A Venture Capitalist's Understanding of Public Schooling and Where It's Succeeding
Ted Dintersmith draws from his visits to 200 schools nationwide and his resulting book What School Could Be to map out more meaningful competency measures and better uses of testing
BY JULI VALENTINE/School Administrator, May 2019

Ted Dintersmith, once a venture capitalist, observed meaningful ways to assess students' performance during a year visiting 200 schools across the country.
Ted Dintersmith had hardly unpacked his bags from touring the country to promote his Sundance-acclaimed documentary film, “Most Likely to Succeed,” when he decided to go back out on another road trip. But this time, instead of press junkets and screenings of the film, he was intent on simply visiting America’s schools as a quiet observer.

So, the venture capitalist, who has become a new champion for public education, traveled at his own expense to all 50 states, visited 200 elementary and secondary schools, almost all of them traditional public schools, and took in 1,000 meetings with educators, students, parents and policymakers in the span of a school year. 

Dintersmith, 66, was concurrently stunned and highly encouraged by what he saw. In schools of all kinds, teachers were connecting learning to the real world and giving students more voice, while coping the best they could with standardized tests of questionable value and other regulations that he thought were leaving dedicated educators hamstrung in using innovative practices in their classrooms.

“I call it everywhere and nowhere,” Dintersmith said. “You can find remarkable examples of learning at its best in every school and community that you go, but it still only reaches a small percentage of our kids.”

One outcome of his journey was the publication of another book, What School Could Be, and a direct appeal to U.S. Secretary of Education Betsy DeVos to take a step back and support the innovation and creativity already occurring in schools across the country. To date, he’s seen no evidence that this appeal has had any influence on her policies and priorities.

The recent interview with Dintersmith was conducted electronically by Juli Valentine, senior editorial assistant at School Administrator magazine.

What led you from being a venture capitalist to being so interested in K-12 public education, and how does your background impact the way you look at schools?
DINTERSMITH: My three-decade career in technology-driven innovation gave me insight into the tsunami of change reshaping our society. The capacities of machine intelligence — computers, software, robotics, artificial intelligence — are increasing exponentially, with profound impact on what we need for career, citizenship and, at some level, meaningful existence in modern society.  

I also came to recognize that our conventional model of education imparts few relevant skills as it diminishes creativity and audacity. In my venture capital career, I actually found that academic success was negatively correlated with the ability to thrive in innovative endeavors.  In our increasingly dynamic world, our schools need to enhance, not diminish, creative problem-solving and collaboration and mindsets such as audacity, curiosity and embracing ambiguity. The extent to which our schools step up to this challenge will define our nation’s future.

As for my own background, I’m a product of public education — Fairfax County Public Schools in Virginia and a state university, College of William and Mary. Our nation’s public education system is the foundation of our democracy.  When we shortchange it, we risk the survival of our civil society. 

What prompted you to embark on a year-long trip to visit schools and school districts across all 50 states? Did your preconceived notions — or your mission — change as you went along?
DINTERSMITH: After my venture career, I took on a new life mission — how to prepare kids for a world defined by innovation. My strategy started by organizing and funding a film on education, “Most Likely to Succeed,” which shows what’s possible when students take on ambitious interdisciplinary projects guided and inspired by teachers trusted to design the learning experience. 

The film has been a huge success. After it premiered at Sundance, I turned down offers from online streaming companies and instead pursued an innovative distribution model. We offered the film to schools, so they could convene community screenings to spark thoughtful discussion about the future of their organizations and their kids. It has now been screened in some 10,000 communities in 35 countries. Recently, we made the film available on iTunes, Amazon and YouTube, but we still recommend that schools use it as a vehicle to energize their communities to reimagine what their schools could be. 

As I traveled with “Most Likely to Succeed” to communities around the country, I was getting important questions: “What kind of learning experiences prepare kids for the world of innovation?” “The school in the film, High Tech High in San Diego, had the advantage of starting from scratch. How can an existing school change?” “What can administrators do to effect positive change in their schools?” “What kinds of policies and assessments set the conditions that let powerful learning experiences flourish in creative non-standardized ways?” All great questions.

So, I did something bold during the 2015-16 school year. I traveled nonstop, going to all 50 U.S. states, visiting 200 schools and convening 1,000 meetings and community forums. I was blown away by the experience, particularly by the many educators I met fighting so hard for their students. Our teachers face the daily challenge of misguided policies, inadequate pay and a lack of trust. Yet, they never give up on their kids. This immersive trip also gave me a much better perspective on the core question of how to transform classrooms and schools to elevate learning outcomes for children trusting us to prepare them for a future none of us can imagine.  

You carry strong views about the failings of standardized testing and the lack of meaningful competencies being measured in schools. Are these views based on your entrepreneurial business background and/or what you’ve learned from spending time inside schools?
DINTERSMITH: Actually, these views are based on the evidence, or lack thereof, offered by the testing companies themselves about their high-stakes tests. The best case the College Board makes for its SAT test is that scores are loosely correlated to the test-taker’s first-year college GPA, a correlation that’s much weaker than the affluence of the test taker’s family.  

I’m waiting for the day when one of these organizations, which generate such large profits on testing, provides evidence that the time spent on test prep helps kids develop any consequential proficiency. I’m not holding my breath. The reality is that these tests soak up large amounts of student time and money, with the only consequence being reshuffling college admissions priorities, not developing important proficiencies. These scores are far better reflections of the tenacity and financial resources of the parents, not the students’ skills and potential.

I encourage people to review a few online sample questions for the SAT, ACT or state-mandated tests. Then ask, “Do these questions get at anything of consequence to me as an adult?” They don’t. In Most Likely to Succeed, which I wrote with the amazing Tony Wagner, we suggested — not tongue in cheek — that we should replace this entire battery of standardized tests with timed performance on crossword puzzles and Sudoku. 

Making matters worse is the entire tutoring industry that’s grown up around these tests, with highly compensated coaches imparting useful but corrosive advice. “Don’t think creatively.” “Do practice drills until you can do these low-level problems in your sleep.” “If you come across a hard problem that will take you time to figure it out, skip it.” Just dreadful messages for kids.

There’s an added dimension to the damage done by these tests. By pushing kids to do well on these vapid exams, we effectively tell them that what matters in life is outperforming your peers on material of no redeeming value to their community. In a very real sense, when we turn our schools into test-prep factories, we hollow out of our children any sense of genuine purpose.  

What have you observed in your travels that gives you confidence we know how to prepare kids for a world we can’t begin to anticipate or predict?

A teacher at High Tech High School in San Diego, Calif., conducts a classroom lesson at one of the schools visited by former venture capitalist Ted Dintersmith.

DINTERSMITH: The subtitle of my book is Insights and Inspiration from Teachers Across America. As I traveled, I was stunned by the many powerful examples of great learning experiences I discovered. You can find remarkable classrooms in any district and community.  Our educators know what to do. The challenge is that these exemplars, while in every community, only reach a sliver of our kids. We must understand what conditions let these authentic, powerful learning environments flourish.

A challenge for me in writing What School Could Be was that the learning experiences I showcase differ entirely in their specifics. I describe kindergartners in Fort Wayne, Ind., designing robots, elementary school kids in South Carolina taking responsibility for their school garden, 8th-grade history students in Fargo, N.D., creating documentaries about their community’s historic buildings, and many more creative, distinctive learning experiences. The antithesis of standardized education. But in reflecting on these exemplars, I came to appreciate that they share certain core principles. These classrooms and schools help kids develop an authentic sense of Purpose, Essential competencies (critical thinking, creative problem-solving, etc.), student Agency, and deep and retained Knowledge. I use the acronym, PEAK, to define these conditions for powerful learning.  

The book also profiles education leaders who create conditions that empower teachers and principals to create PEAK learning experiences. I showcase district superintendents in Virginia’s Albemarle County and California’s Coachella, community leaders and state commissioners who have effected profound school transformation — but not with top-down edicts insisting on a cookie-cutter approach. These transformational leaders energize their community to support change, build consensus on essential student competencies, trust teachers to lead the way with an innovation model based on small steps leading to big change, and engage community resources.  

You’ve indicated you admired elementary schools “that made thoughtful, diagnostic use of standardized tests to ensure young kids develop core learning skills.” But you found in higher grade levels an obsession with test preparation.
America’s education system leads the world in time allocated to preparing for and taking standardized tests. Today, many high school students have taken more than 100 standardized tests during their K-12 years. Piling on, the college admissions process pushes kids to produce sky-high SAT/ACT scores, engage in an AP course arms race and check off lots of extracurriculars for the express purpose of producing a more attractive application. 

It’s essential for schools to equip kids with basic “learning how to learn” skills, and standardized tests can play a constructive role in ensuring kids aren’t getting short-changed on the basics. A school system needs urgent help if many of its middle and high school students are reading well below grade level. That’s an educational code red, which tests can help us identify. But we don’t use these tests in thoughtful, diagnostic ways. We use the scores punitively, demoralizing teachers committed to our most challenged kids. The ironic hypocrisy is that America’s education system showers our rich kids with resources, then shames the educators who dedicate their lives to helping the kids with the biggest out-of-school challenges.   

In a system that emphasizes performance on standardized exams where college readiness and admission is the principal goal, you say that more affluent families can afford better test preparation such as individual tutors and expensive preparation programs. Doesn’t that leave less privileged students at a distinct disadvantage?
Absolutely. As long as school success is defined by scores on exams tied to material that kids find boring, these scores will reflect the tenacity and resources of the parents — not the competencies and determination of the students.  If college admissions continues to prioritize scores, they’ll continue to fill entering classes mostly with affluent applicants, and fight off court cases about how they’re somehow bending the rules when they accept applicants with lower scores. 

But here’s what’s exciting. Imagine if school were about kids creating and carrying out bold, creative initiatives to make their world better. Suppose high school graduation requirements (as is the case in New Hampshire) and college admissions officers (as is the case with a growing number of colleges participating in the Coalition for Access) care most about an applicant’s tangible accomplishments (e.g., science experiments, creative writing samples, thought-provoking analyses of literature or historic events). 

In this world, we’d see all across our country what I write about in What School Could Be — an explosion of engaged learning. And we’d see how often the at-risk kids bring resourcefulness and creativity to do remarkable things, while many rich micromanaged kids struggle with more ambiguous, risk-filled endeavors. This education world, where kids take on ambitious initiatives to make their world better, is far better preparation for kids going forward and would help return education to its historic role of helping level America’s playing field. You won’t hear that visions from education bureaucrats, but it’s the vision we urgently need.

You mention that children should study what’s important to learn, not what’s easy to test. How do education leaders balance that idea with compliance with state and federal standards?
I’ll discuss this in the context of math, a particularly telling example of damaging, nonsensical standards. Just for context, my math background in school and professionally is pretty decent, so I’m not winging it.

In middle and high school, kids take lots of math. Every state requires students to complete an algebra course, and often geometry and/or algebra II. College admissions officers expect kids to do well in calculus, viewed as the pinnacle of high school math. In all of these courses, kids drill on lots of low-level procedures with the goal of being able to quickly and accurately perform tasks like solving for unknowns, factoring polynomials or simplifying closed-form integrals. No one seems concerned that kids never learn how to apply this math, nor do we have any evidence that students retain this math. In fact, studies find that only a small percentage of adults in our country use any math beyond fractions and decimals.

One reason why our kids study so much math they’ll never use as adults is these low-level math micro-tasks are perfect fodder for our standardized test designers, who can bundle together 30 to 45 simple problems to produce a test that generates a perfect bell curve of results. As these tests define our curriculum, our kids study what’s easy to test, not what’s important to learn.  So we live in a world where few kids study the math behind financial literacy, but all study the quadratic equation. Our best math kids take calculus (no scientist or engineer does hairy integrals by hand anymore) and are discouraged from taking statistics (a big career advantage, and of vital importance for citizenship and important personal decisions). We rationalize all of this by saying, in some vague way, that it helps students master the fundamentals, develop grit or learn how to think. All just waving hands to justify a disastrously-obsolete curriculum. 

These failings aren’t limited to math. Kids study the difference between ibid and op cit, but can’t do basic fact checking. Kids memorize formulas and definitions in science, but are clueless about how the natural world works (watch this short video about MIT graduates for a real shock, or this video about Harvard graduates explaining why it’s cold in Boston in the winter). They check off the box with two years of foreign language in high school, but respond with a blank stare when asked, “¿Como está?”

None of this comes as a surprise to educators. They understand the damage done by federal policies and our mile-wide-and-inch-deep college-ready curriculum. And they know what kind of challenges bring out the best work in students. They know what they can do if they’re trusted. Our challenge is how to unleash the potential and pent-up innovation in America’s children and educators. We can continue to adhere to an education model based on precisely measuring our kids’ lack of progress on material they’re unlikely to retain or ever use. Or we can put in place conditions that empower trusted teachers to help students develop distinctive competencies by creating audacious initiatives that contribute positively to their community.  The choice is ours, and every family, teacher, school, district and state has the power to focus on developing the distinctive potential of each child. 

What do you consider next-generation assessments, and how did you see these being applied in some of the places you visited?
In What School Could Be, I describe the remarkable transformation in New Hampshire schools. From 2009 to 2016, under the leadership of State Commissioner Ginny Barry, New Hampshire moved to competency- and performance-based standards, and advanced learning outcomes across the state. It modernized its assessments, linking them to authentic examples of student work. It trusted teachers to lead the way, subject to checks and balances. And while it’s anecdotal, in hundreds of events I’ve done over the years, the very best questions I’ve gotten were from New Hampshire public school students.  

Did you meet superintendents in your local school visits and come away with any impressions of the role they play or don’t play? If you were serving as a local superintendent, what steps might you take to improve learning and life outcomes for children?
First of all, I have enormous respect for the contributions of our district superintendents. This position carries very consequential responsibility, and requires dealing with many fierce constituencies who often are on very different pages. 

The superintendents I’ve met are pretty evenly split among those “doing obsolete things better” and those striving to “do better things.” Honestly, if a superintendent views his or her role as holding their principals’ feet to the fire to boost test scores, I don’t hold out hope for real improvement in that district. This approach is what the U.S. has tried to do nationally for over two decades, with little to show for it.

But it’s inspiring to see what’s possible when a superintendent leads the way in reimagining education. Their leverage is considerable, if they view their role as supporting and empowering their district’s innovative principals and teachers. And I’ve seen entire districts transformed in just two to three years.

In addition to politicians, textbook companies, college admissions deans and billionaires, you have listed “education bureaucrats” among the leading forces that impede meaningful change in schools. Did you see evidence of education leaders standing in the way?
There’s a reason they call it an education “system.” There are lots of non-experts in American education who go to great lengths to tell our educators what they have to do, instead of trusting and supporting educators to do what they know will be effective.

I’ve found, somewhat ironically, that the higher up someone is in the education “pyramid,” the less informed the perspective. America does have real education expertise … in our classrooms, schools and districts.  It would be a beautiful thing if non-educators realized this.

Additional Resources
Based on what he observed of effective education, Ted Dintersmith and his colleagues, along with feedback and contributions from teachers across America, developed the Innovation Playlist, a grassroots innovation model that promotes small steps that lead to transformative change over time in a school or district.

The playlist includes resources that enable principals and teachers to try small innovations in classroom pedagogy.

Dintersmith suggests these other resources:

» What School Could Be by Ted Dintersmith, Princeton University Press, Princeton, N.J. This book details his trip to America’s schools with more in-depth discussion of alternative assessments in schools.

» Most Likely to Succeed: Preparing Our Kids for the Innovation Era by Tony Wagner and Ted Dintersmith, Scribner, New York, N.Y. This book was the impetus for a documentary about the function and focus of American schools. 

» “Rapid Innovation in Public School — Team 19 at Albemarle High School,” a short video featuring a Virginia high school that is piloting an innovative approach to teaching and assessment.