Hey everyone!

So, I have 0 paying users (🎻) with a paid product and I'm about to tell you why I'm totally fine with that. Actually, more than fine.

I designed it this way. I’ve made it deliberately hard to pay me, and I’m genuinely curious if you think by the end of this quick email I need a sanity check or not.

My first version of Little Moments had a paywall sitting right after onboarding. Six feature splash screens → trial paywall with a little "Skip for now" tucked underneath the big button. Two weeks free.

I was excited. I had a gorgeous paywall set up with RevenueCat in minutes and shipped it because I wanted the win of a paid product. Everyone says payment = proof of product market fit, and they are not wrong.

I was also excited because I thought my first few invited friends would become paid members just because, and I’d have paid app users off the bat…

…a cheeky milestone that wouldn’t have said anything about product market fit.

But, of the 4 close people I shared v1 with, 4 skipped the paywall. 100% skip rate.

I asked them why and what they were thinking, even though I already kind of knew the answer. They hadn't experienced any value yet. And like I wrote about last time, my v1 onboarding was also just not very good at communicating the reason anyone should try Little Moments.

My friend Ryan who does growth for a living at a consumer subscription company asked me one question that I should have asked myself but didn’t: "You have to decide what's more valuable right now: Adoption or Dollars."

And around the same time I was thinking about this redo of my onboarding, quite perfectly and serendipitously, I had a very unique call

The real lesson came from an unexpected place. PostHog.

At my full-time PM job, the PostHog team called up me and my VP of Engineering.

I thought it was an upsell, a new tier, a feature we’re expressed interest in but hadn’t started using yet, I don’t know, something related to why companies usually call you up.

Instead, they told us we were spending too much money with them and showed us how to spend less. And then sent me a t-shirt…

That was the entire call—making less money from us.

Amazing. A company that makes you feel like they're on your side instead of trying to squeeze you. It made me speak more highly of them. Refer them more. And honestly, it solidified me as a customer forever. I'd never leave PostHog after that.

So, perhaps they will make less from us this quarter. But I bet you they will make more money from us overtime. Not just because they’ve got more advocates for them on our company, but we came back within a few days and added new products to our plan.

The best selling isn’t selling at all.

The takeaway that I brought to Little Moments is this: Don't make people pay when they don’t need to. Tell them at the right time, when they need to, and then they'll want to. And when they want to, they’ll become loyal fans.

That's what I wanted Little Moments to feel like.

This app won’t make any money if I can’t get people using it and helping me with feedback.

In v2, my onboarding is way better. People experience value in the first minute (see last post). But I still decided to keep any paywall info completely out of onboarding.

Early paywalls get more visibility but worse conversion and lower intent. People upgrade just to get past the gate and cancel later. I’ve done this and I’m sure you have too.

Late paywalls mean fewer eyes but much higher lifetime value and retention.

My bet is that when I get paid subscribers, they will stick around for a long time. I could be totally wrong. But let me walk you through the thinking.

The core mechanic is free. Capture a daily moment with text or voice in under 2 minutes, save it in your Capsule. No restrictions on voice transcription, no cap on how many moments you can capture, and nothing in the way of the daily habit.

You can't lock the feature that gets people to form the habit. Messaging apps don't stop you from sending messages. You can't build habits behind a paywall.

So Capture and Capsule are free. Sharing moments is free too—people share moments with friends, friends might sign up.

Free also includes one monthly Chapter (your monthly recap, generated from your moments if you added 7+ that month) and 3 Threads (connections Ellie finds across your moment: patterns, insights, follow-up questions).

Both cost me money to run—AI processing, model inference, daily analysis across every user's moments. Not expensive today, but not free. But I'm betting that demonstrating actual value through these features will lead enough people to want them for $10 a month or $100 a year.

Premium unlocks unlimited Chapters, unlimited Threads, and more than 1 year of Capsule history.

Premium is for people who care about holding onto moments as an asset they value, and who find joy in reflection and insight. I'm building it for those people specifically.

So where is the paywall? Mostly buried. Intentionally.

A small banner sits at the bottom of the app, and in settings, and Ellie drops personalized messages at specific moments, like after 10 captures, after a Chapter, after viewing a third Thread. All points where upgrading actually makes sense.

But it's not in your face. No pop-ups. No persistent banners. No upgrade badges on every screen. No modals when the app loads telling you to upgrade.

And when you do find it, this is where I think I'm doing something different from any app I've seen.

Clicking the premium card opens a conversation with Ellie instead of hitting you with a sales pitch.

She opens with something like: "This isn't a hard sell. Let me help you figure out if premium is right for you." This is what it looks like.

This is a filter for fit right now, not a funnel for cash.

Ellie explains who premium is ideal for, what you get, and based on your actual usage data (moments captured, consistency, Threads viewed, Chapters received) whether or not you actually need it yet.

Right now? For every single user, the honest answer is no. The app is too new. Nobody has hit the limits yet. I won't tell someone they need to pay when they don't. If someone wants to support me beyond that regardless, of course I'm happy. But I'm not hustling anyone here for a dime.

The user can ask Ellie follow-up questions. There are buttons for common questions, and a permanent "Continue to Premium" CTA at the bottom whenever they're ready.

When they do continue, the flow goes:

This one came from a dinner conversation with Julia.

There's so much negative shit in the world right now. Orange Man bad. I wanted Little Moments to have some positive lever beyond how the app helps the individual, which I think it does. Some small touch of good being added to it.

So, I landed on 5% of all subscription revenue going to causes people care about. When you hit the paywall flow, you pick one of 6 causes, each backed by a real charity or program through Every.org. Pick one and I handle the rest.

To start—since I have zero subscribers—I'll manually pay via Every.org based on allocations. Once there are actually some paying members, I'll automate it with Every’s API and some webhooks with a human sign-off to make it simple.

It's really not a conversion play. I genuinely don't know if it helps or hurts sign-ups. But it felt right so I did it.

I've got many unknowns right now. Does the chat-first paywall help or hurt conversion? Which Ellie questions push people to convert better than others? At what point in a user's lifecycle do they generally go paid — after 10 moments? 30? Their first Chapter?

I'm tracking every step of the premium flow. Every question a user asks Ellie. Every button they tap. Every point where someone backs out vs. continues. The full funnel — from trigger message to Ellie chat to paywall to plan selection — so I can see exactly where people lean in and where they drop.

But even beyond the paywall, the bigger question is: what actions do free users take that predict going paid? Is it capturing moments 5 days in a row? Viewing their first Thread? Getting their first Chapter and wanting more?

PostHog's funnels and cohort analysis will show me how free vs. paid users behave differently. And their AI lets me just ask in plain English — "What's the most common last action before a user hits the premium screen?" — instead of building dashboards I'll forget about.

PostHog gives me 1M free events a month which is a serious free tier, not a trial gate. If you're building something and need to stop guessing what your users actually do, it's worth the setup…which takes just a few minutes.

It's not easy to pay me. And I know exactly how contrarian this is.

Lenny's Subscription Value Loop framework says consumer apps should aim for 80%+ of users seeing the paywall on Day 1. Eighty percent. I'm deliberately targeting close to zero.

Maybe I'm leaving money on the table. Maybe the generous free tier means nobody ever needs to upgrade. Maybe the chat-first approach adds a step that loses people.

But I keep coming back to that PostHog phone call. A company that tells you to spend less with them earns more loyalty than one that pushes you to spend more. I want Little Moments to feel like that.

If you want to see how the flow feels yourself—and I’d love that feedback—hit me up and I'll send you a TestFlight link. It's weird. It goes against everything people tell you to do. But try it and tell me if I'm nuts.

Onwards…
— Jaryd