Subversive

DashPass has stayed at $9.99/month since its launch back in 2018, a choice the person who built it believes is exactly right: Jimmy Liu, the original creator of DashPass.

He joined DoorDash in 2016 to run the San Francisco market, back when the company was losing $12 per delivery there, and spent his early months personally emailing every first-time customer to understand what wasn't working. Those conversations became the foundation for DashPass, and Jimmy used them to convince a skeptical leadership team to bet on subscriptions for food delivery years before it became an industry norm.

He eventually became DoorDash's Head of Product for New Verticals, and DashPass members now place about 75% of DoorDash's US grocery and retail orders.

Before DoorDash, Jimmy founded his own startup called GymFlow, an experience that instilled him with the ownership mentality and hustle that shaped his work at DoorDash from day one.

In this episode, Jimmy breaks down:

• Why DashPass's first version was unprofitable and the three levers that fixed it
• How an A/B test that kept compounding proved DashPass was working
• How DashPass helped DoorDash expand into grocery, retail, and other verticals
• Why Jimmy believes keeping DashPass at $9.99/month can maximize long-term growth
• Why DoorDash could become a personal assistant for the physical world
• How DoorDash out-executed a better-funded Uber and an earlier-to-market Grubhub

Jimmy Liu:

• Website: https://www.doordash.com/
• LinkedIn: https://www.linkedin.com/in/jimmyliu2/
• X: https://x.com/jimmay

Phil Carter:

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

As AI-generated content floods the internet, how do you know what's still human?

Weeks after ChatGPT's release, Edward Tian built the first version of GPTZero from a cafe in Toronto over New Year's, tweeted it out, and watched it go viral overnight. 

What started as his senior thesis project at Princeton became the first commercial AI detector, and three years later has grown into a full authenticity suite, covering AI detection, hallucination detection, and education tools used by millions of students and teachers.

Before GPTZero, Edward took a gap year from Princeton to be an investigative journalist who tracked AI-generated disinformation for the BBC. That experience shaped his mission to "preserve what's human on the internet," ultimately inspiring him to start GPTZero.

Under his leadership, GPTZero grew profitably from $9M to $30M+ ARR in just 18 months without ever turning off its free tier. The company was recently acquired by Superhuman.

On this episode, Edward shares:

• Why teachers drove GPTZero's early growth
• The free "scan box" on GPTZero's homepage and how it drove SEO and GEO traffic
• How the company turned viral media moments into a repeatable growth engine
• How listicle content helped make GPTZero the top AI detector inside ChatGPT 
• Why he believes editing, not the first draft, is where real critical thinking happens 
• How Superhuman's 40M+ user Chrome extension is expanding GPTZero’s reach
• The one thing Edward wishes he had done differently - bought the .com domain early

Edward’s Links:

• Website: https://gptzero.me/ 
• LinkedIn: https://www.linkedin.com/in/ed-tian/ 
• X: https://x.com/edward_the6 

Phil's Links:

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

In the crowded subscription app economy, building a great product is no longer enough.

As AI has made software significantly faster, easier, and cheaper to build, the primary bottleneck has shifted from product development to distribution.

As the serial entrepreneur behind multiple breakout Health & Fitness apps like Fitstar and Zero, Mike Maser has experienced this challenge firsthand. Over the last 15 years, Mike sold his first startup called FitStar to Fitbit, was diagnosed with stage four cancer, made an incredible recovery that he attributes in part to intermittent fasting, and then teamed up with Kevin Rose to build Zero, the world’s #1 fasting app that he has since scaled to $5M+ in ARR and over 10 million registered users. 

Now, he's navigating Zero through its biggest disruption yet - the rise of GLP-1 medications like Ozempic and Wegovy and the ripple effects they are having on the entire fasting category.

Mike breaks down:

• Why Zero’s simple one-screen MVP was critical for generating early momentum
• How a single tweet from Elon Musk drove $1M in revenue for Zero in 24 hours
• Shifting from organic virality to building a sophisticated growth and monetization engine
• How Zero adapted its strategy to the GLP-1 era by helping GLP-1 patients track their hydration and manage their protein intake to maintain muscle mass
• Zero’s ongoing strategies to reduce subscriber churn and build lifetime subscriber value

Mike Maser:

• Website: https://zerolongevity.com/
• LinkedIn: https://www.linkedin.com/in/mikemaser/
• X: https://x.com/mmaser

Phil Carter:

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

Every single person alive has asked themselves the same question: 
"What should I do with my life?"

Tomas Hoyos, cofounder and CEO of Apt, is building an AI-powered career mentoring platform to help millions of people answer this question at a moment when AI is about to make it harder for everyone.

Tomas breaks down:

• Why long onboarding quizzes counterintuitively convert better vs. short ones 
• How switching to a conversational AI quiz lifted onboarding conversion 60%+ 
• Why Apt charges from day one but is still betting on freemium long-term
• The playbook app-layer AI startups need to win vs. OpenAI and Anthropic

Tomas Hoyos:

• Website: https://www.tryapt.ai/
• Substack: https://tomashoyos.substack.com
• LinkedIn: https://www.linkedin.com/in/tomas-hoyos/
• X: https://x.com/tjhoyos

Phil Carter:

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

When Melissa Cash and her cofounders looked at children's apps, they saw two extremes: addictive games designed to maximize screen time and educational apps built around rote memorization.

So they built something different.

Pok Pok is an Apple Design Award-winning app offering open-ended, Montessori-inspired play - more like a box of LEGOs than a traditional mobile game. 

Previously, Melissa designed products for babies and toddlers at Disney and now also works with companies like Solobo Toys and Inkwell Games to create thoughtful play experiences for kids. 

Tune in to learn: 

• Why Pok Pok deliberately removed levels, rewards, streaks, and every other addictive gaming mechanic from its app
• How Melissa thinks about building for kids while selling to parents 
• Why micro-creators are outperforming influencers and traditional paid marketing campaigns for consumer subscription apps
• Why the company waited over two years before launching on Android 
• Why the key to building technology for children isn't necessarily less screen time but better screen time

Melissa Cash:

• Website: https://playpokpok.com/ 
• LinkedIn: https://www.linkedin.com/in/melissa-cash/ 
• X: https://x.com/melissacash_

Phil Carter:

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

"If you wait until it's perfect, you're too late."

This was Tyler Denk’s attitude when he took the growth engine he had built as employee #2 at Morning Brew - the newsletter he helped scale to >3M subscribers and a $75M acquisition - and productized it into a new startup called beehiiv.

He launched with a fraction of the features his competitors had, but built an entire process around seeking out criticism, using it to inform the company’s product roadmap, and then executing relentlessly to delight beehiiv’s customers.

This ethos, paired with a 0% take rate model that counterpositions beehiiv vs. Substack, has propelled the company to $30M+ in ARR in just a few years, and it's not stopping there.

beehiiv’s recent product launches have taken it beyond newsletters to websites, podcasts, and online communities, positioning it to be the operating system for the entire content economy.

In this episode

• Why Tyler built beehiiv on a 0% take rate and calls Substack's model "predatory"
• How building in public has become a secret weapon that propels beehiiv’s growth
• Features in beehiiv’s recent launch, including Community, Copilot, and a new visual editor
• Why Tyler believes AI will ultimately make human-created content more valuable

Tyler Denk

• Website: https://www.beehiiv.com/ 
• LinkedIn: https://www.linkedin.com/in/tyler-denk/ 
• X: https://x.com/denk_tweets

Phil Carter

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

Most AI coaching apps are just ChatGPT wrapped in a personality. Raj Singh and Mark Manson built Purpose to prove there's a better way.

Raj, cofounder and CEO of Purpose and previously the founder of GoMoment (acquired by Revinate), explains how they engineered an AI mentor that over 40% of users already call "life-changing" less than a year into the company's existence.

In this episode

• The prototype that revealed AI could outperform a $300/hour therapist
• How a poker game led to Mark Manson becoming a cofounder
• The playbook that took Purpose from launch to $1M ARR in two weeks
• Why Purpose initially stayed founder-funded to protect its mission

Raj Singh

• Website: https://www.purpose.app
• LinkedIn: https://www.linkedin.com/in/rajsinghla/
• X: https://x.com/RajSinghLA

Phil Carter

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

Sam Chaudhary is the cofounder and CEO of ClassDojo, an education platform used in roughly 95% of US K-8 schools and by tens of millions of children across 180 countries around the world. Born in the UK and raised in Wales and Abu Dhabi, he studied economics at the University of Cambridge, taught at Charterhouse, and advised governments on education reform at McKinsey before leaving to build something himself. In 2011, he cofounded ClassDojo with Liam Don after the two met at a Startup Weekend and went through the Imagine K12 accelerator together. Under Sam's leadership, ClassDojo grew bottoms-up, teacher by teacher, into one of the most widely used education products in the world, reached profitability, and is now expanding into kids’ gaming and AI with Dojo Tutor, Dojo Islands, and Dojo Spark. He was named EY Entrepreneur Of The Year 2025 for the Bay Area.

Key Takeaways

• After meeting at a startup weekend, joining a startup accelerator, and deciding to build an education company together, Sam and his cofounder Liam spoke to hundreds of teachers and even spent time teaching summer school themselves to deeply understand and empathize with the needs of their target customers.
• Their first product - a simple tool that allowed teachers to give positive feedback to their students - quickly went viral, resulting in over ten thousand teacher registrations by the time Sam and Liam had graduated from the Imagine K12 startup accelerator.
• After digging into usage data from their early adopters, Sam and Liam realized that the teachers who were engaging and retaining on ClassDojo over the long-term were those who had decided to not only use the product with their students, but also with those students’ parents. This three-sided network effect became the key to not only driving cost-efficient organic growth, but also extremely strong user retention rates.
• After years of only offering a free product, ClassDojo finally monetized its business through ClassDojo Plus, a premium subscription that offered parents additional features to enrich their children’s education. It maintained a freemium model so that most users could continue using the product for free, which bolstered teacher trust and preserved the strength of the app’s core organic growth loops, but with enough premium value behind the paywall to convert 5%+ of users into paying subscribers.
• ClassDojo is now used in ~95% of US K-8 schools and by tens of millions of students across 180 countries worldwide. Recently, the company has leveraged its scale and network effects to launch three new products - Tutor, Islands, and Sparks - that use AI and gamification to deliver additional value to parents and students.
• Looking ahead to 2030, ClassDojo’s mission continues to be helping every child thrive by giving them access to a great education they love at an increasingly low cost. Sam believes AI will play a key role in realizing this mission by reducing the need for human capital, thereby making education more affordable and accessible to all.

Sam Chaudhary

• Website: https://www.classdojo.com/
• LinkedIn: https://www.linkedin.com/in/samchaudhary/
• X: https://x.com/samchaudhary_

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/

Esan Durrani is the cofounder and CEO of StudyFetch, an AI-native learning platform used by more than 7 million students worldwide. Esan launched StudyFetch in 2023 with his cofounder and childhood friend Ryan Trattner to build an AI tutor that helps students truly learn rather than shortcut their way to easy answers, ultimately earning both of them Forbes 30 Under 30 awards in the education category. The company has raised $11.5M from Owl Ventures and College Board, partnered with NVIDIA and the White House on K-12 AI education, and recently launched Honen, an agentic learning platform for enterprise workforce development. Before StudyFetch, Esan was a serious drummer who played in more than 500 live performances.

Key Takeaways

• After trying several other startup ideas with his cofounder and childhood friend Ryan Trattner, including an AI-powered essay writing tool that they ultimately scrapped because they felt like it was helping students cheat, Esan and Ryan founded StudyFetch in September 2023 as an AI-powered platform to truly help students learn.
• Unlike other AI learning tools like ChatGPT, as well as a previous era of EdTech platforms like Chegg and CourseHero, StudyFetch intentionally does not give students easy answers. Instead, it provides students with highly personalized learning tools including an AI-powered tutor as well as study plans, flashcards, quizzes, and practice tests that are all calibrated to a student’s specific course materials and their understanding of those materials.
• Not only do 92% of active StudyFetch users report earning higher grades while reducing their average study time by 30%, but multiple case studies have shown that StudyFetch most benefits students with learning differences, which helps raise the lowest grades in a class and compress the achievement gap experienced by underperforming students.
• One key to StudyFetch’s growth has been their student creator program, where the company has used an “army of accounts” strategy partnering with hundreds of TikTok and Instagram microinfluencers to generate 150+ short-form videos per day, ultimately driving over 2 billion social media views and helping StudyFetch scale to over 7 million registered students.
• Recently, StudyFetch announced the launch of Honen, its new B2B skillbuilding platform that aims to help companies more efficiently and effectively train their workforce. StudyFetch has partnered with NVIDIA on Honen to get 250k+ high schoolers on a path to AI literacy.

Esan Durrani

• StudyFetch Website: https://www.studyfetch.com/
• Honen Website: https://honen.com/
• LinkedIn: https://www.linkedin.com/in/esan-durrani-576b611b4/
• X: https://x.com/esandurrani

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/

Eugenia Kuyda is the founder and CEO of Wabi, an AI-powered personal software platform that lets anyone create, share, and remix mini apps in minutes. Before Wabi, Eugenia founded Replika, one of the world’s first AI companion apps, which she grew to 40M+ users over the course of a decade. A native of Moscow, Eugenia began her career as a journalist before pivoting to tech and founding the YC-backed startup Luka in 2014, which ultimately pivoted into Replika. She holds a Master’s in Journalism from MGIMO and an MBA in Finance from London Business School, and has spent the past decade building consumer products at the intersection of AI and human connection.

Key Takeaways

• After Eugenia unexpectedly lost her dear friend, Roman Mazurenko, to a hit-and-run in November 2015, she gathered thousands of text messages, fed them into a neural network, and built a chatbot that replicated his personality. This deeply personal project became the inspiration for Replika, one of the world’s first AI companions.
• Replika experienced immediate product/market fit, launching to a waitlist of 1.5 million people. Over the course of a decade, Eugenia and her team grew Replika to over 40 million users, helping people overcome loneliness, depression, anxiety, and recovery from breakups, divorces, and abusive relationships.
• Recently, Eugenia decided to launch a new AI startup called Wabi that aims to usher in the era of personal software with a platform that allows anyone to create their own mini apps in minutes with nothing but a simple prompt. Users can also follow other creators and “remix” their creations into mini apps that meet their own unique needs.
• While Wabi is extremely flexible in what it allows users to create, its platform offers a secure environment and standardized UI/UX elements that help overcome the pitfalls faced by many vibe-coded apps built by non-developers who don’t have the technical expertise required to ensure a high-quality finished product.
• While Eugenia has many ideas for how to grow Wabi through viral word of mouth and ultimately monetize the platform - including revenue sharing agreements for successful creators - she is keeping her team laser-focused on retention right now, given it is all that matters until they’ve demonstrated strong product/market fit.

Eugenia Kuyda

• Website: https://wabi.ai/
• Ted Talk: https://www.youtube.com/watch?v=-w4JrIxFZRA
• LinkedIn: https://www.linkedin.com/in/eugenia-kuyda-638a8a1b/
• X: https://x.com/ekuyda

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/