I remember seeing this interview with Carol Bartz at TC Disrupt: NYC (above).

Arrington: What is Yahoo?

Bartz: What is Yahoo? Yahoo is a company that is very strong in content. It’s moving towards the web of one. We have 32,000 variations on our front page module. We serve a million of those a day. It’s all customized. Our click-through rate went up twice since we started customizing this. People come to check the things they like. “You can just get it together.” Yahoo is one site people always stop at.

And with that, I decided that Yahoo! would not succeed with Carol Bartz at the helm as CEO.

Mind you, I’m no management guru. This is my first time wearing the CEO hat, and I screw up a plenty. So take that as a strong qualifier to what I’m about to say…

The CEO must, first and foremost, define and communicate a clear vision of and for the company.

What is [insert company name]? If no one inside or outside the company can answer the question, then there’s a problem. And problems of that magnitude typically arise from the CEO.

I saw this same problem at Drop.io, the Brooklyn-based startup that shut down this week in an asset sale to Facebook.

For a while, Drop.io was one of the hottest startups in NYC.

But for the longest time, I had absolutely no idea what they did. Mind you, this is when I was living in New York and actively involved in the local startup scene. If anyone was in a position to understand what they did, it was I.

One night, I attended a crowdsourcing meetup at the Drop.io HQ. Drinking beer afterwards, I asked a Drop.io engineer: “Maybe this is a stupid question, but what exactly is Drop.io anyway? What do you guys actually do?”

“Well, Drop.io is a lot of things. We have a robust chat application. We do real-time file synchronization. We…” And he proceeded to list out 10 more seemingly unrelated features. I’m sure he understood his particular task, but there didn’t seem to be any theme or story that unified all the products & features into an actual company.

The New York VCs seemed to love Drop.io, to the tune of $10mil over 3 rounds of investment. Word on the street was that they really just loved Sam Lessin, the founder. Apparently so does Facebook, as Sam’s name was singled out in company press announcement.

I don’t really know Sam. I’m happy he found a place to park the company’s assets and hopefully get his investors their money back.

But it seems like Sam––as much as he is described as a genius and fawned over by the people who actually know him––failed on the marketing front. Not just externally, but internally too.

From what I could gather as an outsider, Drop.io was the limitless company, a product that did everything for everybody, or tried to, anyways…and because of that, after December 15, will end up doing nothing for no one.

This is no personal dig on Sam, mind you, as I’m sure he tried his best.

But a big part of being a CEO involves requires you to decide on a core message––your founding story––then go out and repeat it ad naseaum to everyone who will listen, including bloggers, customers, investors, random people at bars, prospective hires, etc.

It takes repetition for a message to stick, and that means you, as an entrepreneur, have to repeat yourself over & over again in a disciplined and uncreative manner. Uncreative repetition is not why you become an entrepreneur, but it’s necessary to success so long as you wear the CEO hat.

It’s like being a political candidate: You have to go out and give the same damn speech time and time again. And if you want people to believe in you, you gotta do it with gusto. It ain’t easy, and it takes a special temperament to do it.

If you don’t? Well, then no one knows who you are or why you exist. And if they don’t know that, they won’t believe in you or your hallucination, they won’t part with their money, they won’t join your company, they won’t follow you down the dark hole of unknown that is being a startup. They won’t care.

And you fail, selling scraps of the dream, piece by piece, to the highest bidder, if anyone bids at all.