How do you get to be a serial entrepreneur? By doing your first startup. That experience, regardless of your title and position, lets you into a very exclusive club. Investors seek such people eagerly, as do potential employees and the media. The experience is golden, some say invaluable.
To put it into perspective and give you lessons from serial entrepreneurs, I recommend reading The Secrets of Serial Success in the Wall Street Journal, Monday, August 20, 2007. While I do not agree with each person interviewed, this well written article gives insight to the special world of the multiple startup leader. Note how different the lessons are from each founder and CEO in their responses to the reporters.
It is at best awkward and at time scary and dangerous to ride a bicycle the first time. Doing your first startup feels the same way. The WSJ article gives frank examples of that. So if you are doing your first enterprise and have those emotions, you are in good company.
Managing your way through successive new enterprises is tricky. Picking a string of successes, preferably each more successful than the prior one, is very difficult. Statistically each is going bankrupt. Yet the best managers most often pick a string of winners. They impress me with how well each company prospers in spite of all the troubles each inevitably gets into.
Learning from disaster is required. Most likely the worst will happen. How you respond to it will determine a great deal about how well you do your next new enterprise. Drugs and sex or reflection and recovery? People will ask you what you learned and now what you are going to do next. Get ready.
BOTTOM LINE: Serial entrepreneurs are made, not born. They are not lucky. They make their own luck, the hard way. No startup is easy, even if that is what you read in the media. They all are very difficult. As you learn by doing successive new enterprises, your encyclopedia of skills will grow rapidly. Your attractiveness to stakeholders will rise to lofty levels. You will become part of a very significant unfair advantage. Learning that is priceless.