The Little Things

Americans have  been dressing down for years now.  Just look at Mens Warehouse.  Place is empty   When you go to a startup event if you don’t have a t-shirt on you feel out of place.  Essentially you should have on some All Birds, be a bit unshaven and maybe even not fresh out of the shower.  Business casual could be flip flops

I don’t like it.  Sometimes I think I should teach a class in etiquette and the fine art of working your way around a place setting but I digress…

I agree, you cannot tell a book by its cover.  Judging someone by their appearance can be short sighted.  The person that looks and smells like a miscreant might be the most incredible entrepreneur ever.  Remember, in business, you need to be able to flow seamlessly from culture to culture.  It pays to remember, it’s “the suits” that have the money to spend.  You are playing on their field, not yours, when you are selling to them.

I remember when we were interviewing investment bankers to take CME public.  One bank showed up in trading jackets.  Cute.  I laughed but it didn’t help them build any bridges.  We knew they weren’t one of us.  There was no way they could have been one of us.  If they were, they’d have been sitting on our side of the table.  They’d have been better off coming in crisp.  That was our expectation of an investment banker that is going to raise a bunch of money for you when you take your company public.

If you are a startup business and you want a corporation to ensure its employees, customers and business with you, best to be on the safe side and look sharp.  I get that the world is a lot more casual.  We like to poke fun of the guys that wear suits all the time.  When I was trading and a Congressperson visited the floor I often had a polo on, a tie around the neck of the polo, gym shoes and khakis.  It wasn’t until I started dressing better that I gained more respect and got more responsibility in the PAC. When I visited Congresspeople in Washington, I had shined shoes and a pressed shirt and suit.  I was on their turf, so I wore their uniform and spoke their language.

When I see an entrepreneur, I always look at their shoes.  If they are wearing gym shoes, do they look tattered?  If they are wearing leather shoes, are they taken care of?  Do they look crisp, or do they look disheveled?  If we go out to eat, do they know their way around a table setting?  Do they have manners?

One time I was talking with an entrepreneur.  He said, “Do you have any advice for me?”  I said, “Shine your shoes.”  Entrepreneurs that take the time to take care of themselves and their clothes take care of their employees and their businesses.  They aren’t always successful, but they are present.

There are outliers.  I am not saying you should look or be like Downton Abbey.  But, you shouldn’t look like a gangsta rapper or a rock star either.

I suppose it doesn’t matter in the B2C software world where you are creating the next great app for a phone but in our world of B2B Fin Tech you cannot sell in a hoodie and ripped up jeans.  I remember my first boss Harry Toussaint complimenting me on how I ate breakfast and that one of his sales reps had no business taking anyone near a restaurant because of how they ate.

Thank goodness for good parenting and the Air Force Academy.  By the way, you never pass food over an officer.  I learned the hard way.

I was thinking about this because today I have to do a presentation and then go to a black tie.  I spit shined my shoes to glass.  I went out and bought some edge dressing because they needed it.  I knew at the place I was presenting I was going to wear a sport coat, but I wondered if I should wear a tie?  I don’t want to embarrass my host. 

Remember, it’s not always about you.  We all aren’t Steve Jobs or Mark Zuckerberg.  Not all of us are icons.  If you read Shoe Dog, you’ll see Phil Knight went out of his way to look as good as he good given the situation he was in.  Even if you don’t have a lot of money, you can look crisp.  By being crisp and put together, you can set yourself apart.  It’s not the 50’s and we aren’t all Men in Grey Flannel Suits.  This is not hard.

Finding decent clothes these days is pretty easy if you are a standard size.  Cheap too.  A lot easier then it was for me back in the day.  Especially at my size.  I wear size 14A and a 46XL suit.  It’s a pain in the ass to find good stuff at a decent price.  When I buy stuff, I hold it for a long long time.  I have some shoes that are 10-20 years old.  In my first job, I had to call on auto body shops in a suit and tie.  Try demonstrating a grinding disc or selling some caulk dressed like that.

If you are a startup, prior to meeting a customer or a potential funder, do you take stock of how you look?  If not, you should.  You have one chance to make a good impression.  Better to err on the side of formality than not.  What if your competitors are?  It could mean the difference.

I am in NYC today and tomorrow