Fred Wilson talks about the ‘hard raise’ today on his blog. This part resonated most with me:

One of the reasons hard raises can turn into great performers is that they often mean you are doing something others aren’t doing, you are early to an opportunity and others don’t see it. That certainly was the case with USV 2004. That’s the contrarian bet in action.

I have been through periods of easy raises and hard raises.

In 2005 and 2006 it was easy for me to dial for dollars. In 2005, I got excited about a Company in Phoenix called Golf602.com. The Phoenix real estate market was booming and my network was flush. It was an easy raise. Golf602.com became Golfnow.com which was acquired by Comcast in 2007. In 2006 a friend showed me a business plan for Lifelock.com and I invested immediately. I had to push my network a little harder considering how little expertise I had investing in startups. Lifelock is now a $1.6 billion public company. In 2006 I started Wallstrip and because Fred Wilson got actively involved, raising money was relatively easy. CBS acquired it 6 months later.

In 2007 things changed quickly. I had the full on angel investing bug. I was investing my own capital with some wins under my belt and thought everyone would see what I saw. Unfortunately, the market was changing. The world was worried about the banking crisis and the end of the financial system. I was pitching the ‘real-time’ web, web video and Facebook apps while people were losing their homes. Tweetdeck, TubeMogul, Buddy Media and Ticketfly had pre money valuations ranged from $600,000 to $2 million but the venture capitalists were in hibernation. Luckily I was really early to the real-time and Facebook phenomenon so the hard raises were the good raises. Tweetdeck was acquired by Twitter, Tubemogul is a public company, Buddy Media was acquired by Salesforce and Ticketfly was recently acquired by Pandora. The hard raise was good to me for a number of reasons. I was ahead of the curve and the founders that were solving the hard problems were the most motivated cluster of entrepreneurs I have ever worked with.