How Ashlyn got 75 advertiser leads for $60

Hi newsletter operators,

Got some killer info for you in this edition! Been getting some great feedback on both of these episodes, as they both are doing things that most operators are wanting to do but just haven’t started yet.

So if you want to learn from people probably just slightly ahead of you, both of these are great. And Ashlyn’s meta ads looking for advertisers is the biggest unlock for me in awhile. We did a test last night in two markets, and got 7 leads for around 60cents each in both. Getting ready to do this in all my markets soon!

Also, wanted to share something I’ve been working on for months that’s finally ready. It’s called Local Newsletter OS. It’s a platform that helps put all the things my team does to create our local newsletters into one platform. We do all of the creation in this system, then just copy/paste the html code into beehiiv and hit send.

Also, if you have ideas for what you’d want to see in a system like this, please reply and let me know!

Podcast spotlight

Ashlyn from Cypress Digest

Ashlyn really came with the heat for this one! Absolute killer insights from her on so many different aspects of the local newsletter business. How she’s running ads looking for advertisers is probably the biggest, but so many other golden nuggets as well.

She’s quite new in the space but has clearly been taking massive action and trying so many things. And great to see many of them working.

She got me so fired up, I’m working on my directory as we speak (after it sitting for 3 months without doing anything).

This is a must listen episode. DO NOT just read these highlights, you need to check this out in full!

Top Three Takeaways

1) Paid Lead Gen Beats Cold Outreach

Meta lead forms targeting local business owners filled Ashlyn’s pipeline fast. “Get them to your door, then sell.

• $10/day test, 3 images, Advantage+ limited to residents
• 75 leads in ~7 days on ~$60 spend
• Form fields: name, email, phone, business
• Follow with media kit, demos, and tailored packages

I’ve heard of multiple people trying this and failing, but she seems to have figured something out. I’m going to be trying this myself soon, and will report back.

2) Warm the Prospect Before the Call

Outbound works when sequenced. Use tools to skip gatekeepers, then dial.

• Apollo.io (~$30/mo) for direct emails, titles, phones
• Start with IG DM + email; call becomes the 3rd touch
• Prioritize high-LTV categories for live calls
• Track opens to time outreach

3) Build a Monetizable Directory + SEO Engine

Capture the long tail and upsell services while helping readers.

• Directory on subdomain via v0; consistent brand, fast updates
• Listings: $10/mo standard; premium = top placement, logo, richer copy
• Static “Resources” block links it in every send
• Local SEO retainers: Google Business Profile setup, NAP consistency, content; aim for Map Pack where most intent lives

John Apolinar from Scottsdale Scoop

Always love chatting with John. He’s always iterating and putting in the work to chat with local business owners, and use unique sales strategies that most are doing yet.

Sorry his audio was a bit hard to hear in a few sections, I’ll include a link to the transcripts, which you can run through AI to get some good insights on what you missed.

Top Three Takeaways

1) Local Events as Monetization & Brand Builders

John is leaning heavily into hosting local events as a growth and monetization strategy. His first event—a paid happy hour with raffle prizes and sponsorship from a personal injury attorney—is already generating revenue and brand interest.

• 37 people registered and he’s already made over $500 in ticket sales.
• Sponsor covered venue and drinks in exchange for exposure—low-cost, high-impact.
• Raffle prizes (like suite tickets) and a donation drive add community value.
• Future event interest is already inbound (e.g. Rivian wants to host one and pay him).
• He's using events to build trust, in-person connection, and open sponsorship doors for bigger plays.

2) Cold Email + Smartlead = Underrated Sales Channel

John is getting meaningful traction using cold emails to sell newsletter sponsorships, powered by Smartlead and Clay.

• Uses Smartlead to manage warm inboxes across 3 domains and 6 mailboxes.
• Sends 10–15 emails/day per inbox = 60–90/day total.
• Closed 3 sponsors last week alone, all from cold email.
• Avoids Instantly due to predatory pricing practices (Smartlead is <$100/mo all-in).
• Recommends targeting high-LTV businesses like lawyers, med spas, senior living, etc.
• Hires people on Fiverr for lead scraping if you don't want to use Clay.

3) Future Growth: Welcome Flow Monetization + Hybrid Event Packages

John is thinking long-term with a sharp focus on monetizing the welcome flow and layering hybrid sponsorship packages.

• Wants to trigger dynamic landing pages based on survey answers (e.g., homeowners → insurance offer).
• Exploring CPL (cost-per-lead) partners for welcome emails and survey paths.
• Suggests bundling events + newsletter placements into a single ad package.
• Considering launching a Shark Tank–style pitch event with a wealth management sponsor.
• Using platforms like Handshake to hire interns for Instagram content (carousels work best).
• Believes newsletter value is in distribution + trust, and long-term upside is in building a higher-multiple business on top of that (agency, home services, etc.).

Great reads

We’ve Lost Preview Text for Email. Are Subject Lines Next?

I haven’t personally noticed this yet, but definitely concerning if AI is changing this stuff for us. Good to know what’s happening here with the email platforms.

Read it HERE.

He Makes $500k a Year With His Automated Local Newsletter

Highly recommend checking this out and learning what Matt is doing. I’ve talked with him at length about his model, which is super interesting. Different than mine and most everyone else’s, but he’s making more than almost all of us. Worth thinking deeply about what he’s doing.

Read it HERE.

As Local News Faces Mounting Challenges, a New Report Spotlights Reasons for Optimism

Good overview of some positives happening in our space, although primarily talking about legacy local media. Always good to keep an eye on the competition.

Read it HERE.