BlueRain

I started my early career in tech, joining Microsoft in 1992.

Three cool things about working at Microsoft back then:

(1) I didn't have to wear a tie

(2) The Seattle music scene was on fire (Grunge!)

(3) Microsoft was the hottest company in America

(Apple wouldn't become the new darling until Jobs returned as CEO 5 years later. Yeah, I'm that old!)

Since I ran a lemonade stand when I was eight (orange juice, actually) and upstarted four other ventures in high school and college, my entire identity was wrapped in being entrepreneur. Given this, I expected my time in a large company would be limited.

After four short but amazing years, I left Microsoft to co-found my first start-up, Cognisoft.

Now, leaving Microsoft in 1996 didn't make logical sense to anybody, especially to my father. Everybody thought I was crazy. But I didn't have a choice. IFYKYK.

One person who was particularly amused at the prospect of five guys leaving Microsoft was Michael Lewis. So much so that he covered our journey for Slate Magazine (full article).

After Cognisoft, I moved to San Francisco in 1998 to start BlueRain as an antidote to my creative direction disorder. An organization committed to exploring new paths in digital media, consumer internet, corporate software, finance, and food. It made no sense to anyone, except me.

BlueRain was fun. The Dot Com boom. The Dot Com bust. Then Social, Mobile and Cloud. San Francisco was a playground for dreamers and storytellers. I had a great time meeting with hundreds of founders which led me to invest in over 30 private early-stage ventures. I had a few hits. Several misses. And some are still kicking today.

BlueRain was a journey of allocating capital. Today, my focus is about allocating my time.