
TL;DR: Today weâre 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 startupâa GPT wrapperâwould fail. Instead, one year later, itâs thrivingâwith about 500,000 registered users, nearly 3,000 paying subscribers, and over 2 million conversations in the GPT store.Â
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.Â
Today, AI PDF is one of the most popular AI-powered PDF readers in the worldâand 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, Vicenteâs 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 statementsâand even pit AI PDF against Perplexity live on the show. Here is a link to the episode transcript.
This is a must-watch for small teams building profitable companies at the bleeding edge of AI.Â
Watch on X or YouTube, or listen on Spotify or Apple Podcasts.Â
If you want a quick summary, hereâs a taste for paying subscribers:
TL;DR: Today weâre 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 startupâa GPT wrapperâwould fail. Instead, one year later, itâs thrivingâwith about 500,000 registered users, nearly 3,000 paying subscribers, and over 2 million conversations in the GPT store.Â
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.Â
Today, AI PDF is one of the most popular AI-powered PDF readers in the worldâand 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, Vicenteâs 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 statementsâand 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.Â
Watch on X or YouTube, or listen on Spotify or Apple Podcasts.Â
If you want a quick summary, hereâs 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 âupload their whole collection of files,â with some having âmulti-level foldersâ 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 âend-to-end workflowsâ with the documents theyâre 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 âis capable of doing things like creating new files, updating metadata in files, going through the file structureâŠto accomplish a job for the user.â 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 âwrapper-death countdownâ which keeps track of the number of days the company survived since the last time it was âpronounced dead.â Here are his thoughts on how startups can be successful in a market where the capabilities of frontier models continues to expand:Â
- Do one thing really well. Vicente takes the example of Loomâwhich got acquired for a nearly $1 billion for perfecting video recording, a feature that Vimeo and YouTube could have developed but didnâtâexplaining that while OpenAI and Anthropic focus on âthe minimum for core use casesâ to appeal to a broad audience, you can create value by ânailingâ 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 experienceâ at AI PDF by making the tool âlow frictionâ for their users, and ârespecting the intelligence [users] put in creating their folder structure.â
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:Â
- 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 âthe opportunityâ to disrupt the market by âintroduc[ing] a new way of doing thingsâ thatâs âjust too radical, typically, for the incumbents to be able to do.â
- 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 âwe are so early in this AI cycleâŠand the steady state or productivity state of the technologyâ is âshifting as we go along.âÂ
- 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. âWeâre trying to work with the core of our early adopter users and also listen to the ones already moving forward to the next thing,â Vicente says.
According to Vicente, AI doesnât 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 engineersâwhich would inevitably take more timeâhimself. âWith 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.â
- AI meets you where you are. Vicente notes that if youâre already technical, AI significantly increases what you can get done. Taking the example of his cofounder, he says, âeven for him, a world-class engineerâŠAI makes him so much more productiveâŠwhatever level youâre at, you become a lot more capable.â
As we talk, Vicente addresses two challenges facing startups at the cutting edge of AI: the persona of the user youâre building for and whether you should raise venture capital. Â
Who are you building for?Â
- 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 âpeople were risk takers and early adoptersâŠso we build for them.â
- 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 âthat they bring a lot of documents to the platform, theyâre basically trying to get some job done, and they want to do this in the new way, which is the AI-first way.â
To raise, or not to raise?
Vicente shares that when AI PDF was considered raising venture dollars, âthe beginning was fast, and the process started dragging along,â to the point where he was spending a chunk of his time âtweaking PowerPointsâ and âpreppingâ 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.Â
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, âWe want to be very diligent about when we do it, why weâre doing it, and how weâre going to use the capital that gets invested,â he says.
The future belongs to AI managersÂ
According to Vicente, we are moving away from question-and-answer chat interfaces to agents, where the user âgives [the AI] a task, and it executesâ independently.
Vicente views agentic systems as an âopportunity to build for a new experience,â requiring consideration about what tools to give the agents and questions like: âIs the tool good? Is it self-explanatory? Does it do what itâs expected to do?â 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. â[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.â He draws an analogy of how companies can rely on agents the same way âa very wealthy person operates through intelligent agents, [that is], people that they hire.â
Vicente believes humans will be a big part of a future with intelligent AI agents, noting that âit takes leadership, talent, vision, and grit to be able to organize these projects.â
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:
- Introduction: 00:00:35
- AI PDFâs story begins with an email to OpenAIâs Greg Brockman: 00:02:58
- Why users choose AI PDF over ChatGPT: 00:05:41
- How to competeâand thriveâas a GPT wrapper: 00:06:58
- Why building with early adopters is key: 00:20:49
- Being small and specialized is your biggest advantage: 00:27:53
- When should AI startups raise capital: 00:31:47
- The emerging role of humans who will manage AI agents: 00:34:53
- Why AI is different from other tech revolutions: 00:45:25
- A live demo of an agent integrated into AI PDF: 00:54:01
What do you use AI for? Have you found any interesting or surprising use cases? We want to hear from youâand we might even interview you. Reply here to talk to me!
Miss an episode? Catch up on my recent conversations with star podcaster Dwarkesh Patel, LinkedIn cofounder Reid Hoffman, a16z Podcast host Steph Smith, economist Tyler Cowen, writer and entrepreneur David Perell, founder and newsletter operator Ben Tossell, and others, and learn how they use AI to think, create, and relate.
If youâre enjoying my work, here are a few things I recommend:
- Subscribe to Every
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- Subscribe to Everyâs YouTube channel
Thanks to Rhea Purohit for editorial support.
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.
We also build AI tools for readers like you. Automate repeat writing with Spiral. Organize files automatically with Sparkle. Write something great with Lex.
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Ideas and Apps to
Thrive in the AI Age
The essential toolkit for those shaping the future
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can get from an AI subscription."
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