One of the most frustratingly paradoxical things about startups is how outsiders deal, or don't deal well, with your extremes.  Your greatest weakness in one advisor's eyes may be your greatest strength in the eyes of a board member.  Allow me to explain…

Investors, pundits, experts, folks in the community, etc. all want their startup CEOs to be bold and interesting. Some want you to be a contrarian, but not too much.  Others want you to be independent, but not too much.  They want you to enjoy some modicum of work-life balance so you don't lose your mind, but not too much.  You should be outspoken, but you shouldn't rock the boat.  Definitely be inventive, but not so much that you can't find immediately enthusiastic customers willing to write a check.  Be persistent.  But you'd better succeed because as much as we talk about our admiration for people who keep trying Abraham Lincoln style, we really don't respect anything other than bottom-line success.  Network, but focus on your early stage business and your product.  Listen, but stay focused on your strategy and your approach to the marketplace.

Startup CEOs walk a fine line of all of the above, all while representing a business, an opportunity, and the people that make up the organization he/she leads.  Cross the line at all and you'll be judged, often harshly, by people who don't know you or your story.  But whatever you do, don't let it discourage you.  It's at times a lonely life — but it is the cross you bear for choosing "the road not taken".

Now don't take any of this as a complaint — I love what I do.  But if you set out to make everyone happy as a startup CEO, you're in the wrong business altogether.  You have to have a thick skin to run a startup, and sometimes you have to sometimes be "appropriately extreme" at the right time to make the right decisions.  You're going to be a genius to some people and an idiot to others.  Just don't let it get to you, and be the chameleon you need to be to make the right choices in real-time.