The Side Project I am Building to End My File-Request Nightmares

So here's the thing about client work that nobody warns you about: the most frustrating part isn't the actual work—it's getting the materials you need to even start the work.

I can't tell you how many hours of my life have disappeared into the void of "Hey, just following up on that logo file" emails. Or how many projects have stalled because I'm waiting on a signed contract that's sitting forgotten in someone's inbox.

Last month, I hit my breaking point. I was juggling four client projects, and literally half my workday was spent writing variations of "Just checking if you got my email about..." messages. Not billable. Not productive. Just... chasing.

That night, I started sketching out a solution. What if there was a tool that made requesting files as simple as typing what you need, generating a link, and letting technology handle the rest?

Two late-night coding sessions later, PleaseSendMeThis.com was born.

The Concept: File Requests Without the Friction

Before diving into the technical details, let me explain the core idea. I want the entire experience to feel like this:

I type: "Send me your logo in vector format and the signed contract." The system instantly creates a form with those exact fields. I share a link with my client. They click, upload, done. I get notified, they get thanked, and we both move on with our lives.

No accounts. No downloads. No friction.

To verify I wasn't reinventing the wheel, I tried every file request tool I could find. They all fell short in the same ways. Most required too much setup time building forms field-by-field. Others forced clients to create accounts or download apps. Some lacked automated follow-ups, and almost all were too complex for what should be a simple task.

So I decided to build exactly what I needed—a lightweight web tool for quickly requesting files and information from clients without any hassle. The user simply types a natural-language request, and the system generates a shareable link. The client clicks the link to find an instant form and upload the requested files or input information, all without needing to sign up.

Core Features (or How It Actually Works)

Let me walk through the key components that make this system special.

AI-Generated Request Forms: Type Once, Done

The magical part is how you create requests. No form builder. No field configuration. Just type what you need in plain English:

"Please send me your updated logo in SVG format, your brand color hex codes, and a brief description of what you want highlighted on the homepage."

The AI then parses this into an appropriate form with a file upload field for the SVG logo, a text input field for hex codes, and a text area for the homepage description.

This is genuinely the feature I'm most excited about. It cuts request creation time from minutes to seconds. I've been testing this with GPT-4 and it's surprisingly accurate at determining the right field types. For example, it correctly identifies "Send me your headshot" as an image upload field, "What's your availability next week?" as a text field or potentially date picker, and "Share your company background" as a text area for longer content.

And when it's not perfect, you can quickly adjust the generated form before sending it.

Shareable Links: The Magic Delivery System

Every request generates a unique link that works like a mini-portal for your client. When they click it, they see exactly what you've requested, clearly labeled and ready for upload. No accounts. No downloads. Just a clean, simple interface that works on any device.

What I love most about this approach is that it meets clients where they are. No learning curve. No new accounts to create. The barrier to completion is as low as humanly possible.

From a security standpoint, the links are designed to be unguessable. Each link contains a random UUID or hash that's virtually impossible to brute force. Optional link expiration and passcode protection add extra layers of security for sensitive materials.

The Client Experience: Simple. Clear. Fast.

I obsessed over the client-side experience because, let's face it, if it's not dead simple, clients won't use it.

When your client clicks the link, they see a clean header with your request, a simple form with clear labels and instructions, upload buttons that work on desktop (drag-and-drop) and mobile (camera uploads), and a submit button.

That's it. No distractions, no confusion, no friction.

I've shown early prototypes to some non-technical friends and timed how long it takes them to figure out what to do. Most understand within seconds—always a good sign.

Automated Reminders: The End of "Just Checking In" Emails

This feature alone would have saved me countless hours over the years. Instead of manually following up, the system handles reminders automatically. You set a reminder schedule (e.g., 3 days after sending, then weekly). If items remain unsubmitted, the system sends gentle reminders. The client gets a direct link back to their upload page. You get notified when they finally submit.

I'm particularly excited about this feature because it eliminates the most awkward part of client communication. Nobody likes sending or receiving nagging emails, yet they're necessary to keep projects moving. Automating this preserves the relationship while still getting results.

Progress Tracking: Clear Visibility for Everyone

Both you and your client can see exactly what's been submitted and what's still outstanding. This transparency eliminates confusion and provides subtle pressure to complete all requested items. I've found that simply showing progress bars or completion status can significantly improve follow-through rates.

The Technical Side: How I'm Building It

For those interested in the nuts and bolts, here's how I'm putting this together. I'm keeping the tech stack modern but focused on performance and simplicity.

I'm building the app using Next.js for the web frontend and serverless functions, running on the Bun runtime for speed and efficiency. I'm utilizing Supabase for backend services – including PostgreSQL for the database and Supabase Auth for user management. For file storage, I'm using an S3-compatible approach where Bun's S3 client connects to Supabase Storage to securely store uploaded files.

Why this stack? A few reasons:

1. Next.js gives me the React-based frontend I love with built-in API routes and serverless functions
2. Bun provides ridiculous performance improvements over Node.js (important for file handling)
3. Supabase offers auth, database, and storage in one platform, reducing integration complexity

For the AI component, I'm currently using OpenAI's API, though I'm exploring local models for potential cost savings at scale.

The Data Model and File Handling

I'm structuring the data with several key tables in Supabase/Postgres: a Requests table for each request's details, a RequestItems table for individual expected items, a Submissions table for actual submitted data, and a Reminders table to track follow-up status.

File uploads are the trickiest part of the system. I'm leaning toward pre-signed URLs for direct S3 uploads to minimize server load and speed up the process. This approach allows the client's browser to upload directly to storage while maintaining security controls.

Security & Privacy: Protecting Sensitive Data

Since the tool will handle potentially sensitive documents, security is a top priority. I'm implementing several layers of protection:

1. Unguessable URLs with proper entropy
2. Optional passcode protection for sensitive requests
3. Encrypted storage at rest
4. Clear data retention policies
5. Minimal personal data collection
6. Proper access controls at every level

Future Integrations & My Development Timeline

While the core functionality is my immediate focus, I have plans for powerful integrations once the basics are solid. I'm particularly excited about a potential Chrome extension that would let you highlight text in Gmail, right-click, and instantly generate a request link you can paste into your email. That's the kind of seamless workflow I'm aiming for.

I'm building this in the open, with iterative releases planned:

1. Alpha (Now): Core functionality with minimal UI polish
2. Beta (April 2025): Refined experience, basic reminders, early adopter testing
3. Public Launch (May 2025): Full feature set, polished UI, open to everyone

Right now, I'm focused on getting the core request-and-upload flow working flawlessly before adding bells and whistles.

Why I'm Sharing All This

I know this post is unusually detailed for a side project announcement. But I believe in building in public and sharing the full journey—not just the polished end result.

This approach has several benefits. It forces me to think through all aspects of the project thoroughly. It invites feedback from potential users early in the process. It might inspire others working on similar problems. And it creates a comprehensive reference I can revisit as development continues.

If you've read this far, you're exactly the kind of person I'd love to have as an early tester or collaborator.

How You Can Get Involved

If PleaseSendMeThis.com sounds like something that would make your life easier, here's how you can participate:

Join the Beta by signing up at pleasesendmethis.com (*coming soon!) for early access. If you're a developer familiar with Next.js, Bun, or Supabase, I'd welcome collaboration. I'd also love to hear about your file request pain points or feature wishlist. And if you know others who might benefit, please share this post.

Final Thoughts: The Tool I Wish I Had Years Ago

Every time I chase a client for files, I think about how much better this process could be. We've made incredible advancements in technology, yet somehow, the simple act of requesting and receiving files remains needlessly complicated.

PleaseSendMeThis.com is my attempt to solve this problem once and for all—not with more complexity, but with radical simplicity.

Type a request. Share a link. Get what you need. Move on with your life.

That's the promise, and I'm committed to delivering it.