I firmly believe that no entrepreneur can truly be successful without being, at least partly, insane.  Entrepreneurs need to think outside of the box to create things that have never been created before.  They need to test every boundary and create their own rules.  The best innovators whom I have interacted with and have learned about are the ones that have said f*** off to the status quo and seek to change the world.  Let’s try a Boston example of this – IdeaPaint.

If you’re not familiar with them, IdeaPaint has created a whiteboard paint that can be applied almost anywhere to create endless brainstorming space.  One of the reasons I know this company so well is because at MassChallenge, we are home to the world’s largest continuous writable surface made completely of IdeaPaint.  This idea came out of Babson’s E-Tower when a group of Freshman students had a need for brainstorming space and covered their entire walls in white paper.  Not to long after, they were running out of room and had to replace the paper.  The solution – paint that could be used as a white board.  To these student’s surprise, nothing of this sort existed and after a bit of research everyone had told them it was an imposible product to create.  To use a tacky line originated by Adidas and repeated by my boss, John Harthone, Impossible itself says I’m possible.  It’s true though – these students spent the next few years working with chemists and engineers to develop what is now an award-winning product with over 50,000 installations in dozens of countries around the world.

Now, how does all of this craziness and perseverance relate to me?  Well as the Director of the Husky Startup Challenge and an executive board member for the Northeastern Entrepreneurs Club (aka. the #6 entrepreneurs club in the world!) part of my job is figuring out ways to make our weekly get togethers fun, entertaining and a bit scandalous.  One way I have been able to help accomplish that by securing rockstar speakers such as this week’s Jonathan Kay, Ambassador of Buzz at Grasshopper.  The other way is through integrating really unexpected “ice breakers”.

When I was first brainstorming crazy ice breakers that would get members engaged as well as create a fun atmosphere in the club I thought back to high school and other experiences I have had that may have been cleaver.  All I could remember was three truths and a lie, something about cutting string into bracelets and the good old “bring something to a picnic that begins with the first letter of your name”.  These weren’t innovative.  They weren’t outside the box.  They didn’t say f*** you to the status quo.  At our executive board meeting I had an epiphany – I’ve never done an ice breaker involving ice.  I got on the phone with a local Ice Company and a few moments later had a delivery schedule for a 300lb. block of ice and went to buy a sledge hammer to break it with.  It was a huge success – members loved it, no one expected it and I got to meet a few new members thanks to it.

Now, the next problem was finding a way to follow-up an “ice breaker” like this.  I will say, my next idea was not as creative but equally scandalous and entertaining.  As I said, this week’s guest was Jonathan Kay from Grasshopper.  Grasshopper is probably one of my favorite Boston startups because with Jonathan’s crazy ideas and energy they have executed some ridiculous word-of-mouth campaigns.  My favorite - 5,000 Grasshoppers.  True to my insane self, I went out to but about 15 grasshoppers and dipped them in chocolate to bring to this week’s meeting for members to eat.  Most startups will fail and a big reason why people are scared to start their own venture is their fear of failure so I used this ice breaker as a way for members to face their fears and do something they’ve never done before.

Lessons Learned:

• When breaking a 300lb. block of ice with a sledge hammer, have surrounding people wear safety goggles.
• When having people eat chocolate covered insects, buy them from Chinatown NOT Petco – and probably have them sign a waiver before eating.
• Be insane and think outside of the box.  Honestly, nothing is impossible if you set your mind to it so think as crazy as you can and execute like a beast.
• Live your passion and have fun doing it!