Who do you think is the greatest living serial entrepreneur?

Years ago I read "The New New Thing" by Michael Lewis, one of my favorite authors. He profiled Jim Clark, the serial entrepreneur who founded three billion-dollar companies in his career -- Silicon Graphics, Netscape, and Healtheon (now WebMD). For years I considered him the best serial entrepreneur ever. But in "The Coming Jobs War" Jim Clifton (CEO of Gallup) makes a good case for Wayne Huizenga who founded 3 Fortune 500 companies -- Blockbuster, Waste Management, and AutoNation.

Other insanely good serial entrepreneurs include +Mark Cuban, +Richard Branson, +Sean Parker, David Neeleman, +Marc Andreessen, +Reid Hoffman, +Mark Pincus, +Peter Thiel, +David Sacks, +Bill Gross and Steve Jobs.

Mark Pincus is quoted this week in Business Week:

"I’m sometimes called a serial entrepreneur, but that’s only because, before Zynga (ZNGA), I failed to create a sustainable company. After starting two companies in the ’90s, I had a social networking startup, Tribe.net, in 2003. One of the things I try to instill at Zynga is to fail fast, look at the data, and move on, and at Tribe I failed to do that." (Source: http://buswk.co/IBfnsF)

I love the title of Sarah Lacy's 2006 book "Once You're Lucky, Twice You're Good." I think there is something to that. I wonder if wanna-be entrepreneurs can learn more by studying lessons learned by successful serial entrepreneurs than by studying one hit wonders -- no matter how big their company got.

Studying Sam Walton (Wal-Mart) is fascinating because he basically invented modern retail. Walton's innovations included stocking merchandise in aisles and letting customers browses them (before that, clerks used to retrieve products for shoppers), steep discounted pricing, and locating stores in rural/remote areas. But it may be easier for modern entrepreneurs to learn how to succeed today by reading Richard Branson's books or Mark Cuban's blog. They are more timely, relevant, and based on multiple successes, not just one.

It's a great time to be an entrepreneur. The Lean Startup may be the best book for entrepreneurs since The Entrepreneur's Handbook (Richard White, 1977). It definitely captures the "fail fast, look at the data, and move on" philosophy that Pincus mentioned above. The Startup Genome project may be the best attempt in history to study entrepreneurial success and failure on a massive scale, in an effort to improve the success rate with recommendations based on their analysis of the data.

I'm working on a project that will try to improve the chances of startup success for thousands of non-Silicon Valley entrepreneurs. Startups who don't enjoy the benefit of living in the middle of thousands of successful entrepreneurs and investors and talented employees who have "done it before" need a lot of extra help to succeed, in my opinion. The culture of success in Silicon Valley is unique in the world. (Although there are other entrepreneurial ecosystems that have significant value, as reported this week by the Startup Genome: http://tcrn.ch/HGWeng)

My team is working on a taxonomy of decisions that startups have to make at each stage of their existence. We're up to about 300 decision points already. Ideally, we'll be able to match those decision points with case studies and examples from one-time and serial entrepreneurs, at the very time the entrepreneur needs it -- not five years earlier while they're sitting in a class at a college or university.

Here's an example: online startups need to choose key metrics, a web analytics tool, and design a dashboard. Done right, this can become one of the most significant ways to achieve success. Done wrong, or ignoring this decision, online startups will almost always fail. So which analytics program should they use? There are a couple of dozen really good tools to choose from. Which one is right for them, and why? What tools were selected by other successful entrepreneurs, and how did it make a difference? That is the type of questions I hope this project will help answer for thousands of startups.

In order to do this right, I need to locate as many serial entrepreneurs as I can -- especially those who have lectured, written blogs or books, or otherwise shared their keys to success -- especially how they approached specific decisions at key times.

Can you think of anyone?

Please comment and share.

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