Building an AI EdTech Company: College Guidance Network CEO Jon Carson (Part 2)

Sramana Mitra: So let’s double-click down on that. I’m not going to go into all the previous projects because it’s going to take time. You want to focus on the current one. Let’s start with the AI part of that. What is the AI part of what you’re doing in the current project?

Jon Carson: It actually starts with the masterclass part. In 2020, my kid was in Lexington High School, and I was surprised that I couldn’t get a meeting with a counselor. He only got two meetings. Lexington is a well-resourced district, and I’m looking at a $350,000 decision. Something wasn’t lining up.

At the same time, MasterClass had just announced a big financing. I met the lead investor at Al Ventures, and he explained the model to me. I had this idea: what if you built MasterClass for guidance?

Fast forward to two years ago, I met the guy who started the AI lab at McGraw Hill. By then, we had about 250 experts under agreement — everyone from Sal Khan to Malcolm Gladwell, even a president of B.A. It was a real Masterclass. He said, “If you own that content, that’s rocket fuel for an AI guidance counselor.” He told me, “I can build you the best AI guidance counselor in the market on two dimensions: response quality and brand reflection from credible experts.”

So we built it as a RAG (retrieval-augmented generation) model and launched it last September. We’re now up to 400 experts. It’s trained in four content categories: navigating the college admissions process; navigating college affordability, ROI, and aid; navigating career pathways; and parenting and dealing with teenagers who don’t take direction well.

What makes it different starts with the expert training, but we also bundled it with wraparound services. We have a personalized project plan that’s integrated with Ava, our AI counseling assistant. We also run live programming with top experts. For example, last Thursday, we had a LinkedIn executive, a Harvard Business School professor leading the future of work project, and an expert on entry-level jobs in the AI age.

Sramana Mitra: Let’s get the chronology straight. When did you start this?

Jon Carson: We incorporated in late 2019.

Sramana Mitra: How long did it take you to build the initial 250 masterclass-style video lectures?

Jon Carson: We’re at 400 now, and we add about 15 new people a month.

Sramana Mitra: What was your pitch to these experts when you started in 2019?

Jon Carson: One of my investors knew the head of admissions at an Ivy League university who hated his job. He wanted to become our chief content officer on the side. He reached out to his network — this was during early COVID — and invited them to join webinars on specific topics.

It wasn’t easy in the beginning, but the breakthrough was Malcolm Gladwell. Once we got Malcolm, others followed.

Sramana Mitra: Why did Malcolm want to do it?

Jon Carson: He had a message he wanted to get out — he’s strongly against rankings. We did a show on that. We had a list of 40,000 school counselors and promoted the show to them. That gave him leverage to get his message out. He gave us an hour, signed the release form, and then we got Angela Duckworth, Sal Khan, and others. We can get a lot of high-level people.

Sramana Mitra: But what you really need isn’t high-profile people. It’s real experts in college admissions — people with actual knowledge, even if they aren’t famous.

Jon Carson: True. For instance, we did a parenting show with Sal Khan and Angela Duckworth where they talked about how they were raising their own kids.

Sramana Mitra: That makes sense. I agree it’s not hard to get experts to share knowledge. Once you have that content, layering it on a system like ChatGPT gives you great AI counseling capabilities.

Jon Carson: Yes. But the most important feature in the solution is the personalized project plan. If you go to Lexington High School now, you get a generic three-page PDF checklist for each grade — one-size-fits-all.

We built a master checklist. Every item is tied to a specific month and grade, and linked to expert content. It’s personalized to the user. We have almost 1,000 checklist items across different pathways. It tells you what to do, when to do it, how, and why. And it’s integrated with Ava, so Ava knows your checklist progress and vice versa.

This segment is part 2 in the series : Building an AI EdTech Company: College Guidance Network CEO Jon Carson
1 2 3 4