Last night I had the great pleasure of meeting Tony Hsieh, CEO of the massively successful retail site zappos.com.  As a testament to the usefulness of twitter and the approachability of Tony, I found out he was in San Francisco from a tweet, replied to him asking if he was going to be around later, and he invited me to a event he was attending at Mighty Bar (all via twitter), where a friend of his was doing an exclusive tasting of their new premium Liquor called Haamonii, which was delicious by the way.

So off I went barreling into SF with high hopes of meeting someone I greatly admire and respect, even if I only got to chat with him for a few minutes and it took me 45 mins to get into the city, I knew it would be well worth the trip.  While driving in at a slightly faster speed then the posted speed limit to ensure I actually would have some time to chat, I formulated a number of questions, mostly related to growing an eCommerce startup, raising money for inventory and marketing in a horrible economic climate, and getting feedback on our single category approach to online apparel sales.  One of the ways we describe our vision and strategy for hoodiepeople.com is “be for hoodies what zappos.com is to shoes, the preferred online destination for shoppers”.   I closely follow zappos in the news and Tony has helped me out a number of times with quick convo’s via twitter on early stage issues and advice.   He is undoubtedly one of the most approachable, transparent, and successful people in the world and if you get a chance to meet him or hear him speak, just do it, you will not be disappointed.

Upon arriving at Mighty, a cool bar in the  SOMA/Mission area of SF, I quickly spotted Tony and introduced myself.  First thing he did was introduce me to Alex, the UPS truck driver that serves Zappos in SF.  Tony asked how we ship, how much we pay, and a few other details and told me to get in touch with Alex regarding getting a zappos like rate for our small startup.  He specifically mentioned to push for a great shipping rate and that tracking a package and facilitating easy returns is a key factor in creating a great online shopping experience.  Point one taken.

From there I preceded to ask a slew of business related questions, which Tony addressed each time, but also dug a bit deeper and continually brought me back to one central point, is this business going to provide a source of personal satisfaction and happiness even if it never grows into a massive success.

I was literally stopped in my tracks a few times by this question, the truth being I’m not a huge hoodie fanatic or especially embedded into hip hop or surf/skate culture.  Personally my passion revolves around building a great business, being independent, and being  current and connected with the online community.   However, the hoodie is really special, I think its a clothing item that is rooted in self expression, utility, and comfort, hoodies are both useful and stylish.

It was clear Tony is far more interested in helping people find their passions, and guiding them to pursue them, then giving advice on improving conversion rates.  While he is highly knowledgeable in e-commerce and marketing, there is something much more important at play, and he very openly guides you to those big picture questions, so that you don’t end up following a path for the wrong reasons. Point two Taken.

Take a minute to check out this cool Nighline feature on company culture at Zappos to see how much they do to live by their core values and encourage people to be themselves and be great.