The Deal I Lost Before It Even Started

A Freelance Lesson

I was hanging out with a friend one evening, just chilling and having a few drinks. The vibe was good. My friend kept getting phone calls from work. He works for a billboard company which I will keep anonymous.

As the calls went on, I got curious and asked what was going on. He explained how they manage their billboard data. Everything was in Excel. To know which billboard was available or which client was currently using one, someone had to open and check an Excel file. Photos of the billboards were stored in a separate drive folder. On top of that, the Excel file was managed by only one person in operations.

Problems everywhere.

I could not help myself. I started explaining how this could be automated with a simple website. Simple in idea, not in execution. I broke it down for him and explained the value. We talked for almost two hours. I drew rough workflows and explained how the system would work. By the end of the night, he was convinced.

Later that week, he shared the idea with his seniors and it was well received.

They asked for a proposal.

I consulted a friend and a colleague and put together a detailed proposal. ChatGPT helped too. It was my first time writing one, so I took it seriously. The first two weeks were mostly emails and discussions. I helped my friend understand the flow of the system and how to present it to the board. I even helped him prepare for a board meeting where he would pitch the idea.

The core idea was to migrate the Excel data into a proper database. From there, enable full create, read, update and delete functionality. The system would allow updating billboard photos, which they do monthly. It would also allow booking available billboards, tracking clients, and many other features. One important feature was the ability to see the geolocation of each billboard. I explored multiple approaches.

I really put in the work. Every morning was research. I designed role based access for field agents, operations staff, and management.

Later, they asked for a mockup and a prototype. I configured an existing web setup and shared it with the team. At this point, there was still no payment at all.

During one internal meeting, their managing director mentioned that he had a friend who could help with the geolocation feature. The idea was to link my system with their app to get live coverage of the billboards. He insisted they had satellite access. I honestly did not believe this. Even Google satellite images are not updated that frequently. Where I live, recent buildings do not even show.

Still, we scheduled a meeting in town.

It was a Tuesday morning. We met at Java House. I dressed up and went with my friend. We shared our location and one guy arrived first. We introduced ourselves and did the usual small talk. A few minutes later, his developer joined us.

They then started a presentation.

What we had been told was that these guys would only provide satellite information. So my questions were around integration. How would we communicate with their app. I was basically looking for APIs and documentation.

But that was not the case.

They already had a billboard management system. Almost fully built.

That moment hit hard. It felt like a kick to the nuts.

What I did not know was that my friend had shared my proposal and mockups with their team. Another thing I should mention is that these two guys initially thought I worked at the billboard company. When I introduced myself as a freelancer and a developer, I saw their facial expressions change. It was clear what they were thinking. Competition.

During their demo, I noticed that some pages looked very similar to the mockups I had shared. I almost lost my composure but I kept it together. The demo went well. They were great at selling.

I asked technical questions. What stack they were using. How the frontend and backend were structured. It quickly became obvious they were not technical people. They could not answer much. They were sales guys.

Still, the meeting itself was polite and calm.

Realistically, I had no chance. The expectation was to have the system ready by January. I had estimated about six weeks to build a solid version. These guys were more established, connection with the MD and clearly ahead.

I took one of their contacts, thinking maybe I could still help in some way or join the effort. Till date I have never texted him.

I took my L.

I left disappointed. My friend noticed immediately. We went home without saying much. I was angry and bitter. You can probably feel it in this article.

But it was a lesson.

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Brief summary and lessons for freelancers

This experience taught me a few important lessons about freelancing.

First, never do extensive work without clear terms. Proposals, mockups, and prototypes are valuable. If possible, define ownership and scope early, even if it feels awkward.

Second, be careful with trust by association. Just because a friend is involved does not mean everyone in the chain has your best interests at heart.

Third, control information flow. Share only what is necessary at each stage. You can sell the vision without giving away the full blueprint.

Finally, losses are part of the journey. Not every pitch turns into a win, but every experience sharpens your instincts.

Sometimes you do everything right and still lose. The key is to learn fast and move forward.