When Failure Attacks! Startup Edition.

Those who know me would know that I was working on a startup with a few friends/ex-colleagues that I thought had some real promise. We had a couple developers and a couple product managers, and an interesting idea. Recently, the wheels have fallen off. It's been a couple years now, we have a fair amount of code written, we have incorporated, have a bank account, operating agreement, tax documents, computer equipment, a humble web presence, and a bunch of plans. I just wanted to talk about what went wrong and what I would have done differently, and what I WILL do differently when I try again, because I am definitely hooked.

What Went Wrong

1) No Idea Validation - An idea is great in the minds of those who had it. I will admit readily that this idea was not mine, but I still think it's a great idea. The problem is that nobody who was in a position to a) buy the software, b) invest in the company, or c) partner with the company was ever spoken to to find out if this was really a good idea. How far in to the game do you talk to people? Do you worry that those people are going to say "hmm, good idea" and then do it themselves or find a different partner? Do you have faith, draft your NDA and go forth into the fray? Do you trust that it's a good idea and wait until you have something demoable, then go full bore?

2) No Time - We had a large discrepancy between what needed to get done, and how much attention it required, and how much time people were willing to spend to accomplish it. This was a strictly after-hours proposition, and we all worked at challenging jobs, but we all knew that was the deal, and we just didn't make this business a high enough priority. Deadlines weren't met, and worse, they often weren't set. This is an "all-in" game that we were playing, and we weren't giving it "110 percent".

3) No Networking - There are tons of ways to meet people who know people who have ways of helping, investing, or at least validating your idea - there are huge, active communities full of people who live for this stuff, and we didn't harness that at all. Bad, bad, bad. This was totally correctable, and will be one of the first things I do when I come out of mourning.

4) Plans Too Grand - We didn't have good checkpoints. We didn't have a great way to get demoable software out piece by piece. We had a big huge roadmap that included the kitchen sink. It was too much. We were too late in trying to identify the critical path (also see failure #1). We were going to build it all, an entire enterprise software product, in our spare time? Two of us? Yeah right! Who were we kidding? We needed to prove the concept with a small subset of the eventual product so that we could get funded or find a partner. Hindsight...

5) Bad Technology Choices - I take the full blame here. I am a Java developer. It's what I have been doing since I started in this industry. It's what I am good at, what I know, and where I feel most comfortable. So we chose Struts/Hibernate/Tomcat. It's documented, it's established, it's a known quantity. It's also not the fastest way to get something done. If I started again, in 2006, I would have used Ruby on Rails or maybe even PHP. When I start again now, I will use Groovy and Grails. The productivity gains you get from these frameworks are simply too valuable to ignore, especially when you are strapped for time.

So, for these and other reasons, we failed. It sucks, but I will do better next time. Please feel free to comment with any sort of tips or experiences that you've had along the way in your entrepreneurial career.