How Damon Chen beat the crowd and built the most valuable PDF AI website today


Damon Chen is the founder of and I first came across him mid-ChatGPT hype, when everyone was trying to build apps on top of ChatGPT.

I was intrigued because somehow, he was able to beat the crowd (and large enterprises) by building THE PDF AI app of the time.

In this article, we will look at some clever strategies he used to launch a valuable product riding the AI hype, and why I think even if he shuts his entire business operations down he will still make money from it.

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What we will learn

  • How much Damon paid for the and domain names
  • A napkin math to work out how much to pay for premium domain names
  • Is building in public dead?
  • Why successful indie hackers no longer share revenue metrics publicly
  • How to build a product so valuable the product drives it own expansion

Who is Damon Chen?

Damon Chen is a serial entrepreneur and indie hacker who runs, and several other apps. He left his software engineering job at Cisco in March 2021 after his 5th side project starting making money.

When he first got started, he promised his wife that if he couldn’t make $100,000 within 12 months of quitting, he’d give up his dreams and go back to an office job in San Fransisco.

Thankfully that day never came.

He reached his $100,000 goal with within 9 months of quitting, and have since gone on to create another startup popular startup, that is now generating $1.5M(est) in revenue a year.

How Damon Chen rode the AI wave and built the most searched PDF AI tool

As you will learn in this article, Damon has a unique approach to building. Maybe it’s because he lived in Silicon Valley among countless ambitious tech giants, Damon is someone who isn’t afraid of betting on himself.

When Damon first got started, adopted the “ship more” approach shared by many indie giants like Pieter Levels. Just keep shipping projects until something pops.

But. He is not like most other bootstrapped entrepreneurs is are afraid of taking risks.

He took some bets and they paid off.

Here’s 5 things he did differently and how you can do the same:

  1. Use a short, memorable domain – You will learn how this strategy helped him “steal” traffic from large competitors without much work.
  2. Buy, don’t build – You don’t have to build everything from scratch, even if you can.
  3. Link to your product everywhere – See how he links regularly to his products mid-posts.
  4. Share your MRR sensibly – You will learn why he thinks building-in-public is dead (and my take on this).
  5. Pay attention to product-led growth and your upgrade flow – I will show you how he uses a clever way to get people to upgrade to his paid tier.

Let’s dive into each of the 5 ideas above in detail:

1. Use a short, memorable domain

This is perhaps the single most pivotal decision he made for both and – buying premium domains for both.

And it all started when, the earlier product of the two, was mis-quoted by another popular Twitter creator, Joe Speiser. Joe’s tweet went viral, which should have been a boost for Damon.

But unfortunately for Damon, Joe misspelled the website and linked it to instead of

Which mean Damon received absolutely ZERO additional traffic from that viral tweet.

He made a decision that day to spend $35,000 buying, the misspelled domain TLD. And here is how his justified the decision, a napkin math:

Note: An increase in revenue correlates with a 10-fold increase in your business valuation. Obviously this assumes your SAAS can be valued at 10x revenue, which is likely optimistic outside of the US.

Then mid 2023 amidst the peak of the AI hype cycle, he snagged the domain for even less money (just $9,899!).

Judging by how many large corporates are now bidding on the “PDF AI” keyword, buying a short domain with that is a high search volume keyword is perhaps the single most important decision he made in his indie hacking career.

Now every time someone searches PDF AI, his website comes up as the top organic result. Even if he shuts down the entire business he can sell the domain to any of the 4 paid competitors above.

Oh. And the other benefit of using a short domain is you can do something fun like this:

Lesson: Use short, memorable domain for your business. Buy a premium domain if the value of the traffic you stand to gain is higher than the price of the domain.

2. Buy microSAAS, don’t build

As Damon is a software engineer before indie hacking, I would have expected him to build EVERYTHING from scratch.

And for the most part, that’s what he did.

But he did not build

Instead, he acquired the GitHub repo (aka the code base) for an AI PDF interaction product called Looseleaf. Then, he immediately rebranded everything under a more memorable domain and launched the product within days on Product Hunt.

Within 6 days, he made back his initial acquisition cost of the acquisition.

Lesson: Don’t assume you have to build everything. Even software engineers like Damon acquire weekend projects from other developers. Buy if it means you can save time on building and spend more time on marketing.

3. Link to your product everywhere

If you look at Damon’s Twitter profile you will see that he is not shy about linking to his own products EVERYWHERE he can.

Clicking on the image takes you straight to

For some reason, many people are worried about having their posts censored by social media giants like Twitter because the posts include external links.

But if you keep posting without linking to your product, you’re missing out on free traffic. You have to realise that most people are lazy. Almost no one bothers clicking through to your profile just to hunt for a link.

Here’s what another founder, Sandra Djajic says:

Put your links in your tweets!

Lesson: Put your links in your posts. It’s free marketing.

4. Share your MRR sensibly

Many indie hackers adopt the “build in public” mentality – sharing everything from their experiments to their MRR (monthly recurring revenue) publicly.

This approach certainly has its advantages.

It’s much easier to build a community of friends, get feedback and accountability when you share your progress.

But it comes at a cost.

Most bootstrapped entrepreneurs like Damon Chen, Pieter Levels, Danny Postma and many others stopped sharing their revenue metrics online once they reach a certain MRR treshold.

This is to avoid their products being plagiarised.

For many startup founders, having your product copied is a huge risk. And the bigger your MRR, the more people are interested in cloning your business.

No one will ever use a plagarised Facebook clone.

But a cloned version of a small startup without a strong branding?


In the customers eyes, it doesn’t matter who copied who as long as the product they paid for works. Who cares if it’s not THE original idea.

Lesson: Decide for your self if the benefits of building in public outweigh the risks. Share your progress authentically but keep your common sense.

5. Pay attention to product-led growth and your upgrade flow

Product-led growth means creating a product so valuable and user-friendly that it drives its own adoption and expansion. This approach empowers users to experience the product’s value firsthand, which naturally encourages upgrades and advocacy without heavy reliance on traditional sales and marketing efforts.

Damon designed product tours and onboarding campaigns for help free users quickly grasp the platform’s benefits.

Specifically, I think the way he designed his user upgrade flow is insanely clever.

For context, is a software Damon created to help business owners collect testimonials from their customers and clients and display on their website as a “wall of love” easily.

Instead of asking users to upgrade to a paid plan just to collect testimonials (after exhausting their free credits)…

Damon asks users to upgrade to access the testimonials, AFTER the additional testimonials are collected.

This allows the users to immediately see the value of upgrading before asking for payment.

Lesson: Experiment with when you ask your users to upgrade from free to paid.

Juicy ideas to replicate success

Damon Chen is an inspiring software-engineer-turned-indie-hacker who has recently found success by riding the hype of AI with his startup,

Here are the main takeaways from today:

  1. Find a short, memorable domain for your startup. You can also improve your chances of success by using domains that reflect popular search keywords like “PDF AI”. Use a formula like the one Damon shared above to work out whether the premium domains are worth you paying for.
  2. Link to your domain frequently. Don’t fall into the trap of being modest. Link to your product whenever it makes to do so. A short domain makes this easier to do without appearing spammy.
  3. Even software engineers buy projects. Your time is valuable and some opportunities don’t wait. Consider buying someone else’s project instead of building everything from scratch if you need to move fast.
  4. Be wary of over-sharing your revenue metrics. A high MRR will attract plenty of copycats. Don’t assume your customers will care that you are “the original” idea.
  5. Pay attention to when you ask your users to upgrade to a paid plan. Like in Damon’s case, give your users an immediate benefit when they pay.

What’s next

If you haven’t already, check out our other issue on How Pieter Levels built a $2M empire building things he loves or subscribe here to unlock the entire database of articles.

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Growth Strategies of Top Indie Makers Delivered to Your Inbox

Each week, we will reverse engineer the growth and distribution strategies used by top indie makers to grow their startups past $100k annual revenue. Subscribe so you don’t miss the latest issues!