Johnson Cook

Atlanta tech investor. Entrepreneur.

Johnson Cook - Atlanta tech investor. Entrepreneur.

Fun Friday: What Entrepreneurs Wear


Entrepreneur Dress ThoughtsI’ve been avoiding starting a “fun Friday” pattern for one big reason. I know I can be disciplined enough to come up with some content 3-4 times per week, but committing to coming up with funny content: no way!   So don’t expect this to be a regular thing.

{ ///end reader expectation management }

So there I was in Vancouver, BC attending my first Global event with the Entrepreneurs Organization. After a long day of airports and taxis I was finally at the hotel. When you arrive at conference hotels, go through check in, and find your room, there is always that moment where you’re looking around for a familiar face. Looking around nervously to make sure you came to the right hotel… or the right city… on the right date.

After I checked in, I went straight for the elevator, the door opened and there stood 4 guys. Every single one was dressed in jeans, black dress shoes, dress shirt (no tie), and a sport coat.   Ah-HA! I had arrived! That is the unmistakable entrepreneur’s uniform!   We all had a laugh and I was right.  It’s not surprising to share that my suitcase in two had 3 pair of jeans, 2 sport coats, and 3 dress shirts.  So yep.

So I think I’ll start keeping notes on my observations of entrepreneur dress habits. Here we go:

Observations on jean-based concoctions…

  • Nice jeans are the assumed leg coverings when something says business casual. Screw khakis as “business casual.” Those are for people who work for the man!
  • Dress shirt untucked + jeans is ok if you run a technology company.  It’s also ok if you are friends with someone running a tech company. Or if you own a Mac.
  • If you are really high-tech savvy, mandatory t-shirt with your company logo under a sport coat.
  • If you are also the head coder/engineer and the CEO, you can do an untucked T-shirt and jeans. You are really kicking ass if that’s you.   Nobody expects you to dress nicely, you’ve been up writing code and eating pizza all night then running finance and board meetings all day. You are really busy! (Just make sure you wear the thickest rimmed glasses you can find to complete the ensemble. Even if you don’t need them.)

Briefly on ties…

  • A CEO friend of mine says: “I only wear a tie if someone died or we are talking about someone else’s money.”  That seems to work for me.   It’s also why my money manager and lawyer friends have to tie up daily. Constantly dealing with OPM.
  • Ties suck.

Completely random, possibly useless observations…

  • It’s ok to wear a polo.
  • Polo under a sport coat is like superman showing off his “S” by leaving his top button unbuttoned. It tells everyone that the coat is just there to get you through this boring event, and soon after that thing will be thrown in the back seat as you drive to the golf course in your comfy polo.
  • If you want to show off how you’ve lost weight because you are a rockstar and working out: tuck in your shirt to your jeans and pull your belt tight. You are successful AND healthy!  (This serves the secondary purpose of keeping your pants up since they probably don’t fit since you’ve lost weight.)
  • Black polos are as good as suits. They mean respect but you want to be comfortable. So it’s really ok to leave a black polo untucked.
  • To demonstrate that you are living the dream (whatever dream it is), wear shorts and a polo to a breakfast meeting. It shows that you are playing golf later that day, even if you don’t own golf clubs.
  • If you run a creative company, you should look as sloppy as possible. A well-dressed creative person is just out to get my money. I want to hire the creative who looks like he hasn’t showered in 3 days.

I could go on, but this feels a lot like wasted time. More to come later as I continue to observe the strange dress habits of entrepreneurs.

Note, I’m not proclaiming that any of this is “code” or rules” … purely observational.



Category: General, Ideas
  • Dodder says:

    Love it Johnson!

    May 26, 2012 at 1:34 pm

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