Pricing Playbooks for Founders
How founders set, test, and raise prices — packaging tiers, finding willingness to pay, and the pricing changes that quietly doubled revenue. Each tactic is quoted directly from the founder who ran it.
337 tactics · page 8 of 12
“All the apps that have some kind of AI usage are finally accelerating this trend because they've got no other choice. The AIP makes a lot of sense where you can buy credits on top.”
Hybrid monetisation is coming — AI apps are forcing the issue
Thomas Petit has advocated for hybrid monetisation (subscriptions plus credits or consumables) for years, but adoption has been slow because complexity was prohibitive and low-hanging fruit remained in pure-subscription optimisation. AI-powered apps are breaking the logjam: usage-based costs make a credits model economically necessary, and they are pioneering the flows that other app categories will eventually copy.
“We didn't paywall any of the current functionality — you could come in and do everything you did before, in fact we upgraded the free functionality as well — and then we built new stuff and paywalled additional functionality.”
Don't paywall existing features — build new premium functionality on top of a free core
When Rapchat introduced subscriptions after years of being free, Seth Miller was careful not to degrade the existing experience for the 400K MAUs already on the platform. Instead, the free tier stayed intact and improved slightly, and the paid tier unlocked new features — vocal effects, algorithmic song enhancement. This approach protected the viral loop while converting engaged users who wanted the next level.
“Don't say 'unlock well AI plus' or whatever — it's kind of very vague. It's better when your call to action is very specific: 'Start your 7-day free trial' or 'Get started with your free trial'.”
Replace vague "Unlock Plus" CTAs with specific free-trial language
Generic CTAs like "Unlock Premium" give users no reason to act now. Specific free-trial CTAs remove the ambiguity about what happens next and signal zero risk. Bahasarian consistently flagged vague CTA copy as one of the most common quick-win paywall mistakes across every app reviewed.
“You could animate this button and just making it more liveable and in a way that it attracts more attention than just having it static here.”
Animate the CTA button — a static button loses to a pulsing one every time
A motionless CTA button competes equally with every other element on the paywall. Adding a subtle pulse or breathing animation draws the eye to the single most important tap target. This is one of the lowest-effort paywall changes with some of the highest return — most apps ship a static button and leave easy conversions on the table.
“Your CTA should be the most visible thing on your paywall and here all your highlighting and bolding is all in purple — it takes the attention from your main CTA button.”
Never bold pricing text in the same color as your CTA button
When highlighted prices share a color with the CTA button, user attention gets split across multiple elements and the main action becomes harder to find. The fix: use the accent color only for the primary button, and switch price highlights to a neutral or secondary shade. Every extra visual competing with the CTA costs conversion.
“The minimum thing you can do is just do price anchoring — make this not $29.99 per year but get the monthly price of it and show it as broken down to monthly.”
Show the annual price broken down to per-month — not the raw annual figure
Users anchor to monthly numbers because that is how they budget. Showing $29.99/year as '$2.50/month, billed annually' shifts comparison from a big number vs a small number to value-per-month vs convenience. Flow's paywall was cited as the gold-standard presentation: monthly equivalent visible first, full annual total shown below.
“When the trial is on, don't call your product yearly — call it a free trial. You need to communicate enough with the user that this is free: just mentioning it once is not enough.”
When the trial toggle is on, label the plan "Try for free" — not "Yearly access"
One of the most common free-trial mistakes is saying 'Start for free' once in the button while labeling the selected plan 'Yearly access.' The plan label is what users read to understand what they are signing up for. Switching it to 'Try for free' when the trial toggle is active dramatically reinforces the zero-risk message at exactly the moment of decision.
“If they just swap these images with a short video that shows how the app works it's going to perform way better — and always have a title: even if you're using a video, having a title performs better.”
Swap static screenshots for a short demo video — always add a title over it
Static screenshots require users to interpret the app by reading UI elements. A 10-20 second demo video showing the core workflow removes that cognitive load. The key constraint: never run a video without an explanatory title above it — the title both orients users who cannot watch with sound and pulls them toward the CTA below.
“There are a lot of texts — usually this is not good. Don't ever put this amount of text on your paywall, specifically if it's just a one-page static paywall. It just makes everything too crowded.”
Too much text on a static paywall kills conversion — replace with visual carousels
Feature descriptions written out in full sentences compete with the pricing card and CTA for attention. Replacing text blocks with swipeable image or video carousels keeps the paywall scannable and moves users toward the purchase decision faster. For apps with multiple features, a 3-step paywall structure — visuals, then reviews, then pricing — outperforms a single-screen wall of copy.
“I don't know why you want the X button to be this big and this highlighted — you can be much smarter with this X button and still keep it visible but with a different presentation, without the background color.”
Don't make the dismiss X button the first thing a user sees
A large, high-contrast dismiss button primes users to close before they have read anything. The goal is not a dark pattern but a de-emphasized one: remove the background fill, reduce size, or position it where it is findable but not the focal point. Users who want to leave will find it; users on the fence should not be directed toward it.
“I don't know why you want the referral code thing here — it just gets all of the attention. Put it somewhere under 'cancel anytime' or somewhere that doesn't get that much attention.”
Move promo/referral code fields off the main paywall — they steal attention from the CTA
A referral or promo code input on the main paywall creates a cognitive detour: users who have no code wonder if they are missing a discount, and users who do focus on entering it instead of tapping the CTA. Move it below the fold, under the CTA, or into a secondary flow. The same applies to overly visible 'have a promo code?' links.
“If you notice that people are canceling and they're the same people who aren't using the product, it's probably not a pricing problem — it's probably a product problem.”
Low conversion is usually a product problem, not a price problem
Most subscription operators immediately jump to price cuts when growth stalls. But when non-users churn at the same rate as users, reducing price does not help — someone who gets zero value from a product will not pay any price for it. Diagnose the churn before touching price: is it awareness, onboarding failure, binge-then-leave behavior, or product staleness?
“If I use it I'll pay anywhere between five and ten dollars a month, and if I don't use it I will pay nothing. So if you're talking about product market fit in a forever relationship, I'm going to pay money until I die.”
Most subscription products are inelastic — fix product-market fit before cutting price
Subscription products are often step-function inelastic: engaged users will pay across a wide price band, disengaged users will not pay at any price. Robbie uses a party-at-a-bar analogy: fix the onboarding (guests cannot find the food), the product (same songs every week), or the operations (speakers broken) before cutting the cover charge.
“We tested it at 30 bucks a year and we tested at 15 bucks a year too... they were about a wash which is really interesting from a net revenue perspective 15 bucks a year versus 30 bucks year was was basically flat but we went with 30 because it gave us more maneuverability.”
Price Elasticity Can Be Flat Across A 2X Range — Choose The Price That Gives You Optionality
AllTrails cut price from $50 to test $30 and $15 — net revenue was flat between them, meaning conversion volume offset the per-unit difference. Ron picked $30 not for revenue maximization but for optionality: room to discount, offer introductory pricing, and run promo campaigns. At $15 there was nowhere to go. If your test shows flat revenue across two prices, always take the higher one for tactical flexibility.
“An annual subscription uh the auto renews it's like an annuity like it just builds up every single year... if you're able to kind of you know do a pretty good job on on the retention side and just see this thing build up and just raise the tide every single year.”
Annual Subscriptions Are Annuities — Every Year Of Good Retention Raises The Revenue Floor
Ron describes the compounding mechanics of annual subscription revenue as his single biggest business insight. Each year's cohort becomes the floor for the next year — unlike e-commerce where you re-compete for every transaction. AllTrails went from 20K paying subscribers when Ron joined in 2015 to 1M+ by 2021 because each renewal class added permanently to the base. Annual billing, not monthly, is what makes this compounding effect maximum.
“There's a very fun CAC to first payment period — we make sure the CAC is lower than the first payment period and then the renewals are gravy.”
CAC Must Be Lower Than First Payment — Renewals Are Pure Gravy
Cliff's unit-economics discipline is simple: if CAC is covered by the first payment, every subsequent renewal is profit. This framing forces creative and channel decisions to optimize for first payment conversion, not just installs or trial starts. It also means the team can scale spend confidently because they know the math works on day one — they don't have to bet on long-tail retention to justify acquisition costs.
“Post-IDFA, subscription is not enough. I look at it across three lenses: subscription is my core, ads is my secondary, and one-time purchases or upsells is another avenue. I start with Revenue as my North Star since I think that's the best metric for a company.”
Revenue Is the Only North Star — Subscription + Ads + One-Time Are Three Levers, Not One
Ryan Beck argues that post-IDFA, consumer subscription apps need to think about monetization in three buckets simultaneously: subscription (recurring revenue), ads (ad-supported tier for non-subscribers), and one-time purchases (consumables, content bundles). Duolingo is his example: subs + ads + gems. Revenue — not any individual KPI — is the North Star because it integrates all three levers and avoids local optimization that looks good in isolation but misses the full picture.
“If nobody complains about your price you're not charging enough. People are complaining about having to pay — you're doing the right thing. It's a signal that they want it, a positive signal of value creation. Nobody complains about the price of something they don't want.”
Complaints About Price Are a Positive Value Signal — Silence Means Nobody Wants It
When Pray.com introduced subscriptions, some users complained that faith content should be free. Rather than treating this as a crisis, Ryan reads price complaints as confirmation that the product is valuable. An app nobody wants generates zero complaints about pricing. His response to negative App Store reviews: reply personally, get on a call, show people the team cares — and track the data separately to confirm that conversion rates validate the price.
“We know that there's a level of importance of having a certain amount of information that is just readily available for those core user needs but what we have identified is that there are users and specific cohorts within our business that are willing to pay.”
Generous Free Tier + Paying Power-User Cohort Is a Valid Dual-Track Strategy
Weather.com serves massive anonymous traffic with a full free experience (ad-supported), while separately identifying a 'weather enthusiast' cohort that wants deeper radar data and hourly details. Keeping the free tier generous keeps casual users engaged and monetized via ads, while the premium tier targets the narrow but real segment with high willingness to pay. Not every app must choose — dual-track can work when the audiences are distinct.
“So many apps are so focused on getting that subscriber that they're not seeing the forest for the trees — there are so many cohorts that would be casual users that they could still monetize via ads and maybe nurture over time to become a subscriber.”
Freemium + Ads Lets You Monetize Users Who Would Never Subscribe
The Weather Company monetizes its massive casual-user base through advertising while reserving subscription prompts for identified high-intent cohorts. Host David Barnard highlights this as a valid alternative to pure subscription models — especially for utility apps with large traffic. Casual users who monetize via ads today may become paying subscribers later as they deepen engagement with the product.
“Your health metrics are too good — it's like going into the doctor's office and they're like look you need to eat a cheeseburger. I think that's actually one thing I see a lot of writers on Substack that I think are underpriced and they're not realizing their full earnings potential.”
Great Retention Is a Warning — You May Be Leaving Revenue on the Table
Reid DeRamus advises Substack writers (and app operators) that unusually high retention rates are a double-edged signal. Yes, it means subscribers love the product — but it also means many would happily pay more. He urges operators to resist the temptation to 'let it cruise' and instead treat above-peer retention as a trigger to evaluate whether prices have drifted below the market's willingness to pay.
“What we typically see when we've done price increases in the past is that they usually impact subscriber acquisition way more than subscriber retention — if you execute well you won't see much churn from your existing subscriber base but you will see a little pressure on new subscriber acquisition.”
Price Increases Hit New Subscriber Acquisition Far More Than Existing Retention
Across Hulu, Crunchyroll, and HBO Max, Reid DeRamus observed a consistent pattern: well-executed price hikes produce minimal churn among existing subscribers but cause a visible step-function drop in new subscriber adds. The implication for small apps is that the short-term revenue hit of raising prices is mostly a slowdown in growth velocity, not a wave of cancellations — a far more manageable trade-off than most operators fear.
“To really realize the revenue gain from a price increase it's important to figure out a way to increase price for existing subscribers — if you only do it for new subscribers in the future that's a fine approach but just know that you're leaving the vast majority of the impact from a price increase on the table.”
Existing Subscribers Hold Most of the Revenue Upside in a Price Increase
Reid DeRamus frames the price-increase calculus clearly: raising price only for new subscribers captures a fraction of the potential revenue. The real money is in the existing subscriber base — but that requires thoughtful communication, timing, and often grandfathering early supporters at the old price. For early-stage apps with only a handful of founding subscribers, skip the complexity and grandfather them; for established apps, the math on existing-subscriber uplift almost always justifies the effort.
“One of the things a Spotify and a Disney Plus can't do because they are such a big brand is actually test the price increase on new users before they actually raise a price on existing users — if you're not a brand name, if people don't know your price offhand, you can go ahead and see first what the impact is on new subscribers.”
Small Apps Can Test Price on New Users Before Rolling It to Existing Subscribers
Big-brand price changes are immediately noticed and covered by press, making quiet testing impossible. Smaller subscription apps have an advantage: they can quietly raise the price for new signups, measure conversion and retention impact, find the elasticity ceiling, and only then roll it out to the existing base. This new-user testing approach converts a scary all-or-nothing decision into an iterative experiment.
“I think tiers make a ton of sense — without them you're forcing one price on everybody when you know that people have different willingness to pay. I think it's good to keep it as simple as possible — more than three tiers the consumer's brain might start to break.”
Keep Tiers to Three or Fewer — Beyond That the Consumer's Brain Breaks
Tiered pricing lets apps capture revenue from both budget-conscious users and power users willing to pay premium prices, without forcing everyone onto one plan. Reid DeRamus draws from streaming experience to set a practical limit: three tiers is the threshold before cognitive overload sets in. Beyond that, the complexity of the paywall starts working against conversion rather than for it.
“We really wanted to exhaust all the possible ways of bringing on new subscribers — only got to a price increase pretty deep into my time there, after six or seven years of really focusing on paid subscribers and scaling that up as much as possible.”
Exhaust Subscriber Growth First, Then Raise Prices — Crunchyroll's Sequencing Lesson
Crunchyroll spent six-plus years maximizing subscriber volume — through marketing, partnerships, content expansion, and adjacent product lines — before finally raising prices. The lesson isn't that you should always wait that long, but that growing the subscriber base to its potential ceiling is a prerequisite for getting the most from a price increase. Raising prices too early trades long-term growth velocity for short-term revenue.
“It grew 80 90% in 12 months or something in terms of Revenue. There was just a lot of — you could just do the math right. You could go wow there's a lot of people that are using the heck out of this.”
Burning the Boats on Free Users Grew Revenue 80-90% in 12 Months
V1 Sports switched from freemium to free-trial-only, forcing even long-time free users (some had used features for nine years without paying) onto paid plans. The backlash in reviews was real, but revenue grew 80-90% in the following 12 months. The lesson: when users clearly get tremendous value from a product, they will pay — the risk of converting free users is almost always overstated.
“If you're so worried that a 10% price increase is going to run off all your customers, I would encourage you to think through why — and is it because you don't have conviction that your product is really solving one of these people's problems? If that's the case, the problem isn't the price increase, the problem is understanding those customers and delivering the value.”
Fear of a Price Increase Signals You Don't Believe Your Product Solves a Real Problem
When app founders hesitate to raise prices, Alex Prasad reframes the hesitation as a product-market fit diagnostic. True conviction in the product's value makes price elasticity a manageable concern. V1 Sports' subscription held firm through its transition precisely because 21-minute monthly sessions proved users were genuinely engaged — and engaged users pay.
“The revenue maximizing over the lifetime of the customer price may be artificially low versus if you were only selling one tier. Once you have expansion revenue opportunities it radically changes the way you think about that first step — I just want to get you in and start to interact and learn more about you.”
Entry Pricing Should Optimize for Lifetime Value, Not Maximum First-Transaction Revenue
V1 Sports learned from its B2B side that expansion revenue transforms the math of first-sale pricing. Charging the maximum upfront is rational only in one-shot transactions. In a repeat game — subscription apps — getting the user in at a fair price and expanding over time via higher tiers, add-ons, or B2B upsells yields more total revenue than a high entry point that spooks potential subscribers.
“We figured out how to get people to pay — a smaller number — but now we're looking at how do we expand this to many many more people including people using it for free. Our paid penetration is 17% versus Duolingo's 8% — which means we can probably have a lot more people using the product for free.”
Prove Willingness to Pay First, Then Build the Freemium Funnel Around It
Opal deliberately reversed the typical freemium trajectory: instead of building free usage first and monetizing later, they proved payment willingness before opening the funnel wider. With 17% paid penetration and a clear conversion baseline, the move to freemium is a deliberate growth expansion from a profitable position — not a leap of faith.