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

Posted on Wednesday, Oct 15th 2025

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.

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

Posted on Tuesday, Oct 14th 2025

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?

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

Posted on Monday, Oct 13th 2025

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.

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Bootstrapping an EdTech Startup with a Paycheck to over $5M: Karyn Koven, CEO of LanguageBird (Part 5)

Posted on Friday, Oct 3rd 2025

Sramana Mitra: What kind of numbers are we talking about as we go beyond 2015? How many numbers of students, how many instructors, how was the business unfolding?

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Bootstrapping an EdTech Startup with a Paycheck to over $5M: Karyn Koven, CEO of LanguageBird (Part 4)

Posted on Thursday, Oct 2nd 2025

Sramana Mitra: And what were the numbers? 10 people in the beginning, and then how did that grow?

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Bootstrapping an EdTech Startup with a Paycheck to over $5M: Karyn Koven, CEO of LanguageBird (Part 3)

Posted on Wednesday, Oct 1st 2025

Sramana Mitra: Who were these people that you got an audience with?

Karyn Koven: I think it was because I had a background, and it was based on my reputation amongst other counselors and school officials.

Sramana Mitra: They were referring students to you?

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Bootstrapping an EdTech Startup with a Paycheck to over $5M: Karyn Koven, CEO of LanguageBird (Part 2)

Posted on Tuesday, Sep 30th 2025

Sramana Mitra: Let’s go back to the beginning of LanguageBird. When you were thinking about doing this project, were you already thinking of it as an accredited language school that would serve as supplemental education?

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Bootstrapping an EdTech Startup with a Paycheck to over $5M: Karyn Koven, CEO of LanguageBird (Part 1)

Posted on Monday, Sep 29th 2025

Karyn has built a technology-enabled business that is already over $5M in revenue and sits at the cusp of a tremendous scaling opportunity by leveraging AI. If you are mulling AI startup ideas, this kind of tech-enabled service that is fully optimized with AI could create tremendous value.

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