9 Awesome Things You Can Learn From Drinking Coffee With Entrepreneurs

MP900423117300x300-1Since I moved to Portland a little over 2 years ago, I’ve hung out with a lot of entrepreneurs, in coffee shops all over town.

(Yes, I drink a lot of coffee, as befitting my “Starbucker” moniker – although here, I spread my java love around to the local brews too)

For an hour or so, we just chat about their businesses, and about them – and I have to tell you, these discussions have been revelatory for me.

I was a “corporate guy” for so many years (28 to be exact), and while I thought I knew what it was really like to “think like an entrepreneur”, it turns out I really didn’t know.

Because I had not taken that personal risk, and started something up on my own.

That is, until now.

I have my own company now (SOBCon – check out our event in Chicago this May) , and a wonderful partner, but I knew I needed to learn more about what makes these risk takers tick.

Thus, my ingestion of copious amounts of coffee – and learning.

I’m happy to share some of the awesome insights that I’ve picked up from these fantastic people – here’s just 9 of them.

“Go for Broke” faith – These folks are willing to put almost every dime of THEIR money into the pot, because they so believe in what they are doing.

Innovation (with Purpose) –  Steve Jobs has to be smiling from above these days, because just about everyone I speak to wants their product to change the world (or at least make someone’s life better).

(Poker Player’s) Guile – I love how these entrepreneurs will raise the stakes with less than a perfect hand – i.e. like talking about the latest version of a product that is really still in someone’s head.  Putting that bet down is like a self-fulfilling prophesy –  this hand WILL be Aces…eventually.

Ability to Take Multiple Punches (The Wepner Syndrome) – My generation remembers Chuck Wepner, the “nobody” who took on Muhammad Ali back in 1975.  He took punch after punch after punch after punch, and still lasted until the 15th round.  Entrepreneurs have that same resiliency.

Innate Understanding of the value of EVERY dollar – No dollar lost (or gained) is unimportant; there are no rounding errors in a start-up.

“Spongy-ness” (for absorption of data) –  The entrepreneurs I spoke with were all great listeners; I could almost “see” the “spongy-ness” of their brains, receiving all of my feedback in their core processors.

Productive Naivete – At this stage, there is so much benefit to NOT knowing certain things – things that could cause unproductive emotions (like fear), or indecisivenessAlso, this naivete extends to the service and/or product idea itself (i.e. “we’re going to sell MILLIONS of “em!).  

The Need of the BHAG – Speaking of millions, entrepreneurs nurture the BHAG – the big hairy audacious goal – like a mother hen looking after her chicks.   They protect and defend it as if their life depended on it (and come to think of it, in some situations, it does).

So Undeniably, Positively Human  – No suits, no briefcases, no tons of cool acronyms, no executive assistant, (sometimes) no office, (sometimes) no money, no huge staff – just them.  And their dream.  And their love of the dream.   The earnestness is so truly inspiring.

These are the folks that are in the arena” (thanks again Teddy).   Some will fail, some will get by, some will be profitable, and some, well, they just might become the next Facebook.

Kudos to them all.   Keep teaching us.


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