Subversive

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.

Rachel Hepworth, former CMO at Notion and growth marketing expert from Slack and LinkedIn, shares her insights on how community engagement spurred Notion's success in AI. She reveals how the company pivoted towards AI Writer by leveraging user-generated content like templates and demos. She discusses the challenges of catering to both individual users and businesses while scaling internationally. Additionally, Rachel highlights the importance of community champions for advocacy and navigating feedback to enhance authenticity in brand perception.

Zain Abiddin, a seasoned global product builder and leader with over 15 years of experience, shares his insights on Canva's spectacular growth. He discusses how Canva expanded internationally, adapting localized pricing and payment methods to penetrate new markets. The launch of Canva for Teams played a pivotal role in boosting revenue and enhancing user collaboration. Zain also highlights strategies to combat involuntary churn, emphasizing the critical role of data analysis and A-B testing in refining pricing strategies and user retention.

Ravi Mehta, a seasoned product executive with a history at Tinder, Facebook, and Tripadvisor, shares insights into Tinder's explosive growth. He discusses how the app went viral on college campuses, thanks to its innovative swiping and marketing strategies. The conversation delves into Tinder's clever monetization model, featuring multiple subscription tiers and in-app purchases designed to retain high-intent users. Ravi also highlights the challenges of consumer subscription apps and the importance of delivering continuous value to combat user churn.

Ron Schneidermann, entrepreneur and former CEO of AllTrails, shares insights into transforming the world’s largest outdoor platform. He reveals how AllTrails shifted focus from hardcore enthusiasts to appealing to casual hikers, leveraging user-generated content for engagement. The discussion highlights the importance of strategic pricing and SEO for growth, including unique challenges of international expansion. Ron also emphasizes the role of AI in enriching user experiences while advocating for nature connection through innovative outdoor activities.

Greg Stewart, CEO of Ladder, an innovative strength training app, discusses the company's incredible 2,000% growth. He reveals how Ladder pivoted its pricing strategy from $60 to $30 to better align with customer needs. Greg elaborates on the creation of the 'Ladder Quadrant' to identify high-value user segments and emphasizes the impact of turning in-house coaches into TikTok content creators for user acquisition. He also touches on the importance of community engagement and AI in enhancing the overall fitness experience.