9 Awesome Things You Can Learn From Drinking Coffee With Entrepreneurs

Since I moved to Portland about 16 months ago, I’ve hung out with a lot of entrepreneurs, in coffee shops all over town.

(Yes, here I spread my coffee dollars around between the national chains and the local brews).

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, 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 indecisiveness. Also, 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.






  1. says

    Great article and thanks for sharing. I totally agree about the spongy-ness of the brain…that will get you so far. I see some that are very closed minded not do well because of it. They are not willing to learn from others.

  2. says

    My coffee with you was a highlight of my trip to Portland Terry. You were such a gracious host, and it’s very easy for me to bring back the memory of those two window seats we had at the counter of Stumptown Roasters. I’d add to this list something you illustrated for me, an anything is possible enthusiasm and eagerness: What a fabulous contagion to share, mahalo nui.

  3. says

    Hi Rosa, how are you? It was so great to share that time with you, and I look forward to the next time. And you’re right – enthusiasm and eagerness goes a long, long way towards success.
    My best thanks to you, my friend, and all the best!

  4. says

    Thanks, Terry!….yes, I found immersing myself in the company of entrepreneurs was the best antidote for “the unexamined life.” You’ve hit on the exact reason I get up up every day and go to work with this crowd. It’s too interesting not to!

  5. says

    I chuckled at the BHAG acronym. I’ve definitely met entrepreneurs like that. I’m having coffee with one this afternoon (I’m actually in the shop now!). I have a feeling I’ll be running this checklist in my head to see what applies.

  6. says

    Hi Lindsey, I’d be interested in your thoughts on how my list matches up with yours. Enjoy your coffee, and thanks for your comment!
    All the best,

  7. Suzi says

    Great inspirational tips. Thanks. I’ll be visiting more coffee houses and drinking gallons of coffee.

  8. says

    My husband started his own business about 12 years ago. One thing he has always been and one thing that drew me to him is his confidence and positive attitude. As as his company has grown and many people depend on its success for their livelihood (including our family) he has said more than once, “Failure is not an option.” With the economic climate such as it is — it takes constant reevaluation to stay ahead of the competition and streamline costs. It’s a ton of work and worry but if it’s your baby — it’s worth it.

  9. says

    Hi Jamie, thanks for your note, and for sharing your husband’s entrepreneurial resiliency. And I love to hear how confidence and a positive attitude can help us achieve our dreams.
    Thanks again, and all the best!

  10. Steve Lynch says

    Thanks for sharing this. I sometimes feel like I am on an island of my own as I also have been a corporate professional in the IT world now engaging in my own company and the entrepreneur world. And like you, I have been drinking more coffee than I have in my life with other entrepreneurs in my area. It has been invaluable and I appreciate all of their time.

  11. says

    Don’t wish for it, work for it! “The major key to your better future is you!” “Only you can make you successful!” When a entrepreneur know this then they can have a journey to success.


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