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Building an AI EdTech Company: College Guidance Network CEO Jon Carson (Part 5)

Posted on Friday, Oct 17th 2025

Sramana Mitra: What about the financing strategy of this business? You’ve done venture-funded companies before. You’ve had exits. You were coming into this business with your own personal needs. Did you bootstrap the beginning? Did you fund it right away?

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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 AI Startup to $10M from Boise, Idaho: Christian Perry, CEO of Undetectable AI (Part 4)

Posted on Saturday, Sep 27th 2025

Sramana Mitra: Let’s get to the exciting Undetectable AI story. What was going on in your mind? What problem did you want to solve, knowing that ChatGPT was taking off around you?

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Building a Venture Scale FinTech SaaS Startup: Mike Whitmire, co-founder and CEO of FloQast (Part 3)

Posted on Friday, Sep 19th 2025

Sramana Mitra: And how long did that $6.5 million last?

Mike Whitmire: We did extremely well in 2016 and the first half of 2017. We more than tripled our recurring revenue. Then we were approached proactively about raising another round. The investor was great, the terms were strong, and I was ready to scale further. We fielded a few term sheets, found the right partner, and raised our Series B—$25 million led by Insight.

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Building a Venture Scale FinTech SaaS Startup: Mike Whitmire, co-founder and CEO of FloQast (Part 1)

Posted on Wednesday, Sep 17th 2025

Mike has raised over $300M and built an over $250M ARR FinTech SaaS business. Now, AI offers FloQast an opportunity to further strengthen their product roadmap with deep domain knowledge.

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Building a High Growth Vertical AI Company in Healthcare: Ganesh Padmanabhan, CEO of Autonomize AI (Part 1)

Posted on Tuesday, Jun 3rd 2025

Ganesh has executed on a textbook case study of building a vertical AI company in Healthcare with a clear human-in-the-loop strategy that VCs are salivating over. Read on, much to learn.

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