Skip to main content

The Best Advice I’ve Ever Received Came From a Creepy Old Guy

By July 28, 2014No Comments3 min read

As some of you may know, I grew up in the liquor business. Now, I was fortunate enough to have it turn into the wine business, but it started off

as the liquor business. When I was 16, there was a salesman from one of the liquor companies who was always around. He was a real raunchy, 80-something-year-old guy who was about as politically incorrect as you can get. One day he made yet another statement that made me think “you disrespectful dope,” but over the years it kind of stuck, and I think it’s worth sharing:

He said — and I need you to imagine this in an “old man who drinks too much bourbon and smokes too many cigarettes” voice — “Gary, you never know what you have until you sleep with it.” Now admittedly, he was trying to be douchey, but it was in the context of hiring an employee, and in the long-run, it kind of changed the course of my career.

I take a lot of pride in the fact that I have really good EQ (IQ’s emotional counterpart), and am a good judge of character, but the truth is that up until that point, I was crippled by the need to be perfect up front. Processing that statement removed the last parts of that thought process, and lead me to become the manager I am today.

As a leader and a business owner, I’m the kind of coach who is all about making halftime adjustments, and that statement, though raunchy, was absolutely true. You can read a resume, look at a P&L, or do any number of things to prep yourself for what you’re about to get into, but you just don’t know what the reality of the situation is going to be until you’re in it. Once you’re in it, and things maybe aren’t exactly what you expected them to be, you have no choice to make a call and adjust. You’ll never be able to force a different reality on the situation.

So this offhanded, inappropriate comment really had a big effect on me and the way I manage. Yes, you should do your homework, but you don’t really know what you’ve got until you sleep with it.