His GPT Wrapper Has Half a Million Users—And Keeps Growing

TL;DR: Today we’re releasing a new episode of our podcast AI & I. I go in depth with Vicente Silveira, the cofounder and CEO of AI PDF, a leading AI tool for document processing. We get into how small startups building niche solutions can win in the age of AI, when a startup should raise capital, and the changing role of human AI managers as agents become increasingly capable. Watch on X or YouTube, or listen on Spotify or Apple Podcasts.

Everyone told Vicente Silveira that his startup—a GPT wrapper—would fail. Instead, one year later, it’s thriving—with about 500,000 registered users, nearly 3,000 paying subscribers, and over 2 million conversations in the GPT store. 

Vicente is the cofounder and CEO of AI PDF, a tool to help you summarize, chat with, and organize your PDF files. When OpenAI allowed users to upload documents to ChatGPT, the consensus was that his startup, and all the other GPT wrappers out there, were toast. Even when some of his competitors closed up shop, Vicente believed they could still create value for users as a specialized tool. The AI PDF team kept building. 

Today, AI PDF is one of the most popular AI-powered PDF readers in the world—and they did it with a five-person team and a friends-and-family funding round.

I sat down with Vicente to understand, in granular detail, the success of AI PDF.

Vicente explains how staying small and specialized is a key strategic advantage for his business. We get into why lean startups are better positioned than companies like OpenAI and Anthropic to create cutting-edge solutions for users, the role early adopters of technology play in shaping the market for new products, Vicente’s candid take on raising capital as a growing startup, and his thoughts on the emerging role of AI managers who will be responsible for overseeing AI agents. We demo an agent integrated into AI PDF, prompting it to analyze a bunch of recent articles from my column Chain of Thought and write a bulleted list of the core thesis statements—and even pit AI PDF against Perplexity live on the show. Here is a link to the episode transcript.

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This is a must-watch for small teams building profitable companies at the bleeding edge of AI. 

Watch on X or YouTube, or listen on Spotify or Apple Podcasts. 

If you want a quick summary, here’s a taste for paying subscribers:

How you can compete with frontier AI companies

I asked Vicente why customers use AI PDF instead of simply uploading their PDFs to ChatGPT. He explains that AI PDF offers more functionality for this use case than ChatGPT: While the latter has limits on the number of files one can upload, AI PDF allows users to “upload their whole collection of files,” with some having “multi-level folders” and more than 150,000 files in a single account. Vicente says that AI PDF is also a more powerful tool because it enables users to create “end-to-end workflows” with the documents they’re working with. To be more specific, through ChatGPT and Claude, an AI is given access to the documents in question; at AI PDF, an AI agent is given direct access to a cloud drive, which means that the agent “is capable of doing things like creating new files, updating metadata in files, going through the file structure…to accomplish a job for the user.” AI PDF also gives tech-forward users the ability to use models from different frontier companies on the same platform.

Vicente jokes that they have an internal “wrapper-death countdown” which keeps track of the number of days the company survived since the last time it was “pronounced dead.” Here are his thoughts on how startups can be successful in a market where the capabilities of frontier models continues to expand: 

• Do one thing really well. Vicente takes the example of Loom—which got acquired for a nearly $1 billion for perfecting video recording, a feature that Vimeo and YouTube could have developed but didn’t—explaining that while OpenAI and Anthropic focus on “the minimum for core use cases” to appeal to a broad audience, you can create value by “nailing” your use case.
• Make the user journey delightful. You can differentiate your tool from a general-purpose chatbot by designing a better experience for your customers. Vicente explains that they created a superior "product experience” at AI PDF by making the tool “low friction” for their users, and “respecting the intelligence [users] put in creating their folder structure.”

Why small teams will win in the age of AI

This is why Vicente thinks lean startups have an advantage in the age of AI: 

• Having fewer users can be a good thing. According to Vicente, a large, diverse customer base is both the strength and weakness of big companies, leaving them to cater to mainstream use cases, and giving startups “the opportunity” to disrupt the market by “introduc[ing] a new way of doing things” that’s “just too radical, typically, for the incumbents to be able to do.”
• The best way to grow is with your customers. Since startups have the chance to build for early adopters, they tend to stay relevant because their products track how a new market is evolving, something Vicente believes is important in the age of AI because “we are so early in this AI cycle…and the steady state or productivity state of the technology” is “shifting as we go along.” 
• The customer is king, even in the age of AI. The early users of your product are valuable partners because they encourage the development of new technology, while also having a higher tolerance for the risks that come with experimentation. “We’re trying to work with the core of our early adopter users and also listen to the ones already moving forward to the next thing,” Vicente says.

According to Vicente, AI doesn’t just give startups a headstart, it also enables them to do more, specifically:

• Broaden the possibilities of what you can do. From his experience as a product manager at Meta, Vicente explains that AI enables him to do many of the tasks he would have had to delegate to engineers—which would inevitably take more time—himself. “With the tools that we have now, we should be able to be a lot more efficient, and do things that would only be available to larger companies.”
• AI meets you where you are. Vicente notes that if you’re already technical, AI significantly increases what you can get done. Taking the example of his cofounder, he says, “even for him, a world-class engineer…AI makes him so much more productive…whatever level you’re at, you become a lot more capable.”

As we talk, Vicente addresses two challenges facing startups at the cutting edge of AI: the persona of the user you’re building for and whether you should raise venture capital.  

Who are you building for? 

• Bold early adopters. Remember that your audience is willing to try new technology, despite potential uncertainties. When AI PDF shifted from uploading documents through Google Drive and Dropbox links to directly on its website, Vicente found users to be more adventurous than expected, noting that these “people were risk takers and early adopters…so we build for them.”
• People who have a problem. Beyond early adopters, seek out users who have a specific problem to be solved. Vicente says the common denominator between AI PDF customers is “that they bring a lot of documents to the platform, they’re basically trying to get some job done, and they want to do this in the new way, which is the AI-first way.”

To raise, or not to raise?

Vicente shares that when AI PDF was considered raising venture dollars, “the beginning was fast, and the process started dragging along,” to the point where he was spending a chunk of his time “tweaking PowerPoints” and “prepping” for calls with VCs, all while AI PDF users were proactively requesting the team to build new features. At this point, Vicente and his cofounder decided that it would be a better use of their time to focus on refining the product and creating ways to monetize it. 

Vicente thinks that AI PDF might raise a round in the future, but only when the team knows where they would deploy the money, and how it would help the company grow. Careful not to fall into the trap of startups who grow complacent when they raise too much money, “We want to be very diligent about when we do it, why we’re doing it, and how we’re going to use the capital that gets invested,” he says.

The future belongs to AI managers 

According to Vicente, we are moving away from question-and-answer chat interfaces to agents, where the user “gives [the AI] a task, and it executes” independently.

Vicente views agentic systems as an “opportunity to build for a new experience,” requiring consideration about what tools to give the agents and questions like: “Is the tool good? Is it self-explanatory? Does it do what it’s expected to do?” For example, he describes a real opportunity AI agents are creating at his own company: Vicente thinks the onboarding for new users of AI PDF can be improved, and he wants to hire someone to build and manage an AI agent assigned to onboard new users. “[I]t's kind of an interesting way to think about these things, where we feel that as we hire people, they will end up being responsible for certain agents on the product that will have specific jobs.” He draws an analogy of how companies can rely on agents the same way “a very wealthy person operates through intelligent agents, [that is], people that they hire.”

Vicente believes humans will be a big part of a future with intelligent AI agents, noting that “it takes leadership, talent, vision, and grit to be able to organize these projects.”

You can check out the episode on X, Spotify, Apple Podcasts, or YouTube. Links and timestamps are below:

• Watch on X
• Watch on YouTube
• Listen on Spotify (make sure to follow to help us rank!)
• Listen on Apple Podcasts

Timestamps:

1. Introduction: 00:00:35
2. AI PDF’s story begins with an email to OpenAI’s Greg Brockman: 00:02:58
3. Why users choose AI PDF over ChatGPT: 00:05:41
4. How to compete—and thrive—as a GPT wrapper: 00:06:58
5. Why building with early adopters is key: 00:20:49
6. Being small and specialized is your biggest advantage: 00:27:53
7. When should AI startups raise capital: 00:31:47
8. The emerging role of humans who will manage AI agents: 00:34:53
9. Why AI is different from other tech revolutions: 00:45:25
10. A live demo of an agent integrated into AI PDF: 00:54:01

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Dan Shipper is the cofounder and CEO of Every, where he writes the Chain of Thought column and hosts the podcast AI & I. You can follow him on X at @danshipper and on LinkedIn, and Every on X at @every and on LinkedIn.

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