God-tier level copywriter hooks.

Let’s make this real…

Currently, my (other) newsletter (The Water Coolest) begins with…

“Hey there weekday warrior,

Today we’re getting into… [list of the day’s biggest biz and market headlines].”

Don’t do this. Gemini will recap this (likely without any of my humor).

Best case: a reader likes one of the stories and wants to see more. Worst case: they get everything they need from an AI summary and never open anything.

A better approach? Using my opening remarks to tell a reader what they’re about to get: “Elon’s latest move at Tesla is going to impact the SpaceX IPO.”

This email (yes, the one you’re reading) is a masterclass in what not to do as well…

“Depending on who you ask, it’s either the best time ever to launch a newsletter… or eMaiL iS dEaD.

Last week, Google held its I/O conference. Think: Apple’s World Wide Developer Conference, but for people who prefer green text bubbles.”

Gemini’s summary would very likely neuter any personality or voice in my opening lines and focus on the fact that Google I/O does, indeed, exist.

How could I have done better?

“Let’s talk about WTF you can start doing today to defend against Gmail’s AI inbox updates.”

Getting “above the fold” right was already important. In this weird AI world, it just became exponentially more important.

Get tested

There’s no “one simple trick” to know how Gemini is going to summarize your newsletter content. That means the current best practice is to monitor the situation. Set up some email inboxes and keep an eye out for how your email/summary renders. Bonus points for asking readers to submit screenshots.

Oh, and it’s probably worth just asking the free version of Gemini how it would summarize a specific newsletter.

Give readers a reason to open your email.

If you’re simply dropping knowledge bombs in your newsletter, there is no defense against AI summarizing the nuggets a reader needs to get the gist of it. Commodity content can be summarized without significant loss of value. As such, readers would be happy to read it as part of an AI Daily Brief or skim it as part of an AI summary.

So it’s on you to make sure they need to open the email. If your newsletter is appointment viewing, it doesn’t matter how damn good an AI summary is. You will get an open.

And before you say it, thinking you have “killer content” just isn’t enough. Good content is table stakes.

You have to force a reader’s hand (literally) to click and read through your email. ID something (or, ideally, things) that AI won’t be able to replicate in 200 characters or less…

Listen, I didn’t say this was going to be easy, you guys…

But if you get this (and a whole bunch of other things) right, you could be one of the lucky few to break through and ascend to AI inbox nirvana. A place where you manage to land in an inbox, get prioritized in an algo-driven inbox, find yourself in the AI Daily Brief, and make summaries work for you.

Godspeed.

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 on a scale of 1-10?