Ajay Mehta is an accomplished entrepreneur who is currently cofounder and President of Portola, the company behind a viral AI companion app called Tolan. Prior to launching Tolan, Ajay founded other successful consumer startups including Birthdate Co., Therapy Notebooks, and FamilyLeaf, and he has held product and growth leadership roles at Wealthsimple (Canada’s largest FinTech company) and Tilt.

Key Takeaways:

• After finding product-market fit with an AI companion in the form of a Pixar-like alien friend and officially launching its app in February 2025, Tolan has gone viral among Gen-Z women who use it for everything from emotional support to relationship advice to help with homework and everyday tasks.
• The magic moment for users is when their Tolan remembers something they said the previous day and realize their Tolan really sees and understands them. The “wow factor" of this emotional connection has helped the app go viral, similar to how the stunning speed and quality of ChatGPT’s responses made it go viral.
• TikTok has been the top channel for Tolan. Because of the way TikTok’s algorithm works, Tolan was able to generate multiple viral videos even before it had any real online following, which has helped propel its exponential growth.
• Tolan is doubling down on its rapid organic growth by transitioning from a hard paywall to a freemium model and building social experiences into its app that will allow users to create a “solar system” of close friends and their Tolans.
• Like many AI apps, Tolan’s monetization strategy must consider the underlying costs of AI-powered features. However, as these costs have continued to come down dramatically, it has allowed application-layer companies like Tolan to push the envelope on feature development and give more value away to users for free.

Ajay Mehta:

• Website: https://www.tolans.com/
• LinkedIn: https://www.linkedin.com/in/ajayumehta/
• X: https://x.com/ajaymehta

Phil's Carter:

• Website: https://www.philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://www.linkedin.com/in/philgcarter
• X: https://x.com/philgcarter

Cori Shearer is currently a Lead Product Manager at Headspace, where she has spent the last four years leading teams focused on growth as well as engagement with their full suite of human-delivered care offerings like coaching, clinical, and AI-based services. Prior to Headspace, Cori worked at Quizlet as a Senior PM focused on acquisition, activation, and international growth. She is also an entrepreneur, startup advisor, and instructor for Product School.

Key Takeaways:

• Headspace was founded in 2010 by Andy Puddicombe as the first meditation app in the app store after Andy returned from being a monk and wanted to share everything that he had learned about meditation and mindfulness with the world.
• After Headspace acquired Ginger.io in 2021, it evolved from a single product focused on meditation into a platform of health and wellness services that now includes human-delivered care in the form of coaching, therapy, and psychiatry.
• In parallel, Headspace has also expanded from a pureplay consumer app to a B2B solution with Headspace for Work, which offers health and wellness services to companies and their employees.
• As Headspace has evolved on both of these two dimensions, it has needed to stretch its brand in new and different ways while also adapting its product to be able to serve a range of customers with different mental health needs. This has meant slowing down at times to make sure they got things right for their customers, and building a new set of outcome metrics to measure efficacy.
• In late 2024, Headspace launched its AI companion called Ebb, which helps users navigate through Headspace’s various products and services to get what they need to improve their mental health and ultimately live happier lives.

Cori Shearer:

• Website: https://www.corishearer.com
• LinkedIn: https://www.linkedin.com/in/corishearer/
• X: https://x.com/alacodeblog
• Instagram: https://www.instagram.com/alacodeblog/

Phil's Carter:

• Website: https://www.philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://www.linkedin.com/in/philgcarter
• X: https://x.com/philgcarter

Podcast Production by Podders: https://podders.io

Natalia Castillejo is a Director of Product at Duolingo, where she has spent the last decade since graduating from Yale University in 2016. Natalia started her PM career at Duolingo working on the company’s English Language Test and other core product features. More recently, she helped lead the development and monetization of AI-powered features like “Video Call,” “Roleplay,” and “Explain My Answer” that form the core of Duolingo Max, and then transitioned from core product to monetization to help accelerate the growth of this new higher-priced subscription tier.

Key Takeaways:

• Duolingo started investing in AI product features in 2022 after getting early access to ChatGPT. It spent a year building and refining these features before packaging them into its new higher-priced Duolingo Max subscription tier in 2023.
• Duolingo Max wasn’t an overnight success. It wasn’t until the company launched video calls and repositioned Max from “pay more for AI” to “pay more for conversational language learning” that the new subscription tier really took off.
• Duolingo requires all PMs to be daily users of its app, and the company A/B tests every product change. This has led to a world-class product development culture built on both strong product intuition and rigorous experimentation.
• Duolingo always starts with the user problem that needs to be solved and works backward from there. This helps avoid “technology in search of a problem,” which is especially important right now as AI is unlocking all sorts of new technology.
• Duolingo is also encouraging its PMs to invest in AI tools to boost efficiency. This includes using tools like Replit to build prototypes without engineers, and building internal tools to predict the impact of an A/B test based on previous experiments.
  
  

Natalia Castillejo:

• LinkedIn: https://www.linkedin.com/in/natic/
• X: https://x.com/naticsti
  
  

Phil’s Carter:

• Website: https://www.philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://www.linkedin.com/in/philgcarter
• X: https://x.com/philgcarter
  
  

Podcast Production by Podders: https://podders.io

Jacob Eiting is the founder and CEO of RevenueCat, the world’s largest SaaS platform for subscription apps that need help powering in-app purchases, managing customer data, and growing revenue across iOS, Android, and the web. Prior to founding RevenueCat in 2017, Jacob was the CTO of Elevate Labs, a consumer subscription business offering both brain training and meditation apps, and a software developer at multiple other companies, including Apple.

Key Takeaways:

• The cost of building apps is falling exponentially. This is opening up opportunities for products in niches that were not previously viable, but that can now support profitable businesses. However, it’s also dramatically increasing competition.
• Subscriber retention is the most important metric for consumer subscription apps, but retention rates continue to decline as the app stores become increasingly crowded. While there are tactics companies can use to improve retention on the margins, this metric is hard to move and is ultimately driven by product quality.
• The rise of AI has created a “tourist effect” that is driving organic growth through viral word of mouth, but this will slow down eventually. To win in the long run, AI companies need to develop sustainable and repeatable growth strategies.
• Given that 80% of trials occur on the same day an app is installed, optimizing the new user onboarding experience is one of the highest-leverage opportunities consumer subscription apps have to accelerate growth.
• Consumer subscription apps are at a disadvantage vs. B2B SaaS businesses because most of them only monetize users through a single subscription tier. Recently, a lot of apps have begun testing lifetime subscriptions and/or one-time purchases to capture more consumer surplus and increase ARPU.
  
  

Jacob Eiting:

•  RevenueCat Website: https://www.revenuecat.com
•  2025 SOSA Report: https://www.revenuecat.com/state-of-subscription-apps-2025/
•  LinkedIn: https://www.linkedin.com/in/jeiting/
•  X: https://x.com/jeiting

Phil Carter:

•  Website: philgcarter.com
•  Substack: philgcarter.substack.com
•  LinkedIn: linkedin.com/in/philgcarter
•  X: x.com/philgcarter

Podcast Production by Podders: https://podders.io

Yuriy Timen is a seasoned growth and marketing advisor with 15+ years of experience scaling technology companies. Yuriy joined Grammarly as the company’s first marketing hire in 2012 when it had just 10 employees and left in 2020 as Global Head of Marketing and Growth. Since then, Yuriy has advised more than 40 companies, including Airtable, Canva, Oyster, Whimsical, and Otter.ai. He specializes in marketing, product-led growth, and hiring and developing high-performing growth teams.

Key Takeaways:

• Grammarly started by building a web app with a 7-day free trial marketed to students through paid channels like Facebook and Twitter, and through SEO given the high volume of students searching online for help with their writing.
• After realizing the global market opportunity for professional knowledge workers was much larger than for students, Grammarly pivoted its product, business model, and growth strategy to serve this new customer segment.
  • Product: Grammarly created browser extensions for Chrome, Safari, and Firefox, built plugins for Microsoft Office apps, and launched a mobile keyboard, all of which helped it integrate into existing prosumer workflows.
  • Business Model: The company also introduced a freemium business model with a free tier that gave prosumers more time to experience the value of Grammarly's product before needing to make a purchase decision.
  • Growth Strategy: Grammarly cracked YouTube as the perfect channel for explaining its nuanced core value promise to knowledge workers.
• In 2018, the company launched Grammarly Business and began selling to entire teams of professionals, with enhanced admin and security features, function-specific value props, and updated ad campaigns to reposition it as an enterprise solution.
• As Grammarly has gained traction with businesses, it has benefitted from word of mouth within and across professional teams that has helped the company to land and expand within enterprises.

Yuriy Timen

• Website: https://www.yuriytimen.com/
• LinkedIn: https://www.linkedin.com/in/yuriytimen/
• X: https://x.com/TheTimenator

Phil Carter

• Website: https://www.philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://www.linkedin.com/in/philgcarter
• X: https://x.com/philgcarter
  
  

Podcast Production by Podders: https://podders.io

Rachel Hepworth is the former CMO at Notion, where she helped the company expand internationally, move upmarket, and grow by 10x. Prior to Notion, she was part of the marketing leadership team at Slack, founding the Growth Marketing function and scaling the company through IPO. Rachel is now a full-time marketing and growth advisor, helping companies like Clay, Luma AI, and Attio reach their full potential.

Key Takeaways

• After a pivotal company offsite in 2022, Notion’s founders recognized that AI was the future and directed the company’s entire 60-person team to throw out their roadmaps and focus all of their attention on launching AI Writer.
• As a horizontal product with a lot of different use cases, Notion has always relied on its highly engaged community to educate other users on how to get the most out of its product. When Notion moved into AI, it leveraged its community to raise awareness of AI Writer and help other people understand how to use it.
• Specifically, Notion crowdsourced templates and demo videos from users to help people understand the most powerful ways to use AI Writer, and it has continued using this strategy as Notion AI has evolved into an entire suite of AI tools.
• Notion’s community has helped it overcome the challenge of building a business that is distributed both functionally (~80% of customers are individual users but ~80% of revenue comes from businesses) and internationally (roughly a third of the company’s users come from North America, EMEA, and APAC, respectively).
• Roughly 25% of Notion’s B2B workspaces came from individual “champions” who were then able to convince their companies to invest in Notion as an enterprise. The company got very good at using data to identify these champions and then empower them to spread Notion to other people within their companies.
• Over the last couple years, Notion AI has expanded into Q&A, database creation, and a suite of many other tools. These investments have had a tremendous impact on the company’s growth trajectory.
  
  

Rachel Hepworth

• LinkedIn: https://www.linkedin.com/in/rachelhepworth/
• X: https://x.com/rachelhepworth
  
  

Phil Carter

• Website: philgcarter.com
• Substack: philgcarter.substack.com
• LinkedIn: linkedin.com/in/philgcarter
• X: x.com/philgcarter
  
  

Podcast Production by Podders: https://podders.io

Zain Abiddin is a global product builder and leader with 15+ years of experience. He joined Canva in 2020 as the company’s first subscriptions PM and spent four years helping to scale Canva to billions of dollars in ARR, including the launch of Canva for Teams as well as tools to support localized pricing, price migration, and involuntary churn management. Prior to Canva, Zain ran several startups before transitioning into a career in product management. Zain is now the founder and CEO of Hewwi, a startup dedicated to helping people boost their health, wealth, and wisdom. He has travelled to 30+ countries and worked in APAC, EMEA, and North American markets.

Key Takeaways:

• In the last five years, Canva’s valuation has soared from $6 billion to $49 billion, fueled by international expansion and the launch of Canva for Teams.
• Expanding internationally has required Canva to support local currencies, adjust prices to align with local willingness to pay, and integrate alternative payments methods (APMs) for specific regions.
• Canva has also made significant investments in dunning and other techniques to minimize involuntary churn, which happens when users lose access to subscriptions due to failed payment methods or insufficient funds.
• More recently, the company launched Canva for Teams, which has accelerated revenue growth by unlocking larger accounts while also boosting virality given the natural network effects that exist between teams of knowledge workers.
• Going broad through international expansion helped Canva get past its first $1B in ARR, then going deeper with the launch of Canva for teams helped the company get from $1B to $2B in ARR, and now the company is increasingly expanding into enterprise accounts to grow ARR even further.

Zain Abiddin:

• Website: https://zain.blog
• Substack: https://zainabiddin.substack.com/
• LinkedIn: https://www.linkedin.com/in/zainabiddin/
• X: http://twitter.com/zainabiddin 

Phil Carter:

• Website: https://philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://linkedin.com/in/philgcarter
• X: https://x.com/philgcarter

Podcast Production by Podders: https://podders.io

Greg Stewart is the CEO of Ladder, an innovative strength training app that has grown subscribers by 2,000% over the last two years. He has a mix of startup leadership, company-building, and corporate finance experience. Prior to Ladder, Greg served as COO and a founding team member of Bungalo, an operationally intensive consumer-facing real estate technology platform he helped to build and launch from the ground up within Amherst Residential. Before Bungalo, Greg was COO and then CEO of a high-growth SaaS startup also in Austin. Earlier in his career, Greg served as a technology investment banker at Goldman Sachs, first in New York and then in San Francisco.

Key Takeaways:

• After launching during the pandemic, Ladder pivoted its way to product/market fit with a coach and team centered strength training app for fitness enthusiasts.
• When it realized its initial $60/month price point was too high, Ladder rebuilt its subscription pricing and packaging from the ground up until it felt confident its premium product and new $30/month price were aligned with its target customer. 
• The company built a framework to identify its highest-value user segments and worked backwards from their unique needs to recruit the perfect coaches.
• Ladder cracked user acquisition on TikTok (and now Instagram) by turning in-house coaches and creators into short-form content creation machines, converting the best organic content into paid ads, using an onboarding quiz to predict each new user's LTV, and leveraging this pLTV data to continuously optimize its advertising spend.
• Ladder’s innovative growth strategy, combined with category-leading subscriber retention rates driven by its coach- and team-centered approach to fitness, have helped it grow ~2,000% from 10k to 175k subscribers over the last two years.

Greg Stewart:

• Website: https://www.joinladder.com
• LinkedIn: https://www.linkedin.com/in/gregoryfstewart
• X: https://x.com/gregoryfstewart

Phil Carter:

• Website: https://philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://linkedin.com/in/philgcarter
• X: https://x.com/philgcarter

Podcast Production by Podders: https://podders.io

Ron Schneidermann is an entrepreneur who is passionate about building great companies that help people have healthy, authentic, real-world experiences. He is the former CEO of AllTrails, the world's largest and most trusted outdoor platform with a community of over 75 million trail-goers. In 2005, Ron cofounded Liftopia, the global leader in ski lift ticket bookings, and was Head of Growth at Yelp Reservations. Ron attended UCLA, earning his bachelor’s degree in Communications, and lives in Northern California with his wife Jenny, their three children, and their dog Sally.

Key Takeaways:

• After launching in 2010 and establishing initial product/market fit among a loyal early adopter base of outdoor enthusiasts and search and rescue professionals, AllTrails pivoted to a much larger mainstream audience of casual hikers.
• This pivot required AllTrails to change everything from its copy and creative to its user acquisition strategy, core product experience, and subscription price.
• AllTrails leveraged SEO to drive cost-efficient organic growth, particularly for hyperlocal search queries related to local hiking trails, where content created by its user base gave the company a highly defensible competitive advantage.
• More recently, AllTrails has expanded internationally using a playbook where it seeds new countries with manually curated trail guides and then leverages this content to attract early adopters and get its UGC-driven SEO flywheel going.
• While AllTrails relies on AI to boost internal productivity, it has intentionally been slow to create consumer AI features until it recognizes a compelling use case that enhances its core value promise of helping people get outside.

Ron Schneidermann:

• Website: https://www.alltrails.com/
• LinkedIn: https://www.linkedin.com/in/schneidermann/
• X: https://x.com/AllTrails

Phil Carter:

• Website: philgcarter.com
• Substack: philgcarter.substack.com
• LinkedIn: linkedin.com/in/philgcarter
• X: x.com/philgcarter

Podcast Production by Podders: https://podders.io

Ravi Mehta is a senior product executive with experience leading product organizations for globally recognized brands like Tripadvisor, Facebook, and Tinder. Over his career, Ravi has scaled well-known products that have impacted millions of people and built teams to meet the challenge. Ravi is a well-respected thought leader, and his frameworks on product strategy and product leadership have been adopted by thousands of professionals across the industry. Previously, he was Chief Product Officer at Tinder, Product Director at Facebook, VP of Consumer Product at TripAdvisor, and Executive-in-Residence at Reforge. He is an active advisor and investor, primarily focused on consumer tech companies.

Key Takeaways:

• After launching at USC in 2012, Tinder went viral on college campuses across the country by combining mobile-first features like Facebook Connect and its famous “hot or not” swiping mechanic with a GTM strategy focused on frats and sororities
• Tinder expanded beyond college students by investing in features like Festival Mode and Swipe Search designed to create network effects among other user segments
• To overcome inherently high churn rates in the dating category, Tinder has developed a sophisticated monetization strategy that includes three subscription tiers - Tinder Plus, Tinder Gold, and Tinder Platinum - as well as complementary in-app purchases like "Boosts" and "Super Likes" that capture additional value from high-intent users
• Tinder deeply understands the fundamental goals of its subscribers and aligns the premium value promises of its subscriptions and in-app purchases to ensure that it always creates more value for subscribers than it takes back in the form of revenue
• Tinder’s innovative approaches to product development, growth, and monetization have turned it into the top dating app in the world with well over $1 billion in revenue

Ravi Mehta:

• Website: https://www.ravi-mehta.com/
• Substack: https://blog.ravi-mehta.com
• LinkedIn: https://linkedin.com/in/ravimehta
• X: https://x.com/ravi_mehta

Phil Carter:

• Website: https://philgcarter.com
• Substack: https://philgcarter.substack.com
• LinkedIn: https://linkedin.com/in/philgcarter
• X: https://x.com/philgcarter

Podcast Production by Podders: https://podders.io