Lenny's Podcast: Product | Career | Growth · Lenny Rachitsky

How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)

·1 hr 25 min·5 clips

Grammarly doubled upgrade rates by giving free users a taste of paid suggestions—challenging the fear of giving too much away.

Albert Cheng built his career in growth across some of the most successful consumer subscription products in the world: Duolingo, Grammarly, and Chess.com, with earlier work on YouTube streaming and gaming features. In this conversation with Lenny Rachitsky, he walks through his core framework: explore and exploit. Explore is about finding the right mountain to climb — identifying which growth levers or opportunities are actually worth pursuing. Exploit is about focusing resources to climb that mountain well. He warns that teams spending too much time on either end underperform — too much exploration leads to scattered efforts, too much exploitation leads to stagnation. Cheng applies the framework at the micro level, working with individual PMs to find insights before committing resources. At Grammarly, his biggest monetization win came from a counterintuitive experiment: sampling premium suggestions and surfacing them to free users. Most free users experienced Grammarly as a basic spell-checker; exposing them to paid features changed their mental model of the product entirely, driving significant paid conversion. He argues that user retention is the foundation of any consumer subscription business — without retention, the entire monetization burden falls on acquiring paying users on day one. Cheng discusses how AI tools are transforming growth work by accelerating the hypothesis-generation and analysis cycles, and how his goal at every company is to run 1,000 experiments per year to generate a fast feedback loop. He connects his childhood training as a concert-level pianist — including having perfect pitch — to the discipline of running growth: both require consistent repetition, resilience to failure, tight feedback loops, and a structural framework layered with creativity. On team-building, he argues that high agency and clock speed matter more than deep domain experience, especially in a rapidly changing landscape where previous expertise can become a liability. The conversation covers how brand and community unlock growth flywheels that paid acquisition cannot easily replicate, and how each of his companies — Duolingo, Grammarly, Chess.com — had distinct levers that required different approaches.

As heard by us

Growth is treated as product work, retention, and practical experimentation.

Albert Cheng frames growth as connecting users to product value, not as metric chasing for its own sake. The discussion stays focused on why retention matters in consumer subscription businesses, and on how even mature products still need fresh ways to bring people back to…

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