About a year ago, I emailed my investors and told them we were refocusing our company in a new direction… one reply really stood out.

“I have learned that acting from your heart and being bold about it sets the stage for greatness.” George Zachary

While pivots tend to have a negative association, our current company wasn’t failing and by many measures it was very successful. COLOURlovers had more than 2 million registered users, was a 5x Webby Awards nominee for Best Community, doing $500k in annual revenue and had organic year over year growth…

But, I never intended to build COLOURlovers, it was a weekend project that didn’t die when monday rolled around. Over the past 7 years it has connected with tens of thousands of people on a deep level… largely I believe because we made being creative super simple and accessible. I’m very passionate about the community we created and that...

“I missed your talk, but caught the end… You’re doing like suicide prevention for startup founders? Keep up the good work!” That wasn’t what I intended when I spoke recently at FounderFables, an off the record event aimed at founders sharing stories in a private environment, but I took the feedback as validation that I should be talking about what I was sharing and not just to an off the record group.

What I was talking about isn’t spoken about in our industry enough and it affects all of us deeply. Perhaps I’m willing to speak about this because I have a unique background.

I grew up as a rich kid, going to private schools, living in the only mansion in my town… I wore a non-rented Armani suit to my senior prom, and if that sounds pretentious, it’s because I was. But under the veneer of the rich kid popular jock, I was self conscious, depressed and a little lost.

I was the youngest...

My friend’s Jon Crawford and Matt Galligan both wrote about the topic of Work/Life balance this week and I thought I would continue their conversation with my perspective.

To call it a balance implies two sides of a scale where too much weight on one side, tips the other. To struggle for balance is to struggle for equal attention to things at odds with each other. How I choose to run my life is to strive not for balance, but for harmony. I embrace that my personal and work lives coexist in the same 24 hours of each day. My founder brain doesn’t shut off and neither does my personal brain. When two things vibrate at opposing frequencies, their forces can be devastating. When they vibrate together, it’s peaceful. When in harmony, both my personal and work lives are vibrating vigorously, but without fighting each other.

With mental perspectives in mind, I was struck most by this...

Somebody tweeted this the other day and it annoyed me. It’s a horseshit personal empowerment line that comes on posters & placards for entrepreneurs. It’s meant to inspire you to quit your job and begin the glamorous life of an entrepreneur that surely has you becoming super rich.

Two things specifically annoy me about this.

1. It’s flat out wrong. Plenty of people got rich working for other people.

A very timeley example of this is Marissa Mayer, the new CEO of Yahoo. She’s worth an estimated $300 Million and potentially a whole lot more if she can successfully throw a hail mary. How did she become so wealthy? Working for Sergey Brin & Larry Page at Google.

Steve Ballmer. Worth Billions. Got it working for Bill Gates at Microsoft.

There are lots of rich people who got their wealth being early employees at startups that became huge successes. (Facebook just created a several...

The following video came across my feed as a humor link, but how I reacted wasn’t just a laugh. I thought, “shit, I’ve done that. I’m doing that right now!”

http://www.youtube.com/watch?v=VmU6BChuiBs&feature=share

Not as a runner, but as a founder. I know the general direction I’m headed. I know it’s a race to the finish. I feel at times exposed like I’m wearing speedo-shorts. I started with a plan and composure… and now have no idea what I’m doing but am chest out running towards my goal like a mad-man.

“Everybody has a plan until they get punched in the face.”
― Mike Tyson

Mike’s words are true. This is why business plans for startups are largely a waste of time. You can plan all you want, but until you’re out there executing you’re just guessing. Like the runner that started his race, he had a clear plan. Gun goes off. Run. Jump over 10 hurdles. Win. His plan didn’t...

Ahoy! The theme of my writing here on the Svbtle network will be from the perspective of a weathered captain who has been surviving the storms of startup life.

For nearly a decade I’ve been out at sea searching for my brave new world. There have been many storms along the way that have nearly wrecked my boat: I struggled in the developing startup ecosystems in Portland, OR several years ago. I was an outsider to the Silicon Valley elite startup world and desperately wanted to be on the other side of the wall. I’ve gone broker than broke a few times while bootstrapping. …But I’ve also reached some amazing shores: I was accepted to Y Combinator. I raised more than $2M from top VCs & Angels. I built a passionate community up to 2M registered users. I’m on the other side of that wall.

So here is where I’ll write my ideas, advice & lessons learned to help my fellow founders at sea...