As bloggers we spend a lot of time waxing poetic about how not to to make mistakes. Our problem is that we often forget our own hard lessons and all those mistakes that we made over the years that brought us to this point. Just as a change of pace, today I am going to take a look at a project that I worked on about a year ago, Orangeply. All you really need to know about the application itself is that it was supposed to revolutionize online identity and would have been the next collaborative, social, crowd-sourced Web 2.0 super-app (ugh).

Needless to say, it failed miserably. Here are a few reasons why.

Path To Failure

Lack of resources. The biggest mistake was a lack of cold, hard cash. It’s the oldest story in the book. We had a really big idea, but didn’t have the money to put it together. It didn’t help that our credit histories were nonexistent and our total assets equated to a bank rounding error. Had we been a touch more clever, we would have recognized that the problem wasn’t the idea itself but the scope. We were trying to build the Sears Tower out of matchsticks, and when your imagination builds an idea bigger than reality, it’s only a matter of time before it comes back to bite you.

Feature Creep. A corollary to lack of resources was an explosion of scope. When you sit a handful of programmers and engineers in a room and have them plot out the road map to a web application, it’s amazing how quickly a simple idea can become a White Whale. We must have generated a hundred pages of paper before we wrote a line of code. Sure, it’s always better to outline your projects before jumping into them, but if your ALPHA needs weeks of pure thought to make it coherent enough to start, the problem might be the idea itself. Throw in the fact that all of this thinking was unpaid work and you quickly arrive at the next problem.

Distractions. I would like to see the statistics on how many projects die a still birth just because the people involved in them have to cut back in order to keep paying their rent. Distractions comes in many different flavors, but the ones that are attached to dollars can be the most damning. Between classes, work and trying to maintain some semblance of a real life, we were managing to burn the candle at both ends without going anywhere. The lesson here is that before jumping into any project, you would do well to ask yourself just how much you’re willing to commit. Until you get things off of the ground (and even after), you are going to be broke, tired and mostly unavailable to your friends and loved ones. It’s a hard life, be sure you know what you’re getting into.

Team Composition. One thing I try to tell people who want to build a web project is that the team they have is the only source of work they can count on. We had a lot of talent but if we had taken any time at all to take inventory of ourselves we would have seen the gaping holes in our team. More importantly we would have noticed that we had no real plan to plug them. It’s great if you have a whizbang front-end developer, it’s fantastic if you have a marketing guru, it’s stellar if you have an IT guy who builds servers in his sleep, but if you don’t have someone to get the back-end up and running and you have no money to outsource the task, you’re shooting in the dark.

Venture Hunting. When you have no cash, big ideas, no reasonable business model and stars in your eyes what’s the first thing you should go out and do? Look for VC, of course! There is nothing more draining for inexperienced entrepreneurs than hunting for investors. You will get a lot of doors slammed in your face and for good reason — your idea probably isn’t that great. In our case, the chimera we had built was too dependent on network effects. Said differently, we could make a ton of money, if we had 100,000 people using it. When you’re in the trenches, you don’t want to see that it’s your idea that has the problem, not the investors. Blame is a poison that can quickly burn it’s way into the heart of your idea. Once it’s there, it is hard to do anything other than beating your head against the wall and complaining. The only way out of the trap is to understand that you’re only real job as an early stage entrepreneur is to constantly improve. Learn to accept criticism with humility.

Counting Your Chickens. Looking at the rest of these points, you would think that depression would have set in before long. The fact is that just the opposite happened. The more unreasonable it became that we would actually complete anything, the grander the castles that we built in the sky. After you get off the phone with a few big names who, for whatever reason, were willing to hear you yap on and on about your “vision,” it becomes really easy to buy into your own hype. If blame is a poison, over-confidence is a cancer. You don’t have anything that is worth celebrating until you get a real piece of software written. If you find yourself celebrating week seven of brainstorming sessions you are missing the point entirely.

Failure to start. That brings me to the nail on which all of the rest of these hung, we failed to begin. We talked, we planned, we mocked up, with prototyped but we never committed anything to reality. Instead of recognizing that our product had grown too large and scaling it back to the point where we could actually build it, we decided to put our faith in the nameless investor who was supposed to bail us out. When he didn’t show up, instead of finding a way around the problem we let the wall we hit crush us.

There you have it, a cocktail of bad ideas that eventually lead to us quietly shelving the concept. Of course, without ordeals like that it’s impossible to learn the nuts and bolts of building a business that must be second nature if you’re going to be successful, but when you’re pushing against a bad idea it’s hard to look at it in terms of the wonderful lessons you will learn later.

Do you have any “war stories,” if so what did you learn?

(Image) (RSS) (Forum)