Web + Wins #26: Newsletter mistakes I see small business owners make
This Week's Update
We’re getting reaaaally close to the “let’s circle back after the holidays” season. 😅 I’ve got a handful of client projects wrapping up in Q4, and then I’m hoping to carve out some time to actually work on the business. There’s a lot of organizational stuff to I need to tackle – including updating my own website, which is long overdue. I’ve been so busy building other people’s sites that mine has been neglected. I think I’ll share my refresh plan here when I get to it.
And tomorrow — I’m hosting the first Content Club with Jonathan Palance from Soda City Films! It’s a virtual meetup where you can come share a content idea you’ve been sitting on, get real feedback, and make some new connections.
Before I went full-time on Snaply, I used to hop into things like this from my car in a parking lot on my lunch break. But those live moments gave me so much: expanded my network, sharpened my thinking, and kept me moving forward, no matter what I was trying to build (that seemed to change every few months till I found something that stuck).
Signups are still open if you’re curious. Come see what happens!
Get a Web Win: Newsletter Mistakes I See Small Business Owners Make
I’ve been thinking about this one for a while — partly because I’ve made a lot of these mistakes myself, and partly because I’m getting asked about my newsletter more often as more people start their own. So here’s the list.
Before Web + Wins, I started newsletters that went nowhere. The two biggest missing pieces were strategy and consistency. When I finally launched this one, I leaned heavily on two people I’ve followed for years: Josh Spector, who writes about using content to attract the right clients, and Matt McGarry, who focuses on newsletter growth and distribution. If you’re serious about building a newsletter, follow both. (More on Josh in Convo Corner below.)
Here are the mistakes I see most often — from them and from my own trial and error:
❌ Your newsletter is a company highlight reel. Nobody really wants a monthly roundup of your awards and announcements. Make it about the reader and provide something valuable. Definitely work in your business updates — but only when they offer a real lesson or insight.
❌ There’s no clear goal. Why are you sending a newsletter? Staying top of mind? Generating leads? Building relationships? The answer shapes what you write, how often you send, and what you ask people to do. Pick your goal and work backwards.
❌ You’re sending from Gmail — or your newsletter is a PDF. If you’re BCCing a list from your personal email, it’s time to upgrade. An email service platform like Kit (that’s what I use), Mailchimp, or Constant Contact handles deliverability, unsubscribes, and analytics — and it looks far more professional. A PDF attachment has the same problem. Make it easy to read on any device.
❌ You’re not thinking about deliverability. Authentication settings, list hygiene, engagement rates — these all matter if you’re trying to grow. Great content is useless if it’s landing in spam. Most ESPs (email service providers) walk you through the basics when you set up. This can get techncial, but ChatGPT and Claude are there for you.
❌ The content disappears after you send. Your newsletter shouldn’t live and die in an inbox. Turn it into a LinkedIn post, a blog article, a short video. I’ve started doing this on my website and LinkedIn. It extends the life of every issue significantly.
❌ You’re not on any discovery platforms. LinkedIn has a built-in newsletter feature (this is on my list). Substack has its own audience (playing with this one very soon!). Kit has a discovery network. The more places your content can be found, the more people can find you.
❌ You’re selling too hard. Especially relevant for service-based businesses. Your newsletter is a trust-building tool, not a sales page. Share your expertise generously. The goal is to stay top of mind so that when someone is ready — they think of you first. Push too hard and you lose them.
One last thing from personal experience: write a welcome email. Someone just said yes to hearing from you — don’t make them wait two weeks. Automate a short note and invite a reply. It goes a long way.
Web + Wins is still an experiment. But these are the things I’ve seen over the years and the mistakes I’ve made myself. If you’re working on a newsletter, let me know — I’d love to subscribe. 🙂
Convo Corner: Josh Spector
I’ve exchanged comments and the occasional email reply with Josh over the years, but we haven’t had a real conversation yet. Yet. Still, I can’t talk about newsletters without mentioning him.
I first discovered Josh’s content back in 2021. I was working as an account manager, wearing a lot of hats, and we had a new client interested in email marketing. It wasn’t really something we were offering, but we took it on anyway — and I started Googling.
A super helpful Medium article by Josh Spector came up, broke down exactly where to start, and I was hooked. From there I went deep: followed his tweets, then followed him to LinkedIn, subscribed to his newsletter, bought a few of his products, and listened to his podcast when he launched it. (And I'm hoping a book is next!)
His focus is on using content to get in front of the right people — not just more people (be for somebody, not everybody). Which is exactly the kind of thinking that changed how I approached my content. I tried multiple newsletters over the years before this one. They didn’t go very far. But I’m so glad I found him early. He’s 100% worth following.
Let's Talk!
Q4 is a great time to get your website in order before the new year hits. Whether you’re starting from scratch, doing a refresh, or just wondering if your site is actually working for you — I’m happy to take a look.
