This interview is part of an ongoing series profiling interesting builders in the creator economy. I spoke with Lex Roman about paid newsletters, pricing psychology, the problem with Substack’s default CTA, and why creators need to reframe how they think about revenue. This conversation was recorded in May 2025 and has been lightly edited for grammar and clarity.

If you’re building a newsletter, the question of “going paid” eventually hits all of us.

When? How much? Will anyone actually pay?

And maybe most of all: How do I talk about money without sounding desperate, awkward, or apologetic?

That’s exactly why I wanted to talk to Lex Roman.

Lex, founder of Journalists Pay Themselves, is one of the clearest voices out there when it comes to helping creators build sustainable, community-funded media. They work at the intersection of strategy, psychology, and systems — and isn’t afraid to call out what’s broken in the default advice about paid subscriptions.

We spoke about:

Whether you’re already charging for your newsletter or just thinking about it, this conversation is packed with a ton of super specific advice that I found to be so valuable.

[P.S. I’ll share more about this topic in an upcoming article for beehiiv. Stay tuned!]

Q: I saw a post where you said "Upgrade to paid" is dead. Why is that?

Lex: I think that's weak copy from the get. If I was writing the copy for a default button on a platform like Substack, that is just about the weakest three words I could have picked. Who wants to "upgrade to paid"? 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. I don’t want to upgrade to paid. That’s like, "Would you like to pay money?"

It doesn’t make any sense. So I think it's a weak call to action anyway. But also Substack has made us gloss over it. It's in every Substack. It's just completely dead and useless now. I encourage people to write their own CTAs instead of using that weak-ass one.

There’s this culture, specific to Substack but also now on Beehiiv and other platforms, of being apologetic about asking for money. I see writers be like, "It would be great if you became a paid subscriber, but no worries if not!"

Why are you caveating that? Nobody's forcing anybody to pay. This isn't the electric company.

People need to frame their CTA as an opportunity. You can use your publication's mission: "Are you glad this exists? Want to keep it going? Here's what I’m planning next." Or use perks: "Get access to this post, my Discord, early access, whatever."

Q: Why do you think creators struggle so much with this mindset shift around money?

Lex: People really do have to do that mindset work. If people aren’t in therapy or working with a coach, they should. You have to believe you deserve to get paid for your work.

If you're constantly apologizing or acting like a charity, that's not going to work for you long term. And it’s a huge problem in journalism and among writers.

Look at how many creators we’ve lost this year. Several full outlets are gone. YouTubers quitting. These media ventures won’t continue if people don’t support them.

If you don’t monetize, you’ll have to go get a job and your newsletter will suffer.

Q: How should people think about pricing? Especially when they’re just starting out.

Lex: I'm a big fan of the $9 price point. I've done analysis on newsletters and worker-owned newsrooms, and most starter subscriptions are between $5 and $10. $5 was popularized by Substack and Patreon, and now people are leaning toward $10.

I like $9 because it's right before $10. There isn't enough data yet on the psychological difference between $9 and $10, but once you go into double digits, there may be drop-off.

But really, the leap from $0 to $9 is the big one. The difference between $1 and $9 is negligible. The difference between $1 and $100 is bigger.

So charge as high as you can without introducing too much friction. You're pretty safe around $7–$9. Above that, have a reason: team size, perks, niche content, etc.

Q: What about paywalls? Should people promise a weekly cadence or leave it open-ended?

Lex: Don’t lock yourself in editorially too early. Don’t promise "one paid post per week" if you're not sure.

Be vague in your messaging at first: "Get access to all paywalled posts." Don’t promise quantity or cadence unless you’re sure you can deliver.

You can experiment. Maybe you paywall behind-the-scenes content, or deep-dive analysis, or personal recommendations. Max Read and Caitlin Dewey both do that. It builds trust and makes paying feel more meaningful.

Q: When is the right time to go paid? Is there a subscriber number that signals you're ready?

Lex: I think of it more in terms of trust, not size.

People who go paid at launch have built trust beforehand: maybe from social media, a previous email list, or a publication they worked for. You don’t need thousands. You need like 100 people who really trust you.

You can do a one-time reader raise. Andy van Bergen at Escape Collective did that. The 51st raised $250K. The Flytrap raised $50K+ on Kickstarter. I launched my newsletter to 1,500 people and got 40 annual subscribers on day one.

You don’t need to wait. Worst case, nobody bites and it just sits there.

Q: Do you recommend monthly or annual subscriptions? What about lifetime access or one-time payments?

Lex: Annual is better. Monthly churn is high.

Ryan Singel from Outpost said the same: better to have people in annuals. They’ll likely churn before 12 months if they’re monthly. Annual reframes it as an investment. It also keeps people from thinking, "Am I using this newsletter this month?"

Lifetime or one-time offers are fine, but should complement subscriptions. They’re good for cash infusions, but not everyone wants to commit forever. Offer both.

Q: What are some smart strategies for upselling subscribers?

Lex: I see two big levers:

You can also use automation. If someone’s 6–8 months into a monthly plan, send them a prompt: "Switch to annual and save X%."

Q: And what about preventing churn? What helps people stick around?

Lex: Communication. Through automation and manual outreach.

Automation looks like:

Time those email sequences before renewals or during peak churn points.

Manual looks like:

Bergen from Escape Collective does individual outreach. Even with a big list. He wants people to feel seen. That stuff really works.

My main learning from talking with Lex is that we should all be bolder and more strategic in funding our newsletters; we’re running media companies at the end of the day. I was so inpsired by her conversation, in fact, that I launched my paywall here for Creator Diaries.

It’s still in the early days, but I have so many awesome content ideas (like more of these interviews!) that I’d love to explore in the future.

You can follow Lex at: