Rocketship disrupts how technology works in charter schools to give kids a boost.

John lightly suggests that there is an essential randomness about his life’s journey, but it’s clear that he is profoundly driven by social justice. Having “retired” at 30 after taking his internet ad company public, he didn’t use the resulting free time to play golf. On the contrary, he turned to digging down with deep empathy into one of the root causes of social injustice, an education system that has lost its way. “Every person is born with a certain nobility that you need to preserve in their lives. Unfortunately, society sometimes doesn’t do that. So it’s important to fight for everybody’s nobility.

“It’s important that when you see things are wrong, to try and fix them."

John got involved in education following the sale of his business, when he became a Henry Crown Fellow of the Aspen Global Leadership Network. A Jesuit school in his home city of San Jose had approached him for support. That school became his Fellowship leadership venture—instead of just making a financial donation, he got involved, and found something he loved: “When I started, I had a normal substandard understanding of what causes poverty, and why people can’t escape it. Through that school I began to understand that in the US there are pretty significant structural issues that make progress difficult. Education just made sense to me as being an area for leverage.” John was extremely moved by the impact the school had on the community it served: “You could see how much it affected the life of the kids and their parents. Their body language changed, their sense of self changed.”

Soon after, John’s wife was offered a post at Vanderbilt University, and the couple relocated to Nashville, Tennessee. John took the opportunity to improve on both his academic and his practical understanding of the education sphere: he got a masters degree in education and took a job as a teacher. “I did a ton of reading. It solidified my view that social mobility was not a random problem; it had been created by society, and if you were going to change it, you needed something like education to be able to do so."

One insight John gained from teaching is how difficult it is, emotionally and physically. “It was one of the things I did right: to not sit around complaining about teachers, but to go and teach. It’s a high-energy performance for eight hours a day, for virtually no money. It was unlike anything I had done before, really different, and quite difficult.”

By the end of this period, John’s research had convinced him charter schools held a potential solution to the education gap, starting with elementary school. “The most common theory of change in education is if you can bring a student all the way through high school and then watch them closely in college, you have the best chance of them getting through. And our theory of change is different: it really needs to start at elementary school.” He also knew the need was great; whatever he started, he wanted to be able to scale, potentially to thousands of schools: “The idea that we do one great school and really help 500 kids a year when there are 13,000 failing schools, just never made sense to me… unless you can do it at scale, and make a reasonable dent in the problem, you’re doing nice things, but it doesn’t really move the needle very far,” he says.

And he believed he understood a design principle of scaling in this context: “The way to scale education is to remove as much of the labor as possible—to reduce staff numbers in order to reduce complexity; and to have a better-looking budget.

“That’s how we started to work with personalization and technology,”John says of him and his co-founder of Rocketship, Preston Smith.

What emerged is a blended model in which 75% of pupils’ time is spent in conventional classrooms, but 25% is spent in learning laboratories with programs designed to address their individual needs. This reduces the number of teachers required, allowing better salaries to be paid to fewer teachers. At the time, it was paradigm-shifting. “An advantage of my outsider’s perspective is that having lived in a start-up for-profit world, I didn’t really accept conventional wisdom on anything,” John says. “Most educators know that schools aren’t delivering for students, but most would say that the structural problems lie outside of their control. Injecting a non-conformist into that is helpful.”

It was relatively easy to figure out how to build a better school, John says; but “everything else was hard. Hiring hundreds of teachers, building school buildings, getting great results, empowering parents, dealing with politics.”

The other pillar of the Rocketship model is the built-in engagement code: the parents of each student are obliged to volunteer 30 hours each year, including parent meetings. “While many parents initially feel this to be onerous, as they see their children’s dramatic improvement over time, they begin to see the volunteer work as a privilege of giving back.”

Rocketship has been life-changing for families. The approach works: the schools have overall outscored high-income schools. It has moved 91% of its students from the bottom two quintiles of performance in English and Math, to the top three quintiles.

Rocketship has its detractors, but John is sanguine. “They worry about how this will affect unions or how it will affect funding for schools or what it’ll do to the involvement of parents at other schools. Our basic principle is that if we keep starting great schools in low-income neighborhoods, one of two things will happen. One: the detractors will say, I don’t like what he’s doing, and I better figure out something to do about it— so we will see more flexibility in the rules and teachers being given better opportunity. Or two: they don’t respond. And if they don’t respond, we— Rocketship or other organizations— will continue to run low-income schools.”

Through the highs and the lows, John has maintained close ties with his Henry Crown cohort. “We all get together at least yearly, and informally see each other in between. They’re not my Board or my employees, and I can have really good conversations with them. I find that super-helpful,” he says.

In 2013, John left Rocketship and founded Zeal Learning, a blended tutoring platform. It provides daily on-demand tutoring in K-12 schools through a network of independent tutors using Zeal’s platform. Zeal has lowered tutoring costs from standard $30-$50/ hour to $1/hour by blending technology and tutors—so it costs the same as a computer-driven program, yet achieves outcomes that are better than in-person tutoring.

John is clear about why he left direct engagement in schools to go back to his roots as a software entrepreneur.

“I always intended Rocketship to be a five-year process for me. Two or three years into it, I was already talking to Preston about my exit.

“But more importantly, when you get large—we had 5,000-6,000 students and several hundred employees—your job becomes dealing with friction and politics. I was never interested in the politics. I had hoped that the Charter laws had been written well enough that this wouldn’t be the case, but that was not the case."

There was also a frustration which led directly to Zeal: the limited customization possible of online programs for teaching children.

John is confident about Rocketship’s future. “It will fulfill what we intended it to,” he said. “I imagine that there will eventually be hundreds of schools. We originally had a goal of thousands of schools, so I don’t consider Rocketship super-successful. But a lot of schools are learning from the model, so we’re ‘scaling’ in that way.”

Nor is Zeal John’s endpoint.

“I had this little boy when I was teaching, in my 2nd or 3rd year, called Brian. He had an extraordinarily complicated life story. I ended up spending a good amount of time with him trying to find out what made him tick. I think it was helpful to him, but it was more helpful to me. When you’re working with someone who is not buying in, it forces you to go back and work out why you’re trying to make him do this thing.

“I think there have been plenty of Brians in my life.”

John is never going to stand still. “My advice to people who’ve been successful in their careers is this: there is a tremendous inertia when you are at the top of your local status hierarchy. Things are comfortable, people say nice things to you. And so 99% of people won’t break out of that and try to do something else.

“But there are a couple of good reasons to do something else, especially things you are passionate about but feel are broken: first, it’s extremely likely that if something is broken, and ithas been broken for a time, the people in that system are not going to fix it, so you may be the best hope. Second, you will be far happier.

“I meet so many people who are just acting the part of ‘successful X’ but inside they are bored, sad, indifferent. Doing something hard in an area you care about, having a purpose, is ultimately what life is about. Making that first step is the hard part. Then hopefully your timing, skill set and perspective are a good match for creating the change needed.

“I am 50, I have a couple of decades, there’s a ton to do. I would like all 2 billion children in the world to be able to afford their own tutor. When Zeal is done, I will identify what I think is the next important thing in education and focus on that."