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
Replies
Really interesting breakdown, what do you think had the biggest impact on monetization: product value or upgrade flow?
@kyle_bennett6 I feel like product value drives everything. If I don’t see real benefits, even the smoothest upgrade flow won’t convince me to pay.
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@kyle_bennett6 @martha_s_bako 100% agree!
@kyle_bennett6 From my perspective, product value is the foundation. I’ve noticed that when I truly find something useful, I naturally explore upgrades without hesitation.
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@kyle_bennett6 @morgan_nabors I agree! When I get value I use a product even if it's not perfect. (no product is perfect, Claude went down the other day for a few min ahha)
Btw, please give Pretty Prompt a go: https://chromewebstore.google.com/detail/prettyprompt/opjebobgkipcdimgofkboimilnchghpd
@morgan_nabors Your point about value guiding users decisions really fits with friction removal once login is gone, users hit the "aha" faster and immediately see value. It's a good reminder that small UX tweaks can amplify depth and engagement rather than just chasing numbers.
@kyle_bennett6 I completely agree, I've noticed removing friction helps users reach value faster. It makes me rethink how small UX tweaks can drive deeper engagement.
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@kyle_bennett6 I personally lean toward product value being the main driver. If I don’t feel a strong benefit, I usually ignore upgrade prompts completely.
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@kyle_bennett6 @sana_silhah Exactly!
The creator of Gmail says "If your product is Great, it doesn't need to be Good."
(https://paulbuchheit.blogspot.com/2010/02/if-your-product-is-great-it-doesnt-need.html)
@sana_silhah Completely agree, removing login friction seems like a smart way to let users experience value instantly. Even if the product is strong, forcing an extra step can mask the benefit, and users might drop off before seeing why it's valuable.
@kyle_bennett6 I’ve seen this play out many times, users don’t always have the patience to “earn” value through steps. I prefer showing value immediately. For me, login should feel like a natural next step, not a gate.
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@kyle_bennett6 @ilaiszp True.
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@kyle_bennett6 Product value. Cos we saw whenever we had a bug that impacted the actual value of the product, upgrades went down for those days, then when it was fixed, it went up again.
We haven't really spent much time on optimizing the flow yet - so much more to add 🫠
@ilaiszp It's interesting how product reliability and smooth experience directly affect user behavior. I can see how removing login friction would complement this getting users straight to the core value without extra steps probably helps prevent those early drop offs when bugs or minor issues happen.
The customer support point is underrated. Did any support conversations directly influence your pricing?
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@paige_lauren1 Not so much pricing, but they are starting to influence our Team tier.
A few users really love Pretty Prompt, and they are pushing for a team license
@ilaiszp That actually feels like a really useful signal. Maybe not "change the price" but definitely "there is a bigger use case here than we thought." I like when support conversations reveal where the product wants to go on its own.
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@paige_lauren1 Yes! Support convos are a super power of signals (I'm a big fun of doing support as a founder)
That 20 seconds "aha" feels huge. What was the hardest part of getting users to feel value that quickly?
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@oliver_nathan2 making sure it works at scale 😅. Chrome extensions are a different world. It actually lives in the user's browser, so there are infinite possibilities that can happen.
Does the user have other extensions?
Did they update their Chrome?
Did Chrome update to the latest version of your app?
Did they get it how to use it?
Do they have good internet speed?
So many more questions we ask ourselves and try to cover constantly, to make sure users do get to that aha ASAP.
Please give it a go - it's free: https://pretty-prompt.com/
@ilaiszp That makes a lot of sense. It is easy to think the hard part is just showing value fast, but with something like this it feels like half the challenge is making sure that first experience actually works smoothly. If it breaks or feels confusing in the first few sec, I can see how the aha disappears really fast.
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@oliver_nathan2 I think getting a user to an "aha" is really difficult 😅
We question it every day haha
and every day we learn something new from users.
Btw try it out https://pretty-prompt.com/
Love the "dig deeper into feedback" point. What kind of feedback turned out to be most useful for monetization?
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@reid_anderson3 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.
@ilaiszp 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.
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@reid_anderson3 completely agree, here's a great article about it by the creator of Gmail: https://paulbuchheit.blogspot.com/2010/02/if-your-product-is-great-it-doesnt-need.html
@ilaiszp Appreciate it, will check it out.
"Get one person to pay first" is such a solid rule. Do you think most extensions fail because they monetize too early or too late?
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@leah_josephine I don't think they fail because of monetization, probably because of the actual product people don't need, or don't get enough value from it.
Though sometimes they don't even know it exist... But that's a distribution problem
@ilaiszp That makes a lot of sense. The distinction you made really clarifies it.
It's easy to think the prob is when to monetize, but it actually feels more like a value gap. If the product isn't solving something clearly enough, timing almost doesn't matter.
The distribution point is interesting too. Sometimes it's not that people don't need it, they just never reach that "moment" where the value clicks.
Feels like the real challenge is making that value obvious early enough, not just building something useful in theory.
The part about users clicking upgrade but not converting stood out. What exactly changed on that middle page?
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@miles_anthony2 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 Chrome Web Store
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? https://pretty-prompt.com/
@ilaiszp 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?
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@miles_anthony2 Not sure yet, we have a lot more to optimize and test (we're two people only!)
The part about launching and forgetting about it made me smile 😅 I always feel like I need a perfect launch, but here it seems like the real validation came after, not during. That changes how i see things
@rebecca_richard1 The 20-second aha moment is interesting. I have installed many Chrome extensions but uninstalled most of them quickly because I did not get value fast enough. This makes a lot of sense to me
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@alex_j_jemmy did you manage to try Pretty Prompt? I'd love your feedback, and if you get any value within the first 20 seconds! https://chromewebstore.google.com/detail/prettyprompt/opjebobgkipcdimgofkboimilnchghpd
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@rebecca_richard1 It's 100% true! Here's a short video talking about our launch and pivot - it was quite funny, though at the time it was a bit stressful 🤣: https://youtu.be/ATypIGYXAv0
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?
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@martha_s_bako 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.
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@morgan_nabors There's a great essay from Paul Graham I think will help on this matter of going deep into something: https://paulgraham.com/startupideas.html