Jessica Millstone has seen women reluctant to take leading roles throughout her working life: in the scrap metal industry where her family was active when she was growing up, in the ed tech field and more recently in the family office world.
One reason she and her sister chose not to go into the family business was a lack of women role models in the industry.
“On the commodity futures trading side of things, you’ll find a lot of women, but in the actual yards themselves, in the leadership positions, you don’t,” she says. “And these multi-generational transitions are really not led by the women in the families.”
She saw a similar pattern as she began her career in education technology: “It’s mostly women who work in education, and it’s still mostly men who start the companies.”
Now that she and her sister have sold the family business and are co-leaders of their family office, Millstone Investments, she sees that many families include women who are just as educated and experienced in the family business as the men in the family.
“Still, very few choose to kind of step into that power of being able to allocate capital, to take autonomy over some of that wealth and really be in charge of it,” Millstone says.
Millstone has built her own confidence and experience at investing — first by starting a venture capital fund with her father.
“Originally, the mission was for it to be an impact VC fund focused on women entrepreneurs — because my dad had two daughters who did not go into his family business,” Millstone says.
After she moved from ed tech to investing, she found it valuable to join communities of women who are also interested in investing.
“It’s really a confidence game. Being in community with other women who are investing builds confidence, and then you have the confidence to do it on your own,” Millstone says.
She is a member of several groups of like-minded women, including Asteri, a group of women who run their family offices. She has also been a limited partner in a fund called How Women Invest, a fund that invests exclusively in women-led venture-backable businesses. And she has been part of an angel investing club for women, Angels.vc.
“The work that I had done with my dad around building the fund had given me that education background, and then I got to be in a community with these women who were learning this at the same time, either through angel investing or fund investing. We became each other’s support group and sounding board,” Millstone says. “Having a community of people helps me build confidence in the work that I’m doing towards professionalizing the family office, and owning it. I mean owning it quite literally: My sister and I own it, 50-50. But I also mean owning it in the sense of making that my identity and representing our family office.”