
Note: Required reading if you are a newsletter operator who wants to implement an underrated and simple way to close more sponsorship deals for your newsletter.

I was recently on the river fly fishing with no cell service and not a soul in sight - recharging the creative juices - yet my mind kept drifting back to the work.
I realized that 99% of my advertisers for my media company were inbounds. I was manually following up with every single business that wanted partner with Catskill Crew. Educating, pitching, closing (or I was passing). Over and over.
I knew there was a bigger and better opportunity there - local business owners who were already subscribers were the easiest people to sell. But the value prop message kept getting lost in a general newsletter since it was not built for them.
So I did the easiest thing ever, and generated $36,000 in the pipeline (in 7 days)!
Let’s break it down.
In The Newsletter Club, I see many newsletter operators try to sell to everyone through their main publication. This leads to one or both of two things.
Firstly, your readers are bombarded with sales messages that are not meant for them. This can lead to reader fatigue and unnecessary clutter in their inbox. And that is not something you want when you are building a community.
Secondly, your subscribers who are business owners are potential partners. They have different questions, different motivations, and a very different reason for opening your newsletter. Sending them the same thing you send everyone else is leaving money on the table.
I was also running into this dilemma of balancing value and monetization within Catskill Crew.
They have different questions, different motivations, and often a secondary reason for opening your newsletter.

So, I created a second publication to nurture, educate, update, and eventually convert local businesses into partners - through an email sequence.
Go through your QuickBooks, your event history, every business card you have collected. Anyone you have worked with, met, or had any exchange with.
Disclaimer: these potential sponsors are all subscribers to my main publication - they already know the brand and interact with the content.
An advantage here was that many of the potential sponsors were already subscribed to Catskill Crew. My list from doing this alone came to 600 subscribers. Then you stop hard selling and start showing up with:
Updates on what you are building.
Events you just ran.
Opportunities to partner.
Things happening in the community they care about.
Many local businesses don't event realize the returns they might get by advertising in a local newsletter (sometimes I even call it a digital publication).
Of course not every business is meant to be featured in my local newsletter. I'm also hyper-selective about which businesses get to advertise in Catskill Crew. I prefer to work with less and charge more.

The deals close fast when they do because by the time they reach out, they already know what you do, why it matters, and how they fit in.
Steal This
If you want to apply this monetization tactic to your own newsletter, do 3 things this week to get started:
Build your list
Segment your existing list based on non-generic emails from unique domains, adding any other resources from your invoicing to businesses that have reached out to partner and ghosted. Anyone you've engaged with.Set the tone
Draft your first email.
Lead with something you recently did and position as a business update - ensure you let them know why they are even receiving the email.Add one CTA.
"Want to partner with us?" That is it. No pricing or packages are needed (this also gives you flexibility with pricing).
Note: Always offer them an out - a simple button to unsubscribe at the end helps to maintain your newsletter’s reputation.
Do you wanna get my exact email flow I built that has a 70% Open Rate and generated $36,000 in pipeline within 7 days?
Tid Bits
I finally started reading the 800+ page behemoth Lonesome Dove. I find letting my mind drift critical for creativity. This book is heavy and it is great. Highly recommend.
I've never been big on AI notetakers but I realized its not worthy burdening my brain to track all the micro details so I switched over to Granola (thanks for the tip Dhara).
It’s got this interactive feature where you just talk to it about the meeting and it can give you insights right there. Easy. Simple. Valuable.I’ve also been thinking about the importance of creativity in business... in order to do this I turn my phone off around 7pm every night and block off my calendar to disconnect and spend time on a river or in the garden. This is critical for me to reinvigorate energy and ensure I am in the best place for building a long-term business (and all the other side quests I am up to!)

