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We Did a Podcast with Google: What We Shared about Monetizing a Chrome Extension

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There's almost no public content on how to monetize a Chrome Extension.

Google invited us to do a podcast about it, sharing our learnings on how two bootstrapped guys grew Pretty Prompt to 40,000 users, 25% on annual plans, with ~7% weekly growth, with no VC money.

if you want to jump right into it.

My key takeaways from our chat 👇:

1. Launch before you're ready.

We launched on 31st May 2025, my co-founder's birthday 😅, here on Product Hunt. And kind of forgot about it.

Then people started signing up, using the tool, and emailing us asking to upgrade.

That's your signal. If people pull the product from you before you've even asked, you're going in the right direction.

2. Solve your own problem first.

Pretty Prompt started as an internal tool to improve our own AI prompts. Don't build for an imaginary person. Build for yourself first. It's the fastest way to validate a real idea.

3. Earn the right to monetize.

Don't worry about complex billing flows or getting everything perfect. Just get one person to pay.

Step 1: Launch.

Step 2: Did someone pay?

Step 3: Optimize.

4. Get users to "aha" in 20 seconds.

Chrome Extensions work where the user already works. We leveraged this and made it so new users can try Pretty Prompt without even logging in.

5. Customer support is a superpower.

When users contact Pretty Prompt, they speak directly with Charlie or me. The founders.

We try to fix issues in 10–15 minutes. Being personal builds trust, turns users into advocates, and gives you feedback you can't get any other way.

6. Use social proof at every key touchpoint.

We noticed that users were clicking our upgrade button but not converting.

We added an intermediate page, less transactional, more context, more social proof. It helped. A lot.

7. Iterate on pricing.

We started with one plan. Added a yearly option as an experiment. 25% of users converted to annual.

Tie your pricing to the actual value users get, not what a competitor charges.

8. 100 people who love it > 1 million who sort of like it.

Focus on your first 10–100 users. Do things that don't scale. Get close to them. Understand their experience, their issues, their needs. (We took this from Brian Chesky's "Get 100 people who love your product".)

If people love the product, monetization becomes a natural next step.

9. Don't automate stuff in the beginning.

If a user signs up, reports a bug, or shares feedback, we send them a personal note. Work with them to fix it. There's a freshness that comes from real people who genuinely care about their users.

10. Dig deeper into feedback.

When someone says something "doesn't work," don't just say thank you and build what they asked for.

Get to the why. Humans are great at identifying problems. They're not always great at explaining them.

Asking is a form of care, and a faster path to monetization.

Hope this helps! Ilai

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Love the "dig deeper into feedback" point. What kind of feedback turned out to be most useful for monetization?

 I think what a user told me:

"Doesn't matter how many features you add. I just want the tool to work fast, wherever I prompt and just be perfect when I click that one button".

That made us rethink how we tie our monetization to the actual value of the tool. Understanding what users find valuable is super hard. What's the one single thing users would pay for, from your product.

All the rest, are secondary features.

 That is really a good point. It is easy to think monetization feedback will be about pricing or feature ideas, but this feels way more honest. If the core thing works really well, that is probably what makes people willing to pay in the first place.

 completely agree, here's a great article about it by the creator of Gmail:

 Appreciate it, will check it out.

The part about users clicking upgrade but not converting stood out. What exactly changed on that middle page?

 Great question!

So originally you'd click on upgrade and be sent straight to a Stripe checkout page.

But people didn't convert 🫠. And we were not "owners" of that page as it's Stripe's.

So we added this intermediate page, which is a basic static page that has the plans available, features, and some social proof:

Important elements:

  • Only 1 CTA button (per tier) -> Not overcomplicating the page so the user doesn't have more cognitive overload.

  • Simple tiers (monthly/yearly) -> Free - Pro - Team

  • Replaced the title with a review -> You can click on it and it takes you to the

  • Growth nuggets: "Less than 2 lates", "Save 36%", Coming soon features, integration logos, 4.9/5 rating, 40,000 installs, 600k prompts improved (builds trust = "you're not the first one")

    • Make those numbers variables, so you can update them in one place and updates everywhere on the website.

  • Strong review below the plans -> Adds "qualitative" social proof "makes my prompts 50x more effective"

Have you tried Pretty Prompt?

 That makes sense, especially the shift from Stripe → owned page + added trust layer.
Curious what actually drove most of the lift: Was it the social proof (installs, ratings, reviews), or the reduced cognitive load from simplifying the choices and CTAs?

Also did you ever test going even further, like fully replacing Stripe until the final step vs just reframing the path into it?

 Not sure yet, we have a lot more to optimize and test (we're two people only!)

I like how you kept things simple, launch, see if someone pays, then improve. I’ve been stuck trying to perfect onboarding. Did removing login friction significantly impact your early retention or just activation?

 Mainly activation. Retention I think is a different game, which we're exploring now, though it feels pretty good at the moment.

I appreciate how real this feels especially doing things that don’t scale. I’ve been chasing growth instead of depth.

 There's a great essay from Paul Graham I think will help on this matter of going deep into something:

So you have two choices about the shape of hole you start with. You can either dig a hole that's broad but shallow, or one that's narrow and deep, like a well.

Made-up startup ideas are usually of the first type. Lots of people are mildly interested in a social network for pet owners.

Nearly all good startup ideas are of the second type. Microsoft was a well when they made Altair Basic. There were only a couple thousand Altair owners, but without this software they were programming in machine language. Thirty years later Facebook had the same shape. Their first site was exclusively for Harvard students, of which there are only a few thousand, but those few thousand users wanted it a lot.