mediumRetention Blog·April 20, 2026

Simply Sing, Guitar, Draw

📊Affects these metrics

Hey there, it’s Jacob at Retention.Blog 👋

I got tired of reading high-level strategy articles, so I started writing actionable advice I would want to read.

Every week I share practical learnings you can apply to your business.

Retention.Blog is Botsi helps you show the right paywall to the right user to increase LTV by up to 70%. Learn more →

Learn how Simply Sing, Guitar, and Draw, follow a formula to create a huge app business

Before we get there, I need to apologize. It’s been multiple weeks since I’ve sent a newsletter. I feel guilty because it’s not the promise I made to subscribers when they signed up.

I’ve been doing this for over 2 years, have written 100+ newsletters, and written one nearly every week.

I moved last weekend and life has been a bit crazy, but I’m going to try to do better.

Thanks for being here.

Onward!

To get back in the game on the right foot, I looked at Simply LTDs apps:

And somehow I didn’t look at Simply Piano which is doing $3M/mo

And this is only looking at in-app purchase revenue!

I see a lot of their ads going to a web subscription flow: https://join-piano.hellosimply.com/start/motivationsIntro

Wow. I’d be they’re doing millions per month via web2app as well.

Clearly they know something.

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Here is their formula:

Step 1: Create a truly valuable and great product.

Ah, yeah, sorry to burst your bubble. If you’re new here, this isn’t a get rich quick newsletter.

The rest of the strategies they use for Simply Guitar, Piano, Draw, and Sing aren’t going to work for you if there isn’t real substance behind your product.

To be fair, they use different tactics for their web2app funnel, so you could probably replicate these easier with a sub-par product. But web2app is usually not what we’d recommend for a new app and you should likely be doing at least a few $2-4M/ARR+

Step 2: Create a simple onboarding flow with simple personalization

Step 3: Give people the first lesson free

Step 4: Lock subsequent lessons behind a paywall

So why does this work? Because during “Step 3” when people are exploring the app, they get tons of value, make progress on what they’re looking to accomplish, and trust that the app will deliver because of what they’ve done so far, so they’re happy to start a trial or pay.

This is the perfect time to talk about Daphne Tideman’s Price Power Podcast episode on Activation

Daphne Tideman, growth advisor and consultant for subscription apps, explains why most retention problems are actually activation problems, how to distinguish vanity activation metrics from ones that predict real retention, and why the aha moment should start in your ads, not just your product.

But my goal is to bring you insights you can apply today, so let’s get down to business.

You have a decent product, but how do you convince people of that?

Benefits not features, be exciting, aspirational, and emotional

“In a matter of minutes…” pair that with fast value and you have a winning combo

This also removes doubt: “Now I trust they can help me learn with my specific guitar”

Screen 3: “What would you like to achieve?”

Connect the reason for trying this back a person’s motivations

It helps you personalize the experience, but also helps them feel heard

Make it easy on your users, don’t fo rce them figure it all out themselves

Reinforces that they’ll make progress fast. Nothing is more demotivating than downloading, an app, getting excited, and then realizing it’s going to take days or weeks before progress

“….play 3 times per week…

Make fast progress, but also if you stick with it, you’ll learn a lot over the next 30 days

But also, gets people to start thinking about how this fits into their life and commit to a habit

“How did you hear about us?

A extremely helpful question for scaling growth, learn more on that here:

And then into the loading screen!

Looks I have a newsletter for that too…

But the real meat and potatoes are letting your users experience value before asking to pay.

Sometimes you can do this during onboarding, but Simply sees that getting users to actually experience the product is the best way.

They don’t have a 50 screen onboarding flow, they have a few questions, and then get you into the first lesson.

And they’ve created extremely high quality video production to accompany every lesson.

This paywall is also not just a static design.

There is a long audio voice over that talks through all the lessons, the value, and sells you on Simply Guitar.

Simply Guitar is an audio related product, so it makes sense to have audio that is selling you.

Let’s update our formula a bit:

Create a truly valuable and great product.

Focus this product one core use case

During this first lesson, get people to experience value fast

Personalize this first lesson or first experience to cater to their needs or experience level

Create high quality interactive and dynamic experiences that keeps people engaged

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This is getting a bit long - what if I follow up with 2nd newsletter this week that break down the rest of what they’re doing in the other apps?

I’ll also include their web2app conversion flow.

Alright, sounds good, I’ll talk to you again soon

If you can’t wait, here is a Whimsical board with all the screenshots →

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Key Insights

1

Simply Piano generates $3M+ monthly in IAP revenue alone, with additional millions likely from web subscription flows

2

Web-to-app subscription flows can be a significant revenue channel alongside in-app purchases

3

Product quality and value are foundational to app business success