As a venture capitalist, Ted Dintersmith made bets on fledgling tech companies. The work did more than make him wealthy; it also spurred his passion for reimagining education and has shaped his hands-on approach to philanthropy.
Early in his venture-capital career, he gravitated toward company founders with sterling academic credentials, but that’s not where he found his greatest successes. In Mr. Dintersmith’s estimation, the top students clung to formulas and feared risk. Real innovators, he found, excelled in the academic subjects they liked and blew off the rest.
It was a startling revelation for someone with a Ph.D. in engineering from Stanford.
When he was general partner of Charles River Ventures, Mr. Dintersmith, now 65, watched the rapid increase in computing power and computers’ growing ability to learn and improve their performance on their own. Many start-up executives ideas’ involved eliminating the need for human workers. He began to think that any job that a computer could learn would disappear.
Pair those misgivings with his concern about his children’s future, and an education advocate was born.
Mr. Dintersmith started reading everything he could, visited schools, and talked with teachers, principals, and education experts. He’s convinced that the country’s education system is obsolete and discourages children from being bold and inquisitive. But he sees hope in patches of innovation he’s seen around the country.
“This is not something we need to send off to an R&D lab,” he says. “The real issue is how do you take isolated successes and use those to inspire others.”
Critical Thinking
Mr. Dintersmith’s answer, at least in part, was to finance a documentary that highlights the issues at stake. He found director Greg Whitely and put up the money for Mr. Whitely and his crew to make Most Likely to Succeed.
The movie traces the origins of public education in the 1890s, as the United States was industrializing, and how it has failed to keep up with changes in the economy. Then it follows two freshman classes at High Tech High, a school in San Diego that focuses on project-based learning, an approach designed to build critical thinking skills. Mr. Dintersmith co-wrote a companion book, also called Most Likely to Succeed.
The documentary premiered at the Sundance Film Festival in 2015. But Mr. Dintersmith turned down deals from several large streaming services for rights to the film. He didn’t want people to watch it in isolation.
Instead, he makes the film available for groups to buy or rent so they can screen it as a jumping-off point for discussions about how to reimagine education. More than 4,000 school communities have taken him up on the offer.
“Let’s say the two of us and three other people were all involved in the same school. If we each watched it alone from an online streaming source, we would probably say, ‘That’s interesting,’ " he says. “But we wouldn’t even know each other existed. It would not really play much of a role, if any, in helping us work together collaboratively and thoughtfully to help our school reach its full potential.”
“It’s not a cheap thing for me to support, but it’s a totally different world when we say, ‘Bring this film to your school.’ "
A Partnership With Sundance
The project is the centerpiece of Mr. Dintersmith’s giving so far. He estimates he’s spent roughly $2 million on the film and outreach efforts. He won’t specify the total amount he’s given to charity, saying only that he and his wife plan to contribute nearly all their liquid assets in their lifetimes.
During the 2015-16 school year, he made a 50-state tour of screenings. His second book, due out this spring, profiles teachers and schools he came across in his travels that are experimenting with new ideas to transform education.
Mr. Dintersmith believes in the power of film. “The way things change is generally not driven by logic,” he says. “It’s driven by emotion.”
During a talk with Keri Putnam, head of the Sundance Institute, Mr. Dintersmith suggested that the nonprofit could foster more socially minded films by bringing together filmmakers and investors. In 2013, Sundance held its first Catalyst forum, supported in part by a $50,000 grant from Mr. Dintersmith.
Each September, 10 to 12 film teams meet with 35-40 potential investors. The six forums held so far have brought in more than $18 million for 67 films.
Mr. Dintersmith did more than write a check. “When we were first putting Sundance Catalyst together, I was on the phone with him constantly — shooting him ideas, talking with him, asking his advice,” says Caroline Libresco, the program’s director. “He was very present and very engaged.”
An Early Supporter
Making small, early gifts is a hallmark of Mr. Dintersmith’s philanthropy. He says it’s not unusual for him to make a $25,000 or $50,000 commitment by email.
“I’m particularly interested in smaller grants with the chance to be hugely disruptive, where I just move really fast,” he says.
For example, Mr. Dintersmith is a fan of Big Picture Learning, a nonprofit that developed a school design that’s student-driven and relies heavily on internships to enhance real-world learning. He donated $100,000 to help the organization make its internship-management software available to other groups.
And he was an early backer of the Mastery Transcript Consortium, a collective of high schools developing a new way for students to demonstrate what they’ve learned, and NBA Math Hoops, a nonprofit that created a board game that uses basketball statistics to teach math skills.
True to his roots in venture capital, Mr. Dintersmith likes to get in early. “You just bring things like that to a halt when you say, ‘Well, that sounds like a good idea, but come back when you’ve got 10,000 people using it.’ "— Nicole Wallace
