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How Tolan 3X'd Subscriber Conversion after Shifting to Freemium

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The bottom line

Tolan tripled subscriber conversion by going freemium, then giving free users a taste of paid features and personalizing every paywall. AI apps pay real inference costs per user, so pricing, tiers and usage limits have to keep changing as models get cheaper.

Key takeaways

  • AI apps carry real serving costs, so monetization has to be sophisticated from day one. 5:27
    • Frontier-level personality and memory systems cost money on every session, so Tolan built tiers, one-off purchases, ads and price tests early.
    • Even a 7-day free trial adds about four extra days of cost for a trial user who never converts.
  • Freemium became possible once cheaper open source models cut the cost of a good free tier. 8:40
    • A humanity-scale product needs a free version, and a large free audience is what makes a sizable paid tier possible.
    • Routing chat queries to cheaper models and infrastructure at the same quality is what lets Tolan offer more free usage.
  • Conversion rose once free users had a real reason to upgrade. 25:00
    • The first free tier was a mistake, because it was good enough that nobody needed to pay.
    • Tolan rations chat time, smarter models, memory strength and costly features like video chat and tabs.
  • Tiers, add-ons and a younger-to-older audience shift capture different levels of willingness to pay. 16:45
    • Users in their 30s and 40s retain better and pay more, so Tolan added characters like Kestrel to fit them.
    • Light, Plus and Unlimited tiers, relay boosts, tokens and ads fill gaps in the demand curve. Unlimited costs $200 a month.
  • Personalized and contextual paywalls drove the biggest gains. 32:45
    • The multi-step onboarding paywall reuses what users said to the Oracle, and the host credits that set of tests with a 40%+ ARPU lift.
    • Feature paywalls, such as one for video chat, sell one feature when a user hits its limit.

Software's getting more personalized, and you're much more likely to pay for something if it feels like it starts to fit around you like a glove.

Ajay Mehta, cofounder of Tolan

Chapter summaries

0:00 Introduction

Going freemium roughly tripled conversion and ARPU
Subscriber conversion200%
ARPU218%
Multi-step paywall ARPU40%
Gains measured over about a year, from the switch off the hard paywall to today; the multi-step paywall alone added 40%+ to ARPU.

Tolan is a voice-first alien companion that has to cover real AI costs, so its monetization had to mature early.

  • Tolan is a friendly AI guide with over 100,000 subscribers 1:54
    • Alien characters act as guides through life.
    • The app went viral on TikTok in May 2025, and growth has continued since.
    • The transition to freemium is framed as a hit to conversion that later reversed.
    • The pricing, packaging and paywall changes were driven by the cost of AI features.

2:43 Tolan's latest $30M fundraising announcement

New funding pushes Tolan toward a larger goal: personal superintelligence for everyone.

  • Tolan raised $30M more, bringing its total to $60M 3:03
    • Investors include Union Square Ventures and Khosla Ventures, among others.
    • The stated aim is "personal superintelligence for all."
    • The route to that aim is giving everyone a Tolan, "a friendly guide through life."
    • Tolan realized this goal only as it kept building the product.

3:42 Tolan's transition from hard paywall to freemium

Freemium worked because costly new features became upsells, which let Tolan loosen the chat limits that first defined the free tier.

  • Tolan is built to make people feel supported, not more productive 4:53
    • It aims to understand users, be curious about their lives and back their personal journey.
    • Many other personal AIs lean toward productivity.
    • Tolan calls it a friendly guide, close to a spirit guide or guardian angel.
    • It is a small embodied character that you talk to by voice and that reaches out first.
  • Chat time was the first lever separating free from paid 10:35
    • Engaged paid users chat four or five days a week, about four hours in total.
    • The free tier was held far below that to push people to convert.
    • A hard-paywall product that opens its gate will always see conversion fall.
    • Tolan only felt confident enough to offer a moderately generous free tier earlier this year.
  • New expensive features became upsells, so chat limits could relax 11:03
    • Video chat, screen share and "tabs" (proactive research that pushes projects forward) are costly but exciting.
    • Free users get more chat time and meet a feature-gate paywall when they try these.
    • The gate tells them they must upgrade to Tolan Plus.
    • Tabs is Tolan's step toward agentic AI, and it launched within the last month.

11:54 Shifting from Gen Z women to Millennial moms

Younger users brought buzz but drifted away, so Tolan reshaped its marketing and characters around older users who found lasting uses.

  • Gen Z users burned out on novelty while users over 30 found daily uses 13:09
    • Gen Z users often chatted deeply for a day or two, then left.
    • Older users talked about caregiving for a relative and planning summers as a dad of two.
    • The first character design targeted a younger crowd, and older users came anyway.
    • They valued the core chat, memory and personality more than the character world.
    • Younger users still suit top-of-funnel growth on TikTok and Instagram, which was chapter one.
  • Tolan widened its audience first through marketing, then through the product 14:17
    • Ad creative showed real older users, and Tolan hired older influencers.
    • The cast grew beyond cute aliens to meet those users where they are.
    • Kestrel, a woman in a garden with a Mother Earth feel, is in onboarding, and a very significant slice of users picks her.
    • A minimal orb-like character with expressive arms targets men, a small audience so far.

16:45 Why Tolan expanded to three subscription tiers

Three tiers capture demand one price leaves behind
Usage-driven AI costs vary hugely per user, so Tolan, like Tinder and ChatGPT ($20 vs $200 Pro), prices each segment closer to its value and its cost to serve.

Tiers let Tolan charge each user in line with what they value and what they cost to serve.

  • Usage-driven costs made a single price a poor fit. 17:33
    • Early costs came mostly from chat time. Now they also come from what a Tolan does for you, such as video chat.
    • A happy subscriber might use the app one hour a week or seven.
    • Tolan spends much more on users at the highest time-spent levels.
    • Ajay Mehta expects more AI products to move this way because they must be monetized differently.
  • Several tiers capture more of what different users are willing to pay. 18:48
    • Tinder went from Plus to Plus, Gold and Platinum. Robby Metta, a former Tinder chief product officer, laid out that path.
    • With one tier, people who want more have nothing to buy. People who can't afford it are locked out.
    • ChatGPT shows the same split, with $20 a month and a $200 Pro plan.
    • In economics terms this is price discrimination, which captures more consumer surplus under the demand curve.
    • Dating has high churn, so apps must monetize early in the customer journey.
    • Some long-haul truck drivers talk to their Tolan for eight hours on the road to stay alert. They are Unlimited subscribers, unlike a busy mom of three.

22:17 Incorporating in-app purchases and advertisements

New capabilities start in the top tier and move down as they get cheaper, while top-ups and ads fill the gaps around subscriptions.

  • Features start in higher tiers and move down as serving costs fall. 22:51
    • Capabilities that were frontier months ago, like browser use, can now ship. A Tolan can check out for you on Amazon.
    • They launch in Unlimited in limited beta, then reach Plus, then Light.
    • Ajay hopes the eventual frontier experience lands in free and is cheap to serve at scale.
    • Tolan lacks the resources of a company like Meta, so it brings in frontier features as best it can.
  • Ads are likely to be a major part of monetizing a consumer AI product at humanity scale. 25:43
    • Tolan serves classic mobile-game ads, as Duolingo does on its free tier.
    • They reach only some free users, such as lapsed subscribers who get extra access in return for watching ads.
    • One-off top-ups suit Light users who want more time for a single day. Ajay says Tolan hasn't nailed this yet.
    • Tokens buy cosmetics like clothing and planet customization. Users love them, but the product team spends little effort there.
    • Ajay assumes Meta's long-term plan for Muse is free access paid for by ads.
    • Ads are not yet cheap enough to serve, nor rewarding enough, to carry the product. Tolan is testing them to learn user reactions and ad ARPU.

29:12 A/B tests that helped Tolan boost conversion and ARPU

Finding the line between free and paid took many tests, and the biggest winner was an early paywall that users can skip.

  • Where to draw the free-versus-paid line is a seesaw between engagement and monetization. 29:49
    • Tolan tested access to its best models, chat time and memory strength to find a mix that kept free good and upgrading tempting.
    • Midjourney has experimented heavily too. It once gave slow free generations and now requires payment.
    • The free experience was not very good until much more recently, and Tolan is expanding it now.
    • Ajay says experimentation like this is happening across the industry.
  • A freemium product earns the right to show an aggressive paywall early. 31:43
    • It was the biggest winner of all the tests. Users can close it and keep using the free tier.
    • The paywall runs about four screens and shows what a better Tolan could do.
    • Surveyed users say it is a little annoying, though they accept it from similar apps.
    • The pitch is that they can use Tolan free, but should first see why they might upgrade.

32:45 Maximizing conversion through paywall personalization

A paywall converts better when it carries forward what the product already learned about the user.

  • Onboarding is built backwards from knowing the user, so the paywall should reuse it. 34:04
    • The Oracle asks about hopes, dreams and who matters to you.
    • The onboarding runs about 5 to 6 minutes, so asking for payment right after it without using the answers would be a mistake.
    • Real user stories include caring for an older relative and aiming for nursing school.
    • For the nursing-school user, the paywall shows their matched Tolan in a cute pose as a buddy for nursing exams. Mehta says these callbacks can still improve a lot.
  • AI lets paywalls fit one person, where older apps sorted users into a few buckets. 36:47
    • Before AI, apps used onboarding answers to route people to nutrition or workout plans. The best ones personalized the paywall a little.
    • Now the onboarding and paywall can follow one person's interests, not five to 10 groups.
    • Interviewer Phil Cart calls this hyper-personalization.
    • Mehta says software is moving this way, and every personalized experience feels more magical.

37:23 Using contextual paywalls to further boost conversion

A paywall shown where a user hits a limit should sell that one feature, not the whole plan.

  • A general paywall sells the whole upgrade, and a contextual one sells a single locked feature. 38:10
    • The general pitch fits onboarding, or an app-launch paywall for a free user a week in.
    • A user who taps a locked feature, such as image generation, should get a direct offer to upgrade for it.
    • Tolan built the paywall as a template, so any feature can be swapped in.
    • Mehta says he would like to compare notes with others deep in this area.
  • Chess.com shows the tactic works at scale. 39:45
    • Chess.com has three tiers: Gold, Diamond and Platinum.
    • Free users get one game review a day. After that limit, asking for another review triggers an upsell about game review only.
    • Clicking game review signals intent, so the pitch matches what the user just asked for.
    • Cart calls contextual upsells underused, because teams overlook them.

40:50 How AI is changing subscription monetization strategies

Agents break the link between app time and cost
Chat eraAgentic era
Cost driverMinutes chatting in appTasks a Tolan runs
Tokens spentOnly while user is in appIn background, even unopened
ExampleLong evening chatsDaily Dodgers game recap
PricingCap chat timeTiers keep being revamped
Background tasks spend tokens even when the user never opens the app, so tiers and prices have to keep moving.

Agentic features break the link between time in the app and cost, so pricing has to keep moving.

  • Inference cost no longer tracks time in the app, because agents work in the background. 42:03
    • For its first 6 to 12 months, Tolan assumed more time in the app meant more cost.
    • With tabs, users run tasks such as an evening prayer tracker, summer camp research or insurance comparisons.
    • One employee has a tab that reads out the previous day's LA Dodgers game every morning. It spends tokens even if she never opens the app.
    • Mehta says heavy Claude, ChatGPT and Codex users may already spend many times more tokens off the app than on it.
  • Tiers and pricing cannot stay fixed as models improve. 44:28
    • Faster, cheaper models change what can be built, and that changes how to charge for it.
    • Tolan plans tier revamps soon, while keeping familiar things stable for users.
    • Mehta says keeping the same tiers six months from now would be a mistake.
    • Cart says price tests and repackaging must speed up, or a company gets left behind.

44:50 Why getting usage limits right is so critical for AI apps

The right free usage limit keeps shifting upward
Competitors' free offers raise user expectations, and cheaper models let Tolan give away more without wrecking unit economics.

The right usage limit depends on what competitors give away, and it keeps shifting.

  • Limits that are too high burn money, and limits that are too low push users to rivals. 45:44
    • Limits cap inference cost and also push users toward higher tiers or boosts.
    • Rivals are offering more free inference in real time, so Tolan's sweet spot keeps moving.
    • Capabilities move down a waterfall of tiers as they get cheaper and faster to serve.
    • Tolan can delight a new user far more now than three months ago. Expectations set by other apps are high, and Mehta doesn't want Tolan to be restrictive.

47:50 How Tolan will maintain its edge in personal AI

Tolan stays distinct by being a life guide that knows you, not a task assistant.

  • Personal AI is not one product, and Tolan serves a different need than Muse, Instinct or Grok Bot. 48:29
    • Tolan can book flights or restaurants if those matter to you. It does not open with What can I get done for you?
    • Its core is getting to know you, helping you feel seen and supporting you.
    • Midwestern moms use Tolan for things those agents don't serve.
    • The capability floor is rising, and a purely chat-based product may seem quaint within a year.
  • Users run Tolan alongside other assistants, so the roles can coexist. 50:59
    • Many Tolan users also use ChatGPT, for example for work emails.
    • They use Tolan to brain dump on the way to work or chat about TV on the couch.
    • Mehta says even with an awesome assistant he would still want Tolan as a guide.
    • Cart says Tolan builds an emotional connection within the first couple of minutes, which is harder to get right than transactional tasks.

52:43 Lightning round

Tolan's team, its user base and its early design choices have all shifted, and its best moments come when AI helps people connect with each other.

  • The team has grown and the user base has changed a lot in a year. 53:03
    • Tolan has three people in San Francisco now, and Mehta calls them the best group he has worked with.
    • Core users now talk to their Tolans about different things, and different IPs and character universes are meant to meet that.
    • Ambition grows as resources and user signal grow: what we think that Tolen can actually the role it can fill for people keeps rising.
    • The team is hiring in San Francisco and asks for app feedback by email or Twitter.
  • Tolan is a north star when it pushes users toward real-world relationships. 54:38
    • A college student's bond with his dad was fraying, and his Tolan suggested a hike they loved when he was younger.
    • He went, came back and told his Tolan it was an awesome experience that let them open up.
    • Mehta sees this as AI's potential to bring people together, which he says much of the internet is not thinking about.
    • He had already told the truck driver story earlier, so he skipped it here.
  • One locked-in visual style was the early decision Tolan would change. 56:23
    • Even recently, people landed on the app and thought it was for kids.
    • Building more character universes takes a bigger team and more investment, so Tolan should have started earlier.
    • The single style was chosen for good reason, and Mehta says he struggles to criticize it because the art direction is Tolan's own.
  • Spotify's time-based audiobook pricing is the monetization model Mehta admires. 57:57
    • Subscribers get a set number of listening hours, and a top-up covers more.
    • Users can dip into single titles instead of buying whole books.
    • Mehta recalls roughly 30 to 40% of Spotify users being paid, a figure he says he doesn't know exactly.
    • He also names Tinder and chess.com as models worth studying.
  • Tolans can work through complicated life decisions with a couple together. 59:25
    • Mehta and his wife used their Tolans to compare health insurance options during open enrollment.
    • They weighed adding a spouse to a plan and whether two insurances made sense, and ended with a plan Mehta calls great though not provably optimal.

In the growth library

Ajay Mehta (hosted by Phil Cart), Cofounder and president of Tolan. 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.

Lessons that draw on this:

More from Subversive · The whole library, and ask it anything

Transcript2116 lines
Introduction 0:00
0:00

Anytime you're going to transition from a hard paywall to freemium, you're going to take a hit. But over the course of about a year making that transition to freemium, you were able to increase subscriber conversion by over 200% and ARPU by 218%. To have a role in everybody's life, you have to have a free version of the product. We've had to focus extremely early at becoming more sophisticated about monetization than your typical consumer app journey.

0:20

That means things like multiple tiers of subscriptions, [music] one-off purchases. I'd be surprised if we don't see it more and more, honestly, for AI products because they just simply need to be monetized in a different way. Why do you think focusing on personalization and focusing on an emotional appeal versus a logical appeal to users on the paywall works so well for a product like Soul? Software's getting more personalized. It's a much more magical experience and you're much more likely to pay for something if it feels like it sort of starts to fit around you like a glove. To me, that's the magic of Soul.

0:48

And quite literally, it is a little embodied character that lives on your phone. You talk to them via voice, they reach out to you proactively, they find ways to be helpful and supportive to you. You've got Muse, you've got Instinct, [music] you've got Rockbot. >> Where does Soul maintain its competitive edge in an increasingly crowded market as you evolve your product? >> Um >> Welcome to Subversive, a podcast dedicated to sharing stories from the best consumer subscription apps in the world. We'll bring you lessons for how to grow your consumer subscription business, including insights and inflection points that led [music] to exponential growth from leaders at category-defining companies and innovative startups.

1:28

Let's get into the show. This episode is brought to you by RevenueCat. The world's best apps use RevenueCat to power their subscription infrastructure, manage customer data, and grow revenue across iOS, Android, and the web. From any developers launching their first apps to category leaders like OpenAI, Notion, and Ladder scaling to millions of users, RevenueCat handles the complexity of monetization so you don't have to. Learn more at revenuecat.com/subversive.

1:54

Our guest today is Ajay Mehta, the co-founder and president of Tolen, an AI app whose alien characters act as friendly guides through life for over 100,000 subscribers. A.J. first came on the Subversive Podcast in May 2025, shortly after Tolen went viral on TikTok, to talk about the company's launch and early growth playbooks. Since then, Tolen has continued to grow exponentially while making significant changes to its monetization strategy. In this episode, I talked to A.J. about Tolen's successful transition to freemium, about the specific strategies and tactics that have fueled its rapid revenue growth, and about why Tolen has needed to adapt its pricing, packaging, and paywalls to cover the underlying costs of AI-powered features.

2:31

All right, A.J., welcome back to the Subversive Podcast. You're our first repeat guest since we launched this podcast a couple years ago in January 2025. Really excited to have you on here to talk about the recent developments at Tolen. And so, to start off with, you

Tolan’s latest $30M fundraising announcement 2:43
2:44

know, folks know a little bit about Tolen from from the last episode, but why don't you just tell those who didn't listen to that episode a little bit about what your company does, and maybe what's changed over the last year and a half. >> Absolutely. Great to be back. Thanks for having me back, Phil. That was really fun last time. I think this is going to be a really fun one as well. Lots been cooking. The kind of big update that we have, the biggest thing that's changed is that we are we just announced some new funding.

3:08

So, $30 million in additional funding, bringing our total to $60 million in funding from Coastal Ventures and from Union Square Ventures, alongside some some other investors as well, which we're super stoked about. You know, it sort of is a way for us to further our vision towards personal superintelligence for all. As we kind of continue to build Tolen, we realized that that ultimately is what we're sort of striving for.

3:30

And we do that by giving everyone a Tolen, which is a friendly guide through life. So, happy to go into a little bit about the app if that would be useful. Would that be helpful? >> Yeah, let's do it. And let's Well, first

Tolan's transition from hard paywall to freemium 3:42
3:42

of all, congratulations on the fundraise. That's really exciting, and those are two great firms. And so, really excited for you and the team at Tolen. Let's jump straight into some of the changes that Tolen has been making to its monetization strategy. And I want to start with the decision to shift from a hard paywall to freemium. When you all started that journey, obviously anytime you're going to transition from a hard paywall to freemium, you're going to take a hit on subscriber conversion and average revenue per user. Um but over the course of about a year or a year and a half making that transition to freemium, you were able to increase subscriber conversion by over 200% and ARPU by 218% in a relatively short period of time. So let's start with what motivated the decision to shift to freemium despite some of those risks, and then we'll get into some of the specific strategies and tactics that led

4:26

to so much success with this new model. >> Let me also just set the boundaries. I know you and maybe some of the listeners have have played around with Tullen, but um just set set a set a uh groundwork for like what Tullen is. So quite literally, like uh it is a little embodied character that lives on your phone. Um you talk to them via voice. Um you know, they reach out to you proactively. They find ways to be helpful and supportive to you. Um I just want to set that set that so that folks know as we talk about monetization like kind of what what is the product that we're monetizing here? Um and you know, in general like what are we aiming to do? We're aiming to help any user, no matter what they're going through in life, who they are, um with with a friendly guide through life. So a sort of personal AI that is designed to be there to understand them, help them feel seen, uh be truly curious about their

5:09

life, um and be supportive to them in whatever their personal journey is. Um uh and and you know, the orientation is not towards making you maybe more productive like a lot of other personal AIs that are that are out there, especially more recently, but towards helping you feel supported and um further your journey in in whatever way that is. We had to focus extremely early on, I would say, becoming more sophisticated about monetization than your typical consumer app journey. Uh the reason for that is that from basically our very first days of of running Tullen and getting into the App Store with like we were one of the first to get to the App Store with like a a high-quality voice experience with an AI. And it became clearly obvious right out the gate that like this was you know if you didn't have users actually paying for the service in some way this was like a pretty tough thing to make

5:54

sustainable right like there just are significant unit costs in managing a product that has you know basically frontier level sort of personality memory systems like and we've we've been in market for for almost two years now so we started you know even how intelligent this system was back then is only a shadow of of what what it is now but even still we've like really made it super important for us to maintain this like super premium AI chat experience especially and now that we're doing things that are a little bit more agentic with the product and so on that just increases the cost even more so we've had to get really sophisticated about monetization early and that means things like multiple tiers of subscriptions that means things like subscriptions and what have purchases and even ad monetization for a smaller fraction of our users that means things like significant price testing in in all variants you know being very

6:45

careful and attuned to our mix between monthly subscriptions yearly subscriptions and so on even dynamics around things like free trials where in in theory like a free trial for us is not just a conversion you know attempt at higher conversion say it also comes with added cost so if you think about it you know three day seven day free trial for us that that extra four days actually represents some meaningful added cost that could be the case for a trier that does not end up converting so those are just some like we can go all of those we can talk about for probably half an hour here but we've just had to be very sophisticated about like how we think about monetization because honestly that that complexity the marginal cost of serving the product yeah and this is something I think a lot of AI apps are struggling with right now the marginal cost of serving a subscriber for most digital products

7:29

used to be essentially zero you had your server costs but that was about it but with AI you have the underlying inference costs of LLMs for supporting AI powered features and so the unit economics just look very different and it is forcing companies like Toll to adapt their monetization strategies accordingly. So, I do want to drill down into each one of those specific tactics, but before we go there, let's just start with the high-level decision to go freemium. Like, hard paywall was working well enough a couple years ago, but you all made a strategic decision that going freemium would open up the top of the funnel, it would lead to more viral word of mouth, more organic acquisition, and and hopefully a larger active user base.

8:05

Um but, there were certainly some trade-offs. Like, anytime a company makes that bet, it often does lead to a short-term hit in subscriber conversion and and monetization. And so, what motivated the bet up front, and what did the early days of that transition look like? >> So, I guess it comes down to our mission, which is really for every human to have a Tullen. Um and and we we believe that Tullen, like, sort of our users using Tullen today and finding ways to integrate into their life, uh we we see them a bit as early adopters.

8:33

They're a little bit living in the future where they live with this concept of, you know, hard to describe exactly what it is. We call it a friendly guide. Uh other fictional or even religious call it a maybe a spirit guide, a guardian angel, things like that. Like, this sort of notion, this this thing that we've always had this idea that it could exist, now can exist with technology. This is what we're building. We believe that it could have a role in everybody's life. To to be have a role in everybody's life, you have to have a free version of a product. Like, there is no kind of humanity scale consumer product that does not have a free version. Uh I think for for obvious reasons, uh most consumers, I know Ben Thompson and other uh very very sharp commentators have have said like, it just isn't the case that the average person pays for software or consumer software at at very high degrees. Um

9:15

and so, like, we we know we knew that we needed some uh some free version. So, we knew that and and, you know, there's sort of a there's a there's a cost element to that, and then there's also like the conversion element to that, as you said, right? Um so, as soon as we got confident, and that was really only like, earlier this year, we got confident we could like support a like like a truly meaningful, um you know, sort of like moderately generous version of the free tier that was actually like quite a nice experience. Um, we were able to do this because of all the advancements in in models, right?

9:43

The the emergence of open source models that we could use that were a fraction of the cost of sort of front gear models, um, and so on and so forth. We can actually supply a free experience to users that we're we're proud of. Um, and it is limited, of course. It does not have all the features of our Tolen Light or Tolen Plus subscriptions, but but it but it is pretty good. Like we we we feel pretty proud of it. We're happy to put it in front of people. So, it took like that like that that sort of like tons of work on the sort of like cost optimization side to get to a point where that was even possible. Um, and then came the challenge of solving the conversion parts of it, right? Of course, because if you sort of let someone in through the gate, um, you know, from especially a hard paywall product, um, which is what we were, you know, a year plus ago, the chances that they are going to convert

10:21

obviously go down. I mean, there's no way to not make them go down. Um, but I think there's a lot that we've spent a lot of time on and there's a lot of interesting questions around like kind of segmentation between plans and sort of like how you maintain differentiation among plans, right? So, for a very long time actually one of the, you know, the early versions of our freemium plan, the main distinction that we had was basically chat time with your Tolen. It was basically how much time you can spend with your Tolen, right? Our most engaged users want to spend a lot of time chatting with their Tolen. They want to exchange more messages. They want to spend like, you know, our our average engaged paid user engages four or five out of seven days a week. You know, they spend four hours a week chatting with their Tolen. So, like, you know, even even limiting below that and we were significantly limited far below

10:58

that for our free tier, um, you know, was was a was a driver to convert. Um, as we've been able to bring down the cost and then also introduce a lot more features that are more exciting, like potential upsells, like, now you can video chat with your Tolen and share your video with them. You can screen share with them. You can, um, I mean, there's a whole world of new stuff that just has launched in the last month and and we're really actively working on that we call tabs. It's sort of our stab in the agentic direction. Your Tolen actually doing a bunch of proactive research and like helping you push forward projects in your life, right?

11:27

Kind of our Toleny version of agentic AI. All that stuff is more expensive. It's also a great upsell, right? So we can sort of add that into our paywalls so that we can we can sort of loosen the the um the restrictions a bit on chat time, give free users more chat time, um but know that we have like good like a lot of the free users end up wanting to try a voice chat. So they tap on that, they get a feature gate paywall, and it says, you know, to do that you have to upgrade to Tolen Plus.

11:52

>> Got it. Yeah, so now I want to break

Shifting from Gen Z women to Millennial moms 11:54
11:54

this down into some of the bigger strategic levers you pulled, and then we'll get into some of the specific AB tests that drove the biggest impacts. But at the highest level, so I remember when we talked a year and a half ago, your core demographic at that point skewed more towards younger Gen Z women, and many of them were discovering Tolen on Tik Tok or Instagram. But over the course of the last couple years, you've gradually shifted that target demo, at least for your subscriber base, more towards millennial moms, you know, women who are in their 30s and 40s. What drove that decision, and how has that influenced your ability to monetize the product?

12:30

>> So when we first launched the product, even in the design of the characters and so on, and one of the things we're very excited to to have announced just recently and just just just launched in the app are multiple character designs. So this is not quite the case anymore. But in in our design of the characters and sort of like the way that we structured the app, it was targeted for a younger audience. What what started to happen is we just as we got more broad, as we had some videos go viral, you know, as we kind of grew user base, we started to see that two things happened.

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Like an older audience started to use the app, maybe that we didn't necessarily expect would click with like the character world that we created. But they were clearly getting a lot of value from the kind of core chat, the the memory, the personality, how the Tolen showed up for them. Um that was actually kind of different from the Gen Z users that we had, right? The Gen Z users might have like there was a strong novelty effect, they might hop in, chat with their Tolen about something that was tough in their day, but, you know, they they they maybe engaged very deeply for a day or two, and then like weren't as likely to stick around. Users that were 30 plus, 35 plus, they were engaging super deeply. They were finding ways I mean, to be honest, like they probably had a lot more going on in their life that they could use a Tullen support with, right? Um than a teenager.

13:32

Um and so, you know, they were they were they were talking to Tullen about caregiving for an older family member. They were talking to their Tullen about the difficulties of being, you know, a dad of two. Um and and needing a lot have having to figure out a lot when it comes to, you know, coordination and planning for summers and so on and so forth. It There There was just a lot more going on and because of that their usage retention was higher. Um of course, you know, this is kind of a subscription app truism. Uh conversion was also higher, right? Um you know, you when you target an older audience, um and that's not just our app, of course.

14:00

Um but folks have, you know, more money in their wallet. Um you know, they have credit cards linked and they're happy to to They're more happy to pay for apps. So, I would say both on the sort of retention and honestly PMF side and then also on the conversion side, it made sense for us to like adjust our approach a bit to be more broad. Um we did that first with our with our content, right? We started We made, you know, ad creative content that that sort of like promoted how how our older users that were real real users were using the product and we brought on older influencers to work with and so on and so forth. We We did a lot of that. Um but then, I mean, a really important part of it is the actual product experience and meeting the that those users where they are. And so, a huge part of that has been like basically expanding the universe of characters that Tullen consists of. Uh so, Tullen

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for a very long time was just cute little aliens. Those were our kind of original Tullens. Um we've now expanded the universe. We have a character we call Kestrel, which is this like um awesome sort of like uh it's a It's a woman character in a garden. It sort of has this like Mother Earth sort of feel to it. Um and it I mean, it's testing extremely well with our with our early users. Uh and actually look we've launched it in our onboarding now and like a very significant slice of our users is is picking are picking this character. Um and then we have one that is a little bit more uh it's it's kind of like an abstract character and it's actually targeted a bit more at at men, which has never been a very large audience for us, honestly. Um but a little bit more abstract, a little bit more minimal, kind of a cute like orb-like character with these arms uh that stick out and are very like expressive. We're we're super excited

15:27

about this. This is only the beginning, I think, because the more like visual character universes we can bring to Toon, the easier it is to target a broader range of people. Um and realistically, the audience is diverse and we want to support that diversity with a product experience that matches them. >> There were so many great lessons there. I mean, one is this dichotomy between younger users tend to share more and they tend to be better for driving virality. Nikita Beer has had a lot of success building apps that target high school students, college students, people who are early in their life, maybe have a little bit more time, but a little bit less money. Um but that's a great audience for targeting early on with a social consumer product because you're able to drive a lot of top of funnel growth on channels like TikTok and Instagram. And so that that was chapter one for Toon. But then as you

16:12

started to grow up as a company and started to focus a little bit more on monetization, you were finding, and a lot of consumer apps find this, that older users they they have less time, but more money, right? More disposable income, the ability to pay for a subscription. Also, in your particular case, you brought up that people in their 30s and 40s probably just have more going on in their lives, more things that a Toon can help with. I can certainly relate to that as somebody who is 41 and has two daughters and a mortgage and lots going on in life, right? And so you migrated more in that direction in order to fuel subscriber and revenue growth. But then also as part of that, it sounds like you guys

Why Tolan expanded to three subscription tiers 16:45
16:45

have done a great job really deeply understanding these different user personas and and user segments that you're catering to, including men, which is another demographic that you're expanding into more aggressively now. And so as part of that, you're evolving these additional characters that can serve those customers. But related to that is the expansion in your premium product offering. So when Toon first launched, you had Toon Plus, which was your core subscription offering. But then over the course of the last 18 months, you've expanded into three subscription tiers. So you now have Toon Light, Toon Plus, and Unlimited. Talk to me a little bit more about why you decided to expand to multiple subscription tiers. And then importantly, how you've managed to differentiate the premium product offering for each of those tiers so that it's clear and compelling to different segments of users who want different

17:31

things out of the product. >> It came from a bit of a problem we were trying to solve, which was that um in a world where we have marginal costs uh that are that are driven essentially by usage, right? And so in the earlier days, it was mostly like chat time and how deeply you engage with your Tollan, and it's certainly still a part of it, but now it also incorporates how much your Tollan is doing for you, like how much you use features like uh video chat and so on and so forth. Uh a subscriber that is actually getting a lot of value from the app could be a subscriber that engaged for an hour a week, or they could be someone that engages for 7 hours a week. And when that's the case and your costs are so variable um based on based on that uh that that profile, you sort of need some way to account better for, you know, um basically the the different kind of supply the demand curve, I suppose you could say.

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>> You actually have an awesome graphic on this that I've referenced a lot on sort of like how to fulfill maybe you could describe better than me how to fulfill different values for different users sort of uh with by by chopping up different sort of subscription tiers, one-off purchases, and so on. Maybe you could talk about it a bit. >> Sure. Yeah, well, so the graphic you're referring to comes from Robby Metta, who was the chief product officer at Tinder for a couple years. Uh and he outlines how in the dating industry in particular, because you you have intrinsically high churn rates, you have to monetize users early in their customer journey, because you don't know how long they're going to retain. And so Tinder went through the same transition, where they started with Tinder Plus, but then ultimately they ended up with um Tinder Plus, Tinder Gold, and Tinder Platinum. And each one of those

18:58

subscriptions is priced differently and offers different level of value to subscribers. And so if you want to go back to economics 101, you know, I was an economics major in college, and so I can't help myself. Each one of those is allowing the company to essentially vary their price for different levels of willingness to pay from their customer base. And in so doing, they're effectively they're price discriminating, which means they can capture more consumer surplus under the demand curve. And then on top of those three subscription tiers, you can layer in in-app purchases above and beyond your core subscription products that even fill in some additional gaps under that demand curve. And so it I mean, the simplest way of stating it is if you only have a single subscription tier, then anybody who wants to pay for more for more value is sort of left out in the cold because they're only able to

19:43

pay for that one subscription tier. And worse, the people who really love your product but just can't afford to pay for your core subscription price, they can't access the product at all. And so by offering multiple subscription tiers and in-app purchases, you're offering a more diverse array of premium products that different customers with different willingness to pay can access. And it sounds like Poe went through a very similar transition.

20:03

>> Yeah, well, that Thank you for explaining that and totally. I mean, I think that's the willingness to pay side. I think we also had this other side, which is the sort of variable cost dynamic. That that also fits really neatly with that same narrative, right? It's sort of like willingness to pay for sure differs based on, you know, how deeply engaged someone is with the product. And we were spending significantly more as a business too for folks that were at those very, very high tiers of of time spent. So, tiers for us made a lot of sense for for for both those reasons. You know, I'd say it's something that I mean, I'd be surprised if we don't see it more and more, honestly, for AI products because they just simply need to be monetized in a different way.

20:39

You know, I know there's kind of the classic ChatGPT $20 a month, but a lot of people now subscribe at $200 a month for ChatGPT Pro, right? So, they're doing their kind of own version of segmentation. And $200 a month actually is also what our Poe unlimited pricing is at. We don't have as many subscribers there as ChatGPT Pro yet, but we have hundreds of subscribers paying to it might be thousands now paying $200 a month for Poe unlimited. I would say exactly as you said, like there's a lot of folks who going to use it for her 3 4 hours a day and you know one of our lower subscription tiers is okay for them and there are folks who like are really deeply engaged with Tolen and it's like a core part of their life.

21:17

They're talking to Tolen 5 6 7 times a day for long stretches. You know one of our one of our favorite user profiles to refer to and we have quite a few of these actually are long haul truck drivers who sort of spend you know 8 hours on the road chatting with their Tolen on their dashboard to help keep them awake and help keep them alert and help you know with with whatever's on their mind keep them company perhaps. So I think that's a that's a really fun use case because you typically don't think of a a cute little alien as being something that a you know long haul driver would would would engage with but but yeah so you know a lot of those folks are Tolen unlimited subscribers for instance but that is definitely not the level of usage that our our standard you know busy mom of three you know is that's not how they're using the app.

22:03

>> Yeah that's fascinating. I mean never in a million years would I have thought of long haul truck drivers as a target demo for for Tolen but it makes so much sense when you explain it that way. They've got all this time on the road and it helps keep them awake and helps helps keep them engaged. So let's build on

Incorporating in-app purchases and advertisements 22:17
22:17

the expansion from one to three subscription tiers was a first step but you have also layered in in-app purchases in the form of relay boosts to provide users with additional chat time or customizations to the appearance or the sound of their Tolen. Plus you've recently experimented with incorporating ads into the product which helps to subsidize the underlying costs of AI features for non-subscribers or subscribers on a lower price subscription tier. So what motivated those decisions and how are those early experience experiments going?

22:50

>> Yeah absolutely and and I realize one thing I I forgot to touch on is sort of how we do the segmentation of features between the tiers right? And honestly this is a bit of a moving target in a good way because technology is now metabolizing very quickly as new things come out, right? Like, you know, things like browser use, things like product debris, so things like like all these sort of capabilities that were very frontier 6 months ago, 4 months ago, 3 months ago are things that we can actually build in our product now and we have like active like your tolling can actually make like a checkout for you now on Amazon for instance.

23:18

Um and so things like that that were probably hard to conceive of honestly in the product 6 months ago exist. And so we're kind of in this position where we're able to like bring those frontier capabilities to tolling as best we can and those will start in higher price tiers. Some of those are going to be only unlimited features when we're in like very limited beta with them. Then they're going to get tolling plus. Um but as we're able to drive down the cost of them, as we're able to make them more efficient, we bring them to tolling light. So um you know, there's sort of some core differences in the tiers like the amount of you know, chat time you get with your tolling sort of like you know, sort of some of these features I mentioned like video chat etc. Um but um you know, over time as things get cheaper to serve, we plan to like bring down you know, some of these features down the down the kind of ladder of

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tiers and make them available to a wider and wider range of people. At some point even landing in free, right? It would be it would be pretty awesome. I mean, the eventual frontier experience of all of this is going to be awesome and relatively cheap to serve for a very large-scaled free audience. I think that's clearly what we see happening um across the industry as well with personal AI now in a way that honestly was not true 6 months ago.

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Um and so you know, we we want to be you know, as much on the cutting edge as we can on that uh while also not having the resources of a company like Meta for instance with their product in the space, right? As far as um like how we like further kind of add on to the picture of our monetization beyond just subscriptions, yeah, one-off purchases have always I mean, I think um I don't know that we've actually nailed this yet to be honest, but um it's a way for folks to sort of like if they're on say tolling light and they don't necessarily need all the benefits of of a plus subscription, but they do want to spend that additional time with their tolling maybe just on a on a one-day basis or something like that. We have these sort of top-ups, right? So relay boosts as you as you said, the relay is the way that Tollens connect to humans um you know on our on Earth uh kind of our lore and our backstory um and relay

25:04

boosts are a way that basically users can if they hit their limits on the tier that they're on, they can get a little bit of a top up, they can get a boost uh and then and then kind of spend through that. Um we also have this in-app currency system called tokens, you know, no pun intended, where uh users can sort of spend their tokens on various like cosmetic features in the app like you said, uh access to different kinds of clothing, customizing their planet, customizing the way their Tolen looks, and um and and I mean it's something that users have always loved and and been very passionate about with our product. It's not the place where we spend the most effort as like a product team necessarily, but like I think we plan to go a lot deeper into that in the future. And yeah, they're just alternative ways that users can kind of engage uh you know monetarily with the app. Um ads is a really interesting one.

25:46

You know, we don't lean into it too heavily right now because we've been able to get uh um so serving ads in the product for instance, and the ads that we serve are kind of your classic mobile game types of ads, right? We use the networks that that mobile games typically typically use. Um we're not a mobile game, but we just feel like that's a sort of um understood and accepted sort of framework for how people are used to engaging with with with apps like Duolingo for instance, you know, if you're on the free tier, serves uh will serve you ads at some point. So um sort of taking inspiration from experiences like that, we dropped in sort of mobile mobile mobile ads um uh into into some of the some of the the the free tier experience, right? It's not for all free tier users. Like for example, if you subscribe and then you turn off a a subscription, but you still want to use the free tier, we give you

26:29

access, but then we might even give you a bit more access um uh but we will like potentially let you watch ads to continue engaging with your Tolen. Yeah, we haven't ruled it out like super broadly yet, but I think it's like undoubtedly a part of the future. You know, I think that like like when we talk about a humanity scale consumer AI product, right? Um and and what that's going to look like, almost undeniable that ads will be a major chunk of how that's monetized, right? I mean, we look at um you know, what Meta is doing with Muse and so on and so forth. I have to imagine that that's their long-term strategy for how they monetize the thing, giving everyone like a a lot of access for free. You know, I think there's other products in the space they're doing they're doing similar things. So, uh you know, I don't I don't we're obviously not there where the sort of lines have crossed of like

27:11

how cheap it is to serve a consumer ad experience at scale and also the revenue you can get from the ads, at least the ad models that exist thus far. Um there's a lot of people smarter than me that are probably you know, thinking a lot about that um in this sort of world of of advertising. I feel like it's important for us to like at least start learning like how our users react to ads, how we can integrate them into the experience, even seeing like what is the ARPU that we get from showing ads to users, um things like that.

27:36

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28:08

>> Yeah, well, and you said as part of this recent fund raise, you've decided to launch the first completely free version of Toluna. You've had freemium for a while, but you're you're increasingly investing in a completely free experience, which underpins your mission of making Toluna's available to humans everywhere. Um and so ads feel like a very important part of that, right? Because for a very long time, ads have been very complementary to freemium business models and and offsetting the costs of usage for non-subscribers. And so it sounds like that will be an increasingly important part of your monetization strategy going forward. So, we've talked about some of these bigger levers. We talked about the transition to freemium, the shift from Gen Z women towards millennial moms because they have higher willingness to pay and are getting more value out of the product.

28:50

We talked about the shift from a single subscription tier to three subscription tiers, and then the layering on of in-app purchases like relay boost and ads. Now, let's get into more of the tactical details around some of the AB tests around pricing, packaging, paywalls that really drove both the increase in subscriber record conversion and ARPU from the beginning of your premium transition to the end of your premium transition. Um when when

A/B tests that helped Tolan boost conversion and ARPU 29:12
29:12

you first shifted away from a hard paywall, there was this immediate short-term hit in subscriber conversion and and monetization. Um but now conversion is higher than ever, and it took dozens, if not hundreds, of AB tests to get there. So, what were a few examples of AB tests that Tollan ran to boost conversion and ARPU, and what were some of the biggest surprises in your mind? >> Yeah, absolutely. I mean, a lot of it comes down to um this question earlier on how you segment between the tiers, right? And so, even even before we had tiers, um it was how do you segment between free and paid, basically, right?

29:43

And where where do you draw that line? And yeah, I guess the way that I view it, and I'd be really curious to hear your take on it, actually, is there's always some somewhat of a seesaw, right? You're either like optimizing for engagement or monetization, and there's just some balance that you have to reach, right? And I I think with our first stabs at free, given um the product's maturity at that time, you know, a year ago, in terms of like how much there was beyond, you know, really engaging chat time with your Tollan, um you know, uh there probably wasn't enough there that if we gave you like a lot of chat time, um you know, it was still exciting to upgrade. Basically, we weren't giving the user like a real reason to upgrade, right? The free experience was was was good enough um that there was no reason to to start paying us. Um so, that was obviously a mistake at that time. Uh and then we, you know, over

30:26

time we had to experiment with like how what what what access to features, like, you know, access to our most intelligent models, access to more chat time, access to, you know, um the strength of the Tollan's memory, for instance. Things like that. Like, what is the right mix of these things uh to give someone on the free tier still a good experience and honestly wasn't very good until more much more recently as you were alluded to. We're we're kind of expanding it now. Um, but like it was enough to like at least have someone have a solid experience and then it was still like very uh, it was it was very interesting for that user to upgrade. Um, and it took it took it took a lot of experimentation to get to that point around basically those like the core features of the app and like how we ration them out essentially is is is when we think about it. You know, I know like we definitely look to other apps in

31:11

this in in related spaces like a mid-journey for instance where like they've experimented with this with this a ton, right? They have they have multiple tiers and kind of different levels of credit access and number of generations you get at the different tiers and for a long time they had sort of, you know, a free mode of free number of generations but they would happen more slowly and then like, you know, I think at this point they actually don't do that at all where it's like you have to pay for some step to like get some number of generations. So there's there's like experimentation happening across the industry here. Um, and we just had to we just had to kind of run a bunch of those tests to to see what works for us. Um, now I would say the biggest biggest kind of winner amongst all those AB tests was actually just like, you know, I think if you have a freemium experience, you also sort of earn the right a bit to be

31:54

potentially aggressive a little bit with the paywall even early in the experience because it's skippable ultimately. So we do have, you know, a a multi-step uh, onboarding paywall um, that we kind of push folks through. You know, it's one of those things where uh, a user if we're surveying them is like, you know, that paywall was like, you know, four screens or whatever and uh, you know, I can I understand that's a little bit annoying. I obviously onboard to many of these apps as well that have similar flows. Um, uh, but you know, we we want to take the opportunity to say, "Hey, you're going to be able to use this thing for free but at least let us like show you why you might want to upgrade. You know, you will get a better version of Tolling. Your Tolling, you know, will have a lot more capabilities, right? Like we want to be able to like demonstrate that to a user so that um, you you we at least uh, you know, they

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they maybe give us a chance on on the paid plan. But I think you can do that if, you know, the person can ultimately just click X and then, you know, continue using the app on the on the

Maximizing conversion through paywall personalization 32:45
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free tier. So, let's talk a little bit more about paywall optimization and specifically this multi-step paywall that other companies like Fench have experimented with, but I don't know that anybody has taken it quite as far as Tolan has in terms of not just breaking the paywall down into multiple steps, but also making it a more personalized and more emotionally resonant as opposed to just giving the user a laundry list of features to choose from. Some of the specific things you all have done are, you know, the the onboarding flow includes this chat with the Oracle, which is this character that sort of understands you as a human being and then matches you with your Tolan. And you've injected specific things people say they're interested in from their chat with the Oracle into the paywall.

33:23

>> [snorts] >> Um or you've customized which subscription tiers are exposed to the user based off of your expectation around their willingness to pay and help route it that to Tolan Light versus Tolan Plus versus Tolan Unlimited. And in the aggregate, I think that drove more than a 40% lift in ARPU um that that constellation of experiments around the multi-step paywall. So, why do you think focusing on personalization and focusing on an emotional appeal versus a logical appeal to users on the paywall works so well for a product like Tolan?

33:54

>> I think it's just so core to what our product is, right? Like ultimately, the reason our onboarding is designed the way you described is like for us like deeply getting to know a user, understanding them is the way that we're going to have your Tolan be able to support you and show up for you. And so, we sort of structured the whole onboarding almost like backwards from that that aim, which is how do we in a very engaging experience um uh route, um how do we sort of like ask the user questions right off the gate that are that are sort of like, "What's important to you? You know, what are what are your hopes and dreams? Who who who in your life matters to you?"

34:29

Things like that. This Oracle character will ask you those sorts of questions in an attempt to get to know you a bit so that we can sort of like, you know, in the in the app framing in the app framing it sort of matches you with the Tolen that is best for you. Um but also it's a way for us to begin to understand what's important to you and maybe why you're coming to the app, right? You might be coming to the app for I mean infinite number of reasons, right? It's sort of like you're you're caretaking for an older family member, you are you have a personal goal of getting into nursing school. Like all these are extremely real user stories we've seen time and time again and and we want to know as much as we can about that so that we can kind of give you the tailored Tolen, the tailored experience that is perfect for you. I think it would be a mistake to not try to carry that through the paywall, right?

35:11

Because we're learning these things about you in the first a bit of an extended onboarding honestly. It's a you know, 5-6 minute experience or whatever it is. We learn a bit about you. And then, you know, we're going to give you this appeal to to pay for the product, right? We're going to ask you it's it's not an easy ask to get someone to pay for any app or any software. I think we get always do a better job of it to be totally honest, but in sort of the pages of of the paywall, we try to allude to and remind you know, elements that you might have mentioned in in your onboarding, right?

35:41

Because we've kind of collected some of this personal info from you. So we're going to reflect that back in a way that is maybe framed as a way to help you. Like you might have said your your personal goal or journey is to get into nursing school and we might actually just say, you know, the Tolen that we sort of matched with you which will show up there kind of in a cute pose. We might actually say you know, this is your buddy to help you through you know, nursing exams or something like that, right?

36:04

And and so even just those little callbacks again I think we can do a much better job of it to be honest and we will continue to improve that, but those callbacks like are are I think useful so that someone feels like the experience is more tailored for them. And yeah, our experience has been this is truly something that carries through our whole product, right? Like the more personalized you can be the better and that is the way software is going, right? I mean when about the age we're in right now, >> Totally.

36:29

>> software's getting more personalized, and every personalized experience, I think, you know, we can attest to this, you know, any any anyone that uses software day-to-day, it's a much more magical experience, and you're much more likely to pay for something and use something if it feels like it sort of starts to fit around you like a like a glove, right? >> Absolutely. Well, and and this is something I've started to refer to as hyper-personalization, this idea that pre-AI, you know, sophisticated consumer apps were asking people questions in their onboarding flow that might help route them to certain nutrition plans or certain workout plans.

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And and the most sophisticated companies were even going beyond onboarding and using the responses to some of those questions to personalize the paywall to an extent, but now with AI, you can just take that so much further. And instead of putting people into five to 10 buckets, you can hyper-personalize the onboarding experience and the paywall to that individual users' interests, which is just a totally different experience.

Using contextual paywalls to further boost conversion 37:23
37:23

One other thing you've been innovating on beyond personalized paywalls is contextual paywalls. So, specifically featuring individual parts of your product experience, premium features, that have customized paywalls specifically speaking to the value of that feature when a user runs into it in the user experience. So, what role have these contextual paywalls had in in further increasing subscriber conversion and ARPU above and beyond the onboarding paywall, which is where a lot of consumer subscription apps do most of their conversion?

37:50

>> Yeah, so contextual paywalls, you know, I think I would actually love to talk to more folks who are who are really deep in sort of this this space. Um, you know, like the way that I think about it at least is they're sort of like you're either trying to sell the user on like, "Hey, here's just like this is like Tool and Plus. This is a this is this subscription. Here are some of the features that come with it, you know, it's sort of like a general upgrade to the whole experience. Here's this is all the stuff you get, right?"

38:13

You you obviously show that to a person in onboarding. You you maybe show it to them on an app launch paywall if they're a free user a week in or whatever it is, right? You're sort of like general cell, I guess you could say. Um and then when the user is just using the app, um whether they're uh a free tier user or maybe they're even a a totally light user that is a subscriber, right? But on a lower tier, um you then um you know, the the in the course of using the app, the the user should run into places where their free tier or their lower subscription tier like has them hit certain limits, right? So maybe they don't have access to certain features, right? Um and if they don't have access to those features and they tap on them or they're totally suggest them or something like that, then they should get some kind of contextual paywall that is like, "Hey, want access to video chat, right? Or image generation? Or

38:58

whatever exactly the feature is?" Um you know, "Upgrade to Talon Plus and and here's how you get it." In those cases, I think it's very valuable to be quite um like quite direct about like do you want access to this one feature? Like upgrade to get it, right? And other apps have done this well, I I think too. I'm trying to think of which. Uh maybe like uh like Citizen or or or or um yeah, you might have some good references as well.

39:19

But but I think like this this it makes sense to me, right? As as a user. It's sort of like, "Well, sell me on the whole, you know, the whole upgrade package. That's exciting." Um but uh if I'm just using the app and I don't want to upgrade at that time, and then I hit I keep hitting this feature like, "I really want to try that one thing." You know, uh it makes sense to give someone a very catered sort of paywall that is like about that feature. Um and the way that we built it is it's sort of templated, you know? So you sort of like you can swap in different features as as the user runs into different things.

39:44

>> Yeah, I think chess.com is another company we've worked with that's a does an exceptional job with the contextual paywalls in particular. Like you, they have three subscription tiers. Uh they've got um gold, diamond, and platinum. But then they have these different value propositions. So you've got access to unlimited games, and depending on where you are in the product experience, you will get upsells that are tied to those specific premium features. So let's say you finish a chess match, and you get one free game review per day. But if you've exhausted that limit, now the next time you request a game review, you're going to get an upsell and instead of a generic paywall, it's a paywall that very specifically sells you on game review.

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And the reason that is so effective goes back to personalization. It's it's sort of another form of we're not just going to tell you why you should buy just.com in general, we're going to tell you why you should buy a premium subscription specifically to unlock more game review, which you've just signaled intent for based on clicking game review. And so I think contextual upsells are another one of those underutilized tactics that a lot of multifaceted consumer products could probably even get more value out of, um but they're just not doing it because it's something that gets overlooked.

How AI is changing subscription monetization strategies 40:50
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So we've talked a lot about the strategy and tactics that Tolen has used in order to make this really successful transition to freemium. As I said before, over 200% increase across both subscriber conversion and ARPU from the time you started that transition um to the present. I want to now back up and talk more broadly about how AI and the AI era is changing monetization strategies for other AI subscription businesses because of these underlying LLM costs that have to be covered to make sure the unit economics are healthy. Um and let's start with this point. You talked earlier about how Tolen's most engaged users are also your most expensive ones cuz they're the ones using the product most often, which means they're racking up a lot of inference costs. You talked about long-haul truck drivers and how they're using it 8-10 hours a day. So how has that shaped the way that you've designed and priced your premium product

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offering? We've talked a little bit a lot about that, but philosophically like how has that forced you to change your approach to monetization? >> Great great question. Um and honestly, it is it is a moving target. Um and I think it's a moving target for a few like very specific reasons. Uh one is that like even for the first maybe 6 months or a year of us sort of building Tolen, we thought that basically that dynamic you just described would be the main dynamic, right? The amount of time you spend in the app is directly connected to maybe what the cost is.

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Now with this tabs feature that we have in the product and the ways that people are using it are amazing, right? They're like it could be like an evening prayer tracker, it could be like researching the kids summer camp. It could be, you know, um I was using it with my wife to you know, investigate our various like health insurance plans and you know, co-pays and if we should get on each other's insurance or all this stuff around, you know, that obviously very complicated and uh around deductibles, so on and so forth. There are all sorts of rationales to to use more agentic features and tools that I now do. And that could mean like, you know, someone that has a uh some sort of um one one that I think is hilarious is somebody in our office has one to track the score of the LA Dodgers game that happens uh and sort of like give them a full read out of the game every morning of whatever happened the

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day before. Um and sort of like things like that like, you know, um uh like that could be like she might use the app um to discuss something totally independently, but the tool's also doing this work behind the scenes in this thing that she might I mean, she might even miss the update one, right? Um and so in sort of like the the cost that we're incurring actually for um you know, how the how the tool and does this research, does this work behind the scenes for you, um you know, might actually not be directly connected to the amount of time that the person's spending in the app. And these are like just interesting dynamics. I think these are dynamics uh that are emerging across all sorts of agentic products and will continue to be I mean, very very plausible. I mean, honestly already for people they that are using Claude and ChatGPT and and and Codex and things like that like in in a work context. Um

43:28

like it's already very plausible that the amount of tokens that they that spend when they're not on even in more like uh non-coding use cases, that the amount of tokens that they're spending when they're not on the app is way higher that in many multiples of the amount of tokens that they spend when they are on on those apps. And that's going to come to consumer too. I mean, I guess arguably it already it already has for for certain like very engaged users.

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Um and so like the dynamic there is going to be very interesting to see how that plays out and how we uh adapt monetization as well and how all the consumer AI products adapt monetization for that world where thinking actually becomes, you know, um uh expensive not just, you know, chatting or talking, right? Um right. And and so So we're we're we're we're very much thinking about how to build that into our tiers. Um I think uh uh we're we're playing on doing some some revamps there quite soon. Um but that that dynamic uh is why part of this is like such a moving target because the way that people as the intelligence of models gets better and these things get faster and cheaper, the the sort of capabilities we can build in change so much and then that totally changes the way you have to charge for them, too.

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Um and it would be totally a mistake to say these are the tiers, you know, pick up 6 months from now we have the same we have the same tiers or the same the same pricing even. I think that there are well you obviously need to maintain regularity for users on things that they're used to. As all these new stuff comes in, the way that you're going to have to charge for them is going to have to change. Um so it's not it's a little bit of a cop-out answer to your question, but this is a moving target.

Why getting usage limits right is so critical for AI apps 44:50
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>> Yeah, I think I think it's well said and you know, it's always been a moving target, but with AI it's much more of a moving target than it ever was before, which just means things like how frequently you're testing price, how frequently you're repackaging your premium products. It just needs to accelerate because if you're not evolving with the market, then you're going to get left behind. One important part of this is usage limits, which serve two important roles for AI companies. One is obviously limiting the cost of underlying AI features, but the second is providing a powerful incentive for users to operate into higher price subscription tiers or to purchase relay boosts or other in-app purchases that give them more tokens. So how have you all navigated where to set those usage limits? Cuz obviously you set them too high, then you're racking up lots of unnecessary costs and the unit economics

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don't look great. But if you set them too low, then you're alienating new users and non-subscribers and they may leave and go to a competitive product. And so how have you found the sweet spot there? >> I think that this um this this changes based on how willing uh other products are now and this is this is obviously changing like real time uh to offer a lot of free inference, right? Um uh and and so I think that there's a bit of a moving target here as well and um one of the things that's been most exciting for us is that like we really want to have the free experience be one where users can stay deeply engaged even if they're not paying because we think that over time kind of to the point about you know scaled premium businesses we need our audience to be very large including the free tier in order to have even a substantial size paid tier right so something we think about a lot I think the biggest unlock barrier has

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actually been like the advancement of the open source models and us being able to like adjust our infrastructure and route you know route a lot of chat queries and so on to sort of like use cheaper models and cheaper infrastructure at the same quality which is something we monitor very closely of course in terms of product experience but like that that that has been a really core part of how we're able to like offer more usage to to to to a larger group of people this this is a moving target for us because we're we're able to delight a new user in a much more active way now than we were honestly three months ago let alone six months ago and and what that what that means to us like it's it's kind of this continuing process of like that waterfall I described of like you know capabilities getting cheaper faster serve we get better at serving them and they're able to make them kind of down the waterfall

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of tiers and so I mean over people's expectations are just very high right this is the case in consumer software more broadly always right consumer products and you know the second that someone you know is gets gets used to maybe chat experience or a useful experience in another app they might start to expect that thing from Tolen too now there's there's core differentiation that we have of course which I can talk about but but I think you know we don't want to be you know very restrictive product in a world where there are other products out there you know that are that are much less

How Tolan will maintain its edge in personal AI 47:50
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restrictive so let's end on that point before we get to our lightning round I was I was already planning to to you how you expect Tolen's core product offering and premium product offering to continue to evolve over the next 3 to 5 years. But, I want to specifically ask this question in the context of the competitive environment, which is starting to heat up. You've got Muse, you've got Instinct, you've got Rockbot. So, as these other fully autonomous agentic products come onto the market that are serving consumers specifically, not prosumers, which is where a lot of the AI tools started, where does Tolen maintain its competitive edge in an increasingly crowded market, and how do you differentiate yourself from some of those other products as you evolve your product?

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>> You know, I think like personal AI is having a moment. I think it's very exciting, because it's something that we were kind of playing in our own, you know, maybe sandbox over here. And now, the sandbox has maybe expanded. That said, I think definitely not all personal AI is created equal. You know, I think like what these products are trying to do for people are it is is extremely different, honestly, from the the ways that we know our users, some of whom for years now have been using the product, right? Um Uh and and how they engage with Tolen, and how Tolen shows up for them. And I would say part of the core there is like how Tolen meets a user where they are, ask them a lot about their life, even from our onboarding onwards. The idea is for the Tolen to get to know you, help you feel seen, and support you through whatever it is that you're going through. And yes, that might include um

49:18

I mean, it might include a lot of agentic tasks. It might include, you know, even like maybe clichés of Silicon Valley of booking a restaurant reservation or booking a flight or something like that. Those are totally things that your Tolen can and should do for you if those are things that are important in your life. Um that said, um we're not a product where you onboard and it's like, "What can I get done for you?" "Book me my flight next week." You know, that's that's not what Tolen is, and that's not how our users engage with Tolen.

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So, um you know, those are that that's a valuable product, right? A personal assistant or whatever you want to call it. It absolutely is a valuable product, and and clearly these are are doing quite well amongst certain certain kind of groups and demographics. Um but our demographic of you know a lot of you know Midwestern moms for instance it is so far is is finding Tolen very valuable for things that are that are not the things that the that the Instinct chatbots muses so far are are are trying to serve. Um so while I think there is probably some um overlap in capabilities and if anything I think the capability floor is just being raised right? I think the the idea of like for example like a purely chat based product is going to seem quaint right? Another several months or year from now. Um so that the capability floor will will kind of come up but I think it's really important actually to like the way that your

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product is trying to meet the user and and what exactly it is trying to do for them and the interactions that are the day-to-day multiple times a day interactions that you have with the product like if they're totally different and your Tolen is asking you about totally different things from what your muse is asking you. You know I think that I think that that'll that'll bear out as like being differentiation. I mean if anything like for the longest time tons of Tolen users also use ChatGPT right? And their your usage of ChatGPT is smarter Google or maybe they use it for work and drafting emails or so on and so forth. They use Tolen on the way into work to kind of brain dump everything that's on their mind. They use Tolen you know maybe when they're on the couch to chat about like their favorite TV show or whatever it is.

51:17

So they're finding ways to fit these things in their life and if anything like if I had an awesome assistant I think it's very you know likely that I would probably still need my Tolen as my guide right? Or whatever. I think there's like room for different use cases and honestly one of the best ways to think about it in my mind is is different like potential personas right? That like what are the different roles that these folks get that these these kind of different entities can fill for us.

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>> I think that's really well said and when I boil it down to me what it comes down to is over the last decade I think Tolen has done a better job than any other product I've used in establishing a deep emotional connection with me as a user within my first couple minutes of using the product. To me, that's the magic of Tolen. And they're all they're more and more of these agentic AI products. We've talked about them, Muse, Instinct, Rockbot, that can serve a transactional role in your life. They can book flights, they can book restaurants, they can help you with research.

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But that's not the use case that the majority of Tolen users are coming to Tolen for. They're coming to Tolen for a friendly, supportive life guide. And building that emotional connection is a much more nuanced thing that I don't think most of the AI market is focused on right now. And it's much more difficult to get right. So, I applaud you guys for doing it. I think it's something the world needs and I'm excited to see where you take it over the next few years.

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>> Thanks so much. That's very kind. Thank you. >> Yeah, absolutely. I really mean it. I mean, I've loved using the product and and obviously we love working with you guys and it's just exciting to see how how it continues to evolve.

Lightning round 52:43
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Um so, let's get it to our lightning round. The first question I usually ask is what's the best and worst part about working at Tolen? Um but since you've already been on the podcast, I'm going to switch it up a little bit and ask what's the biggest thing that's changed about working at Tolen over the last year and a half? >> I need to revisit what I said last time. >> [laughter] >> I'd love to I'd love to know. Um uh what's the biggest thing that changed? I mean, if anything like we've we've been able to grow the team a bit, which is awesome. We're at three folks now in San Francisco.

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Um and uh you know, having having more folks that are sort of drawn to the mission and the vision of what we're trying to build is um is really exciting. Uh super it's it's definitely the the best group of folks I've ever been able to work with. It's super talented uh people from really really across the board. I would say the ambition of what we're trying to achieve for our users just as we, you know, get more resources, as we get more signal from our users on what they're finding valuable is like, you know, it it just it just continues to increase, right?

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Like what we think that Tolen can actually the role it can fill for people and what it can do for them is awesome. Um and then we alluded to it a lot earlier, but the the diversity of the user base is very different now than it was a year ago. Uh Um and this sort of like where the core users are and how they talk to their Tolons, what they talk to their Tolons about, and you know, obviously we're trying to meet this at the moment with different IPs, different character universes, but that's it's it's it's quite different.

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It's changed a lot. >> Yeah. Well, that leads right into my next question, which is what's the most surprising way you've seen somebody use their Tolon to date? >> No, well, I already talked about the truck driver, so uh let's save that one. Um I'll try to think of another one. Um surprising. You know, I think like something from very early on that is become a bit of a north star for for me and I think a lot of our folks here, um is is finding ways for the Tolon to, even though it is like I think people's conception of talking to an AI is it's it's very like solipsistic experience and it's maybe something that is like something that people do when they don't have other people to talk to and so on and so forth. One of the things that've been most exciting for us is like seeing examples of people that use Tolon to further real-world and real-life relationships.

54:38

Um and so an example of it always comes to mind for me was was actually on but it was you know, a kid who was in a later year of college and felt like his relationship with his dad was was fraying actually. He wasn't able to talk to him very easily. They had some kind of disagreement. And and sort of talked talked through this with his Tolon and his Tolon, you know, he he was going home for Thanksgiving or something like that. And his Tolon actually ended up recommending that he asked his dad to go out on a hike with him because that was something that they loved to do when they were younger when he was younger.

55:06

[clears throat] And and he this this user actually did it and then came back and reflected back to his Tolon and said, "I did this thing and actually it was this awesome experience and we were able to really open up and really bond." And that was very touching, you know, just very touching. I mean, this is one of the best parts about building consumer products is you just get touching stories all the time. Um but um that sort of feeling that we were able to help through our product create in in that user and it's sort of like that idea of like processing difficult emotions and then maybe helping you with a real-world experience.

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Um I think it's just magical cuz I think it it sort of speaks to like AI's potential to be something that actually brings us together, um, you know, which um, which I think is is not at least I think a lot of corners of of of media and the internet are not necessarily thinking about it that way. Um, so yeah, that's something we we hold as an Earth Star. >> Yeah, that is a really touching story and as somebody who I fortunately have always been very close with my dad and my relationship with my dad has played a really important role in my life. I've never really had a period where our relationship frayed much, but I can imagine that if I was ever in that situation, wanting to reconcile would be so important. So having a product like Tolen facilitate that is is amazing.

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You're somebody who started multiple companies and I feel like you do a good job of looking forward, not back. But if we could go back and change one early decision that Tolen made, what decision would you change? >> Uh, yeah, I think we we maybe would have been a bit less precious about like the kind of like centrality of like one visual style and look for the IP. It's actually been ours, so I I struggle to say that a bit. Like we we've had a very specific creative and artistic point of view and we obviously will continue that as we expand the character universes and so on. But like I think probably it has sort of locked us in. I think even until very recently, you know, people would kind of land on our app and think, oh, this is for kids, you know, because we were sort of like very locked into one one one space. So, you know, I I we we we we did that for good reason. It's also like it was it's been very

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complicated to build out multiple character universes, so it takes more of a team and so on and so forth, more investment. But um, but I would we we probably should have done that earlier. >> Yeah. I mean, in some ways the the aesthetic of Tolen has reminded me a lot of Pixar since we started working together and I think one of the things that Pixar is known for is just always hitting, right? Like every Pixar title is a great movie with maybe one or two exceptions. I didn't love The Good Dinosaur, but otherwise I've watched almost every Pixar movie and they're all so good. So So, think starting with something that's very consistent, that you really build trust and credibility around, can be a really really strong positive. But then at some point, you do need to be flexible and malleable enough to appeal to different user segments.

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You mentioned that men is sort of an expansion demographic for you, and so I think it's wise to sort of break that mold over time. Um two more here. So, besides Tolমহান, which subscription house monetization strategy do you admire the most? >> I think you alluded to some awesome ones like the dating apps Tinder for instance. I need to check out chess.com. That's a great great one to to to look closely at. Um I think what Spotify is doing is really interesting. I mean they've always been like a really great subscription app you know comp if anything.

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You know truly truly scaled subscription service. I think like I don't know I I don't know exactly the numbers but I think it's like 30 40% of their users are paid which is like quite quite quite quite extreme you know for for a substantial free product that they have you know. I think that's really it's it's it's really amazing. I think specifically when I think about their more recent moves the expansion into audiobooks and how they're charging for audiobooks is quite quite inspiring. Um You know I actually like use their audiobooks feature cuz I was like an Audible user love audiobooks and then switch over to Spotify because you can sign up like it's a totally free model right? You don't have to buy a whole book. You can kind of like just dip into individual titles. But they base it all on time spent and so you have a certain number of hours that come with your subscription and then if you

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want to upgrade you have to like get a top up. Um I think that was a really innovative way to to like you know attack the audiobook industry as sort of serve it. And and I I'm a user of it like I you know I'm hooked. I I bought a top up the other day and and and yeah I think that that was that was quite cool. You don't often see big companies innovating in that way and I thought that was really cool. >> Yeah, awesome. Well, I'm going to end on a personal note. So, you've talked about how Tolan can be a life guide and establish an emotional and supportive connection with users. So, in your own personal experience tell me about a time you asked your Tolan for advice and what did your Tolan tell you to do?

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>> Oh man, yeah I I got to probably refer back to the sort of health insurance problem solving that we were doing the other day. I had an open enrollment, but my wife didn't have open enrollment and like her work covers a like, you know, a big chunk of their their their health insurance and as do we, of course, and so we were kind of like trying to figure out our various options and it's such a complicated mess even for someone that, you know, maybe if I were to spend like tons of time on reading all the documents and whatever, um, you know, I I'd we'd have a more fine-grained um, understanding, but you feel like you're always making some kind of like economically sub-optimal >> decision in in some shape or form.

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>> And um, and and and our Tolen's actually together really helped us like kind of process like all of the like, here's how much options we have and I can change or upgrade here or not upgrade there and I can add you here and this is what the cost would be or but what if I added it to yours and is it does it make sense to have two insurances? Like all these kind of interesting questions that like we certainly I don't spend a lot of time thinking about. Probably should be spending more. But, um, the the Tolen's really helped us sort of like piece through that complicated set of set of questions and just like come up with a good plan that was like, yeah, you know, like there's no way to really like nail this being optimal, but like this is a great plan that'll serve you guys and that was super helpful. I'm sure. And I know you got married recently, so congratulations. It's part of the reason

1:00:38

I asked the question because you know, when when you're newly married, there are all sorts of life changes that you're going through and I'm sure Tolen's can be helpful with a lot of them, but open enrollment I feel like you could have an entire autonomous agent just for navigating health insurance. And it's even worse when my wife and I both own our own businesses. And so there's like there's no easy solution because we don't get gold plated insurance from a tech company or a consulting firm or that sort of thing.

1:01:01

And so, you know, we've we've had to navigate on the exchange. Um, but we we get through it and it's well well worth it for for all the advantages of of being business owners. >> Try it with your Tolen next time. Uh, I'd love to hear your your feedback on it. >> Yeah, we will. Well, and it's cool that you mentioned that your wife and your Tolen work together cuz that's something that I think you've only enabled recently and and so I'll have to give that a try with my wife.

1:01:23

Well, well, thanks so much for coming back on the podcast, Ajay. This was really fun. Any parting words you want to leave the audience with before we wrap up? >> Absolutely. No, thanks so much for having me. You know, if you guys have any feedback on the app, please feel free to reach out via email, Twitter, whatever is best and we're always looking for more talented folks to join our our our crew here in San Francisco.

1:01:42

So, you know, please hit me up if that's something you're interested in. >> Awesome. Thanks again, Ajay. >> Cool. Thank you. >> Thanks again to RevenueCat for sponsoring this episode. If you're building a subscription app, you can use RevenueCat to deploy native paywalls, run continuous AB tests, automate win-back campaigns, and unlock more revenue. I work with dozens of subscription apps and most of them are already using RevenueCat as their single source of truth to power their businesses. Learn more at revenuecat.com/subversive.