Yes. But would it qualify as 'surround yourself with others you want to be like?' Do you want to be like your typical drug smuggler? Do they have happy endings? ;)

To your first 2 questions - maybe? I have read a few books about drug smugglers, and they're often quite interesting people. I've certainly met some entrepreneurial types I didn't at all like, plus there's plenty of them out there who basically get screwed (down rounds, recapitalization, etc). Assuming entrepreneurship always leads to happy endings seems to be a common fallacy.

And while we always hear about the entrepreneurs who succeed, we always hear about the drug smugglers who fail. It's difficult to estimate proportions in both cases.

The guys who are worth telling popular stories about are the 'good guy' exceptions. The typical large-scale cocaine trafficker is not a nice person.

That being said, you're probably about as likely to get busted as you are to go broke, but at least in a startup you just lose all your money.

This is a good point. We just lack the data to make any predictions whether going the "road less traveled by" leads to success (whatever that means) and assume that "all the difference" equals good (whereas it's rather neutral).

[1] Robert Frost: The Road Not Taken (http://www.bartleby.com/119/1.html)

The article does say, "I’m not talking stupid risks. But smart, calculated ones." :)

If you succed you are basically set for life. If you fail you loose 4-6 years of your life. How is that different from a startup?

In startup, if you fail you dont lose 4-6 years of your life. Moreover people wont consider you a failure if you fail in a startup, as opposed to say landing up in a prison.

This is such a stupid comment, I don't know where to begin. Possible attacks on your argument:

1. "set for life" - not necessarily, plus you would have to sell the drugs, etc.

2. just lose 4-6 years of your life - criminal penalties likely greater

3. horrible effects of prison on your psyche and future work possibilities

4. possible death from involvement w/ criminal underworld

5. with a start-up you get transferable experience

Other reasons why this is a stupid comment:

1. Learn to spell succeed

2. Learn to spell lose

If you are not a native speaker, I apologize for #1 but #2 can be corrected with a spellcheck plugin. But it seems like you just typed quickly without thinking your comment through.

It's interesting that I didn't get the one answer that I was fishing for - that entrepreneurship involves a desire to make the world a better place. I guess that is debatable.

You asked about risk-taking, not entrepreneurship.

Heroine is worth 10 times more. Pick your merchandise right.

The effort and jail time is the same, the profits much much better.