Building an AI EdTech Company: College Guidance Network CEO Jon Carson (Part 1)

Jon has identified a gigantic hole in high school college counseling and is plugging it with AI.
You have read interviews with the entrepreneurs behind Empowerly and Prepory, companies going after the same problem, but with more manual solutions. College Guidance Network is doing so with AI.

Sramana Mitra: All right, Jon, let’s start at the very beginning of your journey.
Where are you from? Where were you born and raised? What kind of background?

Jon Carson: I was born in New York City. I had an unusual upbringing. I was the only child of a single mother. When my father left, she had to get a job. She got a secretary job at a small magazine called Gourmet. Within seven years, she was the editor in chief.

We didn’t have a lot of money, but she started to make her way. Her number one goal was always to provide for my education. I grew up in a household full of grit and resilience.

I was the son of an editor, who in that world was kind of like the CEO. Gourmet was acquired by Conde Nast, and she became almost a celebrity. She worked until she was 75.

I went to Babson College. In my sophomore year, I started a company that delivered kegs of beer to fraternities all over Boston. I had about 16 people working for me by senior year.

Babson made a big decision to focus on entrepreneurship, and the press was always looking for a Babson human interest story. They often featured me, so I got a bit of fame by senior year. Then I graduated—and it went to zero. I was no longer a student. I learned the powerful lesson that it can all go away overnight. Don’t believe your own press clips.

After that, I had two short jobs—one at Boeing, one at McKinsey. I went to Yale for my MBA and started my own consulting firm focused on tech companies. We set up in the Prudential Tower. I grew that to about 25 professionals and sold it in 1989 to an insurance company. At the time, insurance companies were acquiring strategy consulting firms—it was a bit of a moment.

The next important project was building the largest K–12 platform on the internet during the dot-com boom. I sold it to Pearson in 2000.

Sramana Mitra: What was the name of that?

Jon Carson: Family Education Network. I had a big exit—it was a 10x return for my investors.

Sramana Mitra: That was a funded company?

Jon Carson: Yes. That was a 10-year run. I don’t think I was fully qualified to scale a company like that, but you learn as you go. I had a good board, good mentors, and some lucky hires on my senior team. I learned a lot.

The next project focused on social impact. It was kind of an eBay for charities called BiddingForGood. I sold it in 2015 to a roll-up acquiring software fundraising companies for the nonprofit sector. BiddingForGood raised about $800 million for different causes and schools. That was high impact. It was a marketplace, whereas Family Education Network was more about community and content.

The next one was CollegeVine, where I met three Harvard students through the Harvard Innovation Lab. I was asked to be a mentor. They were selling a college advising service and were doing around $100,000 a month out of their dorm room. They really needed some adult help, so they asked me to be their CEO.

I did that for four years. I left in 2019. We raised $24 million and brought in Fidelity as an investor.

The current project is basically MasterClass meets AI guidance-in-a-box for high school families. That’s my journey.