How to convince readers to pay you

“Ugh, I don’t want to have to sell. I want my work to speak for itself.”

I was leading a session in my marketing membership a couple weeks ago when one of my members said this.

Dude, I get it. It’s annoying to spend so much time producing something stellar to then have to turn around and ask for money to pay for the thing you made. Isn’t it obvious why people should pay for this?

But making the thing is different than selling the thing.

I learned this lesson the hard way when I spent two months putting together an audio course and then the next two years learning how to sell it.

You’ll attract paying readers by producing a high quality publication.

But you’ll hit a limit eventually where you know you could have more paid subscribers and the organic routes aren’t bearing fruit like they once did.

That’s why you need to get comfortable with upselling.

Last week, we looked at where those upsells go. This week, we’re talking about what they should say.

📣 Coming soon: Want to grow your paid subscribers? We’re starting up a free monthly mind meld just for solo journalists working to make their writing more sustainable. First session is this Monday, May 6 at 1pm PT/4pm ET. Reply if you’re interested and I’ll add you to the invite.

Upsell with FOMO

Alex Dobrenko cultivates a very personal relationship with his subscribers in his comedy newsletter Both Are True. That makes his upsells feel more like conversations.

Messaging angle: Fear of missing out on what other subscribers are getting, a limited run offer

What it does well: “A number of you asked” and “claim your spot” makes us realize that we might miss the boat. The playful text message-like bits “IT IS NOT A JOKE” and “tysmmmm” make us feel like we’re having a chat with a friend.

Try this out: Humanize your upsells by putting your personality into it. This can even work for newsrooms if you have different writers handle the upsells by signing it or introducing themselves.

“Hey, Earl here. Do you have a question for our upcoming podcast? We want to hear it! Subscribers get dibs on contributing to our show and that could be you. We want it to be you! Get in here, subscribe and ask us a question for the pod.”

Upsell with benefits

Matt Newberg’s multimedia brand Hngry makes their benefits sound like actual benefits.

Messaging angle: Sell the benefits. No like really sell them.

What it does well: The phrase “stay steps ahead” makes the reader feel like they’re a type of insider getting special intel. Keywords like “exclusive scoops” and “members-only” may sound hokey and elitist but they also invite you to be part of something potentially cool and exciting.

Try this out: Play up your subscriber benefits. Even if you don’t offer many perks, highlight what’s unique about your publication. Give your reader the most enthusiastic rundown of what they get access to.

“We write bonus issues just for our beloved subscribers. Not only that! You also get behind the scenes photos from our interviews, our one-and-only guide to NYC bike paths and first pick of tickets to all our live events.”

Upsell with social proof

The Browser features two kinds of social proof on their homepage to encourage you to subscribe and pay: words of their fans and numeric count of readers.

Messaging angle: Social proof. See how many fans we have and read what our fans say makes us great.

What it does well: The sheer volume of “150,000+ delighted readers” is impressive and whenever a newsletter has a lot of readers, we’re primed to think it’s pretty good (that’s the psychological premise of social proof). Including six large testimonials here from some google-able names boosts their credibility and allows their readers to find multiple viewpoints on what makes this newsletter valuable to subscribe to. Both of these tactics I see used commonly in the newsletter operator space.

Try this out: Use real subscriber numbers when you can, especially if they are impressive. Grab a few reader testimonials and work them into your upsells or add them alongside your upsells.

“Rita from Sylmar became a subscriber because ‘The Bad Teacher series last fall saved my son and me a ton of headaches with his special accommodations. This info is pure gold for stressed out parents!’ Be like Rita and join 2k+ subscribers today.”

Our takeaway

Alternate and test your upsell pitches so you can find your preferred style and see what works best with your audience.

Rather than just asking readers to support, write from an angle that makes your subscription appealing to be a part of. Bringing on the FOMO, making benefits enticing, and adding more social proof are just a few of them and we’ll cover more as we get deeper into how these upsells work.

Next week, we’ll be talking about asking for reviews and shout outs.

Are you using reviews? Reply and let me know yes or no.

—Lex (@betonlex)