Nick Pollock stopped chasing sponsors and let them come to him

Nick Pollock runs the Oakville Digest, with 16,000 subscribers, and the Burlington Digest, with 11,000. He started the first in January 2024 while working in tech sales, and he says it has been about a year and a half to where he is now. He tried outbound selling for a while, then dropped it. In this conversation he explains what replaced it, how he prices packages, and the back-office system he built in Claude Code.

Two separate brands, one set of habits

Nick says he put a bit of his salary into ads each month and grew that spend over time. He launched Burlington a few months after Oakville. Together the two have about 28,000 subscribers, plus about 30,000 Instagram followers across their two accounts.

The brands are run separately because the towns sit right next to each other. He runs the ads separately and does almost no cross-promotion. Beyond a quick announcement when Burlington launched, growth has been paid ads and organic reach. When he last checked, 10 to 15% of subscribers were on both lists.

TJ said a welcome-flow prompt offering the sister newsletter converts about 10% for his own brands. Nick said he needs to put more thought into his welcome flow and that this is an easy one to add.

Dinner clubs: real money for little work

Two months before recording, Nick started running dinner clubs through the DNNR app. His first one, in March, was Oakville only. He announced it in the newsletter, posted on Instagram, and got 70 people out. Reviews were good, though some guests were unhappy with their table matching.

The next round drew 50 sign-ups in Oakville, with about 15 of them returning guests, and 32 in Burlington. That was lower, and he is not sure whether the cause was timing. He moved to a Thursday from a Tuesday. He is testing to see whether dinners hold up as steady income or fade.

The first round earned roughly 800 to 900 dollars, and so did the second round combined. He puts it at maybe 500 to a grand. He went to the first dinner with name tags, stayed for the after-party, talked to almost everyone and shot video for a post. He skipped the later ones.

He hasn't looked for dinner sponsors yet. He does think his affluent towns could support higher-priced events, and he floated partnering with an events person on a rev share, so he can focus on marketing.

He tried outbound, then stopped

Nick is blunt that selling ads was never a straight line. Getting in front of companies is hard, and many local businesses aren't educated on marketing or newsletters. Early on, deals were small, a few ads at a time, and most of his inventory sat empty.

Then another operator told him to forget the sales grind. Become the biggest news source and Instagram in town, he was told, and be so obvious that businesses come to you. Nick stopped his daily outreach and put the effort into growth. Inbound picked up, and sponsors began saying they had seen his posts or that a friend had sent them one. He calls that immediate trust at the start of a conversation.

He did a fairly big outbound push for a few months, and it wasn't effective. He thinks outbound gets easier once people recognize your name.

Three-month minimums and custom proposals

Early on, people would buy one or two ads, see no instant results and never return. So Nick moved to a minimum package. He sells three-month or six-month packages, usually two newsletter ads a month. A six-month Oakville package works out to 4,800 dollars.

His pitch is that these newsletters are not Facebook ads. If a sponsor wants quick conversions, they should run a Facebook campaign. He offers long-term exposure to a high-quality audience.

He doesn't send a rate card. He talks with the sponsor first, asks about goals and budget, then sends a custom proposal. If someone pushes for a number, he'll say it runs 250 to 800 dollars a month depending on the newsletter. His media kit has audience numbers but no pricing.

The calendar is nearly full. He is about 95% booked for the next two months, through July, for the first time ever. New sponsors are told they can book now or wait without promises.

Who is buying

Real estate has been the easiest, because listings are the most-clicked items in the newsletter. Each newsletter has an exclusive real estate partner. Others include a pickleball club and a spa. He sees no pattern beyond these businesses having marketing budgets. The contact is a mix of owners and marketing people.

Each package usually includes one Instagram post for every two newsletter ads. A sponsor can tag him or invite him as a collaborator on one of their posts, or he builds a branded carousel for them. He tries to keep sponsor posts from feeling like spam.

Carousels did the growing

For almost the first year, Nick's Instagram pages were weak, with fewer followers than newsletter subscribers. He had been neglecting them. Three changes turned it around:

He found that the stories with the most newsletter clicks usually do well on Instagram too. Once he posted consistently, some posts took off with a few hundred to a few thousand shares. A post shared a few thousand times brings in a few hundred followers. He calls that his best growth formula. His content is nearly all carousels covering news, events and interesting headlines, and he doesn't show his face.

"Digital publication" and the inbox

TJ raised a tip he got from another operator: call it a digital publication, not a newsletter, because "newsletter" can sound like a little thing in the corner. Nick found that interesting. He thinks people rank email below web traffic in their heads.

Nick says that when a sponsor starts talking about an "e-blast," he knows it's already over. The newsletter is part of readers' routines, he says.

The ad back office he built in Claude Code

Before, Nick used a shared Google Drive for each client, manual reminders, email threads for copy and an Airtable for loose financial tracking. It was scattered. He had never used Claude before, though he had tried Claude Code, and built one system to hold everything. It took maybe 20 hours so far.

It has his clients, deals, an ad calendar and dashboards for costs and revenue. Each new deal gets its own client portal. Sponsors see their campaign and each ad, and upload content that goes into his system instead of his inbox. Reminder emails go out 14 days and 7 days before each ad, which ends the 24-hour scrambles.

The portal also has a reporting dashboard linked to the Beehiiv API, showing open rates and clicks. He used to pull that data by hand into spreadsheets.

He says no SaaS could come close, because it is tailored to him. He is now building a newsletter builder for his own workflow and a dashboard that tracks his emails and reminders. He doubts a general SaaS would work, but might consider building these dashboards for others as consulting.

What he wants next

Nick isn't sure yet. One path is to stay where he is, with a stable living and time for other projects, maybe an agency. Another is scaling regionally around Ontario, since he now knows how to build and monetize a brand.

His first vision was 10 or more newsletters, pooled to reach regional or national advertisers. He can't pitch Starbucks or Tim Hortons at 20,000 subscribers, but at 100,000 to 150,000 he could. First he wants a much better newsletter production process and some help, because two newsletters already bring plenty of fires.