Building an AI EdTech Company: College Guidance Network CEO Jon Carson (Part 3)

Sramana Mitra: So, in terms of your chronology, what came in what order? You were doing the recordings—these webinars were a key first step.

Jon Carson: That was the key first step. What I was trying to do was solve the breakdown in guidance in high schools. I didn’t quite know how this was going to work, and it was very anxiety-provoking for a few years.

We started with the Masterclass library and put it into some schools that paid us. The counselors liked it because it was a walled garden of trusted content in an age of misinformation. But parents and students saw it as work. We didn’t get the usage.

We were doing ongoing experimentation—listening, user interviews.

Sramana Mitra: They don’t want to spend an hour listening to an expert.

Jon Carson: Exactly. They don’t want to spend a hundred hours listening to a hundred experts. What they wanted was a plan. So, we built a layer of software on top of the library that allowed you to build a personalized project plan, with content tied to action steps. It wasn’t as big as it is today, but that definitely closed a big part of the product-market fit gap.

We still weren’t all the way there. But we were getting into more schools. We won some state contracts—New Hampshire, Massachusetts. We were starting to get into a lot more school districts. Schools know that guidance isn’t working that well—that’s not a secret.

Then the AI piece came into focus. Two years ago, we started working on it. Steve started to build it out, the team got bigger, I was raising more money. We rolled that out last September.

Shortly thereafter, one of the two big testing companies in the country wanted to buy us. We went through last fall, got a big number—it fell apart at the very end.

But there was an indication they were looking for a solution especially focused on parents. That was a unique angle we had—making parents first. Parents are the ones stuck without the counselor, while the kid is distracted.

The second thing—they said there was a huge market with colleges. Colleges see parents as the economic buyer, and they don’t have a way of engaging them. When the deal fell through, I started talking to vice provosts at colleges. A lot had been on our shows. First call I had, the guy said, “I’ll buy it. How much?”

We’ve now been rolling it out into colleges who are fighting a fierce market share battle. I haven’t met a college yet with a solution for the economic buyer—the parent.

Sramana Mitra: Hold on one second. Let me roll back for a second.

In terms of the product evolution, the first thing you did was these Masterclass-style videos.

Jon Carson: Yes.

Sramana Mitra: And high schools and school districts were paying for that.

Jon Carson: Yes.

Sramana Mitra: But it wasn’t getting a lot of usage because people didn’t want to spend the time listening to experts. Then you rolled in personalized project management—determining next steps, what content to go through, and what to do next. That started getting engagement from students and their parents.

Jon Carson: Yes.

Sramana Mitra: Then came the AI bit—actual personalized guidance and so on.

Jon Carson: Yes.

Sramana Mitra: But this was still all in the context of high school students and parents. After that came the colleges, looking to engage with parents who are the economic buyers. That’s the chronology of your product evolution?

Jon Carson: Yes.

Sramana Mitra: Now, how is this product applied to the college situation?

Jon Carson: I’m only about five months into this. Just to hit pause—CollegeVine, the last company I was at, just priced a round at $800 million based on two AI chatbots for colleges.

What CollegeVine has done is open the eyes of enrollment officers to the power of AI. That’s the background I’m stepping into.

From College Board, I learned colleges don’t have a solution for parents—and they want one.

At Trinity College in Hartford, Connecticut, they’re offering our solution to every parent who inquires about the school, comes for a campus tour, or goes to a college fair. It’s a gesture of goodwill, but because parents fill out a rich personalization form, the college gets a level of data at the top of their inquiry funnel they’ve never had before. They also get sentiment data from the AI conversations.

So for them, this is a very interesting parent engagement solution they’ve never had.

Sramana Mitra: But it’s the same product? The college counseling product is the same, but you’re offering it through the college to the parents?

Jon Carson: Yes. The second version we’re rolling out right now is with the University of New Hampshire. They’ve had multiple budget cuts. They’re going to offer the solution only to people coming on campus tours, to limit the cost. So instead of putting it at the top of their inquiry funnel, it’s for the most qualified leads—those who show up for a tour.

This segment is part 3 in the series : Building an AI EdTech Company: College Guidance Network CEO Jon Carson
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