He went from one newsletter a week to three and the readers stayed

Shane Brady runs BOQ Today in Belleville, Ontario, a town of about 56,000 people. He does it while holding down a full-time sales job. This is the second half of our conversation, and it starts with the question I was most curious about: what happens when you go from one issue a week to three? Shane also tells the story of how he got press releases, and why a paid event calendar "saved my life." If you missed the first half, start with part 1 on writing a newsletter in one hour.

Going from one issue to three, almost overnight

I was about to move to twice a week myself, and I wanted to know if more issues meant more unsubscribes. Shane's answer was a relief. He basically went from one to three in one step. He dropped to two for a couple of weeks when his personal life got crazy, then went back to three.

That first week at three did have a higher than average turn rate. He got a few complaints. But it was nothing close to make or break, and after that, he says, nothing changed with churn at all. It was just what they do now.

Polls on Monday, answers on Wednesday

The extra room let Shane try things he couldn't before. He runs more polls and asks readers more questions. Then he shares the answers in the next issue, instead of waiting a full week.

That timing matters for local news too. Shane covers city council and city updates. If there's a council meeting on Tuesday and he tells people Wednesday morning, it's still relevant. A week later, it isn't.

I made the case that once a week is too rare. If readers see you four times a month, they like you, but you don't feel like a brand that matters to them. Shane agreed. He also pointed to Mikey Pesto, who sends once a week and makes it work with creativity and other ways of getting in people's homes, like physical Monopoly boards.

Sales is why he went to three

Shane has sold for 12 years, and he says he always knew he could sell ads. He also knew that one issue a week wouldn't work long term. So he ripped the band-aid off.

He framed it as a test of whether he was really getting serious. Either he'd find out quickly that he couldn't do it with the time he has, or he'd stay at one a week and never monetize it enough to be worth it. He chose to find out.

Linking to the original source

Shane isn't building a website yet. Long term, he says, yes. For now the newsletter alone is enough to monetize. He tried hiring a local freelance writer a couple of times, and the articles didn't take off. He isn't sure why, and thinks his lack of media background may be part of it.

One thing he changed was where his links go. He used to link to four or five local news outlets. Now he links straight to the first source, like the restaurant or the press release. Some subscribers had told him they didn't want to click through to yet another page. His older readers also don't have Instagram, so linking to a restaurant's Instagram post for a new menu may be part of the problem.

I described the model we're trying: two or three sentences in the newsletter, a button to a longer article on our site, then the restaurant's website, map and Instagram at the bottom. It's much more work. I told Shane that with a full-time job, I wouldn't do it. He liked the idea of a small team writing the stories nobody covers. We also talked about asking a business to write its own 500 words, which is basically a press release.

One week of phone calls for press releases

I asked Shane how he gets press releases at the same time as his competitor. His answer wasn't the easy one I wanted. He took vacation days from his job, and called every place in town that sends press releases. He called, emailed and sometimes walked in. In a town of 56,000 people, that was about 25 to 30 calls. He calls it the week from hell of his life.

It paid off. Now he's on their mailing lists and gets press releases when everyone else does.

He also hated digging through email on Friday when writing Sunday for Monday. So he found where the releases were being posted and hooked up those websites' blog feeds to RSS. They land in a Slack channel, and he picks the ones he wants. That only worked after the outreach was done.

Paying for an event calendar

Finding events was the other big time sink. Shane spent money on an event calendar from a company that does them professionally: City Spark. He found them through 6AM City, which also uses it. He was tired of digging through Facebook and people's sites, and wanted everything in one place so he could pick what to cover at the start of the week.

He says he wouldn't be doing this now, along with his full-time job, without it. The time it saved went to selling ads. He can now reply to every inbound sales inquiry and take the meeting, over Zoom or in person. He no longer sends media kits that "go off into thin air."

He curated Monday's newsletter on the day we recorded. It took about 5 to 10 minutes.

Shane put the top five events in each issue and tells readers to use the calendar for the rest. He said he was about to get a banner ad sponsor for the calendar, so it could pay for itself.

It doesn't catch everything. Businesses that announce events only on Instagram are missed, so he DMs them and asks them to submit events through the calendar. Each newsletter also has a link to submit events.

Where to find Shane

You can find Shane on LinkedIn, and on X at HoodyAndShorts. He calls it a weird handle. His newsletters are BOQ Today and YGK Today. Part of the reason we split this into two episodes is that he screen shared the calendar, and I wanted to show it.