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When I co-presented a webinar on selling your first ads in October, I was actually just starting that journey for The Bentonville Bulletin.
Of course, I’d been the “revenue guy” at Madison Minutes, so I’d done it once before.
But now that I’m back in the saddle, I’ve got some notes on the first 30 days of selling ads.
During the webinar, my co-presenter Allison Mcllmoyl wisely suggested starting ad sales with just a few options for your strongest product. For us, that’s our email newsletter. With over 8,200 subscribers and a nearly 60% open rate, it’s our clear standout.
But it’s also wildly unpredictable. We publish 3–5 articles a week and send them out as soon as they’re ready—we just let 'em fly! In addition, we send a weekly roundup on Fridays, featuring links to everything we published that week plus other local news stories from around the area.
This approach is pretty chaotic, but it’s worked okay so far. Despite the unpredictability, 97.5% of subscribers stay on the story alert list, even though they could opt to receive just the weekly roundup.
However, this does present a problem: you can’t sell specific days if you don’t know when you’re sending. We should probably fix that, but I’ve been focused on other things and don’t want to think about it right now. So instead, we played to our strengths and offered these options:

I made it up. I did little competitive analysis, but I know that it’s a fraction of what more established media organizations in my area charge.
My strategy is to start small, sell out, then raise prices and add new ad options as I learn more about advertisers’ needs. I wanted to avoid analysis paralysis at all costs.
When someone downloads our media kit, our Indie Tech setup automatically adds them to a separate email list. Indie Email has a notes feature where I can jot down details from our conversations. It’s essentially a lightweight CRM for ad sales—no need for anything complicated.
Just to get the ball rolling, we offered readers a deal: if they contributed $50 through our supporters program, we’d dedicate a $300 advertising credit to a nonprofit of their choice. We had six people take us up on the offer. This is a super steep discount, but repeat after me: start small, sell out.

I haven’t been active in the local Chamber of Commerce circles for long. A retired businessman who loves what we’re doing has offered to introduce me to his network. Being connected by a mutual contact is so much easier than cold-calling.
By the end of a week, ad clicks drop significantly—no surprise there, since many audience members have already seen it prominently placed in multiple emails. I plan to start rotating two different ads each week to keep engagement up.
So far, we’ve sold three week-long flights at list price and five logo sponsorships. This doesn’t include the deeply discounted advertising offered to readers.
We’ve got more opportunities in the pipeline, and I think it’s fair to say most relationships take more than 30 days to build. I’m really excited about the potential in the next few months.
And if you think about it, since we started at $0, our advertising revenue has grown by a multiple of infinity. Show me another business with those Q4 results!