As a fourth-generation legacy of iconic venture capitalists, Jesse Draper has had a front-row seat at the investing table since childhood. From great-grandfather General William Henry Draper Jr., to her father, Tim Draper, her access to some of the greatest minds and mentors is nothing to scoff at. But beyond the strategies, successes, and skill sets she’s seen at that proverbial table, one thing remained evident: a lack of women at that table.
Draper, an enthusiastic force to be reckoned with, has made it her mission to not only invest solely in female-founded companies, but to steward the message to women that there is a real place for them in the worlds of finance, technology, and innovation – a truth she has learned herself. Draper, 33, is a wife, soon-to-be mother of two, and founding partner of Halogen Ventures – a successful LA-based fund with 25 companies in its growing portfolio.
Becoming The Valley Girl
Having organically accrued the kind of business acumen and investing insights that would make any budding venture capitalist appropriately confident, Draper simply didn’t know there was a place for her in finance while growing up. Instead, she followed the lead of her successful aunt, an actress, and went into entertainment. There, she could look to many females for inspiration and feel comfortable in her pursuit of success.
But she was a Draper, after all, with an inherited bone for business. In 2009, after a successful run on a popular Nickelodeon sitcom, she decided to leverage her unique strengths to create her own show, The Valley Girl Show – for which she negotiated widespread distribution, received critical acclaim, and instituted a rite of passage for entrepreneurs of every caliber and vertical. A few of the hundreds of guests she’s interviewed include Jessica Alba, Ron Conway, Mark Cuban, Elon Musk, Sandra Day O’Connor, and Sheryl Sandberg.
While she reflects on the show’s tone as “sort of silly, light-hearted, and approachable,” it was also one of the first interview series dedicated solely to talking about technology and entrepreneurs. She used it as a platform to not only make Silicon Valley more relatable, visible, and fun, but to prove the fact that it can, in fact, be pink.
“I love the people who have a chip on their shoulder, who are trying to prove something, who have come up with some new idea out of necessity. They’re solving a problem that they’ve experienced. That’s something I’m passionate about investing in.”
Raising the Fund
Through the show, Draper was able to blend two of her areas of expertise—investing and media—to propel women forward in two ways: emboldening their public presence and funding female-founded companies ahead of their male-led counterparts. She believes there is no shortage of talent, vision, or tenacity among the female founder population; there has just been a historically dry wellspring of investment dollars for them.
To help remedy this imbalance, she had to first raise the fund for Halogen Ventures, which she recalls as “brutal.” Her approach to meeting with investors was aligned with her approach to every ordinary task – be as efficient and effective as possible. While reviewing new ventures, she says, “[The investor] should know right away. If they’re not in after three meetings, they’re probably not going to invest, and you might as well move on.”
Also, according to her experience, having a targeted area of interest can seriously improve your pitch, even while seeking co-investors or mentors. “At Halogen, we focus on early stage funding for female-founded consumer tech, 100% of the time,” she says. “I think it is really important to have a strategic focus and be able to defend that.” Through this specific lens, Draper has been able to identify and help fund some of Los Angeles’ most stand-out startup success stories, including Carbon38, Flex Company, HopSkipDrive, Laurel & Wolf, and Sugarfina.
Betting on Women
With only 4% of venture funding going toward female-run companies, Halogen’s focus is both practical and personal. “We focus on the consumer, and 80% of household purchasing decisions are made by women. Why wouldn’t we be betting on this? They raise half as much money, and they double the returns,” she says. “But I also didn’t have those women [in entrepreneurship and investing] to look up to.” Draper’s goal is to grow Halogen to be a billion-dollar fund capable of breeding the next generation of female billionaires, change makers, and mentors for future generations to learn from.
We focus on the consumer, and 80% of household purchasing decisions are made by women. Why wouldn’t we be betting on this? They raise half as much money, and they double the returns,
The women she’s personally grown to admire, consult with, and consider mentors are many of her peers. “Cindy Whitehead, who sold the first female sex drug [Addyi, often referred to as ‘female viagra’] for $1.5B and is now investing the majority of that into female-run companies, is a personal role model of mine,” says Draper. “She’s someone I work with regularly. We’re on the phone daily and we review deals together. We both come to the table with different perspectives. She’s just someone I really admire.”
She also lists Sonja Perkins of Menlo Ventures, Sheryl Sandberg of Facebook and, of course, her family, as trusted advisors and mentors. “When I bet on these companies, I feel like I’m betting on dreams. But I learn so much from my founders, too,” she says, mentioning that Anna Auerbach and Annie Dean of Werk are people she is constantly learning from.
Among the many lessons she’s learned from these influences, she emphasizes the importance of remaining humble, leading with integrity, maintaining vision, and never assuming you’re the smartest person in the room. “I don’t think any venture capitalist or investor can claim to be an expert. You have to be a bit of a generalist, and always learning.”
Beyond her focus on female founders, Draper has another unique practice that’s a bit unorthodox for Silicon Valley. “I do believe in education, but I don’t always bet on the MBA,” she says. “I love the people who have a chip on their shoulder, who are trying to prove something, who have come up with some new idea out of necessity. They’re solving a problem that they’ve experienced. That’s something I’m passionate about investing in.”