Catskill Crews Creative Monetization Strategy

This episode dives deep into building a durable local media business with Michael Kauffman of Catskill Crew and The Newsletter Club. We unpack why communities crave print again, how to monetize beyond banner ads, and what it takes to turn a newsletter into a multi-revenue platform. You’ll hear how Discord-powered peer learning accelerates growth and why “quality over quantity” in ads is non-negotiable.

Michael shares his upcoming premium, quarterly, wax-sealed mailer, a seasonal “mini almanac” with members-only extras, and the simple validation steps he used before committing. We also cover his “local holdco” approach: products (Catskillopoly games, puzzles, merch), events, and even commercial real estate partnerships that create a flywheel of awareness, distribution, and revenue.

You’ll learn practical ad-sales tactics (educate, de-risk, package, and measure), why one-offs underperform, and how to reverse-engineer campaigns to a sponsor’s success metric (like a 2% CTR). Plus, we talk events that actually work, low-lift dinners, walks, and concerts, priced with flat fees to keep incentives aligned, and the power of polling to validate before you build.

Guest links and contacts: 

The Newsletter Club: thenewsletter.club. 

Catskill Crew: search “Catskill Crew” to find the official site and socials.

#NewsletterClub

#LocalMedia

#CatskillCrew

#NewsletterGrowth

#Monetization

#DirectMail

#LocalEvents

#AdSales

#HoldCo

#SmallBusinessMarketing