ChatGPT's Retention Curves Resemble Past Winners
by Brian Balfour on August 17, 2025
Situation
- Market context: A new AI-driven distribution platform is emerging, with multiple competitors (ChatGPT, Claude, Gemini) battling for dominance
- Strategic challenge: Companies need to identify which platform will likely win to make appropriate integration bets
- Historical pattern: New distribution platforms follow a predictable cycle - competitive market conditions, identification of a moat, platform opening, and eventual closing for monetization
- Current state: We're at the inflection point where a clear winner is emerging but not yet fully established
Actions
Identifying the Likely Winner
- Retention analysis: Brian examined retention data published by VC Didi Doss comparing all major AI platforms
- Engagement patterns: Looked beyond raw user numbers to focus on depth of engagement and retention curves
- Historical comparison: Applied lessons from previous platform wars (Google vs. Yahoo, Facebook vs. MySpace) where winners showed superior retention
- Pattern recognition: Identified the rare "smile curve" in ChatGPT's retention data - where retention initially drops but then increases over time
Evaluating Moat Factors
- Context and memory: Determined that the key moat in AI platforms is context accumulation and memory capabilities
- User experience quality: Assessed which platform was delivering consistently better outputs through context
- Flywheel effects: Analyzed how increased usage creates better personalization, which drives further usage
- Scale assessment: Considered ChatGPT's estimated 10x user advantage over competitors like Claude
Results
- Clear leader identification: ChatGPT emerged as the platform with significantly higher retention rates
- Upward trajectory: Data showed ChatGPT's retention curves shifting upward dramatically over time
- Rare pattern emergence: The "smile curve" in retention data matched patterns seen only in major platform winners like Slack
- Competitive advantage: Despite competitors having potential distribution advantages (like Google with Chrome), the retention data signaled stronger user loyalty to ChatGPT
Key Lessons
- Look beyond vanity metrics: Raw user numbers (MAUs) are less predictive of platform success than retention and engagement depth
- Study retention curves: The shape and trajectory of retention curves provide early signals of which platform will achieve escape velocity
- Recognize the "smile curve": A retention curve that initially drops but then increases over time is an extremely rare and powerful indicator of network effects
- Apply historical patterns: Previous platform wars consistently show that superior retention beats initial distribution advantages
- Make focused bets: For startups with limited resources, analyzing retention data helps identify where to place your single platform integration bet
- Act quickly: The window for capitalizing on emerging platforms is shrinking with each cycle, requiring faster decision-making