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Dave Cotter was 41 years old, an entrepreneur who had built and sold a startup, worked for companies including Microsoft, Oracle and Amazon, and served as an entrepreneur-in-residence at Ignition Partners.

SquareHub’s Dave Cotter at GeekWire Startup Day

And then found himself in the hospital, alone, asking himself where he had gone wrong.

“It was such a surreal moment for me. I had gotten my dream,” Cotter writes. “I got what many of you probably want. I built and sold a company. I was a ‘successful entrepreneur.’  I’d had my successful exit. But you know what I really was? I was empty.  Everything I thought I wanted, everything I’d planned for and built suddenly didn’t matter. I felt alone and unfulfilled. My life was out of whack.”

A big part of GeekWire Startup Day is about sharing difficult lessons learned, and we encourage the speakers to talk candidly about mistakes they’ve made to help others benefit from their entrepreneurial experiences. Cotter, the CEO of SquareHub, took that to heart, sitting on a barstool on stage and talking without notes or slides about his story, and the three lessons he now tries to follow on his journey to the “Big Exit.”

Watch the video above to hear Cotter’s talk, and read his post on the SquareHub blog for more. Cotter is also featured in this piece about Startup Day by KING5 in Seattle.

Thanks to Dave for sharing his story, and thanks to everyone who attended and supported GeekWire Startup Day. We’ll be sharing more highlights from the talks and the rest of the event in the days ahead.

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