Which Chicagoans are best at mentoring women?

TROY HENIKOFF

53, managing director, Math Venture Partners; lecturer on entrepreneurship and innovation, Northwestern University's Kellogg School of Management

"I love helping entrepreneurs," says Henikoff, founder of SurePayroll.com and co-founder of Excelerate Labs, now Techstars Chicago. "It's awesome to see them succeed." Henikoff requires chemistry in a mentoring relationship. "There needs to be something there—I am passionate about the company or person, and the company has to want to work with me," he says. Honesty is also necessary. "Some people think I'm too tough or trying to be a jerk," he says. "I'm not. I'm trying to help."

Amanda Lannert, CEO of Chicago-based Jellyvision, welcomes "unvarnished truth" from Henikoff. "He will tell you what you need to hear so you can get better," says Lannert, 44. She attributes a third of her network to Henikoff, and says he has sent employees, customers and other advisers her way. He's also helped her with venture pitches, one of which just yielded a $20 million investment in Jellyvision, which creates interactive employee-communication software. "I am a CEO because he was incredibly helpful with advice," Lannert says.

Henikoff mentors via 30-minute open-office appointments every Friday, a service he publicizes via Twitter, and through Techstars Chicago. The heaviest mentoring takes place through Math Venture Partners, where he invests time and ultimately money in startups he'd like to succeed.

Even while mentoring, Henikoff protects his network. One example is the way he handles requests for introductions. Henikoff asks for a forwardable email explaining why a mentee wants that introduction. He then forwards it to the person of interest. "I don't want people to feel obligated," Henikoff says. He sends four to five such emails a day with a success rate of 95 percent to 98 percent. "It's really amazing how this community is open to helping," he says.