When launching its subscription service, Dropout theorized it could convert its large YouTube audience over a long period. They discovered that the segment of a free audience willing to convert to a paid product is a finite resource that gets exhausted much faster than anticipated.
The key indicator of a healthy freemium model isn't the specific retention percentage but whether the curve flattens over time. A curve that continuously drops to zero means you are not building a sustainable user base and are simply starting over with each new cohort of users.
The comedy platform's primary customer acquisition channel is organic clips on TikTok, Instagram, and YouTube. Paid advertising, which accounts for only 10% of sign-ups, isn't used for discovery but to amplify content that has already demonstrated strong organic performance.
Many founders mistakenly view freemium as a complete business model. It's actually a top-of-funnel acquisition strategy that replaces marketing spend with a free product to generate leads. The real business model is the subsequent upsell to paid tiers.
Education-based businesses struggle with churn because knowledge, once learned, has diminishing value. To build a sticky subscription, you must offer "consumable" value—something that is used up and needs replenishing, like weekly market data, new ad creative, or trending product blueprints. This creates a reason to keep paying.
Dropout's primary customer acquisition channel is organic social media. Shows like "Game Changer" are intentionally designed to produce viral, context-free clips for TikTok and Instagram, turning the content itself into a powerful, self-sustaining marketing funnel that drives most signups.
Counterintuitively, a high freemium conversion rate (e.g., 7%) isn't always positive. It may indicate the free plan is too restrictive, failing to build a wide user base that provides network effects, referrals, or a long-term upgrade pipeline. The goal is a broad top-of-funnel, not just quick conversions.
Contrary to popular belief, dedicating 50% of your effort to a free weekly newsletter may yield no impact on paid conversions. Tech leader Dave Anderson paused his free newsletter and saw zero change in paid growth, suggesting the free content was a separate value stream, not a conversion funnel.
When a tool gets massive attention but users aren't willing to pay (like Trust MRR), pivot the business model to advertising. Create scarcity by offering a limited number of ad slots and rewarding early advertisers with lower prices. This builds FOMO and generates more reliable revenue.
To profitably scale a SaaS with paid ads (Meta, YouTube), you cannot rely on low-ticket monthly subscriptions. The customer acquisition cost will almost always be too high to be sustainable. You must have a high-ticket enterprise plan to ensure a positive return on ad spend from day one.
Dan Kohler's Kapo Chronicle newsletter converts over 40% of its list by paywalling every weekly issue. Free subscribers only get a monthly email summarizing what they missed, creating a powerful incentive to upgrade. This challenges the common freemium model where substantial free content is the norm.