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Subscription and pricing case studies
What worked, what blew up and what you can steal. The book's original case studies with what's happened since, plus 30 new ones from the AI era, small businesses and Australia.
How Adobe's Hidden Cancellation Fee Cost It $150 Million
Adobe's annual-paid-monthly plan hid an exit fee of 50% of the remaining payments. In 2026 it agreed to a $150M settlement. What went wrong, and the fix.
Amazon, 2025How Amazon Prime Paid $2.5 Billion for Making Cancellation Hard
Amazon Prime still grows 10% to 12% a year, but a hard-to-cancel flow cost it a $2.5 billion FTC settlement in 2025. What happened and what to copy.
Atlassian, 2025How Atlassian Set a Deadline to Move Every Customer to the Cloud
Atlassian is ending Data Center by 2029. The dates, the incentives, why cloud costs more, and what any business can learn about retiring an old plan.
Babylon Health, 2023How Babylon Health Went From $4.2 Billion to a £500,000 Fire Sale
Babylon Health went public at a $4.2 billion valuation in 2021 and sold its UK assets for about £500,000 in 2023. What went wrong with its insurance model.
Book of the Month, 2026How Book of the Month Club Turned 100 by Going Back to Its Roots
Book of the Month Club turned 100 in 2026 with 400,000+ members. How a curated shortlist beat the old mail-order model, and what any small business can copy.
Canva, 2024How Canva Raised Team Prices 300% and Bought an AI Engine to Justify It
In 2024 Canva lifted some Teams plans from $119.99 to $500 a year, citing AI. Here's how it softened the rise, why customers stayed, and what to copy.
Canva, 2026How Canva Reached $4 Billion ARR With a Freemium Funnel and AI Upsells
Canva hit US$4 billion ARR in 2025 with 265 million monthly users and 31 million payers. How its freemium funnel and land-and-expand model work.
Volvo and Jaguar, 2024How Car Subscriptions Stalled: Care by Volvo Quits, and Jaguar Hits Pause
Care by Volvo was suspended in 2024 and Jaguar paused most new-car sales. Why car subscriptions stalled, the economics behind it, and what to copy instead.
Chegg, 2026How Chegg Lost Half Its Revenue When AI Gave Away Its Product for Free
Chegg's homework-help subscription lost half its revenue to free AI answers and Google's AI Overviews. The timeline, why its moat failed, what to do.
Clay, 2026How Clay Unbundled Data From Work and Cut Prices 50% to 90% to Grow
Clay split one credit into Data Credits and Actions, cut data prices 50% to 90% and stopped charging for failed lookups. Why, and what you can copy.
Columbia House, 2026How Columbia House's "12 CDs for a Penny" Finally Ran Out of Road
Columbia House made $1.4 billion a year on 12 CDs for a penny, then closed in 2026. Why subscriptions built on inertia die, and how to build on trust.
Cursor, 2025How Cursor Broke "Unlimited," Said Sorry, and Still Hit $1 Billion
Cursor swapped 500 requests for $20 of usage, said sorry, refunded users and kept growing. What happened, the numbers, and the lessons for your pricing.
Clerri (Kleer and Membersy) and Arbor Dental Group, 2025How Dental Practices Are Replacing Insurance With Membership Plans
How dental practices use in-house membership plans to win uninsured patients, what the Clerri study found, and the steps to build a plan of your own.
Disney+, 2026How Disney+ Tripled Its Price and Stopped Telling Anyone How Many Subscribers It Had
Disney+ went from $6.99 to $21.49 a month in seven years, then stopped reporting subscribers. Why the price rises worked, what they cost, and what to copy.
DocuSign, 2026How DocuSign Stopped Being "Just E-Signature" to Restart Growth
DocuSign grew 54% in 2021, then slowed to single digits as e-signature became a commodity. Here's how its AI contract product reached 10.8% of ARR.
Dollar Shave Club, 2023How Dollar Shave Club Went From $1 Billion to a Private-Equity Carve-Out
Dollar Shave Club's viral video built a $1 billion razor subscription. Seven years later Unilever sold a 65% stake. Why marketing alone isn't a moat.
Dropbox, 2026How Dropbox's Referral Rocket Hit a Ceiling at 18 Million Payers
Dropbox's storage-for-referrals program is a classic. By 2026 paying users sat flat at 18.19 million with 0.9% growth, but a 39.7% margin. The lesson.
Duolingo, 2026How Duolingo's Streaks Became a 12.7-Million-Subscriber Machine
Duolingo's streaks and a June 2026 'Streak Revival' brought back 15.4 million learners. The numbers, why gamification works, and what you can steal.
ElevenLabs, 2026How ElevenLabs Turned a Free Voice Demo Into $330 Million ARR With Credits
ElevenLabs gives 10,000 free credits a month, then a ladder from $6 to $990. How its credit pricing really works, the per-credit math, and what to copy.
Employment Hero, 2025How Employment Hero Grew Tenfold by Selling Everything a Small Employer Needs
Employment Hero passed A$300M ARR in 2025, ten times its size five years earlier, by landing with payroll and expanding. How it works and what to copy.
The Food Boss Academy, 2026How The Food Boss Academy Shows the Shelf-Life of a Solo Subscription
Lauryn built The Food Boss Academy without spending thousands: video modules, weekly live calls, group coaching. What solo subscriptions can learn from it.
GitHub (Microsoft), 2026How GitHub's Users Who "Asked to Pay" Now Pay for AI by the Credit
GitHub's beta users asked to pay. Years later Copilot hit 20 million users, then moved every plan to AI credits from 1 June 2026. Here's why it had to.
GoPro, 2025How GoPro's Subscription Kept the Lights On While Camera Sales Fell
GoPro revenue fell from $1,005M to $652M in two years. Its subscription barely moved, at $106M with far higher margins. What a product-plus-membership teaches.
Groove (now Helply), 2026How Groove's Churn Lesson Grew Up Into an AI Help Desk Priced in Credits
Groove cut churn 71% by emailing users who showed red-flag behavior. Now it's Helply, an AI help desk with free seats and credits priced by task.
HelloFresh and Youfoodz (HelloFresh SE), 2025How HelloFresh's Cancellation Cut-Off Helped Write Australia's New Subscription Law
The ACCC alleges 62,061 HelloFresh customers were charged after cancelling in time. How the case shaped Australia's 2027 law, and what to fix now.
HomeJoy, 2015How HomeJoy's Collapse Still Explains Why Marketplaces Add Software
HomeJoy raised $40 million and shut down in 2015 as customers and cleaners went around it. Why marketplaces leak, and how to stop people bypassing you.
Intercom (now Fin), 2025How Intercom Bet the Company on 99 Cents per Resolution
Intercom priced its Fin AI agent at $0.99 per resolution instead of per seat. How outcome pricing restarted growth, and how to price per result yourself.
Kogan.com, 2026How Kogan First Grew Into a $61 Million Loyalty Engine
Kogan bolted a paid membership onto a low-price online store. In FY26 its loyalty subscriptions earned A$61.4 million, up 14.3%. Here's the lesson.
Looker (Google Cloud), 2026How Looker Went From Developer Tool to Google's "Agentic BI," Priced in Tokens
Looker had 10 customers after a year of selling. Then the market shifted. Now its semantic layer feeds AI agents, and Google meters it in data tokens.
Lovable, 2026How Lovable Hit a $600 Million Run Rate by Selling "a Business That Builds Businesses"
Lovable prices app building in credits per prompt and printed what each prompt costs. How it grew toward $600M ARR, and the credit lessons you can copy.
Microsoft, 2025How Microsoft's AI Price Rise Put It in an Australian Court
Microsoft added Copilot to Microsoft 365 and raised Australian prices up to 45%. The ACCC says it hid a cheaper plan from 2.7M subscribers. What to learn.
Mister Car Wash, 2025How Mister Car Wash Made 79% of Its Sales From a Monthly Club
Mister Car Wash's Unlimited Wash Club hit 79% of wash sales and 2.3 million members, then a $3.1 billion buyout. Why unlimited works for car washes.
Netflix, 2026How Netflix Stopped Counting Subscribers and Started Counting Money
Netflix cracked down on password sharing, added ads and raised prices, then stopped reporting subscribers. The 2023-2026 numbers and what small firms can copy.
Nubank (Nu Holdings), 2026How Nubank Became a Billion-Dollar-a-Quarter Bank
Nubank started with a purple no-fee credit card. By Q2 2026 it had 139 million customers and $1 billion of quarterly profit. The land-and-expand lesson.
Panera Bread, 2026How Panera Learned That "Unlimited" Coffee Needs a Limit
Panera's Unlimited Sip Club became a 30-drink-a-month plan at $14.99. Why it capped unlimited, the annual-plan math, and how a cafe can copy it safely.
Patreon, 2025How Patreon Passed $10 Billion Paid to Creators and Simplified Its Fee
Patreon went from a $5,000 YouTube experiment to $10 billion paid to creators, then swapped tiered take rates for one 10% fee. What changed, and why.
Peloton, 2026How Peloton's 0.73% Churn Became 2.2%, and What It Did Next
Peloton's churn tripled from the 0.73% the book cited to 2.2% in 2026, as revenue fell 40%. How it still turned a profit, and what that means for your churn.
Planet Fitness, 2024How Planet Fitness Raised Its $10 Price for the First Time in 26 Years
Planet Fitness lifted its $10 Classic membership to $15 for new members only, after testing. How grandfathering made a 50% rise almost churn-free.
Pret A Manger, 2024How Pret's Coffee Subscription Went From £30 to £10, and From Free Coffee to Half-Price
Club Pret UK swapped five free drinks a day for half-price drinks at £10 a month. Why Pret did it, the backlash, and how to price a cafe subscription.
Procore, 2026How Procore Kept Usage-Based Pricing Honest at $1.3 Billion
Procore prices on construction volume, not seats. In 2025 it hit $1.32 billion revenue, 95% gross and 106% net retention. What its model teaches any business.
ProfitWell (Paddle), 2022How ProfitWell's "Free First" Strategy Turned Into a $200 Million Exit
ProfitWell gave its metrics away free, signed up about 30,000 companies, and sold to Paddle for over $200 million. Why the free product was the asset.
Replit, 2025How Replit Learned That "Pay for Effort" Needs a Price Tag Up Front
Replit swapped $0.25 checkpoints for effort-based pricing, and some bills jumped. What went wrong, how it fixed it, and how to price variable work fairly.
SafetyCulture (now Mitti), 2026How SafetyCulture Became Mitti, and Why Its Founder Came Back
SafetyCulture grew from a Queensland garage to a $2.7B valuation, stalled, then rebranded as Mitti in 2026 with AI and insurance. What happened and why.
Salesforce, 2025How Salesforce Needed Three Pricing Models to Sell AI Agents
Agentforce launched at $2 a conversation, then added credits, per-user fees and fixed deals. What it teaches about pricing a product of uncertain value.
Slack (Salesforce), 2025How Slack (Inside Salesforce) Put AI in the Box and Raised the Price
In 2025 Slack folded AI into Business+, retired its AI add-on and lifted the price from $12.50 to $15 a user. What bundling AI teaches any subscription.
Spotify, 2026How Spotify Finally Turned 300 Million Subscribers Into a Profit
Spotify spent years as the great product with no profit. How freemium, ads and steady price rises got it to 306 million subscribers and a profit, 2024-2026.
Starbucks, 2026How Starbucks Rebuilt Rewards Around Tiers for 35 Million Active Members
In March 2026 Starbucks Rewards relaunched with Green, Gold and Reserve tiers for 35.5 million active members. How it works and how to build your own.
Strava, 2026How Strava Turned 150 Million Free Athletes Into a Subscription Business
Strava's free social app drives growth, and coaching apps like Runna make the paid tier worth buying. The numbers, the network effects, what to copy.
Stripe, 2026How Stripe's Moat Got Wider: $1.9 Trillion and Counting
Stripe processed $1.9 trillion in 2025, up 34%, and was valued at $159 billion. How transaction pricing and add-on services widened its moat since 2022.
StyleSeat, 2026How StyleSeat Stopped Being Free and Started Charging for New Clients
StyleSeat built its network with free software, then added a $35 subscription and a capped fee on new clients only. How it works and what you can copy.
Superhuman, 2025How Superhuman's Obsession With Product/Market Fit Ended in a Grammarly Acquisition
Superhuman lifted its 'very disappointed' score from 22% to 58%, hit an $825M valuation, then sold to Grammarly, which renamed itself Superhuman.
TechnologyOne, 2025How TechnologyOne Passed $500 Million ARR 18 Months Early, and Aimed for $1 Billion
TechnologyOne passed A$500 million ARR 18 months ahead of plan, with 115% net revenue retention and an A$1 billion target. How switching costs did it.
Uber, 2026How Uber Killed Its Free Rewards Program, Then Won (and Got Sued) With Uber One
Uber killed its free points program for a paid membership. Uber One passed 50 million members, then the FTC sued over sign-ups and cancellation.
Udemy, 2026How Udemy Swapped One-Off Course Sales for Subscriptions, Then Merged With Coursera
Udemy's subscription revenue hit 72% of sales in 2025 as one-off course sales fell, then it merged with Coursera in 2026. The numbers and what to copy.
Greencross Vets and Banfield Pet Hospital, 2026How Vets Turned Check-Ups Into a $660-a-Year Wellness Membership
How Greencross and Banfield turned routine vet visits into wellness memberships, the real prices, what CHOICE warns, and how any clinic can copy it.
Who Gives A Crap, 2025How Who Gives A Crap Took a Toilet-Paper Subscription Into the Supermarket
Who Gives A Crap started with a toilet-paper subscription and a 50-hour stunt. Now it's in Tesco and Whole Foods. The numbers, the moat, and what to copy.
WiseTech Global, 2025How WiseTech Killed Seat Fees Before AI Could Kill Them First
WiseTech dropped per-user fees for CargoWise in December 2025 and moved about 95% of customers to transaction pricing. Why, and how to copy the move.
Xero, 2026How Xero Simplified Its Plans, Raised Prices, and Grew Average Revenue 23%
Xero cut its Australian plans to four, raised prices every 1 July, and grew average revenue per customer 23% in FY26. The prices, the results, the lessons.
Zillow Group (Trulia), 2026How Zillow Turned Trulia's Network Into a Profitable "Home Journey"
Trulia sold to Zillow in a $3.5 billion deal built on network effects. By 2025 Zillow had 221 million monthly users and a profit. Here's how it got there.
Zoom, 2026How Zoom Became a 4%-Growth Company, and What It's Doing About It
Zoom's freemium hook won the pandemic. In FY26 revenue grew 4.4%, online churn was 2.9% a month and enterprise expansion 98%. Here's the fix it's trying.
Atlantic Refrigeration (ServiceTitan customer), 2026How a Heating and Cooling Contractor Tripled Its Maintenance Contracts
How Atlantic Refrigeration grew from 16 to 50+ maintenance contracts, why trades plans pay off in pull-through work, and how to launch your own plan.
US Federal Trade Commission, 2025How the FTC's "Click to Cancel" Rule Died in Court, and Why It Changed Nothing
A US court struck down the FTC's click-to-cancel rule in 2025. Then came Amazon's $2.5B and Adobe's $150M settlements. Here's why it still matters.
UK Government (DMCC Act 2024), 2026How the UK Gave Every Subscriber Two Chances to Change Their Mind
The UK's DMCC subscription rules start January 2027: reminders, easy exits and two 14-day cooling-off periods. What changes, and how to win renewals.