Substack might dominate the paid newsletter conversation, but I have some good news for you. If you don’t want to get trapped in a platform, you want to keep all of your earnings, and have complete control of your upsell automations, beehiiv offers a much stronger alternative. 

This is the guide I wish had existed when I first launched a newsletter. Even after launching and running several newsletters, it feels like the process of how you actually get readers to pay is a topic we all try to dance around. 

I sat down with Lex Roman (They/them), the founder of Journalists Pay Themselves, and one of the most trusted voices when it comes to reader-funded media. They’ve helped everyone from indie creators to pro newsrooms build sustainable, subscription-backed newsletters.

Roman’s advice is direct, tactical, and exactly what most of us need to hear. In the article, I’ll break down how to go paid the right way, and how you can do it step-by-step in beehiiv.

The good news (and the bad news) around paid subscriptions is this: there’s no secret subscriber amount or monthly price that guarantees success. 

According to Roman, the more important factor is trust. Instead of thinking “when should I go paid?” or looking for a magic number, you should look at how much trust you have with your audience.

If you've already built trust—whether through consistent content, a strong presence on another platform, or a successful past project—you may be ready to monetize sooner than you think. That could take the form of:

They shared, “If you’ve built a bunch of trust with any number of people — maybe 100 real people — then you can go paid at launch.”

Some creators and newsrooms even start with a one-time reader raise or a founding member push before launching a recurring tier. And worst-case scenario? Lex says, “People don’t take you up on it, and it just sits there. You get a few people casually. No big deal.”

1,000 True Fans
The Kevin Kelly classic. Can you get 1,000 people to pay you $100/year? That’s a $100K business.

Right-Fit Fans
You may not even need 1,000 people— maybe it’s just 75 people who really need what you’re offering. 

Think niche experts, B2B analysts, diehard hobbyists. If you’re writing high-leverage content, you don’t need mass appeal (and you can charge a higher rate).

As Matt Brown says, “You don’t need millions of casual readers,” Brown explained. “You need a few thousand people who find your work so valuable they’re willing to pay for it directly.”

And if you’re hesitant to “ask for money,” Lex suggests reframing the pitch.

“It’s not a threat. It’s not a mandate. It’s an opportunity. You’re giving people a way to support something they care about.”

So instead of waiting for the perfect moment or chasing an arbitrary number, ask yourself: Have I earned the right to go deeper with this audience? If yes, it’s probably time.

Getting people to join your free newsletter is one thing. Getting them to pull out a credit card? That’s a tougher sell.

This is where most creators fall into the trap of lazy copy or half-hearted asks. Lex Roman puts it bluntly: “If I were writing the copy for a default button on Substack, ‘Upgrade to paid’ is just about the weakest three words I could have picked.”

Why? Because it’s not about paying, it’s about what they get.

“I don’t want to upgrade to paid. I want to upgrade for perks. I want to upgrade to read the rest of the story. I want to upgrade to be part of a community.”

That reframe should shape everything that follows: your pitch, your pricing, and your product.

Here are the strategies that actually work:

Your free readers need to see what they’re missing.

Share a compelling preview. Give them the setup, the tension, the curiosity gap, and make the payoff gated.

Here’s an example of how Roman does this in her newsletter, Journalists Pay Themselves. 

What to try:

beehiiv tip: Use Partial Posts to split free vs paid access and customize the upgrade text.

I’m experimenting with this in my own newsletter, Creator Diaries, where I write long-form interviews for interesting people in the creator economy and share a weekly newsletter on what I’m learning and resources I recommend. 

In a recent interview I published, I did an author Q&A and teased a portion of the full interview for free readers, while gating the rest.

Nobody converts off “I’ll upgrade someday.” Your launch needs a reason to act now.

What works:

Roman suggests aligning this with your mission or roadmap:

“Tell your readers: I want to add a podcast, I want to pay a contributor, I want to host something for you, and here’s how paid subscriptions help me get there.”

Tip: Pair urgency with a personal letter or origin story. See #5 below.

Pricing is perception. Don’t just offer one plan; structure it to guide the choice you want.

Here are a couple of examples from beehiiv newsletters like Status and Garbage Day. 

Common setup:

Roman shared her expertise, “$9/month is a great starting point. It sits just under $10, and it signals value without being intimidating.” 

beehiiv tip: Push annual by setting it as your default CTA.

Conversion goes up when readers feel invested in the journey.

Try:

The Catskill Crew newsletter by Michael Kauffman (although a free newsletter) is a great example of this. He involves his subscribers in every new product launch or new business venture. 

beehiiv tip: You can use beehiiv’s poll feature to embed custom polls on any page or newsletter. 

Instead of a generic sales page, write a personal, honest note. I like how Matt Brown of Extra Points does this often with his subscribers. This approach breaks the Fourth Wall between you and your audience. 

What to include:

Roman recommends this approach to readers: “Frame your call to action as an opportunity. Are you glad this exists? Help me keep it going — and here’s what we’ll do together.”

The founder of Handmade Seller Magazine, Amber Christian, has invested time and energy to build a relationship with her subscribers. So much so that when they made the jump to beehiiv and turned on paid subscriptions, they saw a 34% growth in paying subscribers. 

Sometimes readers just need a little nudge, a cherry on top that justifies the jump.

Ideas:

Example: Extra Points offers the Extra Points Library as an added resource for its audience of sports management professionals. It’s insider information that you couldn’t easily access anywhere else. 

beehiiv tip: You can also use the new one-time payments feature to sell à la carte. Here’s an example from Creator Toolbox. 

Here’s what it looks like in action from some of our favorite beehiiv creators. 

Free subs: 25,000+
Revenue: Sponsorships + paid product 

Sunday Money is one of the fastest-growing personal finance newsletters on beehiiv. As an extension of the newsletter, Collard created the Side Stack Club as a premium product. It includes hand-picked content for side hustlers, tools, success stories, and other valuable content. 

(P.S. See how he uses both urgency (expires in 19 days) and value (20% off forever) to promote the deal. Take notes!)

Why it works: Collard has built a trust with his audience over the years, so it’s a natural next step for his readers to upgrade for more access + content. 

Free subs: 27,000
Paid subs: 2,000+
Annual revenue: $200K+

Brown nailed the niche model. His B2B-ish college sports content attracts athletic departments, industry insiders, and superfans. He charges for the reporting that’s deep, timely, and specialized.

Why it works: The more specific your value, the easier it is to charge for it.

In my conversation with Roman, I realized that too many newsletter creators get stuck overthinking the launch of a paid newsletter—unsure of when, where, or how to make the move. 

But the bigger issue isn’t just when to launch—it's not having a clear plan for A) converting free readers into paying subscribers, and B) retaining the ones you already have. Both are just as crucial to building a successful paid newsletter.

As we mentioned earlier, no one really wants to “Upgrade to Paid.” We give people money because we desire the outcome, whether that’s access, content, or insight.

That’s Roman’s take, and they’re right. Most CTAs ask for money without explaining why the offer matters.

Do this instead:

Here’s an example of upgrade copy I loved from The Fly Trap: 

Don’t just send a Stripe receipt. Make your new paid subscribers feel like VIPs.

What to include in your paid welcome sequence:

Goal: Make them feel smart for joining and excited to stick around.

This is the most overlooked part of running a paid newsletter.

A lot of creators think of their audience in binary terms: free or paid. But your biggest growth opportunity is turning current readers into deeper supporters.

It’s way easier to upgrade someone who already knows and values your newsletter than to convince someone cold to subscribe, Roman explained.

That’s why upsells matter. Whether it’s moving someone from monthly to annual or giving them a reason to jump into a higher tier, this is how you build sustainable revenue.

What to do:

Frame it around momentum. Roman shared two upsell strategies that work:

And don’t forget: this can be automated.

Try this automation:

Roman c​​alls this the “Why Pay” sequence. Here’s an example from 404 Media:

beehiiv tip: You can set up an email sequence (6–8 weeks after joining) that walks them through:

Getting someone to pay once is a win—but getting them to stay? That’s the real challenge (and key) to running a successful paid newsletter.

I see a lot of people focus on conversion and then neglect onboarding, ongoing perks, or just basic check-ins. Roman says, “Retention comes down to communication. And most people just… don’t follow up.”

You can’t assume people will remember why they joined or know how to get the most out of their subscription. Especially if your perks include things like private podcasts, community invites, or Notion libraries.

Lex recommends setting up two key flows:

Bonus idea: You can also run occasional manual outreach — a short check-in asking: “How are you enjoying the newsletter so far? Anything you’d love to see more of?”

I think this is a nice personal touch, and I love to see notes like this in my inbox. 

This is the tactical part. Here’s exactly how I launched a paid tier inside beehiiv — and how you can do the same.

Let’s break it down:

Step 2: Set Your Tiers

Here’s what I am testing for my newsletter. 

Then you’ll want to click ‘Create New Tier’ to create your membership options. 

From there, you can enable monthly, annual, and one-time purchases, and set the rates for each. 

Pro tip: Remember that you can customize the button so it’s more enticing than just ‘buy now.’

When you’re drafting a post:

If you’re using Partial, write a clear preview that tees up the value. Here’s what that looks like in my newsletter. 

To make all of this easier, beehiiv has condensed hundreds of high-impact newsletter automations into a library of ready-to-use templates. Now, you can harness the same automations used by the largest newsletters in the industry to grow, engage, and retain your own audience.

First head to Audience -> Automations.

Then choose from some of the automation templates listed — or you can create your own. I chose this reminder for paid subscriptions. 

From there, you’ll see a full automation sequence that you can customize for your newsletter. You can see there is some template text there, but I recommend writing your own message tailored to your voice and readers. Here’s an example from my automation:

You can customize so much of this process, from how to segment readers to the copy text and more. If you want to learn more, check out beehiiv’s guide here.  

You don’t need to wait until you hit 10,000 subscribers or build the perfect paywall strategy to start monetizing your newsletter. What you do need is a plan for earning your readers’ trust — and keeping it.

And tools like beehiiv take care of all of the technical stuff so you can focus on what you do best. From flexible paywalls to upsell automations, built-in landing pages to one-click upgrade flows, beehiiv gives you everything you need to turn free readers into paying members.

→ Launch your paid tier on beehiiv today

And start building the newsletter business you actually want.