Wendy Lea started OnTarget, a company that raised $0 venture dollars and sold for $150M in 1999. After that she'd worked with venture-backed startups, made a bunch of venture investments, worked with a remarkable startup, and is now working with Techstars.

Ambitious but inexperienced entrepreneurs tend to believe what they are told. As a mentor you should be upbeat and encouraging, but also find a way to break the hash truths. Manage the expectations and ask a lot of questions to the point where the entrepreneurs figure out the answers themselves.

Early in her career, Wendy had an opportunity to get a promotion and move to another state. It was a great opportunity, but it seemed to have a lot of professional risk. Her coach at work explained that it was quite the opposite, and the risk of saying "yes" was rather low, but the potential upside was high. At the end, the move cost Wendy her marriage, but business-wise things worked out great!

Give without expectation of return.