The OpenAI, Datavant, and Education Vets Rescuing K-12 from Itself

a squad of tech and education bros are building a network of schools that don't suck — and an ai stack to support it
Blake Dodge

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Around 2022, Arvind Nagarajan and his niece were both losing faith in school, albeit from opposite ends of the system.

He was running the US arm of a global private school network, watching AI transform every corner of the economy while education clung to the same stale playbook.

“There was just a focus on how do you get one more person in each grade? How do you raise tuition prices by the right amount?” Arvind told me. “And not really enough thinking about, well, actually, what are we educating these kids? What are we preparing them for and why?”

His niece, meanwhile, was just bored. She cared way more about Roblox than school. A lot of parents feared the gaming platform’s addictive pull. But Arvind saw something more optimistic. Out of sheer curiosity, his niece had figured out how to design and sell virtual T-shirts to other users. It became a lightbulb moment: why weren’t schools drawing out that kind of drive?

That question became the spark for Astra Academy — an upcoming network of private schools led by cofounders Arvind and David Chen (formerly of OpenAI and Google) as well as Aneesh Kulkarni (Datavant’s founding CTO). Backed by private equity firms and family offices, their goal is to “restore” student agency in K-12, if it ever existed in the first place, with help from custom AI tech.

School, in their view, has become boring, compliance-driven, and increasingly detached from the challenges kids are facing— including a historic rise in anxiety. Astra plans to address this through a mix of AI tools (e.g. ChatGPT-like teaching assistants) and more conventional strategies (e.g. human relationships), all geared toward helping students find their footing in the real world. Astra will hold its students accountable to real-world projects that they actually care about — and itself accountable to their depression rates. Success, in other words, will be student agency and grit rather than college acceptance per se. Hopefully, this model makes school something to turn “towards” instead of “away from,” Arvind said — a place that’s interesting enough, at least, to hold their attention.

AI isn’t a silver bullet for K-12, Arvind and David told me; nonetheless, it’s opened a door. Between the tech’s capabilities and growing political appetite for “school choice,” more parents are (finally, a little bit) willing to try something new.

“The Overton window is somehow open in this moment to say, okay, how are we actually preparing kids for the future?” Arvind said.

SCHOOL SUCKS

Administrative growth has completely outpaced academic outcomes. The curriculum is largely defined by requiring students to jump through hoops and master brute memorization. Teachers exercise a top-down, “sage on the stage” model, assigning tests, giving grades, and then shooing students off to the next pre-packaged module.

So much of K-12, in other words, is predetermined, not fun, and aimed at a goal (college acceptance) that seems increasingly irrelevant. Bachelor’s degrees aren’t necessarily enough to land competitive jobs, while the cost of acquiring them is increasing. It now costs $100,000/year to attend the University of Southern California — a figure that hits different now that some high schoolers are making millions by spinning up apps with basic AI tools.

You’d think K-12 schools would recognize AI as a wakeup call to address the dysfunctional rot that’s taken over education. Instead, the response has been, in large part, pretty uninspired.

You have a handful of more gung-ho outfits like the so-called Alpha School in Texas using AI to replace teacher instruction entirely, an admittedly interesting approach — though one bound to make kids’ already dopamine-drenched digital worlds all the more virtual.

You have, more commonly, a circular dynamic of basic substitution, where teachers are now using LLMs to spin up lesson plans and assignments, students are using them to do said assignments, and then teachers turn back to LLMs to grade the assignments.

And then you have a lot of educators outright rejecting the potential for artificial intelligence in schooling by trying to ban and detect AI use in a cat-and-mouse game with kids. The instinct, if a touch hypocritical (see: teachers using ChatGPT to generate quizzes), is rooted in fear that AI will turn students, who are reading less and performing worse, into little dumb idiots, while companies like OpenAI look the other way.

Ultimately, banning AI from the classroom won’t get kids anywhere. At least, that’s Astra’s argument. Schools have a responsibility to prepare kids for this changing world — and besides, it’s a lot easier to elucidate AI’s risks and benefits if you’re pulling them into the conversation.

“In so many situations in the K-12 system, we assume the worst of our kids and try to deny them access, block things — instead of treating them as competent humans and embracing them as part of the discussion,” Arvind said.

ASTRA’S TECH APPROACH

Astra Academy’s seminar on entrepreneurship in Durham, NC

Astra is taking tech in-house.

“I joined because I think this moment is a generational opportunity to pioneer AI in education not as a technology vendor, which is the common refrain, but from within a school environment,” David said, adding: “Ultimately the responsibility for innovation in education is with schools.”

Datavant’s Aneesh will lead a small team to guide and implement leading AI tools for kids and teachers. The team will serve as the translation layer between external tools and internal needs. They’ll adopt good tools where appropriate — and build others from scratch.

So far, Astra has made the most progress on its “AI TA,” an LLM wrapper that helps students with writing and entrepreneurial projects. Unlike ChatGPT, it’s trained to ask students questions to guide their thinking, not shortcut it. For example, if a student tells the AI TA to “write my draft,” it asks her to elaborate on the part she’s struggling with.

“It’s more like a coach than a ghost writer,” Arvind said.

Astra is also working on tools to help teachers get through their grading, progress reports for parents, and lesson planning faster — opening up more 1:1 time with kids.

The team at Astra believes these tools will redefine what can be accomplished over the course of a normal school day, allowing both students and teachers to get more done per unit of effort.

In addition to accredited academic programs, for example, students will take on annual “capstone” projects aided by the AI TA — like writing novels, creating YouTube channels, or starting local businesses. Where traditional schools funnel kids into tracks like “college” and “not college,” Astra projects will help them figure out what they should actually do with their lives in more specific terms.

Skilled up in what actually matters to them, maybe they’ll pursue college; maybe they won’t. College acceptance, in the founders’ view, should be a happy byproduct of a good education — not the entire point of it.

The startup’s name “Astra” has a special meaning for its CEO. Deriving from Sanskrit, the word more directly translates to a supernatural weapon. But Arvind has a more mystical take on its meaning: “divine knowledge that can only be acquired through hard work over time,” he said.

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WHAT IF KIDS CAN HANDLE THIS?

Astra’s first pilot school, serving 5th, 6th, and 9th graders, could open in Raleigh, North Carolina, as soon as fall 2026. (Arvind says his oldest daughter will attend.) The team is also acquiring more schools across the Sun Belt, with plans to expand nationally.

To prepare, Astra has hosted two camps and one seminar, with more on the way.

“No matter how cool or great you think your ideas are, all you need is a room of middle schoolers to put you in your place immediately,” Arvind said.

Last summer at Raleigh’s Peace University, Arvind and Aneesh oversaw a weeklong camp where 6th, 7th, and 8th graders wrote short stories. They studied classic narrative arcs — rags to riches, voyage and return — via YouTube. Then came “concept notes” (pitches), character development, and drafting, all with brainstorming help from the AI TA.

But not everyone bought in.

During the pitch stage, Arvind and Aneesh noticed a small group — mostly artsy theater kids — choosing to brainstorm in Word documents, quietly snubbing the AI. When Arvind asked them why, they responded that AI was training on artists’ data without permission or compensation, and they didn’t want to contribute to it. 

“Aneesh and I just kind of looked at each other,” he said.

The men huddled in the corner. Should they force the kids to use the tool?

Instead, they put it to the whole group and reached a compromise. Anyone could work independently, so long as they could keep up with the deadlines. But Arvind made a pitch of his own. AI isn’t going anywhere, and it’s a powerful tool; at least use it to refine your ideas.

“That was the best Aneesh and I could come up with after 30 seconds of discussion,” he said.

The theater kids came around — a little bit. They liked using Arvind’s prompts, but just for feedback (“Can you help me spot where I’m telling instead of showing, and suggest how to revise?”). The conservative approach paid off. Their voices were preserved in their final drafts. By comparison, stories where kids leaned too heavily on the AI started to blur together.

One student, eighth-grader Vanessa, kept working on her story after the camp. She just passed the 10,000-word mark on what she hopes will become a finished novel this year.

I’ve read some of the manuscript. I was impressed.

The story kicks off with a dad’s dramatic declaration from the living room: they were going on “the adventure of a lifetime.”

“That was dad for ‘I’m scared you’ll stop talking to me if I don’t entertain you this summer like your mother would,’” the protagonist quips.

Cue the Hawaiian shorts (“far too short for an almost 50-year-old man”), exclusive four-month cruise aboard the S.Y. Jose-phine, and “tragic accident” of a passenger’s death at sea. Sixteen-year-old Nova Monroe investigates layers of wealth and power to find out whodunit. The message is clear: trust no one; hide your “secrets aweigh,” the book’s working title.

She’s used AI to make the cover art, but that’s it.

Arvind, on the other hand, is using AI to give her feedback, he admitted sheepishly.

“I have not told her this,” he said.

Schools reflexively shying away from AI are missing something crucial. Given the right set of opportunities, students want to work hard. AI notwithstanding.

Vanessa's cover art

TEACHING SUFFERING

Let’s say Vanessa’s novel flops. If she goes to Astra, they’ll talk about it. Out loud.

Generally accepting the reality of suffering will be baked into the school’s culture.

Capstone projects will go sideways. YouTube channels will get 0 subscribers. Teachers, freed up a little by their own stack of AI tools, will help their budding entrepreneurs find strategies for being effective on good days and resetting on bad ones. Astra’s meant to constitute a headstart, in other words, on “figuring out what works for you,” an adulthood-defining struggle that typically starts after 18 years of uninterrupted structure.

“Part of our thesis is that shipping something to the world automatically requires an up and down journey,” Arvind said. “It’s not going to be straight up and to the right.”

Further, Astra plans to measure student rates of depression, anxiety, and excitement for the future as “core outcomes” of the school, holding itself accountable to their happiness.

“The goal is to track how students are doing emotionally and socially, both when they arrive and as they grow, so we can design systems that actually support them,” Arvind said in a text.

Astra was partially inspired by what Arvind described as the “mental health crisis in education.”

Kids today have been dubbed “the anxious generation” for good reason: childhood has been completely rewired by devices, social feeds, and viral content. Every year brings a new algorithmic labyrinth (see: kids falling in love with chatbots). People have implored tech companies to create more guardrails, but the truth is the landscape is changing too quickly for any artificial control — parental or corporate — to keep up. The dangers, same as the opportunities, change overnight.

It’s kind of weird that schools ignore this. If K-12 is supposed to help kids face the world, that increasingly means training them to be stewards of technology rather than sheep.

Astra wants to be that kind of resource in a few ways. It wants students to grapple with technology — weighing in, for example, on tech tools in the classroom and even phone policies. Astra wants phones to be kept in lockers by choice, not top-down edicts. And in general, how tech is changing the world won’t be ignored. It’ll be discussed. Aired out.

During one day of the camp last summer, for instance, Astra held a seminar on “AI ethics.”

A deck displayed various scenarios. One was about making virtual versions of your friends. “Right or wrong?”

Astra camp AI ethics group discussion prompt

The room full of middle-schoolers debated for a half hour.

Did the friend give permission? Would the AI use private messages?

The frequency matters, here; if you start talking to this thing all the time, it could prevent you from making new, real friends, the kids argued.

It was less of a teacher-student dynamic, Arvind said; they all worked together to think through something that was new.

— Blake Dodge

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