Instagram DMs + Chamber Events = Profit

Hi newsletter operators!

I'm having the most insane week ever with this newsletter thing. Like, seriously - the advertising requests just keep rolling in (really struggling with follow ups on these), and I'm getting hit up left and right by people wanting to start their own local newsletters. It's wild how this whole space is suddenly getting real attention from everyone.

Look, if you're sitting there thinking about jumping into this, you're still early to the party - but honestly, probably not for much longer. The window's closing fast, so if you've been on the fence, just do it already.

Our first VIP event was last night because of the newsletter! It was such a blast. That's the kind of cool stuff that happens when you've got a local audience backing you up. Just saying.

Podcast spotlight

In this week's episode, I sat down with John Apolinar from Scottsdale Scoop for his second appearance on the show. During our conversation, I discovered how John built an impressive sales pipeline of 15+ qualified prospects in just two weeks using straightforward, easily replicable strategies any local newsletter operator can implement.

Top Three Takeaways

Instagram DMing is a goldmine for qualified prospects

John's Instagram strategy is remarkably simple yet effective:

• Time investment: Just 10 minutes daily sending 5-10 targeted messages
• Target audience: High-value businesses (lawyers, med spas, plastic surgeons, luxury home builders)
• Message approach: Focus on collaboration rather than selling
• Template example: "I love the creativity of your marketing... I run the Scottsdale Scoop. We feature fun events, local businesses around town. I have a dialed-in audience of 5,000 locals who actually care about what's happening in Scottsdale. Would love to collab or feature you if you're up for it."

As John explained, "It's been generating a lot of really good conversations. I actually just had a plastic surgeon call me back maybe an hour ago." This approach often leads directly to meetings or connections with marketing decision-makers.

Chamber of Commerce events deliver face-to-face opportunities

I've long advocated for in-person networking, and John's experience confirms its power:

• Event types: Morning (7am) and evening (5pm) Chamber meetups, 1-2 times monthly
• Approach: Casual conversations focused on making connections, not pitching
• Strategic targeting: Identifying Chamber members he wants to meet before attending
• Follow-up technique: Finding target businesses before events end to schedule proper meetings

"I'm continuing to hit these Chamber events and just get the word out there and network locally and talk to these business owners in person," John shared. "It's just a more fun environment—these are social gatherings."

Target businesses with marketing departments for faster sales

This insight was particularly valuable:

• Look for: Businesses where the founder isn't running the marketing personally
• Why it works: Marketing professionals understand value propositions immediately
• Budget reality: Marketing directors allocate existing budgets vs. owners seeing costs as personal money
• Conversation quality: More productive discussions about strategy and audience fit

"I'm trying to find these businesses that have high ticket sales, but where the founder still isn't running the marketing," John explained. "I want to talk to an actual marketing person because they can speak the language a little better. They know what exclusivity means and what it entails from a marketing perspective."

Start Implementing These Strategies Today

What makes these approaches so powerful is their accessibility:

• No specialized skills required
• Minimal time commitment (10 minutes daily for Instagram, a few hours monthly for events)
• Focus on relationship-building rather than immediate sales
• Consistent effort yields compounding results

If you're running a local newsletter and looking to boost your advertising revenue, I strongly recommend implementing these strategies right away. The pipeline you build today will fuel your newsletter's growth for months to come.

Great reads

Top 5 Takeaways from the Newsletter Conference in NY

Great read on a lot of the valuable info that was shared at the conference. Not focused on local, but still really great info about the newsletter space in general. Read it here.

The Best Newsletter Ads of All Time

Check this out for some great inspiration for facebook ads. Again, not focused on local, but plenty of great ideas on concepts from these that you can remix. Read it here.