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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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Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 5)

Posted on Wednesday, Sep 10th 2025

Sramana Mitra: So, you were acquiring families through SEO mainly.

Daniel Santos: Yes, primarily SEO.

Sramana Mitra: So, that was not limited to South Florida anymore?

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Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 4)

Posted on Tuesday, Sep 9th 2025

Sramana Mitra: So, you were acquiring families through SEO mainly.

Daniel Santos: Yes, primarily SEO.

Sramana Mitra: So, that was not limited to South Florida anymore?

Daniel Santos: Not at all. At that point, we started working with families internationally and across many U.S. states.

Sramana Mitra: Around 2018, how many families are we talking about?

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Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 3)

Posted on Monday, Sep 8th 2025

Sramana Mitra: Online’s fine. I’m not necessarily thinking that you’re already on AI in 2016–17, because that’s definitely not the time when AI was as pervasive as it is today. So, let’s go back to 2016–17. Tell me more about how the business was progressing. How many schools were you catering to in 2016–17? How were you finding them? How were you doing the sales process?

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Bootstrapping an EdTech Venture to $6M, Ready to Scale with AI: Daniel Santos, CEO of Prepory (Part 1)

Posted on Saturday, Sep 6th 2025

This story is a great example of an EdTech company that has built a validated, bootstrapped, profitable business that can potentially be scaled using AI.

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Building a Venture Scale Two-sided Marketplace for College Prep to 8-Figure Revenue: Empowerly CEO Hanmei Wu (Part 4)

Posted on Thursday, Jul 31st 2025

Sramana Mitra: It sounds like it’s a two-sided managed marketplace. What’s the business model? How much are you paying the counselors? How does this work out?

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Building a Venture Scale Two-sided Marketplace for College Prep to 8-Figure Revenue: Empowerly CEO Hanmei Wu (Part 2)

Posted on Tuesday, Jul 29th 2025

Sramana Mitra: And what did you end up doing to address that itch?

Hanmei Wu: Well, it wasn’t very planned out, to be honest. I was still quite young, only a few years out of college. I was just kind of doing it on my own at first, maybe just charging an hourly amount. I was helping with essays and things like that. Then I decided that I want to get some other people to help me with this.

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Building a Venture Scale Two-sided Marketplace for College Prep to 8-Figure Revenue: Empowerly CEO Hanmei Wu (Part 1)

Posted on Monday, Jul 28th 2025

EdTech is notoriously difficult to build at venture scale. Hanmei is doing it.

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