A conversation with Matt Greenfield, Founder and Managing Partner at Rethink Education.
Addressing adult illiteracy and innumeracy represents one of America’s greatest economic opportunities. With 28% of adults reading at the lowest levels — disproportionately affecting marginalized communities — this educational gap is a persistent barrier to equity and it costs the U.S. economy up to $2.2 trillion annually, if not more.
The communities hit hardest by literacy and numeracy gaps are, as a result, excluded from economic opportunity. The impacts are cascading: parents who can’t help children with homework, workers trapped in low-wage jobs, and citizens vulnerable to exploitation. This isn’t just about individual advancement. It’s about supporting families and entire communities, bolstering American economic vitality, and sustaining a vibrant civic sphere to which all can contribute.
Visionary investors like Matt Greenfield, Founder and Managing Partner at Rethink Education, see transformative EdTech solutions as essential infrastructure for both economic growth and an equitable society. Matt has more than 25 years of experience in venture capital and a robust background in entrepreneurship. We recently sat down with Matt ahead of his upcoming sessions at EdTech Week 2025 for a conversation about investment and innovation supporting adult literacy and numeracy. The conversation has been edited for length and accessibility.
You’re positioning adult literacy as a trillion-dollar opportunity at EdTech Week. Beyond the economic numbers, what’s driving your conviction that this is the moment for breakthrough investments in literacy and numeracy?
Illiteracy has been a problem in the United States for a long time. The Organization for Economic Co-operation and Development (OECD) found in 2012 that 19% of working-age American adults were functionally illiterate. In 2022, that number had risen to 28%. And the federal government puts a relatively small amount of money into adult basic skills training of any kind.
I tutored illiterate adults in Baltimore when I was in my twenties, and I was constantly learning just how difficult their lives could get. For example, you go into a grocery store or a drugstore and are trying to figure out which food or medicine to buy — but a lot of the labels look quite similar. Or what happens if you miss your usual bus stop? How do you find your way back to where you were? How do you manage a calendar and show up for your job on time or a doctor’s appointment?
But it also seems obvious that if your employees are illiterate, that is a huge drag on your productivity and a risk. This is the most basic kind of upskilling and it’s the elephant in the room that nobody is talking about. There are conversations about skills-based hiring and the skills economy, and people are talking about micro-credentials and data awareness and other skills valued by employers — but none of those skills matter if someone is illiterate and innumerate.
What are you seeing in the market that others might be missing?
I think that a for-profit entity might be able to do things in literacy that nonprofits cannot. And I think that employers should be ready to pay for something that works in a scalable way. I also have a fantasy that Medicaid would pay for it as well. Medicaid is already paying for a number of things that are not strictly in the realm of healthcare because they have a major effect on the cost of healthcare or the medical cost ratio.
I can give an example of that, which is in my portfolio. There is a company called Rasa Legal that helps expunge criminal records at the cost of $250 per conviction. They have relationships with two different Medicaid plans because if you can expunge someone’s criminal records, they can get a better job and in some cases better housing — and that ends up costing Medicaid less money.
Literacy is one of the biggest social determinants of health. I would like to see someone at least try to get Medicaid to pay for basic literacy training. It’s a triple win: It’s a win for the individual family, it’s a win for Medicaid, and it’s a win for society as a whole.
So many of us agree that adult literacy matters, but it remains chronically underfunded. What is the one thing that needs to change to unlock real progress?
We cannot count on money coming from the federal government. I think there’s a slightly better chance of it coming from state governments, if you can present them with a clear and effective roadmap to improving literacy in their states. But you have to find a market-based solution where you capture some of the massive positive externalities associated with teaching someone to read.
You can do that through employers, and you can do that through health insurance plans. As I mentioned, literacy is a huge social determinant of health — teach someone to read and they can do a better job of taking care of themselves. You can get an ROI that would be extremely exciting for a venture capitalist, and more or less guaranteed to a funder like Medicaid or to an employer.
At EdTech Week, you’ll be evaluating innovative math products as a “shark.” What makes a literacy or numeracy solution investment-worthy versus just well-intentioned?
I am not looking for a minor efficiency tweak — especially not one that exacerbates the worst aspects of the current system. What I’m looking for is a Trojan horse that fits into the existing system but brings in something new. My favorite example of that is Google Workspace for Education. The value proposition was, “How would you like to use Gmail for free?” Lots of administrators and districts said, “Yeah, that sounds great.” And then they got a collection of cloud-based collaboration tools, which opened up a whole new set of pedagogical possibilities.
If you had tried to sell those pedagogical possibilities to the district and foreground those instead of the Gmail value proposition, administrators probably would’ve turned them down, even if they were still free. They would’ve said, “I’m sorry, I don’t think I can fit that in with all of my other priorities,” or “I don’t think my teachers can do that.” All of the possibilities opened up by Google Workspace would’ve seemed alien and threatening. So you have to smuggle it inside the Trojan Horse. And that is really what I’m looking for.
What about the role of AI? As an investor, is AI a game-changer, or just another tool?
There’s this question about whether AI tools are like calculators during the transition away from slide rules. A lot of people thought that doing away with the slide rule would result in students having a weaker understanding of math. And that may be the case, but we did okay making that transition. But I also think the idea that AI can just write something for you and that you don’t have to learn to write it yourself is incredibly dangerous and wrong.
There is increasing concern that relying on AI actually weakens your own cognitive capabilities — so you definitely don’t want AI to replace the mastery of core skills. You have to deploy it in a way that challenges students to do a better job of developing those skills. I’m not sure that’s what most tools will necessarily do. There’s also going to be a tendency to want to save money and reduce the number of teachers serving a given number of students, and that is dangerous too.
What’s one question that you wish people would ask you?
Maybe it’s a question about how to fix the entire ecosystem. There are a lot of market failures, things that would yield amazing ROIs for Medicaid and Medicare, private insurance, employers, and for society as a whole. What is stopping those things from happening? How do we fix that?
Part of it is just a problem of awareness. Getting the C-suite at large corporations or small corporations to understand — to believe in the ROI of teaching people to read. I would definitely like help from people in getting the message out to those who run health insurance plans. I think they need to be much more proactive in seeking out these health interventions related to learning.
Don’t miss EdTech Week 2025
Join the Luminary Labs team at EdTech Week 2025. We’ll be on site attending sessions on innovation in K-12 and adult education, education infrastructure, and more. Register with the code LUMINARY20 for a discount. Plus, be sure to catch Matt’s sessions:
- Shark Tank: Math in K-20 — October 20 from 10:00-10:45 a.m. ET at Faculty House, 64 Morningside Drive
Math remains a persistent barrier to student success — yet it’s also a gateway to critical thinking, STEM careers, and economic opportunity. This Shark Tank spotlights innovators transforming how math is taught, learned, and applied from kindergarten through college. Expect bold approaches to mastery, engagement, and equity — and a redefinition of what it means to be “math-ready” in today’s world. - Solving Adult Illiteracy at Scale: The Untapped Trillion-Dollar Opportunity — October 21 from 3:00 – 3:45 p.m. ET at Alfred Lerner Hall, 2920 Broadway
Adult literacy is one of America’s most overlooked crises—with one of the highest price tags. Low literacy among adults costs the U.S. economy trillions each year in lost productivity, healthcare inefficiencies, and stalled workforce participation. This session makes the case for a bold shift: treating adult literacy not just as a moral imperative, but as a strategic investment.
