I have a couple of friends who are sharp, technical guys that I may be interested in starting a company with. They are vaguely familiar with web startups (as a career), but are not tapped in to the online startup community. I want to show them the potential of entrepreneurship and all the opportunities there. What books/blogs should I send them to?
My first thoughts were:
Where else should I send people? What will get people excited?
Be very careful with this. People who thrive for this lifestyle already know about it, and are already excited (for example, you).
Startups are very hard to do, with many lows. It's easy to keep people excited during the highs, but if you have a partner that is a negative person, or cannot find intrinsic motivation, when problems hit they will either become part of the problem (ie, will have non-constructive input) or drop out and leave you hanging with the debts/unfinished product/etc.
So yeah, show them the articles you mention, but wait to see if they get some motivation on their own.
Some people are just not made to be entrepreneurs, so don't get a partner who is really smart, but expects a steady paycheck and all the other trappings of an employee lifestyle. You might want to hire that person, but do not make the mistake of making that person a partner. I say this from first-hand experience :-).
EDIT: The reason I say to not try too hard to get your friend into a startup is because you run the risk of making that person feel forced into it (who would want to let down a friend?). If you force someone into this, you will find out later that they are not really cut out for this, and big trouble will ensue (and you will lose the friendship on top of everything).
I agree with gmagana to a great extent. I think the approach is more finding out what they're looking for, what turns them on, where they want to go vs. trying to convince them to do it. Do a soft sell. If they bite, great. If you have to work hard to hard sell them it's probably not going to work.
Some people are cut out for it, many aren't. I've interviewed many people and it's usually pretty enlightening to just ask a few simple questions to see what motivates them. If they talk about wanting to create something, wanting to work with a team, having a passion for the product/service you offer (or are thinking of offering), willing to wear many hats and do whatever it takes to succeed, they're probably a good fit. If they're worried about benefits or what office they'll have or their title or how big their organization will be...then they may not be a good fit.
I'm guessing they either have or aspiring to have good jobs and the urge (if there is any) is not strong enough to take the risk. You can't just be an entrepreneur for the sake of being an entrepreneur. A good writer wants to engage in the act of writing and not just go on book tours.
Oli has an interesting story about this subject. I would seriously consider sitting your friends down and finding out what they really think about your ideas. You may learn something about the viability of your ventures.
If it's an option at all, drag them to some entrepreneur meeting (this is my list for Silicon Valley, but if you live elsewhere, either pick a great local group, or get on a flight and stop by the valley - don't go to a place with 3 losers all crying about why no one does startups). Hopefully, the energy in the room will trigger something. If it doesn't, don't insist: entrepreneurship is not for everyone.
Watching a video online or reading an essay is usually less effective. It may be better for a second step, once they catch the bug, as they should research the startup space and get to know more of the pros and cons.
Excellent question and I've been wondering the same for a long time.
Sadly, I have never truly succeeded in transmitting my passion to a friend, which brought me to the conclusion that I'm either bad at it or that the drive for entrepreneurship is something that one must earn on its own. Oh well, on a second thought, I probably just suck at it: it feels so natural to me that I have a hard time figuring out how to get people excited about it.
That being said, I would strongly recommend the following essay by Paul Graham : How To Make Wealth. It is probably the most inspiring text for entrepreneurs I have ever read.
At the end of the day, a lot of starting a company sucks. If the passion for the specific idea isn't there, then no amount of being a "natural entrepreneur" or wanting to be a serial entrepreneur as a career will change things. You have to get up in the morning and work on something that's gigantic and scary and maybe failing at that moment, so you'd better believe in that specific something.
So, don't concentrate on the career path; concentrate on the idea. If you can't sell them on the idea, try a new idea! Besides, few people who start companies want to be "entrepreneurs" -- they want to do something they care about. A lot of people want to be a CTO, or whatever, at the right company with the right product, even if that is an early-stage company.
Probably the best strategy is just to get together over beers and brainstorm. In a few weeks or months or years you'll all find the opportunity that's right for you.