Journal of Chet Kittleson

Originally published on GeekWire

I’m an entrepreneur with a day job. For a while now I’ve been asking myself if this is reasonable, and I’ve recently decided that it is.

The caveat: I believe day job entrepreneurs can only still consider themselves an entrepreneur if they actively pursue the betterment of the entrepreneurial self.

Put in another way, if you’re not taking advantage of the many resources your company likely has to offer to learn about all the things you know little about, you’re wasting lots of time and making a huge mistake.

I’ve thought about this a lot over the past 18 months at UP Global, and wanted to share a few of the things that I’ve kept front of mind. Read more

Originally published on Fast Company

It started over a decade ago when I was a 15-year-old microwaving gas station food and endlessly scrubbing diesel off of the concrete slab beneath the avocado green fuel pump. Fast forward a few years and I’d been a dishwasher, a pizza delivery driver, a door-to-door salesmen, a shoe stocker, a clothes folder, a cold caller, a boat cleaner, a lawn mower, a cell phone dealer, and a house painter. Each of these jobs taught me something, but as I get older I realize more and more how much they’ve played a role in who I’ve become and the perspective I carry with me day in and day out.

There are four things in particular about my years in these jobs that I felt groomed me for the entrepreneurial community I’m proud to be a part of today: perspective, empathy, customer service and understanding how to be lead by non-leaders. Read more

Originally published on GeekWire

I’m not sure if there’s a term yet coined for those who start companies in their spare time, so henceforth I propose those with full-time jobs and startups on the side shall be known as “side-project entrepreneurs.” It’s time people like us identify with each other. Read more

Originally published on Huffington Post

If A Story is Told but Nobody is Around to Hear it, Does it Make A Sound?

What is it about a city like New York or San Francisco that has entrepreneurs everywhere mesmerized? Is it the number of startups they’re pushing out every day? Is it the amount of money that these startups are being bought and sold for? Are their entrepreneurs smarter? More educated? Better raised? What is it that puts the New York’s of the world at the center of everything? Read more

Originally published on Huffington Post

As an active member of the startup scene for the past several years, I’ve had the privilege of working with and watching a handful of what I’d consider to be some of the most exceptional entrepreneurs of our time. Innovative, talented and respectable people that seem to know exactly what they’re doing and where they’re going. How does one get to that place? How do they manage to not only hold it together under all of the pressure and stress, but to excel and to lead in the midst of it all? Read more