Andrew Grauer is the CEO of Learneo, a holding company valued at $3.6 billion that owns multiple learning and productivity businesses including Course Hero, QuillBot, CliffsNotes, Scribbr, LitCharts, LanguageTool, and Symbolab. After cofounding Course Hero in 2006 when he was a sophomore at Cornell, Andrew spent 15 years growing it into one of the world’s largest EdTech businesses before folding it into Learneo. Over the last few years since Learneo acquired QuillBot, Andrew has been focused on transforming that product into a multimodal generative AI platform for students and professionals.

Key Takeaways:

• Andrew started Course Hero in 2006 when he was a sophomore at Cornell because he wanted a platform that could help student like him find and study academic materials that were highly course-specific.
• Course Hero developed an elegant model where students could access content either by uploading their own course materials, which made the entire platform more valuable, or by paying for a subscription, which generated revenue.
• As more students contributed content to Course Hero, the platform became more valuable for other students, leading to more sign ups and even more content. The company accelerated this core growth loop by investing in on-campus marketing, search engine optimization, and other user acquisition channels.
• From 2020 and 2023, Course Hero formed a parent company called Learneo and expanded into math, literature, and writing through its acquisitions of Symbolab, LitCharts, CliffNotes, QuillBot, Scribbr, and Language Tool. This strategy allowed Learneo to expand horizontally while keeping each of its portfolio companies narrowly focused on building great products within their respective verticals.
• Now, as generative AI unlocks new opportunities for learning and productivity, Learneo is focused on leveraging its existing assets and capabilities to build new multimodal creation tools, starting in the writing space with QuillBot.

Andrew Grauer:

• Website: https://www.learneo.com/
• LinkedIn: https://www.linkedin.com/in/andrewtategrauer/
• X: https://x.com/atgrauer

Phil Carter:

• Website: https://www.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

David Futoran is cofounder and CEO of Honeydew, a skin health platform called Honeydew that helps people struggling with acne and other skin conditions get effective treatments and expert guidance from licensed dermatologists. Prior to founding Honeydew in 2022, David was the Head of Product and Growth at Somatix, an AI-powered remote monitoring service that uses a wearable device to help senior citizens live longer and more independent lives. He holds degrees in Biology and Healthcare Management from the University of Pennsylvania, where he also wrote a masters course and served as President of the Wharton Undergraduate Healthcare Club.

Key Takeaways:

• David’s personal decade-long struggle with severe cystic acne and the difficulties he faced getting access to effective care inspired him to partner with a nationally renowned dermatologist named Dr. Joel Spitz to cofound Honeydew.
• Unlike other telederm startups that sell commoditized topical treatments for mild acne cases, Honeydew is laser-focused on democratizing access to Accutane to treat patients with moderate to severe acne who have the most acute need.
• After launching in New York, Honeydew overcame multiple operational and regulatory hurdles to expand nationally, and is now licensed across all 50 states.
• This scale has also allowed Honeydew to lock in exclusive supplier partnerships that already made it the lowest-cost provider of Accutane in the United States.
• While Honeydew’s best-performing acquisition channel has been Google given the company’s ability to target specific high-intent search queries related to acne treatment, they’ve also had more recent success with paid ads on Meta and Reddit and with UGC content generated by microinfluencers on TikTok.
• Looking forward, Honeydew is excited to go beyond acute acne treatment to offer lifetime skincare, expand to additional skin conditions like eczema and psoriasis, and use AI to improve diagnostics, streamline support, and cut operational costs.

David Futoran:

• Website: https://www.honeydewcare.com/
• LinkedIn: https://www.linkedin.com/in/david-futoran/
• X: https://x.com/davidfutoran

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

Brandon Gador is the Product Growth Lead at onX, where he has spent the last 2+ years helping to scale and evolve the company’s growth team to support vertical-specific apps across hunting, fishing, offroading, and backcountry. Prior to onX, Brandon spent 10+ years in product roles at multiple FinTech businesses including Gusto, Lending Club, and Intuit. He is an avid hunter and outdoor enthusiast and a proud (though misguided) Green Bay Packers fan.

Key Takeaways:

• Since raising its $20M Series A in 2018, onX has grown ARR >10x, expanded its team >300%, and diversified its product offering beyond hunting with additional apps for offroading, backcountry, and fishing.
• onX’s growth has largely been driven through organic word of mouth among its highly passionate user base, which the company has amplified through partnerships with online influencers and ambassadors in the outdoor space.
• As the company has scaled, onX’s growth team focused first on accelerating its experimentation velocity and then on fine-tuning strategy to increase its A/B test hit rate and impact per experiment, all of which has driven compounding growth.
• While supporting four vertical-specific apps creates additional challenges, it has allowed onX to better tailor its UX specifically for hunters, offroaders, backcountry enthusiasts, and fishermen, all of whom have different feature needs.
• While AllTrails and onX are often compared to one another, they target different customers with different strategies - AllTrails has built a freemium experience for casual hikers with an SEO-driven growth strategy, whereas onX is focused on a more passionate and sophisticated group of outdoor enthusiasts that relies on word of mouth to drive growth and a hard paywall to maximize monetization.

Brandon Gador:

• Website: https://www.onxmaps.com/
• LinkedIn: https://www.linkedin.com/in/brandongador/
• X: https://x.com/brandongador

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

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