Subversive

Tanay Kothari is the cofounder and CEO of Wispr, the company behind an AI-powered voice dictation app called Flow. Prior to starting Wispr in 2021, Tanay has been a serial entrepreneur for 16 years since he taught himself how to code as a child. He has founded multiple companies, many of them focused on the next generation of personal computing after Tanay was inspired by the character J.A.R.V.I.S. in the movie Iron Man. He has also held product and engineering roles at Cerebra Technologies and Microsoft and served as a Computer Science teaching assistant at Stanford University.

Key Takeaways:

• Tanay Kothari and Sahaj Garg cofounded Wispr in 2021 with the vision of using a native voice interface to power the next generation of personal computing. Since then, the company iterated through seven other products before ultimately finding strong product/market fit with an AI-powered voice dictation app called Flow.
• The biggest thing Wispr Flow has done to differentiate its product vs. other voice dictation tools is tackle the upfront technical challenges that allow their product to work horizontally across any other single application. This year, Wispr Flow has been used successfully across over 25,000 different apps and websites.
• Unlike other voice dictation tools that transcribe what a user speaks verbatim, Wispr Flow waits until a user has finished talking and then transcribes a polished version based on what the user would want if they were writing. It uses context awareness to understand what type of message the user is writing (email, text message, etc.) and then makes formatting decisions based on that context.
• Two KPIs that Wispr Flow uses to measure product/market fit are zero edit rate and average time to send after completing a message. Wispr Flow’s zero edit rate is currently 81% and its average time to send is half a second, both of which are best-in-class vs. other voice dictation apps (including Apple and Google).
• Wispr Flow has early adopters across a broad range of users, including founders and business leaders, engineers, creative influencers, and senior citizens. Its horizontal use case and simple and intuitive interface have also driven viral word of mouth, allowing the company to rapidly expand across international borders.

Tanay Kothari:

• Website: https://wisprflow.ai/
• LinkedIn: https://www.linkedin.com/in/tankots/
• X: https://x.com/tankots

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

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/albertc248

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

Max Marchione is the cofounder and President of Superpower, a startup that is reinventing digital health by offering patients a comprehensive panel of 100+ labs, an online panel that centralizes all of their health data in one place, and access to world-class longevity clinicians to help them lead longer and better lives. Prior to Superpower, Max has spent the last five years as an investor and serial entrepreneur as the founder of Next Chapter, Ultraviolet Ventures, and Fractal Capital.

Key Takeaways:

• After years of struggling with chronic health issues, Max was inspired to cofound Superpower to help democratize access to the world’ best concierge medicine.
• Superpower launched with a manifesto highlighting the brokenness of the current healthcare system and quickly went viral, building a waitlist of hundreds of thousands of people looking for a better way to manage their health.
• The company now offers a $499/year subscription that gives members biannual labs to test 100+ blood biomarkers, 24/7 access to concierge medicine through a dedicated health team, and the ability to purchase diagnostic tests, supplements, and other medical products and services through an online marketplace.
• Similar to models like CostCo and Amazon Prime, Superpower ultimately hopes to make healthcare more convenient and less expensive by bundling a comprehensive set of medical products and services into a single membership.
• Eventually, Max expects that AI will surpass human doctors, unlocking profound new possibilities for diagnosing and treating medical conditions that will make healthcare significantly better, faster, and cheaper than it is today.

Max Marchione:

• Website: https://superpower.com/
• LinkedIn: https://www.linkedin.com/in/maxmarchione/
• X: https://x.com/maxmarchione

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

Olivier Lemarié is the VP of Growth at Photoroom, one of the world’s largest and most popular photo editing apps. Olivier joined Photoroom in 2020 as the company’s second employee and helped it scale to >$50M in ARR in less than 3 years. Prior to Photoroom, Olivier held sales and marketing roles at Google, Wooga, and Molotov TV. He is also an experienced growth advisor who helps mobile app startups with user acquisition, product-led growth, monetization, hiring, and culture.

Key Takeaways:

• Photoroom was founded in 2019 and launched publicly in 2020 with a focus on using powerful photo editing software to help creators and entrepreneurs market and sell their products online.
• The key to Photoroom’s differentiation vs. other photo editing apps comes down to their superior technology, which allows them to equip online sellers with photo editing tools that are faster and more accurate than anyone else.
• In early 2023, Photoroom launched an AI-powered feature that allowed its users to remove and replace photo backgrounds faster and better than ever before. This product launch became an instant hit within Photoroom’s creator community, which led to rapid organic growth through viral word of mouth.
• Photoroom’s AI photo editing tools created such a powerful “wow effect” that they also dramatically improved the efficiency of the company’s paid ads, reducing CPIs so significantly that Photoroom was able to expand into new international markets like Thailand, Mexico, and Brazil that were previously not inaccessible.
• Over time, Photoroom developed country-specific playbooks for expanding into international markets, including hiring agencies in Japan and Korea to navigate the local culture and offering weekly plans in Thailand, Mexico, and Brazil where consumers often have less money to pay for monthly or annual subscriptions.

Olivier Lemarié:

• Website: https://www.photoroom.com/
• LinkedIn: https://www.linkedin.com/in/olivierlemarie/
• X: https://x.com/olivier_lemarie

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

Miranda Paine is the Head of Growth at Runna, where she has contributed to its rapid expansion and recent acquisition by Strava. Prior to Runna, Miranda held growth and marketing roles at two other London-based fitness startups, including another fitness app called Fiit and a boutique kickboxing-inspired group fitness studio called Flykick. She holds a degree in Marine Biology, and credits her background in science and data analytics for helping her succeed as a growth leader.

Key Takeaways:

• Since being founded in 2020 and launched in 2022, Runna has rapidly grown into one of the largest and most popular running apps in the world, using AI to give runners personalized training plans that adapt to their unique needs.
• The key to Runna’s success has been building features that adapt to each runner to provide them with hyperpersonalized experiences, including pacing tips, real-time audio feedback, and dynamic goals that change based on performance.
• Once Runna had product/market fit, it built an ambassador program and focused on creating strong relationships with runners, both online through UGC on channels like TikTok and Instagram, as well as offline at races and other events.
• Runna has deliberately crafted an aspirational brand at a premium price point, which has influenced its ad creatives, product positioning, new user onboarding experience, and approach to free trials and discounts.
• As a result of its rapid growth, Runna was recently acquired by Strava, which has provided the company with additional resources, expanded its reach, and unlocked all sorts of additional growth opportunities.
  
  

Miranda Paine:

• Website: https://www.runna.com/
• LinkedIn: https://www.linkedin.com/in/miranda-paine-55b573a7/
• Instagram: https://www.instagram.com/miranda.paine/
  
  

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

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/thatsjonsense
  
  

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

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