I had a great time last week with Lex Roman and a bunch of Outpost member publishers (and some folks that were just Outpost curious), answering questions about what we see helps Ghost/Outpost publishers make the most money.
Lex did a great job of keeping things moving fast and keeping all the astronauts from getting bored.
Here's the recap for those of you who missed it!
Recap
Question: Why did you found Outpost? Where did this come from?
Ryan's Answer:
- Started at WIRED, frustrated by the clunky way reporters had to manually link to previous stories — that frustration led to building Contextly
- Contextly's goal was to build loyal audience communities, but publishers didn't care during the Facebook traffic era (just slapped ads on traffic)
- In 2020, discovered Ghost and saw it as the future — memberships, subscriptions built in
- Outpost is a continuation of what Contextly set out to do; now nearly 5 years in as a cooperative
Question: What are the roles between Ghost and Outpost? How are they different?
Ryan's Answer:
- Ghost handles core publishing — getting content out, managing permissions and subscriptions
- Outpost extends Ghost with things better handled outside the core CMS: group subscriptions, CTAs, autoresponder/welcome flows, retention offers, special offers per tier
- Not competitors — Outpost is like a "power tool" plugin layer on top of Ghost
Question: What are best practices for Welcome Flows for free newsletter subscribers?
Ryan's Answer:
- First email is the most important — lean into your mission, founding story, and why your work matters
- Include links to favorite pieces and always offer a discount
- Don't worry that discounts dilute your brand (build pricing with discounts in mind from the start)
- Don't be afraid to write long — be yourself, not generic
- Remember: new subscribers often know nothing about you beyond one piece they read
Question: What welcome offer works best to convert people — monthly or annual? (Re: Riley's question about discounts feeling too big a jump to annual but monthly feeling low-commitment)
Ryan's Answer:
- Strong preference for annual over monthly — monthly churn is significantly higher
- Would rather have someone pay 40% of annual price than full monthly price
- Make the annual discount look dramatically better than monthly in the email (show the comparison)
- Something in the works: 3-month intro subscriptions that graduate to annual
- Avoid the "$1 for a year" trap
Question: How do you get people to open and read welcome emails?
Ryan's Answer:
- Mix up styles — if the first email is long and earnest, make the second short and snappy
- Be honest and conversational (Tangle is a great model — look at their free sign-up flow)
- Enlist readers into your specific mission, not generic "support indie media" messaging
- Stay within your publication's tone, but push as far toward fun and honest as you can
- Make readers feel like they're joining a mission, not just handing over money
Question: What's the recommended pacing for the welcome sequence? Should emails go out 90 days later? (Lucy's question)
Ryan's Answer:
- Cap the welcome flow at 2–3 weeks max
- Propensity to pay is highest right when someone signs up — drops significantly after 90 days
- For the 90-day+ segment, use campaign emails tied to seasonal moments (St. Patrick's Day, Pi Day, etc.) instead
- Don't be afraid of selling hard early — the risk of losing someone from overselling is low
Question: What's the recommendation on deepening discounts across the welcome sequence?
Ryan's Answer:
- Each later email in the sequence should offer a deeper discount (e.g. 25% → 30% → deeper)
- Early subscribers never see the later offers, so there's no "devaluation" risk
- Even a deeply discounted subscriber at $20/year is a win — cost of free vs. paid subscriber is the same to you
- Never say "this is the best offer you'll ever get" — locks you in
- Avoid sharing the same discount over and over (10%, 10%, 10%) — diminishing returns
Question: Do you recommend everyone uses a metered registration wall (reg wall)?
Ryan's Answer:
- More publishers should use it, especially nonprofits worried about access — it doesn't block readers, just requires email registration
- The Guardian does this successfully — it's a proven model
- It's set up in Outpost so only people who read a full article (not partially paywalled posts) have it count against their limit
Question: What's the recommended number of articles to allow before the reg wall kicks in?
Ryan's Answer:
- Start in the 3–5 article range; 3 is a solid sweet spot
- 3 articles in 30 days signals genuine interest and justifies asking for an email
- Setting it at zero (wall immediately) may be too aggressive
- It's easy to adjust — just change a number in Outpost settings
Question: When should someone put in a metered paywall (for registered free subscribers)?
Ryan's Answer:
- Start with the registration wall first — see how it performs for a month or two before adding a paywall
- Set the metered paywall number higher (5–6 articles) since these are already registered free subscribers
- Think of it as identifying people who should be paying but aren't
- Treat it as an additional conversion lever, not the core strategy
Question: Where do you see publishers promoting tip jars, and how should they use them?
Ryan's Answer:
- Tip jars are underutilized — put them in emails, sidebars, and CTAs
- People aren't annoyed by tip requests — it's normalized
- Even paid subscribers will tip extra — it adds up, and occasionally you get large surprise donations
- Outpost now has design controls to customize colors and tip jar language/page
Question: What about tip jar language for non-tipping cultures? (Théo's question)
Ryan's Answer:
- You can fully rename the tip jar page in Outpost (URL, title, language)
- Consider calling it a "support fund" or tying it to a specific goal (e.g. "investigative journalism fund" or "help us hire a public records reporter")
- Goal-specific framing converts better than a generic "donate here"
Question: Any recommendations on tip jar preset amounts?
Ryan's Answer:
- Default presets probably lean too low — consider raising them
- Psychology: most people pick the middle option, so make the middle amount the one you'd "really love"
- Have a "ridiculous" high option that makes the middle feel reasonable
- Make the bottom option a slight stretch (e.g. $15 rather than $5)
- Have fun with the amounts — e.g. $27 (Bernie Sanders-style), $51 (The 51st) or $1337 for the top
Question: What's the bare minimum retention setup you recommend?
Ryan's Answer:
- Send both renewal reminder emails (don't turn them off — be transparent with subscribers)
- Focus retention offers in the 45-day window before renewal
- For canceling monthly subscribers: send a deeply discounted annual offer — most effective retention tactic seen; discounting monthly for monthly subscribers doesn't work
- Turn on all retention offer emails; go deeper on discounts as you approach the final one (e.g. 25% → 40–50%)
- Tone should be respectful — acknowledge "if we're not for you, that's okay" but make the case to stay
Question: What's the recommended timing/spacing of retention emails?
Ryan's Answer:
- Final email should be 1–2 days before renewal (not hours before — too late)
- Spread the earlier emails across the 30–45 day window before expiration
- If you have paid-only perks (ad-free podcast, full-text RSS), Outpost can send a separate email when that access is about to be removed — include a renewal offer there too
Question: Should publishers reach out personally when someone cancels?
Ryan's Answer:
- Yes, if you have the bandwidth — a personal email can reveal why you're losing people (too many emails, topic drift, financial hardship)
- More valuable for qualitative feedback than just win-backs
- Outpost sends a notification to you when someone cancels so you have the opportunity
- Automations handle most of it, but personal touch helps at the margins
Question: What CTAs do you recommend for list growth?
Ryan's Answer:
- Use a pop-up or slide-up — not both (unless you publish very long articles)
- Pop-ups outperform slide-ups
- In-article CTAs: the top-of-post and bottom-of-post placements perform best; mid-article CTAs rarely convert (people don't stop reading to subscribe)
- Set pop-ups to trigger on scroll (e.g. 60%) or after a time delay — don't hit readers the second they land
- Customize CTA language beyond the default — express your voice, your mission, even a sense of urgency if your topic warrants it
- Homepage CTA also works well for some publishers
Question: Thoughts on sliding scale / pay-what-you-want pricing? (Chas's question)
Ryan's Answer:
- Intrigued but Outpost hasn't built it yet
- Molly White (from Citation Needed) has a custom implementation — it's actually fixed price tiers, not true PWYW but interesting to check out
- Technical challenges with Ghost/Stripe make it difficult to implement cleanly
- Not high on the roadmap currently, but worth watching
Question: How does Ghost's native welcome email compare to Outpost's welcome flows?
Ryan's Answer:
- Ghost's version is fine for small/starting publishers
- Outpost gives you multi-email sequences, analytics, per-tier offers, and the ability to route different subscriber groups through different flows
- Ghost's new retention/cancellation offer (just announced) is complementary to Outpost — it hits subscribers at the cancellation moment, while Outpost handles the backup retention flow
Question: Is it more effective to market free or paid subscriptions? (Théo's question)
Ryan's Answer:
- Funnel thinking: concentrate on making your free content great — it's the pipeline to paid
- Even Tangle, which keeps ~80% of content free, converts 16% of their audience to paid
- Occasionally send your paid-only newsletter to your entire list as a "taste of what you're missing" conversion strategy
- For most publishers: get people reading → get them on the free list → demonstrate paid value → convert
Question: Is there a way to move people up to a higher tier with a discount? (Courtney's question)
Ryan's Answer:
- Ghost's native offers won't show to existing paid subscribers
- Outpost can do this: create an offer for a higher tier with a discount, send via campaign email to lower-tier subscribers
- Outpost handles proration automatically (applies unused portion of current subscription to the new one)
Question: Can you track who clicks on a sales campaign and send a follow-up only to those people? (Lucy's question)
Ryan's Answer:
- Not yet — but it's on the roadmap
- More analytics features coming soon, along with events functionality
Question: What do you think publishers are sleeping on most with Outpost?
Ryan's Answer:
- Lead magnet tool: drop a PDF or EPUB into a post, gate it behind free or paid membership — underused
- Group/organizational subscriptions: two versions — a simple tiered option on your site, and a behind-the-scenes invoicing system for organizations (universities, law firms, nonprofits, businesses)
- Real money available in institutional subscriptions — one publisher added 200 organizational members in a single month
(summary compiled with the help of an LLM)
