
In 2024, Naptown Scoop ran 728 ads for 95 clients in 240 newsletters. We also produced about 10 unpaid stories per newsletter. Needless to say, staying organized is essential. A business built on fresh content every day is only as good as its systems.
So, here’s how Naptown Scoop stays organized in the ads department.

It all starts with a good ad scheduler. We use Newspaper Manager but started with Notion. I’ll be writing a deep dive on schedulers soon but I need to get a demo of one final software next week.
Btw, a simple spreadsheet works in the beginning. All you want to do is make sure whatever you use can be exported as a CSV for importing into a “proper” system if you ever outgrow a homegrown solution.
Step 0.5: Research and Brief
In the vein of Joseph Sugarman, I learn everything I can about a client before we advertise for them. This includes having them complete our advertising brief (which you can access in the Members Lounge) along with our own research of their online profile and sometimes even an in-person conversation.
🤖 AI Tip
I’m starting something new today. I believe AI is such a powerful tool that if you’re not using it every day, you simply aren’t trying hard enough and will get left behind. So I’ll be sprinkling lots of AI tips into Life of Scoop emails from now on.
You can use ChatGPT Agent Mode to do this research for you. Ask it to scour the client’s online profile (website, reviews, social media, etc.) and write you a one-page advertising brief. You can even tell it to add the info to its memory which as you’ll see, will come in handy later.
Step 1: Creative
At the start of every month, we send each client a complete list of their ads for that month – along with any from the first week of the next month so we don’t get behind the 8 ball. Pretty tough to produce an ad for the second of the month when you ask for creative on the first.
In the diagram, this step is called Runsheet. It’s easily generated with a couple clicks in Newspaper Manager.
From here, things go one of two ways.
The easy way is Copy. That’s when the client sends us ready-to-publish ads. Usually because they have a crack in-house marketing team or we’re reusing ads we’ve written for them.
The hard way is Guidance. That’s when the client tells us what they’d like to promote and anything else we’ll need to produce a great ad.
Once we have Guidance, it’s time for Writing. Naptown Scoop offers copywriting services to all clients at no charge. It’s a huge value-add, especially for clients with no marketing staff or knowledge.
Early on, I wrote all the ads. Then I hired a copywriting-as-a-service provider (10/10 do not recommend). Then I hired a college student. And a few months ago, I built an AI agent taught with all the same lessons I was along with a few of our best performing ads to write ads for us.
It works brilliantly. So brilliantly that my operations assistant (see org chart) now creates 95% of Naptown Scoop’s ads. I still approve them all before clients see, but I rarely make changes.
Once an ad is written, we email a proof to the Client. They either love it (most of the time) or request changes (rare). Another Naptown Scoop hallmark is unlimited revisions. Many publications charge after one or two. We work until it’s right. And it rarely takes many rounds.
After clients approve, ads go directly into Beehiiv ready for publishing and into our advertising folder on Google Drive where each client has their own folder.
Step 2: Reporting
Running ads for clients without reporting is like the plumber coming to fix your toilet, telling you he’s done 10 minutes later, and leaving without showing you that it’s actually fixed.
Some ad schedulers (like Sponsy) have integrated automatic reporting, but you’ll likely have to do it manually.
On the last day of each month, we send each client the same Runsheet we send at the beginning of the month, except this one has unique opens, clicks, and clickthrough percentage for each ad.
We also use UTM links so savvy clients can check on results themselves. Some clients provide us Bitly links for the same purpose.
And some clients prefer “manual” tracking such as including things like, “Show this ad and say the Scoop sent you” to count conversions. Our veterinarian offers a free ice cream chew toy to new clients who come from Naptown Scoop and counts the amount she gives out each month to track conversions.
The purpose of this step is to show your clients a positive ROI on advertising with you. Because if clients pay you $1 and get $3 back, they’ll renew that contract year after year.
Step 3: Billing
I actually do not recommend you do billing like I do. I need to change it but the pain of switching is too much right now.
Scoop’s way (bad)
On the first of every month, we send invoices for all ads run the previous month. The invoices are due 30 days later.
So if you had an ad on July 31, your invoice comes August 1 and is due September 1. Basically net 30 billing terms (payment due 30 days after services).
But if you ran an ad on July 1, your invoice comes August 1 and is still due September 1. Basically net 60 terms. Good for you. Bad for Scoop.
Invoices are sent to all clients at the same time with just a few clicks in Newspaper Manager which is a very nice feature.
We remind clients about unpaid invoices once a week. Invoices that aren’t paid on time get 1.5% interest added immediately and every additional 30 days they remain unpaid. That said, we rarely exercise this right. It’s not worth the hassle.
What you should do instead
The best way to get paid for ads is to get paid upfront. Once you’re sending big enough contracts, this isn’t feasible for all clients but it will still happen.
The second best way to get paid is subscriptions in Stripe. It charges clients automatically every month and sends receipts. You can customize the amount and add PO numbers if needed. There’s just one caveat: the amount must be the same every month.
That doesn’t always work for us because a client might run 3 ads in June and only 1 in July. A workaround is to average the total contract amount by the number of months and create a subscription with the average monthly bill.
And the third best way is to store credit card info and manually charge clients each month. Make sure you store it securely (in a compliant place like Stripe). This is still good because it guarantees you get paid, it just takes a little more effort.
Whatever you do, just don’t be in the business of collecting money.
Quick billing tips
Don’t accept checks. Unless it’s from a client paying upfront. Monthly checks are super annoying.
Require a deposit for new clients. We charge new clients 20% of their contract value upfront if we’ve never worked with them.
Include a late fee in your contract, but rarely enforce it. Local newsletters are small town businesses. Late fees piss people off. Pissing people off in a small town business ain’t good. Plus, you’ll look like a benevolent publisher when you tell overdue clients that you have the right to charge a late fee but you won’t, just this once.
P.S. Late fees don’t exist if you bill automatically.
How much work is this?
It sounds like a lot, but it’s actually not. Also, basically everything you just read is handled by our operations assistant. The only thing I do is generate invoices each month and meet with new clients if they’re spending above a certain amount (usually $5k in a year).
How much does this cost?
Newspaper Manager is $90 per user per month. We have three users (me, sales rep, operations assistant).
ChatGPT Plus is $20 per month but it’s such a powerful tool that it’s really not a cost of this process. At this point, it should be considered a standard cost of doing business.
Google Drive is free for a personal account (fine for starting out) and Business Starter is $7 per month per user. Again, this is a standard cost of doing business.
As you learned on Wednesday, my operations assistant makes $1,720 per month. Again, this is a standard cost of doing business for me. You probably won’t have this luxury when starting out, but that just means you’ll have to work a little harder.
🤖 AI Tip
If you don’t have a VA when starting out, you can automate much of this process using Zapier or a similar tool. Just feed the process into ChatGPT and ask it how to automate it. It’s so good at giving you step-by-step instructions if you aren’t an automation wizard.
That’s it for today
If you have any questions (about this or anything else), always always email me. I’m happy to help. And your question might be something everyone else is wondering, too, so they often inform how I write emails just like this one.
How can I help you?
I can get you 20% off beehiiv, my favorite place to send local newsletters