Jesse Draper is cracking up. The 28-year-old is looking out at the open road, telling me the stories of her childhood in Silicon Valley, and she just accidentally referred to the family dinner table "the business table."
Draper is a fourth-generation entrepreneur, the first female in the family to take the path, so her description of the dinner-turned-business table isn't off mark. Draper's brothers are entrepreneurs and her father is Timothy Draper of Draper Fisher Jurvetson and a well-known venture capitalist.
During our chat, Draper paused every few moments to apologize for talking too much about herself. She's used to being the one doing the interviewing. She is the "Valley Girl," the founder and host of a show on which she interviews tech moguls. After six years on the web, the show recently inked a television deal with Cox Media Group.
Draper grew up in the Valley, surrounded by suits. Venture capital, IPO, startups — those were common household terms. As kids, she and her brothers tested out hardware that their father brought home. They were some of the first users of AOL Instant Messaging.
When she was in third grade, Draper realized there were no female business leaders in her life. Her mother stayed at home to care for the children, and the only working woman she knew was her aunt, an actress.
So, she decided to pursue acting. Draper graduated from UCLA's School of Theater, majoring in film and television. Right out of college, she landed a role on Nickelodeon's "The Naked Brothers Band" — a show that her aunt produced and her cousins starred on — and stayed for three seasons.
"I think I've analyzed it now and realized that's the reason I wanted to be an actress," she said. "The only woman I was close to and my working inspiration was my aunt."
Before the final season, Draper had an epiphany. She didn't want to spend her life in audition rooms, surrounded by 50 girls who looked exactly like her and who were just as talented. Acting was not her passion. Technology was.
"Looking back, my dad was my number one hero," she said. "I just felt I didn't have a woman in that position. As a little girl, you're trying to find your idol."
After moving back to the Valley, Draper set up a studio in her parent's garage and set up "The Valley Girl Show." Draper saw her father's colleagues and friends being grilled about their numbers on primetime television. They were great people — people to look up to — and she wanted to showcase that. She wanted to become the "Ellen DeGeneres of Silicon Valley," and used her father's Rolodex to find candidates to interview, starting with Google's Eric Schmidt.
The first year, Draper interviewed 25 men and three women, and it upset her that it was so difficult to find women in business and technology. So she made a promise to herself: The interviews she conducted would be 50% male and 50% female each year from then on. And she's stuck to that promise ever since — though it hasn't been easy.
"Women are afraid to put themselves out there, so any time I speak or in front of people, I say please get yourself out there, do press, put your face out there and be that role model that I didn't have in this world," Draper said.
Draper has found a passion for getting women interested in business in technology — so much so that she launched her own angel fund that primarily invests in female founders. She attends demo days and startup launches to find interview candidates, then follows them throughout their careers.
After six years of the show, she gets a lot of requests from startup CEOs wanting to be on the show, but Draper is always pitching herself to big names in the tech world. She has formed strong rapport with people in the industry, so they know she won't try to embarrass them or ask about sensitive issues. Draper simply wants to show that technology — and the people behind it — are approachable and fun.
"I really like to get them to open up," she said. "I like to make them feel very comfortable, I compare myself to Ellen because she is so positive, such a huge hero of mine."
Draper has interviewed people such as Sheryl Sandberg, Elon Musk, Jessica Alba, and Drew Houston. She has played segway polo with Steve Wozniak and learned yoga poses from the president of Kiva, Premal Shah.
"Most interviews, they'll say something and then say, 'I don't know why I just shared that with you.' Or, 'I don't know how you got me to talk about horses,'" she said. "I love telling people's stories, and understanding a whole person."
In her own words...
What are your hobbies?
"I have the coolest group of girlfriends of all time. Any extra time I have I spend with them, we have some standing monthly dinners and things like that. I love hiking and I go on a lot of hikes, it's how I get my exercise. I am weirdly obsessed with Pretty Little Liars, which I cannot believe I even started watching. That's my zone-out mode."
What type of music do you like?
"I'm a huge 80s fan in every sense of the 80s. I think 80s pop is my favorite Pandora station. My friends always say when we're listening to music at my place, it's always like time traveling. I love Journey, I love Queen, and I could listen to those albums endlessly."
Who are your mentors?
"People ask who are your mentors and no one ever says their girlfriends. They are my mentors, I send them all my ideas first. They're the biggest support and they all are in different industries and very driven, smart women. I really look up to all of them."
What is the best advice you've ever received?
"I learn so much from people on the show. I always say just do it, it's such a basic thing. When you're starting a company, just do it. Just go. People spend so much time convincing themselves not to do something, whatever you're doing you need to love. My grandfather always said, 'If you do what you love the money will come.' Now he did not explain how difficult it was to make that money come, but I always sort of had that in the back of my mind."
Lyndsey Gilpin has nothing to disclose. She doesn't hold investments in the technology companies she covers.
Lyndsey Gilpin is a former Staff Writer for TechRepublic, covering sustainability and entrepreneurship. She's co-author of the book Follow the Geeks.