• The biggest risk you can take is to not ever take any risks at all. And you know you’re risk averse, I know you’re risk averse.
• If you care about someone or someone cares about you, but you neglect them for your work, they’ll eventually walk away.
• Read a lot and read widely to spot trends in different industries. Then position yourself to benefit from them. It’s too late to catch the iPhone tide, so look for something new.
• Don’t be inhibited by not being an expert in something. Expertise is temporary. If you’re learning or creating something brand new, you can become an expert in a very short amount of time.
• Moreover, it’s often the non-experts who aren’t confined by existing industry traits.
• Be arrogant enough to challenge the status quo and persistent when people tell you that you don’t know anything or that you’re wrong.
• At the same time, be flexible and constantly test and revise. You’ll probably rewrite your business plan 20 times based on your experience.
• To get meetings with people you probably don’t deserve to meet with based on your lack of credentials or experience: Lie.
• Sometimes risks can be taken in making use of very old technology thought to be dead.
• Sometimes you fail, and sometimes you don’t. This guy chose to pass on investing in Google in 1998. So it goes.
• Unless you want to be a lawyer or a doctor, you can learn what you need to learn without going to school. (As an update, Fred Wilson just posted on this same topic, perhaps inspired by the same entrepreneur.)

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