[adamt]

I agree with a lot of what the author says, but I am not sure I agree with the main premise in his title.

Luck and timing often play a big role in setting up a business. I think there are some people who saw an opportunity through being in the right place at the right time and created a business out of it. Often these evolve into being what people call lifestyle businesses. In my mind these people don't fit into the 'compress 40 years of work into 4 years' camp and are non-serial entrepreneurs.

To me, the mark of a serial entrepreneur is someone who has started a business up, got it to the point where it's been successful, and then having had the option of staying on very comfortably with either a lifestyle business, working in a bigger company, or early-retirement has decided that they want the buzz and excitement of a startup again.

A good serial entrepreneur is by extension of that someone who can do this more than once successfully. To create a single business that works out can often involve a lot of luck/timing; to do it 3 or 4 times is something else.

[swombat]

That's an interesting angle, though I would argue that what you're defining here is a very successful serial entrepreneur, rather just a "serial entrepreneur". I'd say that someone who willingly jumps into startup after startup is a serial entrepreneur - successful or not. Max Levchin was clearly a serial entrepreneur already after his 6th company, even though he hadn't started Skype and Slide yet...

[loceng]

We could look at through a different lens and state that if you aren't jumping into startup after startup - successful or not - are you even an entrepreneur?

[swombat]

Well, that's sort of my point... serial entrepreneurs are the norm. Perhaps we should come up with a term for those rare entrepreneurs who are satisfied with a single attempt at the business game...

[loceng]

I would just say it's something entrepreneurial they are doing, doesn't per say make them an entrepreneur - perhaps it does though; If you're learning a musical instrument, are you not a musician? Maybe not a professional. Professional Entrepreneur vs. Amateur? :P Serial Entrepreneur has a better ring to it, though it really is just someone who is an entrepreneur IMHO.

[amirmc]

Businessmen?

[guth]

Skype?

[jaredsohn]

that should be PayPal

[swombat]

Oops! Yes, it should!

[Dn_Ab]

This is a great point. I also think it is worth noting that by the third or fourth time, even if they were peniless, the person would be starting from a far better position than a first timer. Networks and Reputation are a powerful form of currency and more useful than money if you want to do hard things.

Confidence from repeated success - do not underestimate pressures from family and self doubt in their contribution to start up cave ins.

[vannevar]

...to do it 3 or 4 times is something else.

Doing it 3 or 4 times is in fact much easier, which is why so many entrepreneurs who are successful the first time go on to have further success. It's much easier to raise money with a track record, you have connections with skilled people on both the technical and financial side, and you have your own experience to avoid pitfalls and give you confidence. If entrepreneurship is a marathon, it's a marathon where every mile gets easier and easier as you run.

In such an economic race, it's no wonder there is a growing disparity between the leaders and the rest of the pack.