The best $20 you’ll ever spend

If you want to start a business, the best $20 you’ll ever spend is to find successful entrepreneurs and take them out to lunch. They can be from your industry or other industries — it doesn’t matter. For example, if you’re interested in hospitality, you could pick up a hospitality magazine and see who’s doing interesting work. Then email them and ask to take them out to lunch.

Spend 90% of the time talking about them:

  • Ask them how they did it.
  • Ask them what mistakes they made along the way.
  • In the final few minutes, you can ask about your idea. Is it crazy? What should you be thinking about?

After you meet two or three people, you’ll start to see patterns that you hadn’t recognized before. And that’s when you realize how powerful it can be to ask others for advice.

Yes, advice is cheap: Most people love talking about themselves. But entrepreneurs have a curious fascination with helping other entrepreneurs succeed. (At PBwiki, a Silicon Valley collaboration startup I co-founded, a bunch of us spend time each week meeting with first-time entrepreneurs and helping them brainstorm…and this is a common thing in Silicon Valley.)

People want to help you. All it takes is you reaching out.

J.D.’s note: This is a powerful technique, and not just for entrepreneurs. Over the past year, I’ve had lunch with several people I admire, and always come away feeling inspired and filled with ideas. If you have the guts to ask, the rewards can be enormous.

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