Meet a former VC who has a plan to prepare American students for an AI-disrupted future

“It’s a world where all of these jobs are going to just vanish. We don’t have time to mold this for 10 years,” Dintersmith told Fortune. “Would you rather spend thousands of hours on math you’ll never use in school, or get really good at something that can help you pursue a career you find fulfilling and can support yourself. What do you care about: the future of a kid or data for the state rankings?” 

Dintersmith, in his new book, Aftermath: The Life-Changing Math That Schools Won’t Teach You, argues that the education system is designed to fail students. It’s still teaching kids to learn things a machine can easily do, and it isn’t offering real world knowledge. He argues that math taught in schools has little relevance to real work or life, and it’s undermining American society. Kids should be learning real-world probability and statistics instead of algebra and calculus equations.  

The book is the culmination of 15 years studying the American education system strengths and weaknesses. He sees a system that defines academic success on “high-stakes” standard exams that ask questions that a computer could easily answer, while failing to give students skills that would prepare them for their lives and careers. If the American education system doesn’t change, millions will enter adulthood unprepared, sowing “the seeds for democracy’s collapse,” said Dintersmith.

Beyond math, he believes Americans need to rethink the automatic high-school-to college-pipeline, in a world where more college graduates feel like their degrees are not worth the cost.  

In 2023, Dintersmith visited a school district in Winchester, Va., a small town of about 28,000 located an hour and a half outside Washington, D.C. He met students learning at the Emil & Grace Shihadeh Innovation Center, a technical training center for high school students. While technical education offerings are typical of many secondary schools across the country, Winchester’s approach is different, Dintersmith said, because vocational education is not stigmatized as a place to dump students who weren’t college-bound.  

It wasn’t treated like an afterthought, Dintersmith said, and he found that about 90% of the district’s high schoolers take a class at the center. What he saw inspired him to make the film Multiple Choice in 2025. It was shown at the Sundance Film Festival earlier this year. 

An unlikely advocate

Dintersmith, 73, is an unlikely candidate taking up the charge of transforming American education. After attending the College of William & Mary in 1974 and getting a PhD in engineering from Stanford University in 1981, Dintersmith worked at a microchip startup for seven years, before becoming a venture capitalist and general partner at Charles River Ventures, where he worked for more than 20 years, and has since stayed on a partner emeritus.

While at CRV, he managed a number of funds ranging from $50 million to upwards of $450 million. He was even ranked by Business 2.0 as the country’s top-performing venture capitalist between 1995 to 1999. But Dintersmith credits having children later in life for his seemingly abrupt career shift.

Turning his attention to education, Dintersmith said, came as a surprise to himself as well. 

“I never imagined doing anything related to school,” Dintersmiths said. “And then, honestly, when my kids got to middle school, I just said, ‘Whoa. None of this makes any sense to me.’” His interest started in 2011, when his son’s middle school began offering a program on life skills, but Dintersmith didn’t find any of the skills relevant to real life. His son and daughter are now in their 30s, he said. 

Since then, Dintersmith has written three books and produced nine documentaries about the failures of the American educational system. His work also led him to take an education odyssey during the 2016 school year, he visited 200 schools across 50 states to see how different schools across the country functioned. And detailed the experience in a book What School Could Be, published in 2018. 

Vocational training opens doors

At Winchester’s Innovation Center students didn’t have to choose between welding or Advanced Placement Chemistry to convey that they were an academically rigorous student to colleges because vocation training was the norm. They could take classes on carpentry, welding, plumbing, and electrical work, or train to be EMTs, lab technicians, firefighters, and nursing aides. The courses are tied to the needs of the local economy, and many instructors are business owners or experts who work in the area and volunteer their time to work with the students. Several students have gone on to start careers at their instructors’ companies. 

Liz, a student featured in the documentary, is now a pre-law student at the University of Virginia who wrote about her experience taking welding classes in her college applications. Another student, Malachi, came to a firefighting class asking the instructor for “guidance in life and discipline.” Outside of his classes, he became a volunteer firefighter, and the local station became a place where he could be mentored or just have a place to call home.  

“They were really focused on helping every kid find their lane, and it was tied to what skills would help that local community,” Dintersmith said. 

Winchester can serve as a model for other schools, Dintersmith said. Many high schools offer some form of career and technical education, so “they’re not starting from zero,” he added. Community input is key, he explained. To build the 54,000 square-foot Innovation Center, a local philanthropist donated $1 million, and the State of Virginia and the local community also contributed to the project. 

“It’s really just bridging the gap between finishing high school and being able to say, I’m good at something that matters to the adult world,” he said.