10 Leadership Lessons from 10 Inspiring Entrepreneurs


Photo by Mike Shur

Yesterday I was honored to once again be the emcee at the Oregon Entrepreneurs Network (OEN) 2nd Annual Summit, featuring 15 successful Oregon entrepreneurs sharing their stories in 12-minute “TED-style” speeches.

The theme was the “School of Hard Knocks” – apt because the event was held in Portland’s cool and unique Kennedy School hotel and event center.

There was a diverse group of businesses represented, including restaurants, social media platforms,non-profits, clothing, bio-med, farming, software, and bicycles.

While there was a wide diversity in business type, there was a real commonality in the lessons these entrepreneurs shared  – the “hard knocks” leadership lessons.

These were realizations that came directly from their experiences  – revelations that pushed them past being just a “boss”, but into the higher strata of more human leader.

A strata that became a lynchpin to the successes they so graciously shared with us on this day.

There were 10 lessons in particular that struck a chord with me, and I’m sure they’ll do the same for you too.

  1. “Wherever you work, it has a culture. The question is, do you own your culture, or is culture happening to you? “– Luke Kanies, CEO, Puppet Labs  (@puppetmasterd)
  2. “The future is humble humans working with intelligent machines.” – Marshall Kirkpatrick, CEO, Little Bird (@marshallk)
  3. “Coach more. Shoot less.” – Jim Plymale, President, Clinicient ,Inc (@jimply)
  4. “Respond to conflict with empathy and professionalism.” – Emma Mcilroy, CEO, Wildfang (@irishem333)
  5. “Bring other people into your business, don’t try to control everything.” – Micah Camden, owner of 17 restaurants, including @BlueStarDonuts
  6. “Sharing knowledge is much more powerful. Things have meaning.” – Natalie Ramsland, co-founder, SweetPea Bicycles (@SweetpeaBikes)
  7. “It’s not the idea that is brilliant, it’s the implementation that is brilliant” – Cory Carmen, founder, Carmen Ranch (@carmanranch)
  8. “Don’t let outsiders influence the risk you take” – Ted Pappas, owner, Big Bottom Whiskey (@bbwhiskey)
  9. “If you trust the world it will disappoint you. But if you don’t trust the world you’ll be absolutely miserable.”– Greg Bell, Founder, Water The Bamboo Center for Leadership (@WaterTheBamboo)
  10. “You must have confidence to take creative risks. Humility helps us learn from the mistakes we dare to make.” – Sam Purdue, CEO, Indow Windows (@sampardue)

It was an inspiring day, and I’m already looking forward to next year.

Lead well!



  1. says

    Ten great lines or ten great quotes– for whatever activity domain you find yourself a leader in. Love them! I have a favorite though and it is number 9: “If you trust the world it will disappoint you. But if you don’t trust the world you’ll be absolutely miserable.”- Greg Bell, Founder, Water The Bamboo Center for Leadership. Brilliant!

  2. says

    Love the first one on being intentional with your culture. It’s so easy to forget that if we don’t like the culture in our business, take a look in the mirror and ask what you can do to create change.


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