Brad Feld: Jeff Nolan from SAP Ventures has an excellent post titled Pick Your VC Carefully. This is a must read post for anyone that has either taken or is considering taking venture capital money.
I’ve co-invested with a wide range of VC’s in all of the categories Jeff describes. Some have been outstanding partners, some have been horrifying, and some have been in-between (shocking, I know.)
However, in almost all cases, I couldn’t have predicted where they would have fallen out based on my shallow perception of their reputation prior to getting to know them. Of course, there’s nothing like working with someone to decide whether they are useful or not, but often that’s not an option – especially for a first time entrepreneur or someone who is developing a new entrepreneur to VC (or VC to VC relationship.)
Partnership is a two way street, so I always encourage entrepreneurs and potential co-investors to talk to anyone about anything concerning me. I try to be completely open book about my strengths, weaknesses, interests, and desires. Surprisingly, very few people go really deep in advance of developing a relationship. Yeah – there’s plenty of “due diligence” – but usually that’s a series of relatively useless reference checks from the “first list of people” that provide little to no insight (I’ve been on the receiving end of a number of these calls lately and it amazes me how much time “serious, experienced people” waste on simpleminded, “check the box” reference calls.) In contrast, I try my hardest to “force” entrepreneurs who are considering working with me to meet with entrepreneurs that have deep (and often – multiple company) experiences with me – a phone call doesn’t qualify – go build a relationship (and – your worst case is that you now have another entrepreneur in your network.)
I’ve learned that I don’t want to work with someone who I don’t have a real feeling for – both in good and bad situations. Fortunately, most everyone now has had some bad experiences (or else they checked out and farmed sheep in New Zealand from 2000 to 2002) so it’s a lot easier to get detailed information about potential business partners. I’ve learned that how someone explains their failure is much more enlightening than how they explain their success, and a real conversation (and potentially shared experiences – but please, not bowling) – rather than a series of “interview questions” – can provide real insight.
A prime example of this done correctly is an experience I had recently with Dave Sifry at Technorati. The company was one that was very interesting to me and in an area that I had both domain knowledge and another investment (NewsGator). My partner – Ryan McIntyre – was uniquely qualified to help this company due to his entrepreneurial experience as a co-founder of Excite and was extremely excited about an investment. I supported Ryan (and shared his excitement) and watched while Dave shook him down pretty hard – spending a lot of time evaluating Ryan, his potential contribution to Technorati, and his cultural and functional fit with the team. However, he didn’t stop there – I spent three hours on the phone on a Saturday talking to Dave in the middle of this process. An hour was “get to know you chit chat”, the balance of the time was a real discussion about where the market his business was in was going, his vision, what I thought about it, why I cared, how I could help, and how I / we thought about companies like his. I’m the back seat driver on this investment (it’s Ryan’s investment), but Dave still went after me hard as part of his evaluation as to whether or not he wanted Mobius as an investor in his company.