I joined a company called SPRY in 1993. SPRY sold the first commercial internet product called Internet in a Box. What was unique about it was that we were the first company to license the Mosaic source code from the University of Illinois where a young Marc Andreessen was still a student and hadn't yet co-founded Netscape. Sometime in mid 1994 we were all standing around our computers looking at the newly launched FedEx website. You could enter a tracking number and it would show you where your package was. That blew us all away. I fell in love with the web at that moment. Yahoo wasn't yet even a search engine. Just a handmade directory of links. Not long after SPRY sold to CompuServe I was referred to a company in Seattle called Progressive Networks. They had this idea to deliver audio over the Internet. I joined in 1994 and they subsequently called the company RealNetworks. During my 5 years there, the smart engineers figured out not only how to deliver audio but also video. I remember that our big tradeshow demo was showing live radio station feeds from a Stockholm radio station streaming over the web to our tradeshow floor! The RealPlayer and the Rhapsody Music service became a household name. I learned so much and feel very lucky to have worked with so many smart people.
Nobody has ever asked me this question before but it's actually something that challenges me. We start companies ourselves like Imagekind and our latest venture called Inkd: The largest marketplace to download newsletter templates, flyer templates, brochures, business cards and other types of print creative. However, we also invest in companies such as SEOmoz where we don't have day to day responsibilities. But we still feel it is important to be as supportive as we can so we need to back away from our computers and sometimes go to meetings and try to help tackle tough questions that our portfolio companies have for their own businesses. As you can imagine, when we start our own companies we hold a larger stake but I still feel it is just as important to try to be as helpful as possible for our portfolio companies. When I think about the challenges that Curious Office has, the answer is always the same - not enough time in the day.
This one is easy. Adrian has an incredible risk tolerance. He brought the Seattle Sounders to Seattle as a Major League Soccer team this year for example. He is one of my oldest friends and I respect him so much because he thinks for rationally and calmly in every situation...even when very large amounts of money are at stake. The Seattle Sounders was a far bigger bet than any technology investment.
In my experience, fundraising seems to be just as much about relationships as it does about your idea and your technology. If you are contemplating fundraising then get involved in the events and venues where investors and other successful entrepreneurs go. Sometimes its easier to get close to other successful entrepreneurs than it is to get close to investors but that's a great way to start. It is also important to remember that previous success is the best way to raise money. Even if your first success is small, that's better than no previous track record. It's sometimes smart to establish a first base hit for yourself. That makes all investors feel more inclined to take a risk with you.
I'm interested in working with people who deeply understand the subtle nuances of driving lots of traffic through all available channels. There are those who are learning and there are those who know. I don't know what the next big thing is but the best bet is to bet on smart people. Guys like Andy Liu of BuddyTV or Ben Huh of ICanHasCheezburger are great Seattle examples. They understand how to come up with concepts that have a viral hook and they understand how to drive and build traffic to their destinations. Someone who divulged all those secrets would sell a lot of e-books :)