The Exchanges

Q And how did then GupShop, idea of GupShop came to you and what, what was the process of building it? Sure.

A So I think, um, that started, uh, you know, initially, um, so Rakesh Mathur is a good friend and he was in, he's a accomplished entrepreneur in Silicon Valley. He was, um, you know, he had started, he started many, many companies and so on, but I think he was, um, you know, starting something and he pulled me as I was leaving Elance, uh, you know, he, We sort of got together and we started with this. The initial idea was something different. We called it Weberoo and it was about offline search. I mean, we were, you know, but that idea didn't work. And, um, then we were just looking around, right. Uh, what are the other options, what we could do? And that's again, very commonplace in startups where. Sometimes, you know, things that you think will work don't, and then you have to pivot and adjust and so on. Um, so at that time we realized that, uh, you know, the mobile revolution was happening. Now, you know, this is in, um, 2007 or eight or something and, you know, mobile, uh, many parts of the world. I mean, that was the biggest thing going on. Uh, but most of it was on feature phones, right? It wasn't on, uh, smartphones that, um, Came a little layer later in terms of the mass market adoption. But, uh, what we found was the lowest common denominator was SMS, right? So we realized, uh, sort of the ubiquity of SMS makes it incredibly powerful. You know, and, uh, messaging is a, …

AI assessment note: “we realized sort of the ubiquity of SMS makes it incredibly powerful”

Q You were there at Elance or Upwork. Uh, what was the scale when you left and why did you leave?

A Oh, okay. All right. So fast forwarding a little, um, you know, Elance did a million dollar round and then we raised twelve million dollars from Kleiner Perkins and a few other investors. And then we did a fifty million dollar round from growth investors, uh, and, and so on. Now, fortunately, we did this funding round just before the 2001 stock market collapsed, right? The dot-com bust, uh, as they talk about it. Fortunately, we had enough money to survive those difficult days, right? Which was again, very, very challenging. Um, one of the things that happened was, uh, you know, at that time, um, the, uh, The conventional wisdom was that, uh, you know, B to, uh, B to B, uh, or rather B to C is, is going to be dead, right? Because acquiring consumer, building consumer businesses requires a lot of marketing, uh, because acquiring consumers, customers is harder. And, you know, uh, so, so, and with the.com bust, it's not going to be easy to have a lot of huge marketing budgets. So it's very hard to build B to C businesses, but B to B, you know, businesses still have money and they still need software and, uh, and so on. So we kind of, you know, gradually transformed in about 2002 or three, we sort of started, uh, for, uh, we hired, uh, a CEO who's very experienced with the enterprise business, the B to B business. Uh, and, uh, you know, I was there for quite a while, even through t…

AI assessment note: “it was becoming a different kind of, uh, slightly a different kind of business”

Q And how was the journey, you know, during those seven years at Upwork? What were the key pivotal moments?

A Oh, uh, I think it was, uh, quite, uh, a rollercoaster, right? I think, um, so in the beginning, you know, starting out now, you know, as an, as an immigrant in the US, right, you have, uh, limited resources. There's no family money. I mean, you just, you know, you come here with, With maybe a little bit of pocket money and then you'll figure out your own way, right? So, and it's too early in your career to have a lot of savings and such. So, uh, so that was, uh, but, but what we did have was a wealth of, Networks and relationships, right? Either friends or, uh, classmates or alumni, uh, you know, in my case, uh, from IIT and other places, but, uh, you know, so just getting started itself was hard. Where do you get the initial funding from?

AI assessment note: “I think it was, uh, quite, uh, a rollercoaster, right?”

Q what are, what are the three mistakes, you know, which you would advise your son or daughter, uh, in between that maybe you committed in your two businesses that you would advise them not to commit? And what are your three right decisions? You know, if you have to highlight between the, the two businesses, uh, or the recent one, which you would advise your son or daughter to imbibe?

A Oh, um, Okay. I think there's, there's just so many that sometimes it gets a little challenging, but let me, let me pick a few, right? I think, um, you know, one is, uh, do get started on this entrepreneurial journey for the right reason, right? Uh, it can't, uh, simply be making money. Of course, you know, money is a way to, uh, keep score. It's a way to track progress. Uh, but there's lots of other easier, less stressful ways of making money than entrepreneurship because Here it takes over your life. It, it becomes you, right? Um, so, so I think, uh, it has to be something that you're passionate about and really excited about because, uh, you know, even if nobody paid you and there were no returns, this is what you'd be doing because you are, you like, you know, tinkering or problem solving or figuring things out and persuading and convincing and so on. So anyway, That's one part of it. Uh, the other is, uh, just, um, you know, grit and perseverance and sort of the, uh, the emotional and the mental fortitude that you're going to need to go through it because it's a, you know, it's a rollercoaster journey and you have to, you know, the highs are super high and the lows are extremely low. Meaning, you know, you get a funding round and you think, wow, we're going to conquer the world. And then, you know, something bad happens or a competitor, you know, a large competitor launche…

AI assessment note: “let me pick a few, right? I think, um, you know, one is”