Startup.com

 Startup.com drove me completely insane. These people did not have it together, seemed to really only have half of a clue as to what they were doing and they brought together all of these people with this half baked idea and then failed. Catastrophically.

Towards the beginning of the film there was a potential investor that our boys Kaleil and Tom had gone to go get some money from who told them they had a bad idea that wasn't going to be financially viable. After leaving Kaleil proceeds to say "this guy doesn't get it" but I must say: If after leaving an investment meeting you have to say "this guy doesn't get it" then perhaps you should reconsider your position. Maybe the idea is bad, maybe you presented it poorly. Either way your takeaway should be that you need to rethink and refine either your plan or approach before you move forward.

Later on they're in a big meeting trying to get a huge investment and they literally had their lawyer on speakerphone to talk through the deal rather than taking the time to have the lawyer actually review the offer. This is insane. This is the kind of thing that only people who have no ability to patiently plan and follow that plan will ever do. If you are in a position to enter into a major legal agreement and feel that you just absolutely can't take the time to have your own counsel review the agreement prior then that should not only be a red flag but it should come with flashing lights and alarms! Take the time, review the deal, do what's safe and right for you and your partners.

Throughout the whole documentary everything they did felt rushed at ever juncture. It felt as though they took everything personally and treated every situation like it was a fire that needed extinguishing rather than a problem waiting for a thoughtful solution. Ultimately I think that in their hubris they didn't really refine the idea or listen to the people who could have helped along the way. Towards the end of the line there's a scene where the lead developer is talking to Tom just desperately grasping and trying to figure out what exactly the software needed to do as they've already launched the site and are trying to function as a company. If you get to the point where you have clients and service live but your developers still don't really understand what you're trying to do then you have a problem. Either you've got some incredibly strange developers who can build magic software without knowing what it does, or you have such a fundamental breakdown in your communication and understanding that you might want to review everything you've done up to that point. I think you can bet which one of those situations is more likely.

In the end at all comes crashing down. The overly-personal investment, the high energy rushed attitude, the failure to refine an idea into a service they could provide. It all crumbles and falls out of the sky in a fireball approximately the size of one webpage. Tom went on to be not at all noteworthy and some years later Kaleil went to prison for accounting fraud. Stellar examples of thing not to do if you'd like to be successful.

On a side note: They were using Ask Jeeves at the beginning and that was delightful.