Most venture capitalists spent their twenties building startups or working at Goldman Sachs. Matthew Greenfield spent his teaching Shakespeare to undergraduates.
Now he manages a venture fund that has deployed over $100 million into companies serving students that traditional education fails: incarcerated learners, neurodivergent children, immigrant families, and struggling readers. The path from literature classrooms to boardrooms runs through a simple realization: classrooms alone cannot fix broken systems.
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From Yale to the Classroom
Greenfield earned three degrees in English from Yale University: a bachelor’s, master’s, and doctorate, all focused on American and Renaissance literature. Yale awarded him five academic prizes and competitive fellowships from the Mellon and Whiting Foundations. He served on the editorial board of the Yale Journal of Law and the Humanities.
His teaching career started at Bowdoin College, where he joined the admissions committee and helped create interdisciplinary programs for first-year students. He later taught at the City University of New York’s College of Staten Island, running graduate seminars in literature for New York City public school teachers. His specialty: Shakespeare and Edmund Spenser.
The Pivot to Venture Capital
By 2012, Greenfield had left academia to co-found Rethink Education with Andre Bennin. The White Plains venture firm focuses exclusively on education technology companies.
Before launching the fund, he co-founded Rethink First, a special education software company that grew to over $100 million in revenue before its acquisition by a private equity firm. He also founded Stonework Capital, an ethically oriented hedge fund, and made early angel investments in companies including Wireless Generation, later acquired by News Corp.
Rethink Education has since made 123 investments across early-stage and growth-stage companies. The firm has achieved 26 portfolio exits.
Who Gets the Money
Rethink Education does not invest in companies selling premium tutoring to wealthy parents or test prep services for private school students.
The fund targets companies serving specific populations:
- Students from low-income families
- Neurodivergent learners
- Incarcerated individuals seeking education
- Immigrant communities
- Elderly populations
- Anyone facing discrimination in traditional education settings
Greenfield describes the investment thesis as backing companies that address “actual human suffering.” The firm looks for what he calls “authentic entrepreneurs” who come directly from the communities they serve.
Portfolio companies include Amplify Education, which developed science-based reading curricula now required by legislation in 32 states. Another investment, Ignite Reading, provides daily one-on-one tutoring to struggling readers, primarily in public schools serving low-income students.
The Equity Problem
In 2021, Rethink Education launched Rethink Equity, setting aside $5 million specifically for underrepresented founders of color.
The numbers behind the initiative: white men receive 77% of all venture capital despite representing 30% of the population. Latinx founders receive 2%, and African American founders receive 1%, according to Crunchbase data from that year.
Ebony Brown, who joined as principal to lead the initiative, told Business Wire that Black and brown founders often lack the networks and capital needed to bootstrap companies to viability. The firm now reports that 14% of its portfolio consists of companies founded or led by Black and Latinx entrepreneurs.
Marriage to a Literary Family
On November 1, 2003, Greenfield married Molly Jong-Fast at the New York Palace Hotel. Rabbi Sarah Reines officiated.
Jong-Fast comes from three generations of writers. Her mother, Erica Jong, wrote “Fear of Flying,” a 1973 bestseller that became central to the sexual liberation movement. Her father, Jonathan Fast, teaches social work at Yeshiva University. Her grandfather, Howard Fast, wrote “Spartacus.”
Jong-Fast works as a contributing writer at Vanity Fair, hosts the Fast Politics podcast on iHeartMedia, and appears regularly on MSNBC as a political analyst. She previously co-hosted The New Abnormal podcast for The Daily Beast.
The couple has three children: Max, and twins Darwin and Beatrice. They live on Manhattan’s Upper East Side, where Jong-Fast hosts political gatherings.
Cancer Changes the Calculation
On January 8, 2023, Greenfield discovered he had a tumor in his pancreas. Three days later, doctors confirmed it was a neuroendocrine tumor, the same type that killed Steve Jobs.
Unlike pancreatic adenocarcinomas, which tend to be aggressive and often fatal, neuroendocrine tumors are generally treatable. Greenfield underwent surgery to remove the tail of his pancreas. As of early 2025, he has received clean scans for 18 months.
In a Medium article published January 9, 2025, Greenfield wrote about the three days between initial diagnosis and confirmation, when he thought he might have limited time left. He asked himself whether he would continue working if he had six months to live.
His answer centered on Ignite Reading, the tutoring company in his portfolio.
He wrote about his early experiences tutoring illiterate adults in Baltimore in the 1980s and later trying to start a program at New Haven’s Hillhouse High School, where three sophomores died in shootings over a 10-day period. Those experiences, he wrote, drove him to make his first education technology investments starting in 2003, five years before the term “impact investing” was coined.
The article cited literacy statistics: two-thirds of fourth graders cannot read fluently, 54% of adults read at or below sixth-grade level, and 21% of U.S. adults are functionally illiterate. Those who do not become fluent readers are four times more likely to drop out of high school.
Current Board Work and Recent Investments
Greenfield serves on the board of Southern New Hampshire University, a non-profit that operates the largest online university in the country. He chairs the board of Engrade and sits on boards at CareAcademy, GetSetup, Major League Hacking, Stellic, and Lynx Educate.
Recent Rethink Education investments include Aanaab, a Saudi education technology company, and montamo, a German company that trains heat pump installers. The geographic expansion reflects the firm’s broader focus on workforce development and climate-related education.
The fund operates what Greenfield calls an “impact operator” model, publishing detailed metrics on outcomes and asking portfolio boards to include members who reflect the lived experiences of end-users.
Twenty-one percent of American adults cannot read well enough to navigate a job application, compare medications at a pharmacy, or help their children with homework. Matthew Greenfield taught literature for years before concluding that venture capital, deployed correctly, might do more to fix that problem than any number of Shakespeare seminars ever could.
