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How To Build a Revenue-Generating Newsletter Community
Why traditional strategies may be limiting your growth — and what you can learn from the “creative monetization” model
Taylor Cromwell
March 24th, 2025
By most measures, Michael Kauffman, founder of The Catskill Crew, bucks conventional wisdom.
Instead of aiming for more subscribers, Kauffman prioritizes quality. Instead of chasing ads, he’s building products. Instead of focusing on social media, he’s creating real-world experiences. and his brand generated an impressive $57,000 in revenue in one month alone this year.
Kauffman has found success, not from traditional newsletter monetization strategies like sponsorships or subscriptions, but through a mix of community-driven offerings.
Kauffman’s approach, what he calls creative monetization, redefines what a newsletter business can be. Instead of relying on a single revenue stream, he’s cultivated a thriving audience that actively participates in shaping the brand.
Kauffman’s story is proof that if you’re just thinking of your newsletter as a standalone product, you’re leaving a massive opportunity on the table. In this article, I’ll break down the following topics:
How to build an engaged community through your newsletter
Michael Kauffman’s approach to creative monetization
Ways to experiment with audience engagement
A step-by-step revenue playbook you can apply to your own business
Table of Contents
Many newsletter creators still view their publication as an independent media business, relying on ads, sponsorships, or paid subscriptions as their primary revenue source, but Kauffman is part of a new wave of entrepreneurs who see newsletters as a top-of-funnel strategy to drive engagement, loyalty, and diversified revenue streams.
“I never wanted to start a newsletter to be chasing ads,” Kauffman explained. “Who you advertise with is a deep reflection of your brand.”
Instead of trying to scale quickly for sponsorship deals, Kauffman focused on community-building and authentic engagement. His goal? To create a brand synonymous with fun, trust, and participation — a brand his audience genuinely wanted to support.
“It’s about nurturing this trust and authenticity. I’m building a brand that is synonymous with fun and community and then leveraging that to promote, validate, sell, and drive awareness to any of these products and services.”
This philosophy led to an unconventional but highly profitable model — one where the newsletter itself serves as a relationship-building tool rather than the final product.
Kauffman’s multi-revenue model is a fascinating case study. Read on and learn how you can apply some of the same principles to your newsletter.
What Is a Community, and Why Is It Important?
Before diving into strategies, we should go over some basic terms. For starters, let’s talk about the meaning of “community” and why it matters.
According to Christian Bryant, founder of InboxHype, we have a bit of a definition problem here. He explains that “community” has become a buzzword and has lost its meaning in the process. “It's often thrown around in marketing materials to make sales positioning feel less commercial.”
“We should view a newsletter community as a gathering of individuals united by shared interests, values, and objectives. Rather than referring to our audience as ‘subscribers,’ we should see them as members who can forge connections with like-minded individuals and experience a sense of belonging. That's where the real magic of community lies.”
In theory, a “community” can be created in several ways. Your email subscribers or your social media followers can be considered a community. That’s a start, but not the full picture.
In my opinion, a community is a platform/channel/space that you are intentionally curating that has a common purpose/goal and members who are able to connect with one another.
Communities can take a variety of shapes, whether in real life or virtual, but usually they require some platform to facilitate the group, such as:
Slack
WhatsApp
Discord
Circle
Mighty Networks
Skool
Meg Hovious, founder of Change is Here, is another newsletter creator on beehiiv who is building community as the foundation of her newsletter. Change is Here focuses on actionable tips to support mental health that can help readers feel less stressed at work.
The community, a Slack group that offers peer support for modern mental health challenges (phone addiction, work burnout, loneliness, etc.), is a natural extension of the brand.
In my experience, most people create the community first and then focus on distribution and promotion, but what if you could do it the other way around?
Traditionally, newsletters have functioned as standalone media businesses, monetized through advertising, sponsorships, and, in some cases, direct reader payments.
Creators and publishers would focus on growing their subscriber list, aiming to hit critical mass in order to attract advertisers or convert a fraction of readers into paid subscribers.
The challenge? This approach is highly dependent on scale, and it can be difficult for smaller newsletters to generate meaningful revenue without massive subscriber bases.
For many newsletter creators, this approach meant a reliance on high cost per mille (CPM – cost per thousand impressions) rates from sponsorships or ad networks.
But with increasing competition and fluctuating ad rates, this model became less sustainable, especially for niche newsletters with engaged but relatively small audiences.
Granted, there are a lot of newsletters on beehiiv still crushing it with this model, but the important point I want to make now is that it is not the only way. The new model offers an alternative for newsletter creators.
Today, many successful newsletter creators like Kauffman are flipping the script.
Instead of treating their newsletter as the final product, they view it as the top-of-funnel (TOFU) strategy that leads into a deeper, more engaged community. This shift allows them to create multiple revenue streams that aren’t dependent on advertising alone.
This is a brilliant business model because you are able to learn about your audience as you go and create content and products that deeply serve them.
Kauffman calls this model “Creative Monetization,” which is essentially finding new ways to monetize through your community. Ads and sponsorships may be part of it, but so are IRL experiences, paid community, products, etc.
Kauffman remarks that an important point to make here is that there isn’t really one playbook that you must follow.
Instead, you should learn these principles and apply them to your own business, niche, audience, etc.
Start a newsletter on any topic - then turn it into a community.
$25k-$100k per month is a reasonable base revenue target for community-focused NLs with multiple rev streams.
The playbook works. Build on @beehiiv. Get creative. Give a damn. Have patience.
— Michael Kauffman (@MikeyPesto)
10:26 PM • Jan 23, 2025
That being said, here are some of Kauffman’s top pieces of advice for building community through a newsletter:
Step 1: Build an Engaged Audience Through Free Content
Before monetization can begin, you need to establish trust and engagement with your audience. Kauffman emphasizes that it’s not about sheer volume — it’s about quality.
What’s most important here is that you’ve curated a niche corner of the internet that truly cares what you have to say and trusts you as a creator.
How To Do It:
Deliver unique, valuable content: Kauffman’s newsletter creates a sense of belonging and shared experiences for Catskill locals.
Involve your readers: Encourage participation through polls, Question & Answer sessions, and user-generated content.
Foster conversation: Use email replies, Discord, Slack, or community meetups to engage subscribers beyond the inbox.
Example: Brett Dashevsky, Creator Economy NYC
The Creator Economy NYC newsletter is another awesome example of a newsletter-turned-community that’s killing it right now.
The playbook for Dashevsky? URL ←→ IRL
The community is built around in-person events in NYC but also includes learnings and insights in the newsletter that’s valuable to a wide audience. Both pillars lead to the growth of the other.
Dashevsky explains, “I launched the Creator Economy NYC newsletter to connect with my community routinely and uplift and recognize what was being built in this community, as well as for everyone outside of the New York City Creator Economy.”
Step 2: Define Your Community’s Purpose
Before monetizing, define the core value proposition of your community. What is the main reason people should join beyond just receiving a newsletter?
Ask yourself the following questions:
What does my audience struggle with that a community could help solve?
Do they crave exclusive knowledge, networking opportunities, or personal connection?
Would they pay for deeper access to industry insights or mentorship?
The possibilities here are endless. Maybe your audience consists of new moms who are running businesses or investors who are training for a marathon, or middle-aged women who are taking on a new hobby.
Bonus: Give Your Community a Voice
What I like about Kauffman’s approach here is that he’s actively building alongside his community. They have a voice in every new product, meetup, etc.
“You have a voice. You vote on the direction of where the newsletter goes,” Kauffman says of his subscribers.
Step 3: Create a Strong Entry Point Into the Community
Once you have an engaged audience, the next step is to create a structured way for them to enter your community. There are several approaches to this:
Free vs. Paid Tiers
The biggest thing you’ll have to decide here is how you want to monetize.
For example, you might opt for a free community, like Creator Economy NYC or Catskill Crew, and monetize through other revenue streams, like event sponsorships or products. For some creators, this creates an easier entry point for new members.
At the same time, it might make more sense for your business to create a paid community that’s more exclusive in nature.
Perhaps your community is looking for access for specific knowledge, like Sam Parr’s company Hampton, which is a community for founders with more than 1M in revenue – extremely niche but high value for those in it.
Kauffman has experimented with paid memberships, too. He currently runs Newsletter Club, a community for newsletter operations to connect and learn from one another.
Step 3: Monetize With Multiple Revenue Streams
Your community should offer more than just access to a chatroom. Successful community-driven newsletters integrate multiple monetization methods to maximize revenue.
Proven Revenue Models
Paid Memberships: Charge for premium access (e.g., Trends.vc offers deep-dive reports and networking for $299/year).
Workshops & Courses: Teach specialized skills via live or recorded sessions.
Affiliate Marketing: Recommend tools/services with exclusive discounts for members.
Brand Sponsorships: Partner with companies for sponsored content or exclusive deals.
Live & Virtual Events: Host community meetups, masterminds, or retreats.
Really think outside of the box. Kauffman, for example, has found enormous success with Catskill-opoloy — something that has been a perfect fit for his brand and audience.
“It’s the silliest way I’ve ever made money, but guess what? It’s fun. It’s community-oriented. It’s on-brand with the Catskill Crew identity.”
Beyond games, Kauffman has also sold discount cards, hats, shirts, pins, and even limited edition art prints — all tied to his newsletter brand.
The point to remember here? Most newsletter creators are thinking too small. Don’t stop at just your weekly (or daily) editions.
If you put in the work to build a meaningful, engaged community, you can continually create new products to serve them.
Keeping a Community Engaged (and Paying)
Monetizing is only half the battle. You also need to retain members by providing ongoing value.
How To Reduce Churn & Increase Retention
Keep up a consistent content cadence: Provide weekly updates, monthly deep dives, or live Q&As
Gamify member participation: Use leaderboards, exclusive challenges, and badges
Start community-led Initiatives: Let members contribute content, host events, or mentor others.
Gina Bianchini, founder and chief executive officer of Mighty Networks, has some fascinating thoughts on the topic.
Bianchini’s tip? Make communities a space where people can connect with one another and build valuable relationships.
As Bianchini puts it, the goal is that “the party goes on even when you leave the room.” Communities that are entirely dependent on access to one person are much harder to keep going in the long run.
Bianchini’s team has even coined a unique phrase for this called “people magic.” It’s essentially a metric that can show if a community can healthily grow over time.
As someone who’s joined dozens of communities at every price point over the past few years, I can see this to be incredibly true.
There are some communities you join that just feel special, as if the creator has curated a select group of people in this room, and we all have something to learn and share from one another. (And it’s not just some gimmicky approach by the creator to add monthly recurring revenue; please, please don’t do this.)
Again, Kauffman’s advice is valuable here. The relationship with your audience should remain a two-way street.
Ask your audience what they’d like to see next and how you can help them and continue enhancing your newsletter and brand to better serve them. That’s the foundation of a rock-solid business.
Leveraging beehiiv’s Website Builder for Community Growth
beehiiv’s Website Builder is a powerful tool that enables creators to manage their entire newsletter-driven business from one platform.
With features designed to streamline community-building, beehiiv allows newsletter operators to seamlessly integrate memberships, content hubs, and monetization strategies.
By now, I hope I’ve made it clear that newsletters don’t have to rely on ads and sponsorships. They can be powerful launchpads for creative monetization — if you’re willing to think outside the box.
If you want to turn your newsletter into a thriving, revenue-generating community, you must take the following actions:
Prioritize engagement over scale.
Experiment with revenue streams beyond ads.
Give your audience a voice in what you create.
Leverage real-world events, products, and memberships.
Start by listening to your audience. Then, use your newsletter as a foundation for something bigger.
Want to learn more? Join beehiiv to start building your own community-driven newsletter today.
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