A spirit of experimentation, entrepreneurship and risk-taking has guided Jessica Millstone into and out of a career in education technology and through the build-out of her family’s family office.
This mindset is a legacy from her father, she says, who built the family’s wealth through a scrap metal business started in the 1940s by her grandfather in Rockville, Md.
“I wouldn’t say it’s an extremely future-forward business,” Millstone says. “But my father always was very entrepreneurial within that space, trying a lot of new things and experimenting.”
That attitude now informs the way Millstone and her sister are approaching the work of the family office, Millstone Investments, which they co-own.
“One of the huge money values that was passed down from my father was this idea that all of this is to do something with. It is not to just sit on, it is not to hoard, it is not to grow and count all your coins at the end of the night,” says Millstone, who is managing partner of the family office. “That’s what we want to do with the legacy that he left us: continue that work, get the money out there, build new things — have it be in circulation, working in the world, not in bank accounts somewhere.”
Branching out
Neither Millstone nor her sister chose to go into the family business as their father had hoped they would. Instead, Millstone got involved in the first days of the internet and website development while at NYU. This led to a career connecting education and technology: working as a teacher, for foundations and nonprofits, and for ed tech companies.
While she and her sister were building their own careers, their father was running the family business and investing, starting the first version of the family office.
Since their father passed away in 2021, Millstone and her sister have sold the scrap metal business and are working toward a more cohesive strategy for the family office.
“My sister and I really think of our family office as this evolution of our family business, one that is structured around family money as opposed to scrap metal,” she says. “I think the version that my dad had cobbled together during his lifetime as the main wealth creator was like a proto-family office. Now we’re trying to build one that’s more intentionally structured to handle the family’s assets.”
Going “from family business to family money” is a psychological change, she says.
“Growing up in a family business, it was the organizational structure of the family in many ways,” Millstone says. “That’s what we’re so comfortable with, and want to evolve, but also replicate: the way it feels to have that core entity that everybody kind of rallies around. I want to imbue as much of this with those values as possible.”
Experiments in investing
Millstone’s transition from ed tech to investing started at the beginning of 2020, when she suggested to her father that they explore venture capital investing. She had left her ed tech job and knew that her father was investing outside of the family business, primarily in publicly traded stocks and real estate. They teamed up to form a venture capital fund called Copper Wire Ventures — a nod to the scrap metal business origins. They didn’t raise outside capital but used family office funds for early-stage investing.
They launched the fund at the beginning of 2020. When the COVID-19 pandemic began shortly afterward, “the ed tech space exploded,” Millstone says. “All of a sudden everybody in the world was using all the products, technologies and pedagogies that we had been working on for 30 years. Everyone thought I was a little too excited about a global pandemic hitting town — and, like many things, it doesn’t turn out as great as you think. There were a lot of emergency uses of these technologies that did not go well.”
Copper Wire Ventures, which they had started as an experiment to support women entrepreneurs, turned into an ed tech fund “for what was a very exciting, very volatile couple of years,” Millstone says. But the market became extremely challenging after that time. Due to those challenges, plus their father’s death, she and her sister decided not to raise a second fund but instead apply the lessons they had learned to the family office.
“I credit starting this fund with my dad as the reason that we were able to take over as seamlessly as we did. It seemed very bumpy at the time, but I think, in retrospect, it was a pretty smooth transition,” Millstone says. “Through the creation of the fund, I met all the people, I knew the portfolios that he was holding, I understood the chaotic flow chart of how things flowed between our family assets and the family business.”
Her father had kept much of this information in his head, and the creation of the fund provided what Millstone calls “a neutral opportunity” — not connected to an illness, for example — to transfer this critical information to her. Her sister had gained similar perspective while working with their father on a real estate fund.
“We both got that very authentic education through the creation of these funds together with him,” Millstone says.
A new vision
In the years since their father’s death, Millstone and her sister have been working to realize their vision for the family office. They sold the operating business, though they still own the real estate associated with it and lease it to the new owners. They have started outsourcing some functions, including using a multifamily office, Pennington Partners, for some back office work.
They have continued their father’s risk-taking and experimentation.
“About 80% of our investments are market rate: We’re really looking to make money, and they’re not specifically thesis-driven,” Millstone says. “And then we have about 20% of our portfolio in impact-specific initiatives. I think 20% is more than most people allot to that, and those are the areas that my sister and I spend the most amount of our time on.”
That 20% includes Millstone’s angel investing in education, as well as investments in women’s sports, a passion of her sister’s. They are part owners of the Portland Thorns of the National Women’s Soccer League, and they have invested in the Calgary Wild, part of a new Canadian women’s soccer league.
“We really want to build something that is almost like a circular economy, where we have income-producing investments that then go into the private equity investing, that then feed back into other holdings, like real estate,” Millstone says. “We want it to be a really sustainable and sustaining organization.”