This post is an essay by Matthew Pittinsky, a sociologist of education who founded the ed tech company, Blackboard.  Here’s a link to the original.

In it he assesses the value of my work for people in the field of educational technology, where he has constructed his career.  I’m flattered by his praise, but I thought it was worth posting here because it shows that at least some leaders in the ed tech industry want to understand the field of education before intervening in it.  Too often, as Larry Cuban has shown so vividly, ed tech sees education as a dysfunctional machinery for generating student learning that needs to be blown up and reinvented.  Pittinsky is the rare tech person who is seeking to understand how schools work and wants the ed tech industry to focus its efforts on helping this system work better.

This is his bio:

 

Three Books, By One Author, That Every      EdTech Entrepreneur Should Read…         And Why

By Matthew Pittinsky, Ph.D

April 21, 2026

“Know Thy Industry” is a well-worn and celebrated Silicon Valley value. You need to zoom in and zoom out. You need to understand the historical context. You need to appreciate the logic and illogic behind how things actually work at the system level. Stripe’s Collison brothers are a recent(ish) celebrated example. Two young entrepreneurs from a small village in Ireland, Patrick and John didn’t go from spotting a problem in payments to code. Instead, they treated the industry like a system to reverse-engineer – cold-emailing PayPal engineers who knew where transactions actually fail, acquiring-bank executives who could explain why merchant onboarding is slow by design, and card-network insiders who laid out the constraints Visa and Mastercard impose on everyone downstream. They dug into ISO standards and bank rulebooks most startups never open. Their efforts weren’t simply about networking. They were mapping a system. And when they launched Stripe it felt complete and aligned – because it was.

And then there is tech entrepreneurship in education, where Know Thy Industry seems to often be taken as optional.

Everyone has been to school. Fewer have studied it.

The reason EdTech founders often skip their homework is disarmingly simple. An entrepreneur entering payments hasn’t processed a transaction. An entrepreneur entering logistics hasn’t run a warehouse. But an entrepreneur entering education has twelve, sixteen, maybe twenty years of firsthand experience. Or so they think. Being a student is not the same as understanding education as a system – it’s like saying you understand hospitals because you’ve been a patient. What students experience is the consumer-facing surface of an extraordinarily complex social organization. Indeed, even in the same school students’ experiences can vary dramatically. And yet the field is full of confident outsiders arriving certain they knew what was broken, armed with their own school memories and a deck. The Collisons swiped a credit card too, presumably. It didn’t make them experts in payments.

So how do you go deep? When we were building Blackboard in the 1990s, my required reading was Henry Rosovsky’s The University: An Owner’s Manual and, for those who needed a primer on tech, Robert X. Cringely’s Accidental Empires. When I return to Blackboard in November 2026, I will recommend that Bb’ers engage the writings of a single author, David Labaree. 1

Labaree is a historian and sociologist of education at Stanford who, over three decades, has built a coherent, rigorous, and happily readable theory of why American education looks the way it does, behaves the way it does, and resists changing the way it does. He is not a reformer. He is not an advocate. He is a diagnostician. And that, I’d argue, is what the EdTech industry needs more of – people who understand the patient before prescribing the cure. Three books of his in particular cover K–12, higher education, and the underlying purposes that shape both. None of them will tell you what to build. All of them will tell you what you’re up against and why.

The system rewards the credential, not the learning.

The first book is How to Succeed in School Without Really Learning (1997). Despite the snarky title, it is not about students gaming the system, it is about the system itself. Labaree’s central argument is that American education has always been pulled in three directions at once: democratic equality – preparing citizens for civic life; social efficiency – producing productive workers; and social mobility – education as a private good that confers individual advantage. These three purposes are often in tension. And that tension underpins the system. Over time, social mobility has quietly won the public imagination, turning school from a shared civic project into a personal competition. Getting ahead and getting an education have become dangerously intertwined – and often confused for the same thing.

As an aside, this is the real story behind the panic around academic integrity, not grade inflation, not AI, and not the Internet before it. Those are tools and symptoms. The cause is a system that has taught generations of students that the credential matters more than the learning. Students cheating with ChatGPT are behaving perfectly rationally. The system built that rationality in. Consider the implications for EdTech. AI has genuine potential to improve learning outcomes – to help a student who previously earned C’s earn A’s. But if grades function primarily as a sorting mechanism, then everyone earning A’s is a problem for the system, not a triumph. Harvard’s recent move to rein in grade inflation is a timely example. Is grade inflation driven by expanded achievement of mastery a problem? Not necessarily, unless the point of a grade was never just to measure learning. Ugh.

The mess is not a bug. It is a feature.

The second book is A Perfect Mess: The Unlikely Ascendancy of American Higher Education (2017), and the title is both accurate and instructive. American higher education is, by any rational standard, a mess, or at least the absence of a system. Nearly 4,700 institutions, from Ivy League research universities to community colleges to quasi diploma mills, with no central authority, no coherent national plan, no single governing logic. The outsider may see this as a problem to be solved. Labaree sees this as a feature. The apparent chaos – the wild stratification, the mix of populist access and elite exclusivity, the blend of civic mission and naked credentialism – is precisely what made American higher education the envy of the world. It was never designed. It evolved, under market pressure, competing missions, and relentless consumer demand. That evolution produced something no planned system has matched. 2

For the EdTech entrepreneur, the humbling message is this: higher education is not a system. It is many systems at once, each institution operating under different pressures, different incentives, different definitions of success. A product that works brilliantly for a community college serving first-generation students may be irrelevant to a research university protecting its reputation for selectivity. When you fail to scale, don’t blame the customer. Learn the (non) system before you try to change it.

The grammar of schooling resists change.

The third book is Someone Has to Fail: The Zero-Sum Game of Public Schooling (2010), and the title is the argument. K–12 in America rests on a fundamental contradiction. We want schools to provide equal opportunity for every child and, simultaneously, to secure advantages for our own. In principle, we want the best for all children. In practice, we want the best for ourselves. That contradiction is not a failure of policy or imagination. It is baked into the institution. While the “industrial” model of organizing the process of schooling is often and correctly described as something close to K-12’s original sin, Labaree adds another layer to the challenge. It explains why school reform, despite generations of effort and billions of dollars, has produced so little lasting change.

Labaree builds here on one of the most useful concepts in the literature: the grammar of schooling, a term coined by education historians David Tyack and William Tobin. Grade levels, class periods, Carnegie units, teacher-centered instruction – these structures are so deeply embedded that reform efforts tend to accommodate them rather than change them. Most EdTech is premised on reform. The grammar has other ideas. Innovators arrive with new ideas and find themselves slowly reshaped by the institution rather than the other way around, often without realizing it is happening. I’ve written about the need for EdTech entrepreneurs to act with radical incrementalism: the change you seek has to be transformational in ambition but incremental in execution, aligned with where the sector is today. In other words, A leads to B, B to C, C to D. Rarely does A lead directly to D. And beware the unintended consequences – the history of school reform is full of interventions that achieved exactly what they set out to do and created a new problem in the process. The history of EdTech is not exempt.

Start with the patient.

Three books by one author. They won’t tell you what to build but will strengthen the way you think about what you are building, for whom, and with what mental model for adoption. Of course, there is nothing magical about these three books specifically. Labaree is my choice because no one else covers the purposes, history, and reform dynamics of both K–12 and higher education with the same range, rigor, and readability. The point is to seek system-level insights: that education has no single purpose, and therefore no single logic to optimize against; that what looks like dysfunction is often the system working exactly as designed; that reform has a nearly unbroken history of being absorbed, deflected, or co-opted by the institutions it sought 3 to change; and that the credential, not learning, is what the system has come to reliably produce and protect.

Even former teachers who know the classroom can benefit from a deeper dive into the operating logic of the sector as a system. I’m hopeful the next generation of EdTech founders will treat them as required reading, just as I expect Bb’ers will come this November.

Matthew Pittinsky is the incoming CEO of Blackboard, which he co-founded in 1997 and previously helped lead as CEO and Executive Chairman. More at matthewpittinsky.com. 4