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LONG STORY SHORT WITH LESLIE WILCOX
Ted Dintersmith

 

As a child who played a lot of baseball in rural Virginia, Ted Dintersmith wanted to be a Major League Baseball pitcher. By serendipity, he says, life took him on a completely different path, when he got a job at a high-tech startup. For 25 years, he made a name for himself in the venture capital realm, before leading the charge in America as an advocate for transforming education. He is Executive Producer of the documentary Most Likely to Succeed and a co-author of the book by the same name. In the 2015-16 school year, Dintersmith visited all 50 states to meet with parents, students, educators and politicians, and encouraged communities to work collectively to re-imagine school and its purpose.

 

This program will be rebroadcast on Wednesday, Nov. 8, at 11:00 pm and Sunday, Nov. 12, at 4:00 pm.

 

Ted Dintersmith Audio

 

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Transcript

 

So, you start to realize, what is the point? Is the point of school to weed people out and to rank people on relatively irrelevant measures, or is the purpose of school to help every individual, every child develop their full potential? I think right now, in American education—this is not a Hawai‘i statement, but a fifty-state statement, the purpose of school is to rank kids’ potential on a very artificial limited measure that gives outsized advantage to the affluent. And we have to do better than that.

 

He’s on a personal crusade to bring about change to the American school system. Ex-venture capitalist turned champion of education reinvention, Ted Dintersmith, next on Long Story Short.

 

Long Story Short with Leslie Wilcox is Hawai‘i’s first weekly television program produced and broadcast in high definition.

 

Aloha mai kākou. I’m Leslie Wilcox. After a career as a highly successful venture capitalist, Ted Dintersmith of Virginia found a new calling as a crusader and philanthropist committed to seeing the reinvention of our education system. He’s been traveling eighty percent of the time, and dedicating millions of dollars of his personal finances to bring about change and innovation in the U.S. school system. To show how classroom education could be more effective, Ted Dintersmith produced a documentary called “Most Likely To Succeed”. Starting in 2015, Dintersmith took the film to all fifty states to encourage communities to rethink how children are educated in this country. Among the states where he’s found real promise and breakthroughs in innovation is Hawai‘i. More on that later. Ted Dintersmith grew up in a small town just twenty miles from Washington, D.C., but the family wasn’t much interested in the political scene. The family struggled to make ends meet with blue collar wages.

 

Oh, my dad, you know, for most of the time I was growing up, was a carpenter. You know, my mother stayed at home. She was really the intensity in our family. And so, she was the one who, in a fierce way, fought for her kids and wanted life to be better for us. Had a lot of good aspects to it, it had some things that might not be entirely positive. But we were just sort of, I’d say, fairly, you know, lower income, lower middle income. We didn’t have a lot of money, for sure. And you know, it was one of those neighborhoods where there were no fences. People just rolled out of the back. Every family had two, three, four, five kids. And we would just play all the time. Back then, school was maybe a third, maybe less than half of our life, and the rest of the time had nothing to do with it. You know, very little to no homework, just kinda do things.

 

You didn’t have play dates?

 

No. No. You know, it was like, it was just random. And you know, you realize the incredible value of growing up in a situation where you just are given that kind of space to go figure out yourself.

 

You learned something about your father after you grew up.

 

Yeah.

 

And it made all the difference in understanding him.

 

So, my dad was in World War II. And he enlisted in the Navy before he was eighteen years old. So, didn’t finish high school. And within a month or two, he was on a destroyer in the Pacific Rim, and he went through six combat exchanges. You know, the really bad one. People blew up around him, he came close to dying multiple times. But you name a major Pacific Rim exchange in that window, he was in it, and affected. And in number six, something happened. I obviously wasn’t there. And he was discharged with a partial nervous breakdown.

 

What was the battle?

 

I think that was Iwo Jima. And so, he came back home, and met my mother, and they got married. You know, in the postwar, you know, euphoria, they got married. And you know, then they had kids. And he was not easy to be around, growing up. You know, angry a lot. You know, my mother pushed him a lot to do more with his life. You know, there were some difficult things as a kid in that family. And my siblings, we talk about it, and I think we’d all share that perspective. You know, we grew up the whole time knowing kind of that he was in World War II, but nothing about being discharged with a nervous breakdown.

 

Even your mother?

 

She knew. But this was not to be talked about. Now, what that dynamic was, whether they both agreed never to talk about it, or whether … well, I don’t know. And only when he died, did we find—now, he died twenty years ago. So, I was forty-five-ish when he died, and then we found out. And for all of it was like, oh, my gosh. You know, like had we known growing up.

 

Had you known, what? I mean, what would you have done differently?

 

You know, as a kid, when you’re seven years old and your father is furious at you, you don’t think: Oh, so he’s got an issue going on from his past and it’s not me. You think: What did I do? Like, you know, like it ripples down generations.

 

Did you feel he thought you weren’t good enough?

 

I think I probably felt that at some level. I certainly felt enormous pressure to do well on behalf of the family. And I felt—you know, it’s like always feeling so nervous around the house, because you never knew what would trigger something.

 

Was he violent, as well?

 

Never hit; nothing ever physical.

 

Your father, you say, was a carpenter.

 

Yeah.

 

And I believe your grandfather was bricklayer.

 

He was.

 

Were you expected to follow in the family tradition of, you know, blue collar work?

 

Well, no. And I actually speak about this a lot, because I think we underestimate the power of learning by doing. We underestimate and don’t give kids a chance to do more. My vintage was vocational education or career and technical education, so I actually today have sort of come full circle. But when I was growing up, my mother was crystal clear; all of her kids were going to college, period. And in those years, right, college was, you know, kind of an equalizer. I mean, my college tuition, senior year—so, I went to a public college in Virginia. for the entire year, the tuition was two hundred and fifty dollars. Not for an hour, not for a course, not for a quarter or semester; two hundred and fifty bucks. You know, I mean, I could make that much money easily in the summer, you know, minimum wage. I bagged groceries in a grocery store. You know, today, it’s a totally different story. But for my mother, that was really an important value. And we all did go.

 

What about your dad? Did he want you to go to college?

 

Honestly, in our family, with our dynamic, my father wanted what my mother wanted. You know, it was pretty clear who the CEO of our family was. And it was my mother; no question about it.

 

So, you went to college.

 

I did.

 

And majored in?

 

I majored in, which people will say, Ah, he must be a Gemini; I majored in physics and English. I did. And I am a fierce advocate for the liberal arts. Those are great vehicles for developing the skills and the mindsets that help you later in life. I often tell people that majoring in English helped me a lot more in a career in business and technology, than the physics ever did.

 

Well, what did you do after attending your college?

 

I got into a graduate program in physics at Stanford. I said: Don’t know if I’m really gonna want to stay in physics, but California, that sounds pretty good. And they have a lot of different things, so it would give me different options. Best decision I ever made. And I got there, and I’d say within a month, I said: Uh-oh, you know, like, these people that I’m in graduate school with are way smarter than I am in physics, and far more interested than I am in physics. That’s not a good leading indicator. And I just said: I’m going to be a mediocre physicist if I stay here. Then I started just meeting and talking to other people, and I found this different program that was, for me, very interesting. It was sort of math modeling, applied math to real problems. Switched into that, got my PhD there. And I was just happy to be in Silicon Valley, where every month or two, a new building would pop up for Intel, or Apple, or you know, all these companies, many of which have disappeared at this point. And I just kind of said: You know, this high tech stuff sounds interesting, like maybe I should do that.

 

Ted Dintersmith of Virginia pursued his interest in high tech, and was hired at Analog Devices, a company at the forefront of the digital revolution. In 1981, he made the move from Palo Alto, California to Boston, Massachusetts, and at age thirty-two, Dintersmith became the general manager of one of the company’s businesses.

 

But I was miserable, and I wasn’t good at managing people, and I didn’t like it. And I did it for like, three and a half years, then I finally just said: Oh, I just can’t do this anymore. And that’s how I ended up in venture capital.

 

Well, okay, that’s not a natural. How did you end up in venture capital?

 

When I joined them, they were pretty small, Analog Devices, and they just got bigger, and bigger. I had some ideas to start a business. And then, somebody said: Oh, if you’re gonna start something new, you ought to talk to these people in Boston called Venture Capitalist. And so, I put together a little outline of the business, and used some friends and connections, and started meeting with some. And in one of the meetings, kinda like this, somebody said: You know, your business, that might be interesting, but have you ever thought about being a venture capitalist? We have a search underway to find a new associate, and you’ve got a really good background for it. It was one of those where I said to myself: Do I be honest and say, honestly, I don’t have an idea of what—I mean, I don’t know what a venture capitalist is, I know nothing, or do I say, which I did, you know, that’s always been something I’ve thought about and wasn’t sure whether this was the right time, but that would be a discussion I’d like to have.

 

It was kind of a fake it ‘til you make it.

 

Yeah, yeah; a little bit. Try not to say something totally dishonest. And I ended up joining this group. And you know, as difficult and as unhappy as I was as a manager of a business, it was just a totally different world for me in venture capital. I just loved the business. It, you know, went well, and those were great years for me.

 

So, you were shaping businesses, even though you hadn’t really owned a business yourself?

 

Right; right. Oftentimes, this is kind of the kiss of death in venture is, you fail every single time if your attitude is: I want to work with people that will listen to me and do what I tell them to do. You want to back people who know what they want to do. I mean, it’s great if they listen, and they should be open-minded, but I always said to people: If you don’t reject nine out of ten of my suggestions, I’ve backed the wrong person. Because if I’m making a bunch of suggestions to you, somebody else is as well, and somebody else is as well.

 

Talk about a judgment call on your part. Because the money is big.

 

Yeah; sometimes. And I did feel like, you know, I picked people well. I mean, if I have any claim to fame in venture, I think I did over forty early stage, kind of one to three person startups. And I don’t have these exact, it’s been a while, but eighty-five percent were successes. You know, it’s an industry where if it’s one-third that succeed at that stage, that’s pretty good. So, my hit rate, my success rate was really quite good.

 

And it’s the Charles River …

 

Charles River Ventures. And so, our eighth fund, which we raised in 1997, on a fund, not on a given investment, but we raised a hundred million bucks, and we returned twenty times that. It’s one of the best funds in the history of venture capital. And it was a cross of a bunch of different companies.

 

As a partner in the Boston-based firm Charles River Ventures, Ted Dintersmith became one of the most successful venture capitalists in America during the mid to late 90s, funding innovative startup companies. High risk, high reward; it was a great run. After a quarter century as a venture capitalist, Dintersmith shifted priorities.

 

My kids were like five and seven. And I said: You know, like, I can either keep doing what I’ve done for the last twenty-five years, and knowing that there’s way too much money in the industry and it was gonna be really tough, or I could just say I’m gonna really spend time with my kids.

 

And how old were you at the time?

 

I was about fifty.

 

Okay.

 

Yeah; fifty, fifty-five.

 

And did your kids go to public schools?

 

I figured if they charged money, they’ve gotta be better. Big mistake. They were in this private school in Central Virginia. Then I got this note to parents saying: Brown bag lunch, come listen us, we’ve got these new programs to teach your kids important life skills. And it got me thinking. Like, why do you need a new program? Isn’t it obvious that schools should be preparing kids for life? I mean, a new initiative to teach kids life skills? I mean, isn’t that what school is all about? And I went to the program, and it was about, you know, like we’ll teach kids to drive safely by showing pictures and videos of car crashes, we’ll teach kids not to smoke by showing them tar-infested lungs and people who’ve had their larynx removed. And it’s like, you know, like I get that, but you know. But I made this list, and I said, you know, like important life skills, irrelevant life skills, and started paying attention to what my kids were doing in school. And very little, almost nothing was falling into the important life skills category, and a lot was falling in the irrelevant. But I had to add a new column, which was: harming them. What was actually going to damage my kids going forward? Because I knew, having lived and breathed innovation, how kids need to be prepared for a world where everything’s changing on a regular basis. And I knew, you know, you ask a million questions, you know, learn how to learn, think outside of the box, question everything. You know, like certain things that I just had seen over and over were the success predictors for people in these innovative companies. Not that they had to start the company, but just to be part of it and on the team, and do well.

 

M-hm.

 

You need to have certain mindsets. And I said, these are all disappearing, right in front of my eyes, for my kids in this school process. And this was a school most parents thought was great, certainly was expensive. I said: Whoa, you know, if this is going on in a school people think is great, what’s going on in other schools? And that just sort of led to complete immersion. I wasn’t feeling like they were doing good things, and I went in and met with the headmaster, and sort of laid out my concerns. And to his credit, he was honest with me. He said: I agree with you completely, but if I tried to do this, my board and the parent community would fire me. And as I say, I joke, but it’s not really a joke. That’s when my life turned into a cause. You know, like a lot of the things that normal people do, certainly at a point where they could retire, I don’t do anymore. And I just sort of am, this is the issue, and I feel it’s the most important issue of our ages.

 

Ted Dintersmith of Virginia put to use the analytical skills and out-of-the-box thinking that made him a successful venture capitalist, and he observed and reimagined what he calls an obsolete American education system.

 

I think one of the most misunderstood things in education is, what’s it mean to learn something? Lawrenceville Academy, which is extremely exclusive, very expensive, feeds all the Ivy League schools, and they took kids who had done really well in courses in a year, and when they came back in the fall, they gave them a subset of their final exam questions. Just the essential concepts they thought every kid had mastered. In two years across all these students, the average grade went from a B-plus to an F, and not one kid retained every concept that the faculty thought every kid had retained. And you start to say, the best of our best students in a school that’s on most people’s list of the top twenty private schools in the country, if they’re not really remembering …

 

I’ve heard that, too, from Ivy League grads who said they retained information as long as they had to.

 

Yeah. I think the main skill that gets developed in a lot of schools is short-term memory. We don’t even give them courses on memorization techniques. A teacher in high school in Minot, North Dakota related to me this. He said he told his high school juniors, one class period a week you can work on whatever you’re interested in. He said over half the kids did a Google search: What should I be interested in? And you know, when I relate that anecdote to audiences, the pattern is always the same. Lots of laughter, and then it settles in. And people realize, my gosh, are we hollowing out all the passion and interest, and joy from the kids, all in the sake of covering every possible smidgen of content that some committee has decided they need to know.

 

And how did all of that happen with our school systems?

 

Well, I think the short version is, thoughtfully invented a hundred and twenty-five years ago to prepare people for a world of routine worked well in manufacturing, from manufacturing to paper processing and shuffling, and bureaucracy still worked well.

 

But that was a long time ago.

 

Long time ago.

 

During the covered wagon era.

 

Yeah; long time ago. And then, I’d say over the last twenty years, we sort of made a choice.   And I frame it this way. Do we do things better, or do we do better things? But instead of saying: Let’s reinvent, let’s reimagine, let’s do something really different that makes sense for a world where content is at your fingertips and where you’ve got to solve big bold problems, instead, it was a lot easier to say: Hm, test scores are flat, let’s do everything we can to get test scores to go up. Five years later, ten years later, with No Child Left Behind, they’re not budging. Oh, I know; let’s hold teachers accountable to those test scores. Ah, still not going up; what do we do? And so, doing things better, or I always say doing obsolete things better, you know, doesn’t do anybody any good. We need to reimagine education.

 

To help inspire innovation in American education, Ted Dintersmith funded and produced an education documentary called “Most Likely To Succeed”. The film premiered at the Sundance Film Festival in 2015, and Dintersmith took the film across the nation, all fifty states, for community screenings and discussion. He wanted to convey the value of project-based learning, and yes, the need to rethink how to educate children.

 

I mean, after I came to this epiphany about life skills, and were my kids really being prepared for life, and then saying not only are they not, they actually may be damaged through this process, it may be actually harmful, I said: I gotta do something. And so, I went through a process. I said, so I’m anonymous. You know, like I’m not famous. I’m not Bill Gates; I’m like, Joe Bag of Donuts. And I said, like, I could write a book, and you know, like, yeah, maybe somebody would read it. I just sort of thought of like, I’m telling you what you guys know so well. I mean, how do you change people’s mind? Visual, something with emotion. And so, I said: This could fall flat, it could be a waste of time and money, but if we could somehow come together and produce something really remarkable, that would have a chance to sort of start changing the discussion broadly.

 

The things I think in life that give us some of the greatest satisfaction is making something that wasn’t there before.

 

I can’t wait for that moment, when it does work and I’m completely done with it. And it’s like always, it’ll be…

 

Kids have that feeling that’s transformative; I made this, and everyone’s going to look at it.

 

We filmed for two years, six hundred hours, times two, two cameras. And just got lucky with something that really does kinda get people energized about what could be done in school, and shows them kids learning in a way that doesn’t look like normal school, that they ordinarily might view as summer camp, you know, that you know, you watch these kids and they’re building things, and making things, and working in teams. And if I’d written about that, people would say, “that sounds good.” When they see it, when they see how it affects those kids, when they see teachers trusted to teach to their passions and do what they entered into the profession to do, it just makes an indelible mark on the audience. And so, we only do community screenings, we’ve done two here with you guys, which have been great. And we wanted to bring people together for discussion.

 

And you’ve had many discussions.

 

Yeah.

 

All over.

 

Over four thousand around the world, four hundred in Hawaii alone. And you know, but it’s what you guys know; right? It’s what’s so special about what your work is all about. It’s community, it’s family, it’s bringing people together.

 

In 2016, Ted Dintersmith made his first visit to Hawai‘i to show the film. He also met with local leaders, and visited a variety of island schools. He saw a fertile field for change, and he’s come back again, and again. His national crusade was intensive, and he’s not yet.

 

And so, this was not just like come there and have a meeting or two. I mean, I had for nine months, fifty states, every day from seven-thirty in the morning ‘til ten at night, meeting, after meeting, after meeting, after meeting. You know, from governors to commissioners of education, but lots, and lots, and lots of school visits, meeting with teachers, meeting with parents, meeting with students.

 

And out of those fifty states, you find yourself revisiting two states.

 

Two states.

 

Would you tell us about that?

 

The two states which are very, very different states, and I’m on the plane tonight to the second one, but North Dakota and here. And for very different reasons. But North Dakota, tomorrow I’ll be there, it’ll be the eighth time in two years. And I’ve gone all over the state, and working really closely with their governor and their superintendent of public instruction. And you know, we’re funding some things that they find helpful, and they’re just very all-in at the state level for preparing their kids for a world that’s really different. And they’ve got a lot of things that I think are great, and I think they’ve got a real chance. And I did almost every town, and we had community events. But with me on all these events were either the superintendent of public instruction or the number two, one of the top two or three from the teachers union, one of the top two or three from the chamber of commerce. You can go to a lot of states where those two people won’t even be in the same city.

 

And you bring money to the table, as well as insight?

 

I give some grants. And so, you know, I don’t charge for any—I mean, it’s always an embarrassing thing, because, you know, when I give these talks, what I know is that I’m doing it all on my own nickel, and I’m actually supporting things. And it sounds braggy to say that. But then it gets like, when you come to North Dakota or Hawai‘i, and you say: You guys can do amazing things, you know, I’d hate it if people in the audience say: Well, somebody must be just paying him to say that. You know, what drew me back here, honestly, I wouldn’t keep coming back if it weren’t for this guy Josh Reppun.

 

And he’s a former educator.

 

A former educator, and now just passionate about his state, about the heritage of the state, about what people can do about giving these kids opportunities. So, that first week was unbelievable. You know, they did a documentary on the visit. And the reason I keep coming back here, you know, the people here doing the innovative work in education—

 

In Hawai‘i.

 

In Hawai‘i. Are the best of the best. I would challenge anybody to go to any other state in the country, and I’ve been to them all, and find other examples that are better. You’ve got remarkable innovations going on in your schools here. But if you want to get really energized about education, you know, go to, you know, Waipahu. See what Keith Hayashi’s doing there. I mean, it’s just like, whoa, this is like, education at its finest.

 

And he is the principal of Waipahu High School, who, you know, left the number two position in the DOE, because he wanted to be at his school.

 

Yeah. Go to Waianae, go to Candy Suiso’s, you know, media arts program. I mean, you sit there and you talk to these students, and if you ask them: What are you working on, and why does this matter to you? They have great answers; right? Most places I go to, if you say to a student: What are you working on? They’re not even sure. You know, you go observe a lab and you say: What are you doing? They’ll say: Step 3. What’s more inspiring than what these kids have in this state? And so, I just say, like these people, they just care about it. So, for me, it’s tiring ‘cause I travel all the time, but it’s inspiring.

 

Former top venture capitalist Ted Dintersmith says he’ll continue to be a change agent for education by personally funding and gathering resources for innovative learning approaches such as those shown in his film, “Most Likely To Succeed”. Mahalo to frequent Hawaii visitor Ted Dintersmith of Earlysville, Virginia for sharing your story with us. And thank you, for joining us. For PBS Hawaii and Long Story Short, I’m Leslie Wilcox. Aloha, a hui hou.

 

For audio and written transcripts of all episodes of Long Story Short with Leslie Wilcox, visit PBSHawaii.org. To download free podcasts of Long Story Short with Leslie Wilcox, go to the Apple iTunes store, or visit PBSHawaii.org.

 

I was in West Maui, and I’m talking to these kids. I said: Well, tell me what you’re interested in. When I ask kids even in sixth grade that question, the question they’re often hearing is: What career should I have? And I always say: Don’t worry about that. Right? You’re in sixth grade. You know, and I tell them, you know, that I did fairly well in business, and if you’d asked me at age twenty-eight what a business was, I didn’t know.

 

 

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