How Michael Kaufman Built a Profitable Newsletter Business

Want to turn your newsletter into a full-fledged business? Michael Kaufman, founder of Catskill Crew and News Club, shared his playbook on creative monetization in a recent beehiiv webinar. And trust us—it’s packed with gold.

With under 20,000 subscribers, Michael brings in $57,000 per month without relying on traditional ad models.

Instead, he focuses on brand-building, events, and unique monetization strategies that anyone—yes, even you—can apply to their newsletter.

Table of Contents

• Who Is This Video For?

• Top Takeaways & Action Steps:

• Actionable Next Steps

• Key Resources & Tools Mentioned:

• Closing Note:

Who Is This Video For?

• Newsletter operators who want to diversify revenue beyond traditional ads.

• Creators looking to build a long-term brand rather than just chase quick wins.

• Business owners exploring community-driven monetization models.

• Anyone struggling to find the right timing and strategy for monetizing their audience.

Top Takeaways & Action Steps:

1. Your Newsletter Is a Business—Treat It Like One

“A newsletter is a competitive advantage. It’s a direct conduit to your subscribers—your customers.”

• Most newsletters only monetize with ads and affiliates, but there are hundreds of other ways to make money.

• Your audience is already telling you what they want—listen and build products or experiences around that.

2. The Power of Creative Monetization

“Creative monetization gives you the most bang for your buck. It’s what lets you build a real brand—not just sell ad space.”

Michael’s revenue streams include: ✅ Events (Happy hours, pop-ups, experiences)
✅ Merchandise (Hats, t-shirts, discount cards)
✅ Physical Products (A Catskills-themed board game that sold out in 17 days)
✅ Paid Community (The News Club for local newsletter operators)
✅ Real Estate & Business Investments (Leveraging the newsletter to invest in local businesses)

3. Trust & Patience Are Everything

“If you come out of the gate slinging offers on day one, you’ll burn your audience. Build trust first.”

• Build community before monetizing—don’t start with sales pitches.

• Engage your audience by giving them a voice (polls, surveys, Q&A sessions).

• Protect your subscriber experience—don’t overload them with sponsorships and weak upsells.

4. Use Polls & Surveys to Validate Ideas

“I don’t launch anything without testing it first. Polls and surveys are a goldmine for insights.”

How Michael uses beehiiv’s polls and surveys:

• Gauge interest before launching products – Example: A Monopoly-style board game only went into production after 96% of his audience approved it.

• Segment his audience – He creates sub-groups within his community based on interests (e.g., hiking, fly fishing, art).

• A/B test pricing and demand – Before setting prices, he lets his audience vote on what feels fair.

5. Give Subscribers a Say in Your Brand

“Flip the script—don’t just give them content, make them participants in what you build.”

• Let subscribers vote on new initiatives (e.g., event locations, product designs, new content types).

• Co-create experiences, meetups, and products with your community.

• Subscribers who feel involved in your brand will spend more money and stick around longer.

6. Start Small, Grow Organically, Then Scale

“If you can’t grow your newsletter organically at first, you probably can’t grow it at all.”

• Start with organic tactics (Facebook groups, Reddit, partnerships with local businesses).

• Only start paid ads once you’ve nailed your messaging and audience fit.

• Slow, consistent growth beats a rapid, unqualified list.

Actionable Next Steps

🚀 Step 1: Start Engaging Your Audience Today

• Use polls to learn what they want.

• Respond to every email and comment—build relationships.

🎨 Step 2: Brainstorm Your Unique Monetization Strategy

• What non-ad products or services can you create?

• What experiences can you offer your community?

📊 Step 3: Run a Poll or Pre-Sell a Product

• Before launching anything, ask your audience.

• If they don’t want it, pivot before you waste time and money.

🏆 Step 4: Launch Your First Creative Monetization Play

• Pick one idea (event, merch, digital product, etc.).

• Execute it with a small test group.

• Iterate based on real feedback.

Key Resources & Tools Mentioned:

• beehiiv Newsletter Platform

Closing Note:

The biggest takeaway? Think bigger than ads.

Whether you’re running a local newsletter, niche publication, or passion project, the playbook is the same: Listen. Engage. Experiment. Monetize. Scale.

Michael’s story proves that with creativity and patience, your newsletter can become the foundation of a thriving business.

Now, it’s your turn. Which creative monetization idea will you try first? 🚀