I previously posted about one serial entreprenuer I know, Andy Klein, founder of Wit Capital and Soleil Securities. Andy and I had an interesting lunch meeting during the holiday week over in Noe Valley. I've only met Andy in person a handful of times, but have had the pleasure of investing with him for several years. Andy has teamed up with Anthony Scaramucci to form a new venture called SkyBridge Capital. I'm an investor in the deal and will be hush hush on the details until his new firm starts making waves. However, my lunch with him reiterated why I love to invest with serial entrepreneurs:
1. The Hunger - Some people don't like backing a guy who has hit too big of a homerun before. Marc Andreesen, Steve Case, Mark Cuban...the list goes on and on, successful entrepreneurs who are not as hungry as before. But every once in a while you will find a guy who is still hungry, who knows that the main currency in the world of business is his most recent venture....you are only as good as your last game...try to find guys that care about their reputation.
2. The Truth - The truth of the serial entrepreneur is that he or she does not know all there is to know about all kinds of businesses. The serial entrepreneur knows that he is best at building businesses and creating value. If given a blank organization chart, he knows what boxes need to be created, in what quantity, in what price, and in what time frame the boxes need to be created and connected. If he doesn't have deep domain experience, his partner definitely will.
3. The Rolodex - The contacts of a successful serial entrepreneur are second to none. They have made people money time and time again and they can raise funds from angel investors, venture capitalists, friends, and a wide circle of people who have introduced him to other people. What this means is that the serial entrepreneur knows the value of relationships and will do whatever he can to maintain and cultivate valuable relationships.
I will post next on the topic of angel investing. Andy and I had an interesting conversation about this topic and I was surprised to hear his opinion that he would prefer to invest as an angel versus through a vc fund.
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