Monetization via Newsletter Ads, Job Boards and Events

Hi newsletter operators!

So trying something new starting today. Going to start sending out a newsletter after each episode I release. Doing this for a few reasons:

It’s been super difficult time wise to focus on creating a specific newsletter with all the pieces I want in it. And so I’ve been slacking. So instead of doing nothing, I think giving quick ones with the takeaways from specific episodes should be valuable.

Plus notifying you when new ones come out. Win win here. And I do still plan on trying to put out more full newsletters with a lot of my thoughts that aren’t in the episodes, but this way I don’t have to stress about getting them out.

Let me know what you think about getting them this way a couple times a week (whenever I record really).

And make sure to let me know if you want to be a guest. If you read this, you likely would be great!

Last day of soccer. Getting too hot here in Austin already!

Podcast spotlight

In this episode, I sat down with Landon from Wichita Life for our second chat to dig deeper into the business side of running a successful local newsletter. As the operator of a newsletter approaching its five-year anniversary with nearly 30,000 subscribers, Landon shared invaluable insights that can help you grow your own local newsletter business.

Strategically Structure Your Ad Inventory

• Create a tiered ad system to maximize revenue potential
• Landon uses three distinct positions:
• Primary: Top placement with logo inclusion
• Secondary: Mid-newsletter placement with image
• Baseline: Text-only at the bottom before events section
• Price points vary by position (primary costs ~25% more than secondary)
• Landon: "I set it up just like I think most of us do. Have the primary ad at the top, secondary is a little bit further down, same format with an image. And then baseline is like kind of the bottom before I get to my events."
• This approach creates natural upsell opportunities for advertisers

Job Boards Can Be Profitable With Minimal Effort

• Landon generates thousands in net profit annually with minimal work
• Using Nice Board platform ($179-229/month)
• Two-tiered pricing structure:
• Regular listings: $99
• Featured listings: $199 (includes newsletter mention)
• "It's just free money," Landon explained
• Pro tip: "Seed" your board with existing job listings before promoting
• Only takes 5 minutes to add jobs by importing from Indeed

Community Events Build Brand Recognition

• Annual anniversary events deliver tremendous value through networking
• His recent event:
• Broke even financially
• Distributed 110 branded hats to influential locals
• "That's a net positive for me," Landon pointed out
• Partner with established local event organizers to extend reach
• Sponsor "best of" awards to get your logo displayed year-round in local businesses

The Power of Organized Ad Management

• Biggest challenge: Managing ad inventory across four weekly newsletters
• Current solution: Simple Google Sheet tracking system
• For scaling operations:
• Consider HoneyBook for streamlined workflow
• Provides proposal → contract → payment systems
• Keep flexibility in your schedule
• "I don't have every ad slot filled up because sometimes you never know." - Landon
• This allows for last-minute advertiser requests or self-promotion

Looking to the Future

• Specialized real estate content opportunities. Having a full real estate section with multiple property listings in it:
• High-end home features ($1M+)
• Affordable properties
• Interesting Airbnb listings
• Multiple potential sponsors:
• Real estate agents
• Brokerages
• Title companies
• Mortgage businesses
• Key to growth: Diversify revenue streams while providing genuine value

Another awesome episode with Landon sharing some great insights. Make sure to listen/watch and let me know what you think. Hopefully we’ll have him back on soon!