8 Newsletter Questions From Curious Business Owners
After a short presentation on a newsletter's value, the importance of one as a trust-building tool, and get started now tips; there were questions. Here are my answers.
I had the privilege of being asked by Laura Wolff to share my thoughts on the value of newsletters with her clients this Tuesday. Give her a follow, she regularly shares great advice about leaning into yourself.
After totally getting the date wrong, and a frantic drive from my Dad’s in Sulphur to my Mom’s in Lake Charles about 45 minutes before the start (that’s in Louisiana; WhoDat and pass me dat boudin, sha) for her more stable Internet connection, it went well. Probably better than if I had time to “plan” more (fritter away time, worry, and not really improve anything).
My emphasis on getting the intention right by thinking of a newsletter as first a trust-building tool (but also one that should lead to revenue) and then a few pieces of practical advice for a simple start was well-received.
Better yet were the questions. We had, I think 15 folks online. I’ve moderated webinars with 1,000-plus folks listening live and gotten fewer questions. That was fantastic!
Here they are, asked and answered, and lightly edited for readability and added context in a few spots where my brain shorted out in real time.
For context, this post might help.
Segmentation — what’s the strategy, and how much does it matter?
Until you actually have a list, it doesn’t — so I’ll start there. My whole career has either been small-scale, like I am now, or larger-scale at AIIM, which was a national trade association with about 60,000 members [this feels low, but it was over a decade ago and I have no access to numbers]. So I’ve either been at the 300-person scale or a much larger scale. [I did spend 4 years doing inbound marketing as a HubSpot agency for copier dealers, but none of them paid for the segmentation tier. We did segment by splitting lists based on purchases and interests, but it wasn’t as sophisticated as we could have done for them and their 4,000 to 10,000 customers/leads.]
The one tool I really know is HubSpot. The basic buckets are intent and interest. On intent, it’s tofu, mofu, bofu — top, middle, bottom of funnel. Someone new is top of funnel. Someone in the decision or interest stage is middle. Someone ready to buy is bottom. The other way you split is by interest — so for you, that’d be fasting, the courses, and so on.
[I misspoke here. By interest, I was thinking topic – document imaging, records management, standards, workflow, etc. to use examples from my AIIM time. What I said out loud was segmentation by product, which is a third way to segment your audience.]
Say you had four segments with a few thousand names each. You’d only send the fasting course to people who signed up for the fasting lead magnet — you segment them out instead of blasting everyone. It does boost revenue, but you have to get to that point before it matters. I wouldn’t trust my word on the exact number, but 500 feels about right to start, if you’ve got two main product lines. Beyond that you get into “these people bought these three ebooks and not these five,” and you start upselling and cross-selling. That’s structured thinking, which is not what I do well. I know just enough to be dangerous — I get inside a tool and poke buttons until it happens.
[The poking buttons is true, but with a little more planning and intent behind it. I’ve done some lightweight segmentation work for email campaigns. Once you have more than one thing to sell, segmentation becomes a possibility:
These folks have bought thing 1, so let’s not send messages about buying thing 1 to them.
But, let’s send emails to the purchasers of thing 1 to see if they would also like thing 2.
From there, it starts to get complicated.]
If reading that made your eyes glaze over, you’re not alone — the technical side is exactly where most people stall out and quit. That’s the part I take off your plate. Newsletter in a Box means you don’t have to learn the buttons. I do that. Click here to learn more.
How long should a newsletter be?
My rule of thumb: shoot for 500 words. That’s about enough to cover one topic or introduce a couple. But the real answer is write until you’re done. I think it was Strunk and White — write until you’ve said what you wanted to say, then stop. [Actually, I think this was Mr. White, my sophomore high school English teacher. “Friends are like shoes. You get ‘me, use ‘em.” was another expression of his.]
A newsletter is a container word, like “book.” What goes inside can be anything. It could be a single 2,000-word piece. There’s one I get — Newser or something like that — where the guy pulls ten bits of news, writes a short bit up top, tweaks the headlines and decks, and links out to the original source. Nearly pure curation (he makes revenue from sponsorships/ads). [Others add commentary to each item then link to the source.] I still think of newsletters like a magazine because I did that so long — features, departments, an agony column like Irma Kurtz’s in Cosmo. It can be whatever you want.
And you mix and match. Over time you run experiments — sometimes short is what your audience wants, sometimes long. Nobody knows until you start doing it. I used to make fun of consultants for saying “it depends.” Then I became a pseudo-consultant, and yeah — it really does depend.
I’ve written about this in detail in these two posts, I only touch on length in the 22 tips piece, but I think the advice is relevant for you if you’re reading this and having a hard time starting.
Substack vs. my own email list — how do these interact, and do I need both?
[I didn’t quite grasp the “why are you doing the same thing for a slightly different audience” nature of this question at first though a question later got us there.]
I probably wouldn’t run both long-term. You could absolutely just use Substack as your newsletter platform because it has the discovery features. But Substack has no real email campaign or management capability — even the most basic email platform beats it. You can send a one-off email to your subscribers in Substack, so it’s bare-bones email marketing, but if you’re doing anything complicated, keep them separate.
If you’re trying to simplify, ask yourself: is your activity on Substack growing the list and bringing in customers? If it is, keep leaning on Substack. If your own self-contained list is doing well and people are finding you and you’re getting business, why drive yourself crazy running both?
On video — YouTube is one of the top sites in the world, so being there is good, but you still have to make the video somewhere. The way I want to use mine: shoot on my phone, drop it on YouTube as a holding place and where it can be found, embed that video in the Substack article it came from, then put it up on LinkedIn, since video does well there for B2B. One thing, distributed multiple places. I think of YouTube as just my video hosting platform that also happens to be one of the largest search engines. It’s not my “home” online; that’s Substack. Figure out where your one home is, then point everything else at it.
A quick aside on gut vs. rules
For how a newsletter feels when you’re making it — trust your gut. But for the technical stuff like subject lines, ignore your gut sometimes, because your gut is a moron. At AIIM I’d write a boring, dry, informative subject line and the open rate would climb. Then I’d get a clever, funny one, everybody would laugh — and it would tank. A couple months later, back to normal. So follow the rules sometimes and you’ll do a little better.
Is it ethical to invite my Substack subscribers onto my main newsletter list?
I’m pretty sure this is fine — I get queasy about sketchy stuff, and this feels okay. Check my work though! These are people already actively hearing from you who said yes to you. You’ve got this other thing over here. So send an email: “Thanks for being a subscriber — I do this other stuff over here too, are you interested?” Let people say yes or no.
It’s close to a re-qualification campaign — like when you’ve got a dead list of names you don’t want to just dump. I did this for a company a couple years back. They had three or four thousand names from trade shows they’d never touched. We set up a short sequence: “Thanks for being here, haven’t heard from you in a while, still interested?” As long as you don’t keep emailing the people who never reply, you’re fine. And always, ALWAYS, have an easy unsubscribe process.
Why would I have both a Substack and a newsletter — and if I do, do I copy one to the other? [This is a continuation from the question earlier]
If you’re just starting out with nothing, go to Substack. Why keep ramming your head into a wall when there’s an option with built-in findability? A WordPress blog just sits out there alone — Substack has the discovery, the Notes, the built-in network. I’d ditch the standalone newsletter, import your list, and run it on Substack. Most of us hit the first friction point and quit. Substack is dead easy, works on your phone, and removes some of that friction.
On copying one to the other: if it’s the same content going to two different lists, you’re just making work for yourself — combine them, pick one. From the reader’s end, nobody cares whether it came from MailChimp, Kit, or Substack. That part is irrelevant. The only real exception is a launch sequence — schedule a masterclass, reminder email, sell-sell-sell, then close. You can’t really automate that in Substack; you’d have to send each one manually. I half suspect Substack will eventually bolt on some light email-management tool and charge for it.
[This also gets at name confusion, which I talked about in the presentation – is Substack a newsletter? An email? A Twitter-esque feed/micro-blog ? A blog? Yeah, it’s all of those. I wrote specifically about what a newsletter is here to get folks thinking about the content, not the container, as the important thing.]
You said a CTA in every newsletter — but isn’t that just selling?
Yes, a CTA in every one. And yes — it is selling. It absolutely is. You have to hold two things in your head at once – you need to use your newsletter to build trust by sharing helpful/useful information AND you need to sell your services/products. Kinda like propaganda and marketing are flip sides of the same coin — same mechanics, the intent is what’s different.
So if you coach people-pleasers: write a post that says “stop doing that,” and your CTA is a class — “I can teach you how not to do that.” That’s sales, and that’s fine. I put a CTA in every newsletter for Newsletter in a Box. I can’t think of a single newsletter on Substack that’s serious about using it to market/sell what they do that doesn’t have at least one CTA per issue. Some people put it at the top; I do a middle one and a PS at the bottom.
So 80% helpful, 20% sell?
I’ve seen people do that. Mine is more — some are like, you would have like 95%, you’d have a very tiny CTA or message at the end. I’ve seen others, you have maybe a 1500 word post, and then they’ll have a three or four hundred word description of an upcoming whatever they’re doing, like a cohort or what have you. A CTA is a container word like “newsletter” — it can be a buy-now button, a simple subscribe button, a short description with a link, or a half-page description of your service with a button or link.
You said you’ve spent eight years thinking you had to send eight purely helpful issues and then one with a CTA. It took me a couple years to get past that too. Ask for the money in every one. You are a business. It’s OK to ask for the sale. Don’t be a jerk about it, don’t be pushy — but tell people you can help them. Selling is helping. When you truly believe that, you realize you’re doing people a disservice by not making the offer.
And, yes, I still feel that awkwardness too, but all it does is hold you back from succeeding. Work to overcome it without becoming the stereotypical used car salesman.
A random thought here to your point about the eight and then one. I think there is space every now and again to just be like, “Hey, I do this. Here’s what I do. Here’s how I help.” as your newsletter issue. I’ve not done it because it feels a little bit weird, but I have thought about the idea of writing a “here’s how I work with you” sort of thing, which is basically an entire sales post semi-hidden behind a “hey, this is complicated, you SURE you want to do it yourself” type post. It’s a pure sales pitch and I haven’t brought myself to do one (yet).
What’s the actual difference between a newsletter and email marketing?
Think of your newsletter as your asset — the thing people love. Email marketing is what happens when someone clicks on a CTA (possibly, depending on the offer in the CTA) and kicks off an automated email campaign. Say you’ve got a CTA in your newsletter — “interested in my slumber party this weekend, we’re having slushies?” That CTA feeds into an email marketing campaign, maybe four emails.
First: “Thanks for your interest, here’s what’s happening.”
Second: more detail — who’s coming, who’s already pitched in. Each one has a harder sell at the bottom.
Third: Hey, register now and we’ll give you a free pillow so you’re not unarmed in the pillow fights!
Fourth: I think of this as the shit or get off the post email: “Last time we’re asking and buh-bye for now if you’re not interested.”
The newsletter builds the trust; the email campaign does the direct selling off the back of it.
I’m going to build a webinar off of this presentation. It won’t be a goo-roo pitch of 15 minutes of content surrounded by 45 minutes of “Buy my services.” In fact, here’s the pitch I’ll include (because you do need to ask for the sale and I like a good scotch now and then): hey, I do this stuff. Need help? Let’s talk. Details are on the last slide and you know how to find me on Substack.
If you’re interested, drop your name below and I’ll make sure you get the details as soon as I figure them out.
PS — Got a question I didn't cover here? Ask away. And if the answer is "I just want someone to handle all of this," that's Newsletter in a Box, send me an email: bryant@simplyusefulmarketing.co.
Musical fun.
Can’t pass up the opportunity to share one of my favorite sitcom intros! The full song follows for a double-dose of nostalgia.
That, of course, kicked off a stream of 70s-era tunes, here’s the one I picked out, which I’ve always thought is the definition of melancholy wistfullness.