Esther Dyson: Feign smarts by listening more

High-tech thought leader shares advice to entrepreneurs and lessons as an investor

Esther Dyson, who came in recently to share her story to me about possibly rocketing to space, is widely regarded as an Internet/high-tech luminary, thought leader, and respectable investor, having put money in some of the hottest startups, such as Flickr and del.icio.us (both part of Yahoo), and more recently 23andMe, which is backed by Google.

In this "Lessons learned" segment, Esther offers her advice to entrepreneurs and lessons learned to investors.

Her first is to listen. "Whatever the context, people will think you're smarter," she said. 

The second is to be focused and not be distracted. "More companies die of indigestion," she said. "Pick one opportunity and do it well, rather than do five or six things badly... opportunities will always be there."

The third one is "always make new mistakes."

The lessons she's learned as an investor are trickier and not so straightforward. The challenge for her has always been identifying the mistake in a failed investment and knowing how to apply that lesson to the next investment she's made. By and large, however, she realized that one way to get around this problem is to identify an entrepreneur she feels confident can be flexible and adaptable to bring in the right team when things change. 

"No matter what you invest in, it won’t be the same," she said. "You need a person who can change when the companies change and bring in the right people to lead that change."