Phil Cart
Where to hear and read about Phil Cart1 episode or test
Phil Cart is the interviewer in a conversation with Tolan cofounder Ajay Mehta about moving an AI app from a hard paywall to freemium. The thing most worth learning from him is to match each paywall to what the user just did or said, and to keep retesting pricing as models get cheaper.
Phil Cart: the story and the lessons
1Phil Cart's conversation on Tolan's move to freemium
Cart walks a founder through pricing, tiers and paywalls for an AI app. In his talk with Ajay Mehta, he covers Tolan's shift from hard paywall to freemium, three subscription tiers, ads, A/B tests and usage limits.
Tolan has over 100,000 subscribers and has raised $30M more, bringing its total to $60M.
Cart frames freemium as a conversion hit that later reversed. The conversation presents the move as a drop in conversion that Tolan won back by redrawing the free and paid line, adding tiers and personalizing paywalls.
The headline results are subscriber conversion up over 200%, ARPU up 218% and a 40%+ ARPU lift from one paywall test series. They come from Cart's framing, with no baseline numbers, test results or revenue figures shown.
2Cart's views on paywalls and upsells
Cart calls paywalls that follow one person's interests hyper-personalization. Mehta explains that AI lets onboarding and paywalls follow one person's interests, not five to 10 groups. Cart gives that a name.
Mehta's example is a user aiming for nursing school who sees their matched Tolan pitched as a buddy for nursing exams.
Cart thinks contextual upsells are underused. He points to Chess.com, which has Gold, Diamond and Platinum tiers and gives free users one game review a day. Asking for a second review triggers an upsell about game review only.
Clicking game review signals intent, so the pitch matches what the user just asked for. Cart says teams overlook this tactic.
Cart says price tests and repackaging must speed up in AI. Faster, cheaper models change what can be built, and that changes how to charge for it. He warns that a company that does not iterate gets left behind.
Mehta agrees, saying that keeping the same tiers six months from now would be a mistake.
3How Cart reads Tolan's edge in personal AI
Cart sees emotional connection as harder to build than transactional tasks. He says Tolan builds an emotional connection within the first couple of minutes, which is harder to get right than a transactional assistant.
Mehta adds that many users run Tolan alongside ChatGPT, for example for brain dumps on the way to work, so the two roles can coexist.
How Tolan 3X'd Subscriber Conversion after Shifting to Freemium
Tolan moved from a hard paywall to freemium and fixed the conversion hit by redrawing the free and paid line, adding tiers, and personalizing paywalls. The result was subscriber conversion up over 200% and ARPU up 218%, with one paywall test series driving a 40%+ ARPU lift.
Cart walks a founder through pricing, tiers and paywalls for an AI app. In his talk with Ajay Mehta, he covers Tolan's shift from hard paywall to freemium, three subscription tiers, ads, A/B tests and usage limits.
Tolan has over 100,000 subscribers and has raised $30M more, bringing its total to $60M.
Cart frames freemium as a conversion hit that later reversed. The conversation presents the move as a drop in conversion that Tolan won back by redrawing the free and paid line, adding tiers and personalizing paywalls.
The headline results are subscriber conversion up over 200%, ARPU up 218% and a 40%+ ARPU lift from one paywall test series. They come from Cart's framing, with no baseline numbers, test results or revenue figures shown.
Cart calls paywalls that follow one person's interests hyper-personalization. Mehta explains that AI lets onboarding and paywalls follow one person's interests, not five to 10 groups. Cart gives that a name.
Mehta's example is a user aiming for nursing school who sees their matched Tolan pitched as a buddy for nursing exams.
Cart thinks contextual upsells are underused. He points to Chess.com, which has Gold, Diamond and Platinum tiers and gives free users one game review a day. Asking for a second review triggers an upsell about game review only.
Clicking game review signals intent, so the pitch matches what the user just asked for. Cart says teams overlook this tactic.
Cart says price tests and repackaging must speed up in AI. Faster, cheaper models change what can be built, and that changes how to charge for it. He warns that a company that does not iterate gets left behind.
Mehta agrees, saying that keeping the same tiers six months from now would be a mistake.
Cart sees emotional connection as harder to build than transactional tasks. He says Tolan builds an emotional connection within the first couple of minutes, which is harder to get right than a transactional assistant.
Mehta adds that many users run Tolan alongside ChatGPT, for example for brain dumps on the way to work, so the two roles can coexist.