Been There, Done That: The Serial Entrepreneur

Video: Secrets of a Serial Entrepreneur, Mike O’Donnell

Like most people, entrepreneurs learn from their mistakes. And they meet people along the way. And they’ve a track record—i.e. they’re a known quantity. These are three reasons a serial entrepreneurs has a better chance at success than first-time entrepreneurs. Apparently there are even more. In his blog: Skill versus Luck in Entrepreneurship and Venture Capital, Sanjay Parekh quantifies that “the predicted success rate of entrepreneurs with a track record of success is 30.6%, compared to only 22.1% for serial entrepreneurs who failed in their prior venture, and 20.9% for first-time entrepreneurs.” This gives new meaning to the adage, “If at first you don’t succeed, try, try again.”

Que bummer for us first-timers! How are we supposed to prove ourselves against those who failed the first go round but still statistically do better than us the second? There are many things we can do to up the odds:

  1. Partner with a serial entrepreneur
  2. Build an advisory board of successful entrepreneurs/visionaries in your industry
  3. Bank some seed capital from notable angel investors who have backed other successful entrepreneurs.
  4. Ask a notable industry visionary to join your board
  5. Stick around long enough so that your odds go up via pure persistence–i.e. 1) you have time to learn from your mistakes; 2) you meet people the first zillion times to Sand Hill Road; 3) you become a known quantity.

I did all of these except # 4, and yet a successful first-time entrepreneur friend swears that 4 was the only reason he landed his Series A. He just happened to have a neighbor (whom he didn’t know very well) who just happened to be a retired mover and shaker in the industry in which my friend was launching his company. This said neighbor just happened to have some extra $ to invest and just happened to be open to joining the board of my friend’s fledgling company and … just happened to know a Managing Director at a notable VC who ended up leading their Series A. This kind of thing happens in Silicon Valley. Alas, my San Franciscan neighbors are artists, therapists and ne’re-do-wells. Oh well, at least we have fun block parties.

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Below is a full list of Entrepreneurial Reluctances/e-Publishing lessons from my Top 10s blog post.

Entrepreneurial Reluctance

1. The Catalyst(s)

2. Good $ vs. Bad $

3. Risk Reduction

4. The Network Effect

5. Been There, Done That (serial entrepreneurialism)

6. The New New Thing

7. Emergence & Maslow

8. The Analogy of the Watch (moving parts)

9. A Clean Cap Table

10. Perseverance or Blinders


e-Publishing Reticence

1. False Deadlines

2. Readers & Editrs

3. Genre Opportunities

4. Target Marketing

5. Self-Promotion

6. Creating you Brand

7. The First Review

8. The Network Effect

9. Amazon Ranking

10. The Book Tour

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