Think Different?

Stuart J. Ellman Jan 03, 2012 Back to blog


The New York City tech scene has become hip and has integrated into our culture.  This brings many positive factors into our fair city including an entrepreneurial spirit and a more risk taking culture.  I love that.  But, it has also brought a little bit of snobbery about what and who are “cool”.  I guess I noticed this about something that is really meaningless; how people dress.

Most of the younger guys at RRE wear the downtown uniform: skinny jeans, converse sneakers or funky shoes, untucked flannel shirt, and either scruff or a beard.    They looked at what I was wearing and rolled their eyes into the top of their head.  When they saw me wearing a suit and tie to the office when coming from a non-profit meeting, I saw them cringe.  Ditto for khakis and preppy shirts.  Heaven help me if I actually wore pleats.   Suits are for Wall Street guys, khakis are for people from Silicon Valley and pleats just stink.

Wanting not to appear out of step, I changed my wardrobe when I lost weight and needed new clothes.  All pleats went away.  Khakis went into the donation bins.  Slimmer jeans from J-Brand, AG, and Seven ended up in my closet with cashmere sweaters and better blazers.  My 18 year old niece mocked me for trying to look too hip.   My hair was even getting cut with a razor close to the sides of my head.  I was feeling good.

Then I went downtown for a board meeting with Recyclebank.  The CEO we have down there, Jonathan Hsu, is one of the best.  Brilliant, savvy, hard working, and analytical, Jon is fantastic.  Then I looked at what he was wearing.  The opposite of hip.  He dresses in Brooks Brothers blue or grey suits, white button down collar shirts and boring ties.  Don’t forget the black lace up shoes.  And then it struck me, why does this matter?   I wouldn’t trade Jon for a van of Varvatos-wearing, vespa-riding dudes.  So why does anyone care how I or anyone in technology dresses?

Steve Jobs’ brilliant campaign of “think different” comes to mind.  Apple used to be hip and cool AND different.  Now, everyone knows the Apple stuff is stylish and beautiful, but it is not different any more.  When everyone is “different” then different becomes the status quo.  And those that are not in the majority can get looked down upon.  And this is antithetical to the startup culture.  Bill Gates, Steve Jobs, and Steve Wozniak were hardcore geeks, not hip guys.

This is a business where success comes from great leaders entering new and unproven markets.  And there is a lot of failure.  I don’t care how they dress.  And if they care what I am wearing, then they are focused on the wrong things.  I bought two new pairs of khakis over the holiday break.  I guess I am just comfortable with living dangerously.