A Lesson For My Future Investing Self

Few people are entrepreneurs. The smartest follow the crowd, setting off for Corporate America to collect a monthly payment called a salary. 

But for the resilient few, entrepreneurship is the only path. It’s for the creators, the dreamers, the thinkers who lie in bed late at night brainstorming the next big thing, the ones who are never satisfied. 

Some entrepreneurs or early employees have been fortunate enough to become investors. Take Dave McClure, an early employee at PayPal and now ringleader of 500 Startups. Or ex-Googler Chris Sacca and Lowercase Capital. Or Dave Morin, co-creator of Facebook Connect and Slow Ventures (and a recent addition to our Go Board). 

We are all part of an evolutionary cycle: investors help grow companies and mold entrepreneurs only for them to continue the cycle for the next generation. It’s a cycle of awesomeness. If I have the chance to become an investor after my entrepreneur days are done, here’s a list of what I always want to remember:

1. Invest in people’s dreams, not business plans. Entrepreneurs dream, and dreams become lifelong passions. Ideas will come and go, but people fight for dreams. You can make dreams into business plans, but you can never make business plans into dreams. You want to invest in those dreamers—the fighters. Ultimately, they will win.
2. Entrepreneurs risk everything. Placing one’s entire life on the minute chance that an idea will succeed is foolish. But that’s being an entrepreneur and that includes everything: family, relationships, potential jobs, bills, foreclosures, defaults. It is, and always will be, the truest test of will and character.
3. People’s rent money. Money you invest into a company is more than just helping build a product. It pays for the lives of many. Whether you recognize it or not, you’re paying others’ rent, grocery bills, etc. For someone who has put his blood, sweat and tears into a dream, it’s the most heroic action. 
4. Fairness. Always be fair and be fair to all. 
5. Take email seriously. Entrepreneurs care more than you know. Always reply. Always.
6. Education beyond the classroom. There are many investors who push money into ventures. There are few that teach. Be a teacher. 
7. Have fun. Creating and launching a venture is scary enough. Enjoy it, be a lively person and make a difference in each company you invest in. 
8. Do the stuff you say you will. If you commit to helping someone, help them. Your word is all that you have—don’t abuse it. Also, always be truthful.
9. Dream often. You will miss many great opportunities. The world will always be bigger than any investment anyone ever makes or any company that is funded. Ultimately, better yourself and better the lives of the people around you.
10. If it’s too good to be true, it probably is*. The old adage is always useful, but the asterisk is important too: There will be another Steve Jobs and Mark Zuckerberg. If you find him or her, don’t let them leave the room without a signed sheet. 
11. Know where you’ve been. You stood as an entrepreneur once. It is not easy, but is the most exhilarating and exciting journey imaginable.

There are people who risk everything to dream—to make something different—and face impossible obstacles. For now, I am one of them. But hopefully one day it will be my responsibility to continue the cycle and make others’ dreams become reality.