VC Cliche of the Week

Most entrepreneurs are smart, many are very smart.

But one of the things that entrepreneurs need to watch out for is being too smart for their own good.

We call that "too clever by half".

It’s a cliche I’ve used and heard used for as long as I’ve been investing, but I honestly have no idea where it comes from.

I did a little work on the web, and the best I could come up with was this.  I suspect the origin of this cliche is british, but beyond that, I have no clue where it comes from.

Whatever the origin, its a good phrase.

I remember one of my earliest investments.  The entrepreneur was really smart but whenever he had a deal to work on, he’d always try to optimize it way beyond what was necessary.  He’d get too cute and in the end all the complexity worked against getting the deal done.

I recall another deal early in my career where the entrepreneur had a company interested in buying his business.  It was a good deal.  But he tried to carve out a part of the busines that he thought the buyer wasn’t interested in.  The buyer didn’t really want that part of the business but they thought the entrepreneur was trying to pull a fast one on them and the mistrust that developed killed the deal in the end.

The phrase "keep it simple stupid" is really great advice for anyone who is really smart and prone to overcomplicate and overanalyze things.

The tendency to overcomplicate things often shows up in business plans, business models, product plans, and the products themselves.  And things that seem really interesting and attractive on paper often don’t end up being very attractive in real life.

I have come to believe that the act of reducing something to its essential elements and focusing laserlike on them is the best thing an entrepreneur can do.

Because being "too clever by half" is often the kiss of death for a business.

#VC & Technology