Sramana Mitra: Interesting. What is the trajectory of your company? How did you get started? Where does the AI expertise come from?
Rohan Gupta: It’s a stereotypical startup story. My co-founders and I were in school. My co-founder, the CTO, is a college dropout. My third co-founder was one year out of school and he quit his full-time job. We started with a Google Translate interface. It just took off. We started seeing a ton of organic traffic. It motivated us to pursue it full-time.
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Sandeep Sardana is Founder and General Partner at BluePointe Ventures. We had a terrific discussion on how we each look for a startup story through financial metrics.
Sramana Mitra: Let’s start by introducing yourself to our audience. Tell us a bit about your journey. What path brings you here?
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If you haven’t already, please study our Bootstrapping Course and Investor Introductions page.
Here is yet another story of a high-growth SaaS company that was bootstrapped first. When I spoke with RJMetrics Co-founder Robert Moore in 2016, the company had gone on to raise $22 million. RJMetrics was acquired by Magento and is now part of Adobe Commerce Cloud.
Sramana Mitra: Let’s start at the very beginning of your personal story. Where are you from? Where were you born, raised, and in what kind of background?
Robert Moore: I was born in Annapolis, Maryland but actually grew up and spent the majority of my childhood in a town called Glassboro, New Jersey, which is in southern New Jersey. My journey really begins in high school where I started my first business and really fell in love with entrepreneurship. Everything grew out of that.

I started one of the Internet’s first fashion e-commerce companies in 1999. It was very expensive to do so at the time.
Today, an online fashion business can be launched in an extraordinarily capital-efficient manner.
>>>Sramana Mitra: Very interesting. I have had a blog for 17 years. I’m always a bit annoyed by the rubbish that gets produced out there.
Rohan Gupta: I am too. As a company that started content marketing, we need to eat our own dog food and produce content in a very thoughtful way.
Sramana Mitra: It’s a funny industry. Recently, we started working with Udemy. We have thousands of hours of entrepreneurship curriculum. We started packaging these into Udemy courses. We’ve released 30 courses on Udemy.
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You may be a brilliant computer scientist or even a genius. To become a successful entrepreneur, though, you must not only know how to code but also understand the fundamentals of launching and growing a business.
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Rohan discusses AI-empowered writing as an emerging field. The company has 12 million users and has recently been acquired by Course Hero.
Sramana Mitra: Let’s start by introducing our audience to yourself as well as to Quillbot.
>>>Sramana Mitra: Once you had the Series A, what was the next major inflection point? What strategic moves did you make to get to that?
Jeremy Swift: I would say it was about just further refinement of what our ICP was and figuring out go-to-market too. That was a hard thing to navigate. It took us years to figure out. Just because you raise venture capital, it doesn’t immediately change those things for you. There’s still a lot of hard work.
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