What makes publishers the most money with Outpost's Ryan Singel

Ryan Singel remembers the days when publishers had one moneymaking play.

Step 1: Get traffic from social media
Step 2: Serve ads on articles
Step 3: Profit

After all, every reader is just eyeballs and clicks, right?

Who cares if they stick around and read more?

Ryan cares.

Ryan’s a journalist and a technologist who saw the potential for news software that runs the business while ensuring the reader’s experience is *actually good.*

When he met his co-founder, Andrew Nikolaenko, they jumped on this opportunity to help publishers build loyal fans.

Not just fans—but paying fans.

Together, they’ve created a thoughtful monetization tool called Outpost.

I reached out to Ryan to hear more about their vision, their latest inventions and what’s making reader-centric publishers the most money right now.

Meet Outpost: Your monetization engine

If you want readers, publish articles.

If you want paying readers, get Outpost.

Of course, some of your readers will pay you no matter what, especially in the early days. Launch momentum is real. Just asking every once in a while works too.

But if you want MORE of your base to stick around, read more, share more and become paying contributors, you’ll need some mechanisms.

Why you need Outpost

You’re busy publishing your articles and newsletters. Who’s selling your subscriptions?

That little “upgrade to paid” button you put at the bottom of the issue? Nah. That’s not gonna pay the bills!

Enter Outpost.

What Outpost does:

1️⃣ Allows you to sell subscriptions in the background
While you’re out reporting your next story, Outpost is welcoming your newest subscriber and running them through an email sequence you customize to get them building a habit with your publication.

Features: Autoresponder, member management, welcome emails, nudge.

2️⃣ Matches right message, right time, right place for your readers
Whether your reader is on your website or in their inbox, Outpost knows their status. Are they a returning reader? A paying contributor? Or a brand new visitor? Then, Outpost shows the right set of actions to them—anything from “get on our newsletter” to “become a paying member” to featuring your upcoming event promotion.

Features: Autodisplay, intelligent upgrade buttons, internal content recommendations

3️⃣ Offers more ways for readers to pay you
Subscriptions are ideal for most of us small fry publishers because we don’t have to chase everyone down for $5 every month but it’s also great when you can offer one off contributions or when you can enable a whole organization to buy a pack of 10 subscriptions. Plus, it never hurts to have automatic ways to address churn, especially the churn that happens when someone forgets to update their credit card.

Features: Tip jar, metered paywalls, failed payment flow, gift subscriptions, group subscriptions

Ryan describes Outpost as the “intelligence center” of your publication. Their zone of operation picks up where Ghost leaves us wanting more.

Oh yeah…that’s the catch. You’ve got to be publishing on Ghost to use Outpost.

Not on Ghost? Don’t stop reading! You’ll want to hear what Ryan said could bump up your cashflow.

What makes publishers the most money

I asked Ryan which features were surprising moneymakers.

💡 The tip jar, he replied without hesitation.

They built the tip jar for The Lever, their first ever Outpost customer. Ryan says “It's been way more successful than I thought it was going to be” and that clients have seen both big dollar donations and small ones come through there.

💡 Another winner? Group and institutional subscriptions.

The scenario Ryan gave was a law firm buying a subscription which allows anyone on their email domain to sign up and get access to your publication.

On the publisher’s side, it’s a nice chunk of change in Stripe when those come in.

On the reader’s side, it makes admin way easier than managing individual subscriptions.

💡 Of course, a paywall always helps open wallets.

Ryan reminded me that Hell Gate reported a 20% increase in monthly recurring revenue when they added a paywall in July.

A freewall can also drive revenue. The team at 404 Media said on their anniversary podcast that adding a free email gate brought in 1000 new paying subscribers.

Both publishers use Outpost.

Outpost also offers a metered paywall (for example, 3 articles free then pay) and the team is looking at how to make paywalls auto-apply on certain conditions (like locking older articles after the breaking news cycle).

Unlike most news software which tries to do WAY TOO MUCH, Outpost remains focused on your members and your money.

What’s coming next from Outpost

“Does this make our publishers more money?” is the question the team asks before building the next thing. You know I love to hear that!

They’re currently working on:

• Smarter, more personalized CTAs based on reader behavior

• Flexible campaigns to send targeted emails to groups of readers whenever you want (like an end of year campaign or an event promotion)

• 1st party ad integration if you sell your own ads or sponsorships (with options to turn them off on some posts or for some readers)

• More options for group and gift subscriptions (send invitations, revoke them, control pricing in granular ways)

• Their own theme for Ghost is also a glimmer in Ryan’s eye (though he shouted out Bright Themes in the meantime)

In my mind, the best “feature” of Outpost is actually just how their team operates. They work collaboratively with publishers like you (or maybe actually you!) and they adapt and build WITH their base, not tossing stuff at them like most tech companies.

You might wonder (like I did) why isn’t Ghost handling more of this themselves?

Sounds like they don’t want to. They’re keeping it simple. Ghost doesn’t have so much as a welcome email built in. Founder John O’Nolan wrote about the vision for the Ghost ecosystem last week.

Get the most outta Outpost

If I was setting up my Outpost account today, the feature I would beeline for is called the Welcome Flow and it’s inside the Autoresponder.

I’d set up a couple emails that welcome new free readers and pitch them on upgrading to paid. I’d stagger them farther out than what you see below—maybe 2 months, 3 months, 6 months after the first welcome email.

If you tuned out, your take home assignment is…

Automate your money asks in the background as much as possible.

If you’re on Ghost, you definitely need to try Outpost. They have a 21 day free trial and it’s a subscription that pays for itself.

If you’re not on Ghost, look for automation options that can take more of the selling and fundraising off your plate.