Sramana Mitra: Take me to the inflection point where you hit upon the healthcare focus. What was the impetus for that? Ayush Jain: So that was actually around the time of COVID. Moving forward, we focused on making internal changes—hiring our own sales team, setting up foundations, and so on—because we were always striving for
Sramana Mitra: So, six to seven years of Upwork. What revenue level were you able to reach? How many people did you have in the company?
Sramana Mitra: I can resonate with the time that you’re talking about. In the last ten years, I would say things have really progressed. But at that time, it was still a bit early, especially for these kind of ideas. EdTech is notoriously hard to sell. And schools are notoriously hard to sell to.
Sramana Mitra: What was the startup that you were working on? Ayush Jain: At that time, I was working on launching a website focused on exchanging old and new books. The idea was for people to list their books online, similar to eBay, but specifically for books. Other people could then buy them. As a
Services companies are easy to bootstrap, but often, they grow slowly in the beginning. How do you accelerate? This discussion is about the levers of acceleration.
Sramana Mitra: Category creation is interesting. Let’s talk about category creation. Ryan Millman: Undigital is a category creator. We’ve invented what we call in-package personalization. Category creation is extremely different. When you go out to a company as a category creator, nobody has you in the budget, right?
Sramana Mitra: Okay. All right. So I understand your business. Where do you go from here? Ryan Millman: I spend all my time focusing on Undigital, my newest endeavor. It is a little bit related, but it is more of a pure technology company. From a personal perspective, when the companies get big and mature, a lot
Sramana Mitra: Relatively soon after that [around 2004], this market started to develop, including with venture funded competitors, right? There were a number of very successful venture funded competitors that hit this market. How did you deal with that competition?