The word "cliche" comes from back in the printing press days: Its pronunciation mimics the sound of a printer's mold striking molten metal, dating back to the 19th century.
While cliches have a natural ridiculousness to them—catch yourself if you find yourself rolling your eyes the next time someone talks to you about "going the extra mile"—a cliche also works as a heuristic, a quick guidepost that, if used sparingly, can clue you into what the hell is going on and help you navigate the future.
There's a contrarian libertarianism that bubbles up in the startup conversation: Like Y Combinator partner Paul Graham once wrote, innovation and heresy are basically the same thing. Like Uber and Airbnb have found, you can go after big, society-shifting innovations, but you can't ask for permission from the incumbents (or, in some cases, the government).
"I won't invest in a "ask for permission" deal," he writes. "They don't work."
Wilson argues that the entrepreneurs who have "just done it"—you could call it the Napster effect—end up in better places. Writing in 2006, Wilson predicted that YouTube would be able to get record labels and other content creators to play ball after building their audience and making their platform fun to use.
"Every time a company runs out of money and comes back to the VCs for more," Wilson observes, "you have to assess the management on how well they are doing, whether they are accomplishing the results that everyone wants, and whether it's worth putting more money in."
He says that Union Square generally wants to support their companies, but if the results aren't good, a company can't keep doing the same thing. This is why, Wilson says, "the price of new money" includes "material change" in the direction of the company.
"Leadership is figuring out where everyone is going and then getting in front of them and saying 'follow me'"
While Wilson admits that this one isn't really a cliche, it comes from his mentor Bliss McCrum, the King of Cliches who helped teach him the venture capital business. McCrum, he recalls, came from a big family—so this particular cliche-to-be comes summons the image of the venture capitalist rounding up all his children and running to the front of the line. That spirit of spearheading, Wilson says, applies to family and business life equally.
"Leadership isn't always about figuring out where to take your company. Many times, the company knows where to go better than you do," Wilson says. "So you have to listen to the company, and the other stakeholders; the customers, the board, the shareholders, etc. and make sure that you always know where they want to go. Then get in front and lead the way. It's that last part that is so important."
Have a cliche that's more heuristic than just a bunch of buzzwords? Let us know in the comments.
[Image: Flickr user Baltimore City Paper]