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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?

Karyn Koven: Year over year we kept growing. The first year was about 10. The second year was probably closer to 50. The next year after that was closer to 100. So, it kept growing incrementally.

Sramana Mitra: And that all came through referrals?

Karyn Koven: Yes, correct.

Sramana Mitra: And you were convincing them personally.

Karyn Koven: Yes.

Sramana Mitra: A hundred students and you were convincing them personally. Okay. So, that brings us up to 2015. What happens in 2015?

Karyn Koven: In 2015, I had a critical mass of students where I was able to look at educational data to show proof that this was working. It was successful—the students enjoyed it, they were making progress, they were improving.
This was a viable and flexible way for this age group to learn, which worked well for busy students. In terms of technology, I had a vision to build a platform like the one we have now.
I couldn’t do it then—I didn’t have the resources or the right people, and I didn’t know how. But I could conceptualize what it would look like.

At that time, most scheduling systems were built for in-person setups with everyone in the same time zone. What complicated things was dealing with different time zones.

I hired someone to help build it. They said they could, but I made mistakes in vetting them. In the end, they took a bunch of money and disappeared. So, I just kept going with what we had.

Technology-wise, for a long time, I was “frankensteining” solutions—finding ready-made tools that could be pieced together to do what I needed.

Sramana Mitra: What was that technology? What did you find?

Karyn Koven: Aside from video chat, there was a student information system (SIS) that was off-the-shelf. It needed to be customized—it was designed for traditional schools, not what we do. In supplemental education, we don’t have six class periods and teachers taking attendance the same way.

We didn’t need a lot of the functions; many we did need were missing.

Sramana Mitra: Sounds like the scheduling function a school system wouldn’t have.

Karyn Koven: Correct.

Sramana Mitra: So you had to build it. What ended up happening?

Karyn Koven: The first time I tried to build it, I had a vision, but it didn’t happen.
I couldn’t find the right people and didn’t know enough.
Looking back, I was lucky. Had I built it then, I would’ve built the wrong things—not what we grew to need.

Sramana Mitra: Timeline-wise, what’s happening from 2015 onward? When did you reach some level of technology-enabled scalability?

Karyn Koven: It took a long time. We kept piecing things together until we grew to a point where it was clearly necessary. LanguageBird is bootstrapped, so I prioritized hiring on the academic side to ensure a great student and instructor experience.
Technology was pushed aside due to rapid growth. We just focused on getting students in and figuring things out.

Sramana Mitra: You were manually scheduling and just getting on with the business.

Karyn Koven: Correct. We had some functionality in the SIS system to match students, but most of it was manual and required approval.

This segment is part 4 in the series : Bootstrapping an EdTech Startup with a Paycheck to over $5M: Karyn Koven, CEO of LanguageBird
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