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

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.

Here's the link 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

(I wrote the full article here)