Subversive

Albert Cheng is the Chief Growth Officer of Chess.com. Prior to joining Chess.com a year ago, Albert served as the Head of Product Growth and Monetization at both Duolingo and Grammarly, two of the world’s most successful consumer subscription businesses. Earlier in his career, Albert also held product and engineering roles at YouTube and SoFi, as well as a couple smaller startups. Outside of work, he is an avid chess player and diehard San Francisco 49ers fan.Key Takeaways:Chess.com was founded in 2005 after Erik Allebest and Jay Severson acquired the domain for $55,000. The company now has >90% market share of the online chess market, with 200 million registered users, 40 to 50 million MAUs, 10 million DAUs, 1.5 million subscribers, and north of 20 million games played everyday.For years, Chess.com grew slowly but steadily by investing in its core product experience and underlying infrastructure to provide the best possible gameplay experience for users. This attention to detail was the foundation for its success.Then in 2020, the combination of the COVID-19 pandemic and the release of a massive hit TV show called The Queen’s Gambit led to a chess boom that drove a quadrupling in Chess.com’s daily registrations.Chess.com has grown almost 100% organically driven by strong SEO and ASO performance thanks to its domain, as well as a powerful word of mouth flywheel supported by online tournaments, partnerships, and strong relationships with celebrity chess players like Magnus Carlsen and Gukesh Dommaraju.Going forward, the company is focused on instilling a product-led growth culture rooted in high-velocity, hypothesis-driven experimentation to continuously improve key metrics like user retention and subscriber conversion, which it hopes will drive compounding long-term revenue growth.Albert Cheng:Website: https://www.chess.com/LinkedIn: https://www.linkedin.com/in/albertcheng1/X: https://x.com/albertc248Phil Carter:Website: https://www.philgcarter.comSubstack: https://philgcarter.substack.comLinkedIn: https://www.linkedin.com/in/philgcarterX: https://x.com/philgcarterPodcast Production by Podders: https://podders.io

Max Marchione, cofounder and President of Superpower, is a serial entrepreneur reshaping digital health. He shares his journey of launching Superpower, inspired by personal health struggles and the shortcomings of the current healthcare system. The platform offers comprehensive lab tests, concierge access, and an online marketplace, aiming to democratize health management. Max predicts AI will revolutionize diagnostics, potentially surpassing human doctors by 2030, creating a future where health management is as convenient as subscribing to a service like Amazon Prime.

Olivier Lemarié, VP of Growth at Photoroom, has played a pivotal role in scaling the photo editing app since its inception. In this discussion, he reveals how an AI feature transformed their background removal tool, leading to explosive growth. The conversation delves into Photoroom’s strategic evolution and how viral user excitement drove organic growth. Olivier highlights successful subscription strategies and the innovative advertising techniques that enabled expansion into international markets, showcasing the profound impact of AI in enhancing user experience.

Miranda Paine, Head of Growth at Runna, previously worked in growth and marketing roles at other fitness startups. She discusses Runna's rapid success, leveraging AI for hyperpersonalized training plans that adapt to individual runners. Community-building, particularly through user-generated content and strong ambassador relationships, played a crucial role in their marketing strategy. Miranda emphasizes the importance of distinct content approaches for platforms like TikTok and Instagram, and how these strategies contributed to Runna's successful acquisition by Strava.

Jon Noronha is the cofounder and Head of Product at Gamma, where he's creating a new medium for presenting ideas. Gamma allows anyone to generate a presentation, document, or webpage in minutes using AI, just by writing a topic or pasting an outline. Before starting Gamma, Jon was the VP of Product at Optimizely, where he helped companies integrate rapid experimentation into their product development process.Key Takeaways:After launching in 2020, Gamma struggled to find product/market fit until early 2023 when it bet the company on a big launch focused on AI-powered presentations. By August of that year, the company was profitable.Gamma unveiled this launch on X with a viral post that read: "The most valuable skill in business is about to become obsolete. Designing a killer slide deck used to take days. Now AI can do it in seconds for anyone. Introducing Gamma: your AI design partner for presenting ideas beautifully."One key to Gamma's early success was using cheaper, faster models even if it meant sacrificing some performance. This allowed the company to run lean with lower costs, and it also minimized latency leading to a better user experience.Gamma has benefitted from multiple organic growth loops that allowed it to scale cost-efficiently, including word of mouth (users telling friends and colleagues), casual contact (users discovering Gamma through another presentation), and SEO (users creating websites and presentations that get indexed by Google).Gamma offers two subscription tiers, Gamma Plus and Gamma Pro, each with monthly and annual plans at relatively low prices compared to other AI products. It loses money on a small percentage of its users, but this is a tradeoff Gamma is happy to make to keep its premium product offering simple and delight its best customers.Over 90% of Gamma's users and over 75% of its subscribers are from markets outside the US, and the company has invested in product localization, support for local currencies, and international price optimization to serve these users.Jon Noronha:Website: https://gamma.app/LinkedIn: https://www.linkedin.com/in/jonnoronha/X: https://x.com/thatsjonsensePhil Carter:Website: https://www.philgcarter.comSubstack: https://philgcarter.substack.comLinkedIn: https://www.linkedin.com/in/philgcarterX: https://x.com/philgcarterPodcast Production by Podders: https://podders.io

Ajay Mehta, cofounder and president of Portola, discusses the viral AI companion app Tolan. Tolan, designed as a Pixar-like alien friend, has captivated Gen-Z women by providing emotional support and relationship advice. Ajay reveals how Tolan's surprise memory feature creates deep emotional connections with users. He also explains the power of TikTok in driving the app's explosive growth and the transition from a paywall to a freemium model to enhance user experience and community building.

Cori Shearer, Lead Product Manager at Headspace, shares her journey from a Senior PM at Quizlet to her role in enhancing mental wellness. She discusses Headspace's transformation from a meditation app to a comprehensive wellness platform after acquiring Ginger.io. Cori explores the integration of AI through the feature Ebb for personalized mental health support. She emphasizes adapting to consumer needs and the ongoing evolution of mindfulness practices, highlighting the importance of user feedback in product development.

Natalia Castillejo, Director of Product at Duolingo, has been instrumental in the development of innovative features like Duolingo Max. She shares insights on how AI-driven functionalities like video calls and personalized feedback revolutionized language learning. Discussing her journey from intern to director, Natalia highlights the importance of user-centric design and A/B testing in product development. She emphasizes that successful monetization requires understanding user needs, paving the way for engaging educational experiences.

Jacob Eiting, Founder and CEO of RevenueCat, discusses profound insights from the 2025 State of Subscription Apps Report. He highlights the plummeting costs of app development, presenting opportunities for niche markets amid increasing competition. Retention rates are declining, emphasizing the need for top-notch product quality. Eiting also addresses AI's transient impact on growth and the importance of improving user onboarding experiences. Lastly, he shares anecdotes from his entrepreneurial journey, showcasing the critical elements of differentiation and innovation.

Yuriy Timen, a seasoned marketing advisor and former Global Head of Marketing at Grammarly, shares insights into the company's incredible growth journey. He discusses the strategic shift from targeting students to knowledge workers, revealing how this pivot opened new market opportunities. By implementing a freemium model and leveraging YouTube for marketing, Grammarly successfully reached a broader audience. Yuriy also reflects on the challenges of transitioning from B2C to B2B and the importance of building trust through word-of-mouth and AI-driven solutions.