Raviraj Jain

Partner, Lightspeed Venture Partners

Raviraj Jain is a Partner at Lightspeed Venture Partners, a venture capital firm focused on accelerating disruptive innovations and trends in the Enterprise and Consumer sectors.

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Rohit Mittal: Hi, I’m Rohit. I’m the cofounder and CEO of Stilt. And today, we’re talking to Raviraj.

Raviraj Jain: Hey.

Rohit: Raviraj is currently a partner at Lightspeed Venture Partners, and he’s originally from India. Graduated from IIT Bombay, where he started two companies, HelloIntern and Bookmycab. Both were acquired, so good exits. Then he went to Harvard Business School. And he worked in Product Management in LinkedIn and Fundbox. Now, he’s a partner at Lightspeed Venture Partners, where he invests in early and growth-stage enterprise and deep-tech startups. He has invested in companies like Aurora, which is an autonomous vehicles company; AnyVision, which is a computer vision company that is trying to solve real world problems; and FortressIQ, which is using AI for business process mining. And he has a few investments in stuff that are going to come out soon. Welcome.

Raviraj: Cool. Thanks a lot for giving me the chance to speak to you and talk to your audience.

Rohit: Thoroughly, I’m super excited about this one. For some of us-- some of our viewers who don’t know about Lightspeed, can you tell us a little bit about--

Raviraj: Absolutely. So, Lightspeed is a global venture capital firm. We manage around $7 billion of capital around the world. We have teams and offices in China, India and Israel, outside the Bay Area. We back companies in various stages, various sectors and across geographies. We have actually been supporters of lot of immigrant founders. We were the first big institution backer for Nutanix, which is a multi-billion-dollar company stated by Dheeraj Pandey. We were early investors in AppDynamics. We were early investors in Zscalar. You know, we were early investors in [inaudible 00:08:48]. A lot of these founders are all immigrant founders. So, we’ve been very fortunate to work with a lot of exceptionally smart and driven immigrant founders that have created epic, sort of once-in-a-lifetime kind of companies.

Rohit: Yeah. And these companies are-- multiple of these companies that you mentioned have IPO’ed. They are in the public markets and doing really, really well.

Raviraj: Yeah.

Rohit: Cool. And how long did you-- how long ago did you join Lightspeed?

Raviraj: So, I’ve been at Lightspeed for more than two years now. I joined in January 2017, and I focused on early-stage-- primarily early and growth-stage enterprises.

Rohit: So that’s Seed and Series A, primarily?

Raviraj: Seed, Series A, Series B. I opportunistically look at a later stage as well.

Rohit: Awesome. So, with that context, let’s start with your background. Give us a sense of where you grew up. And you also went to IIT, where you started multiple companies. So, it would be really curious to understand how you decided to start companies at such an early age, like in 2006.

Raviraj: Yeah, yeah, yeah. So, I actually was born and brought up in Jabalpur, which is a city in central India. It’s kind of like middle of nowhere. For those who don’t know India, it’s kind of like-- think of it as Nebraska of India, which is like far from any big city. Yeah, I grew up there, finished all my schooling and went to IIT Bombay. At IIT Bombay, I studied Engineering Physics. So, I was always very curious about cutting-edge technology. And I spent a lot of time in the first year at IIT actually looking at Robotics and sort of new kind of like technological innovations in various fields. It was amazing for me because coming from Jabalpur, I was not exposed to a lot of different things. Now at IIT, I had exposure to a lot of extremely smart and driven people, both students and professors. But at the same time, I had all the resources to actually try out and build things. And it was pretty amazing. IIT Bombay, fortunately, also had a very strong early kind of like entrepreneurial ecosystem. They had an institute called SINE, Society for Innovation and Entrepreneurship, the [inaudible 00:11:04] Innovation Centre, and the Entrepreneurship Cell. So, I got exposed to a lot of entrepreneurs through that. To me, it felt like, you know, it was so amazing to see people actually building businesses that everyone in the country or lot of people in the country use. So that was like the motivation. It was like, “Hey I need to do something like that.” When I was actually looking for a summer internship in the second year, it was huge struggle for me and my classmates to find it. I was like, “Well, there is a job site like Naukri. Why can’t there be a platform for people to find summer internships?”

Rohit: Right.

Raviraj: You know, I learnt a lot about how summer internships are such a valuable part of the Western education system. But they weren’t quite there in India. Large part of that was because there was no bridge between companies and students. And that’s what I wanted to do. So, I teamed up with a couple of my classmates and started HelloIntern.com when I was in the second year at my IIT Bombay days. And it was amazing. I realise that sitting in my dorm, I was able to help students across the country find internships and actually lay the foundation of their career, which was extremely, extremely satisfying, more than anything else. And I didn’t start the company because I wanted to build a big business. I started a company because I wanted to solve a problem that me and my friends faced. And then it became something much larger, and that was very, very satisfying. Then I realised-- it was at that part I realised that technology had the ability to help you scale, help make a massive impact just beyond yourself. At that point, I kind of decided that I want to pursue ways to actually implement and expand that so that businesses use the technology.

Rohit: That’s awesome. And this was in 2006, right? So, 2006, start-ups were not popular, as I remember in India. I was also an undergrad. Like, no one was thinking about these things, specially technology startups. Was there any turning point, any experience that made you more inclined towards this? As a child, were you already doing businesses when you were in High School in Jabalpur? Or because of coming to IIT Bombay, once you got exposed, it just opened your mind to a whole new set of possibilities?

Raviraj: Yeah, I mean, my dad is also an engineer and he works for the government. So, I didn’t really have a business background. I didn’t do any of those things. It was largely influenced by the ecosystem at IIT Bombay, which made a huge difference to us. And I think once we started getting feedback on what we were doing, it just made us feel like there’s so much more that can be done as an entrepreneur. And that’s how we [inaudible 00:13:50]

Rohit: Awesome. And how long did you do HelloIntern?

Raviraj: So, I worked on it throughout from 2006 to 2008. At that time, you realise it was not really a large business, but it was actually creating a lot of impact. So at that time, I kind of stepped out that business and started focusing on other things.

Rohit: And were there any initial lessons that you learnt — this is about 13 years ago — as you were doing your company? Whether it’s about talking to your customers, making assumptions, maybe google market strategy, things like those that are-- those words are pretty common now, but they will not be common--

Raviraj: Yeah. I mean, I think, honestly, we had no business background. We did not much guidance on actually how to build a business. So, we were just trying to figure out things ourselves. And I feel like what we realised was that we were trying to kind of like building a marketplace between companies and students. And now it’s common-- Like building marketplaces is hard, right? You need to get--

Rohit: Right.

Raviraj: --either supply or Demand. And without one, you can’t really get the other. And that’s a very obvious thing now. For us, you know, second year engineering students, it wasn’t very clear. So, it took us a long time to actually build that, right? We had to really like hack our way through it. So, we would reach out to recruiters and say, “Hey, do you want to hire interns?” and they would always say no, right? It was like a challenge for us. And we spent like four months just trying to find postings on our website. Then we realised that that’s not the right path because a lot of people in the recruiting world in India only wanted to take care of the full-time jobs. So, what I did was we started actually-- we took a bold move and we started reaching out to the CEOs of the companies. And started telling them that if you wanted to attract the best quality talent, you really need to go early and hire the best tools upfront. So we had folks from [inaudible 00:15:46], you know, a lot of other big companies in India and also startups — entrepreneurs who all came to-- like we reached out to them and they all got back to us and said like, “Hey, it makes sense for us to hire interns.” We kind of like went top down, which is very interesting because now people talk about in Enterprise Sales that you should go top down. We didn’t know that. We just went to the CEOs and they would say, “Hey, you know what, we’ll give it a shot.” and a lot of them just like hired one intern through us and then it became like, “Oh, it was valuable.” And they started hiring more and more though us.

Rohit: Yeah. And I’m just trying to think of the context here. So, (A) there’s no tribal knowledge as such around best strategies through sales with enterprises. Second, it’s in India. Third, there’s no internship culture now that I recall my time. It’s not that-- companies are not clamouring to hire the best interns.

Raviraj: Right. That’s correct.

Rohit: So, you had to sort of think five steps ahead. And you were already doing at that time what people are doing now. And that kind of thinking basically shows the forward-thinking, the innovativeness--

Raviraj: Yeah. I mean, I think we kind of like bumped into this problem. I feel like the whole thing is like I didn’t realise in hindsight that we were kind of ahead at that time. Because I think there’s an internship website in the US that because popular in like five years back., while we started that in India 13 years back. So, I feel like we were kind of like little bit ahead at that time.

Rohit: Yeah, totally. Makes total sense. And that’s why I was super interested in HelloIntern ’because I see many companies doing that now, and they may be successful now. But, at that time, it was definitely innovative. Cool. So, you did HelloIntern for a while, and then you moved immediately to US or how did that happen?

Raviraj: Yeah, so I spent a few years working before I moved to the States for business school. I also tried my hands at other startups. Some of them didn’t really go anywhere. So, I feel like-- I talk about these two, but there are four or five others I tried my hands on. In education. In personal finance. And for many different reasons, they didn’t work out. And I feel like that’s the journey that most entrepreneurs go through, which we don’t really talk about as much. But I had periods of frustration where I would like to think about a business and like some things go wrong and we had to shut it down. So, I worked on a few different ideas. I also worked at a strategy consulting firm for a short period. Then I started with my cofounder Avinash, a company called Bookmycab.com, which was like a website to book taxis--

Rohit: Uber--

Raviraj: But much before all of that. We thought about that back in 2009. And it was like-- again, we had a fixed time. Smartphone penetration in India was like 4%. 4-5%. Like very low, right? 3G wasn’t there, right? Mostly people were using 2G. Kind of very early. And the way you should book your taxis was actually call us and we will reroute you to the taxi. So, like it was-- like again, it was an interesting idea, but kind of like before it’s time.

Rohit: And that’s kind of fascinating to me now that you tell me you’ve done so many startups. So, you’ve always been looking for the next interesting innovative thing. That’s, I think, a quality that also helps in venture capitalising. One question about startups is — you had cofounders — how did you meet your co founders? How did you decide to start a company with them? Were they like best friends and--

Raviraj: Yeah, I mean, I think, it’s actually both cases. It was like really good friends, who had helped start the companies. At that time, again, there was no formal process that I knew how to find cofounders. I knew people and they were friends from IIT Bombay. I really thought they had complementary skill sets and they were really driven as well. So, it’s like, “Okay, it’s a good fit. We just work together and figure it out.”

Rohit: Cool. So, after you graduated, you were at a strategy consulting firm for some time. How did you decide to come to Harvard? Why not go to IIM for example?

Raviraj: Yeah, I think that’s a good question. The IIMs are great schools. I think what I realised were a couple of things. One is what drives me. What drives me is to be at the cutting edge of technology at a global scale, right? It’s never-- I wanted to be good, but not just good in India. I wanted to be good at global scale, and that really mattered to me. The second is I realised a lot of my ideas were also kind of like ahead of its time in India. And I think the kind of things that I wanted to do, I felt like all of that was happening like in the States at that time. Now, it may not be true completely right now. There are a lot of new innovative businesses around the world. And we’ve seen that happen at Lightspeed as well. At that time, it felt like-- I would look at Discovery Channel as a kid and I would see like everyone who’s doing cool stuff is either in MIT or in Palo Alto. And I was like I want to be that person. I don’t want to be-- I have this whole thing around I don’t like being the audience. I want to be the performer. So, I would not look at the show and say, “Hey, wow, that person is doing something awesome.” It’s like, “Why am I not doing it? I should be the one doing it.” So, for me, getting that global platform to enable myself to work in cutting-edge technology that will transform the world, and not one geography, was extremely inspiring and exciting, and that’s what I wanted to accomplish. And I also realised that I cared-- so I love technology, but I think of technology as a tool to solve problems. I think of myself as a business problem solver with using a lot of like cutting-edge technology. So, I felt like, during my time at HelloIntern, during my time at Bookmycab, there were a lot of other things I could have done better had I had formal education in business. And I felt like if I have to do that, I think Harvard is a great place. That’s like where a lot of theories around strategy, general management originated. A lot of high-quality research in management happens at Harvard. So, for me, it was great place to explore, studying and build the foundation of long-term business skills.

Rohit: That’s awesome. But coming to Harvard is also expensive. Not a lot of people can afford to come to Harvard. US education is not that cheap. Especially the elite business schools. So how did you take that leap of faith to spend so much money?

Raviraj: Yeah. No, I think that’s a very important question. Just going back slightly, like when I was in Jabalpur and high school, I was preparing for IIT, but I used to at people from MIT and like Stanford doing things. That’s where I wanted to go. I want to be at the cutting edge, and I think, I really lucked out that I got a chance to go to IIT for undergrad. But I feel like-- all the time I felt like, “Yes I want to go there, and I can get there.” But I just didn’t know how to finance it. Because, you know, my dad used to work for the government and obviously, we didn’t have the resourced to actually go out and you know, just pay for an expensive education. So, I had no idea how to do that. That’s why US education was not top of mind for the longest time. But I did have some of my seniors from IIT Bombay who went to HBS and Stanford. And I learnt from them that like there’s a pretty meaningful scholarship component and pre approved loans that Harvard and Stanford provide to students. So, the theory at Harvard is that like if you are good enough to attend this school, then no matter what your means are, we will find a way for you to actually fund it. And I think, that to me appealed to me a lot. And I think it was one of the big reasons or big criteria I had in terms of selecting a business school, where my education can be financed because neither did I have the resources, nor I think you could get the loans of that amount in India to actually support a Harvard education. It’s around 200K, 2 years. That’s a huge amount, right, for someone. So, it was big deal, but I think the good think that was that I knew that’s not an issue at Harvard. And that’s why I chose Harvard [inaudible 00:24:26] I got a pretty meaningful scholarship, but also a big loan, which was approved the day I got admitted and accepted the offer. So, I didn’t have to go through the loan process, which was pretty amazing. And I think that has enabled so many people to actually take an education in HBS.

Rohit: Yeah. I assume-- I’m sure there are a lot of other people in India who are probably very capable. They’re intelligent, they’re hard-working, but they are not able to get the quality education that they probably want because they are not able to find the means. So, Harvard basically helped significantly. I think that’s amazing for Harvard to do.

Raviraj: Otherwise I don’t think-- I can’t imagine myself being able to afford an education in the US.

Rohit: Yeah. That’s awesome and that’s great for Harvard. That’s why so many big founders and CEOs and consultants and-- Harvard graduates are in every field. Doing really well. So, you had thought how Harvard and MIT are going to be when you were in India. Did they live up to your expectations? How was it when you actually moved to Harvard? How was your experience?

Raviraj: It actually did. It actually exceeded my expectation. I think the quality of education at HBS was just phenomenal. I think the professors at HBS are like really invested in actually not just research, but also improving the bar, increasing the bar on education, right? And I think it was amazing, right? I think the amount of involvement that the school had and how much investment they made in actually helping you improve no matter what your background is, was phenomenal. Because think about, at HBS like there are people from I think, 60+ countries and from various stages of life and different industries, and they are all very different, right? When I joined Harvard, that was the first time I was in the States. I had never been here.

Rohit: Do you have family or friends--

Raviraj: No family, no extended family in the States when I moved here, right? It was like a completely foreign land to me, and I had never been here before. So, I think for someone like me and then there were people who went to Harvard undergrad and you know, worked in Boston and then joined HBS. So, we had very different entry points, and I think HBS did a phenomenal job of making us all feel at home, and you know, empower to learn and grow. So, I think that was an amazing experience.

Rohit: And do you remember some of the things that took you by surprise when you were at Harvard? When I ask people, one of the things they always say is like how smart everyone else is, and that makes you feel like you are not that smart. But, in terms of learning, you knew things that you did not possibly probably expect.

Raviraj: Yeah. I think one of the big things that I learnt was not necessarily always academic, but also like just more on the people’s side. Being an engineer and focused mostly on the hard skills, I think for me, it was a great opportunity to learn and develop my softer skills, right? So it’s understanding you know, people dynamics, how do you actually build relationships with people who are very different from you, how do you relate to people who have very different background and build a bond with them, and in the end, like become a good citizen in terms of like, being helpful to everyone. So, I think that softer aspect of it was extremely, extremely important. And the other thing was that HBS taught me to think really, really big. They actually almost like hammered you like, “Hey, you know you can be a leader. There are people who went to this school that became big leaders at the global scale, and you can be one of those. So, you need to start thinking big and making big moves in life.” So, I think that that was pretty amazing. I feel like a lot of us are like, very capable, but sometimes, we just limit ourselves by how we think about things. HBS pushes you to actually think bigger, and I think that really helps a lot.

Rohit: That’s awesome. So, they take the most talented people from maybe the humblest of the backgrounds and provide them with resources and make them think big. They allow them to think bigger.

Raviraj: There are people from all sorts of places, right? There were some classmates who were like sons and daughters of billionaires, and some of them were CEOs. There were people from all across. But the amazing thing was that everyone was just very friendly, and we actually learned together, and the ecosystem was great.

Rohit: Awesome. So, you had a good two years at Harvard, you graduate, and you go to LinkedIn in product management. How did you sort of choose a product management, and then maybe decide what type of companies you want to work at? Then also like, give us a sense of how you decided to work at Fundbox, ’because LinkedIn is a more social network and Fundbox is more of a fintech company.

Raviraj: Yeah, yeah, yeah. So, I think LinkedIn and product management was pretty straightforward for me. I am a builder and I think a product manager’s job is closest to like a businessperson can be a builder. And it was very entrepreneurial job. So that was very clear to me that product management was the right discipline. LinkedIn because I wanted to manage products that I use every day, and if you remember a few minutes back, I said I reached out to a lot of CEOs and asked them to hire through HelloIntern in 2006-2007. I did it on LinkedIn.

Rohit: Okay.

Raviraj: So, I joined LinkedIn-- I was like one of the early folks on LinkedIn from India, right? So, I used that, and I had been using that product a lot, and I got a chance to connect with a lot of senior individuals in India and abroad through LinkedIn for many, many years. And I felt like that platform was so powerful. And it enabled me and opened so many doors for me that I felt like I really want to be a product manager of something like that. So, I think that was a pretty straightforward decision for me. It’s like, I loved the product, I would love to be a PM there. So, I think that was the reason for LinkedIn. And it was great. I had an amazing time learning from a lot of people. It was also a bigger company, so I learnt kind of the ropes of product management at LinkedIn from really good senior leaders and learnt about how big organisations work because it was also my first time doing that. The other thing was that it allowed me to be in the Bay Area. That was why I joined LinkedIn. After close to three years at LinkedIn, I decided I wanted to do something more entrepreneurial. And I think, as a lot of immigrants have, it’s not very straightforward to start a company on your H-1. So, I think while I started thinking about different ideas, I felt like I still want to do something more entrepreneurial where I have control of what I’m doing. And I think, for that, I wanted to join an earlier stage company. And actually, a classmate of mine from IIT Bombay was at Fundbox and--

Rohit: Who was that?

Raviraj: Shantanu.

Rohit: I actually talked to him. His story is also very interesting. I’ll tell you about it later, but--

Raviraj: Awesome. So, yeah, Shantanu is a good friend. And he had joined Fundbox and spoke highly of them. I met the team and it seemed like a phenomenal-- very, very interesting business they were in. And I thought that would be a good place for me too.

Rohit: When you joined Fundbox, how many people do you remember were there?

Raviraj: I think, 40-45 maybe.

Rohit: So, Fund box is a very high growth company.

Raviraj: Yeah.

Rohit: Incidentally, yeah, the CEO of Fundbox is also an investor in Stilt. But--

Raviraj: Eyal is amazing.

Rohit: Yeah, Eyal is amazing. I always go to him for advice anything [inaudible 00:32:34] related. Prashant is also an investor. He’s the chief [inaudible 00:32:27] officer.

Raviraj: Prashant is awesome. He’s had such great experience leading products at Facebook.

Rohit: I remember-- just as a side note, I remember meeting him and this is after the investment and we were thinking about product. We had like 145-minute meeting and he just gave us so many insights. I just remember scribbling like three pages of notes in my notebook. So, Prashant has been super helpful. So, there were 45 people at Fundbox when you joined. How did the team increase and how did your sort of role change? I’m assuming you had more responsibilities.

Raviraj: Yeah. So, I there to lead a new product line for them. But, you know, as in any startup, you wear multiple hats and you solve whatever needs to be solved. So, I was working on multiple different projects at the same time, setting up teams, you know, hiring more engineers in the team, and designers and so on. That’s pretty much like any startup has. Yeah, so it was a great experience. But I was there for a short period.

Rohit: Okay. So Fundbox also has team in Israel.

Raviraj: Yeah.

Rohit: Did you work with the Israel team?

Raviraj: Yeah, I did.

Rohit: The reason I’m asking is ’because I want to know your thoughts on working with remote teams. That’s a big trend nowadays. How was working with a team that’s 10 hours ahead of you?

Raviraj: Yeah. It is challenging, but, I think, what I tell you after two years in venture is almost every company now has a remote presence or multiple offices or a distributed team. Just need of the hour. Like, Bay Area is getting extremely expensive. Not just expensive, it’s just getting extremely hard to hire, you know, high quality people in the Bay Area. And the talent’s everywhere, right? So, you really-- I’ve seen more and more companies have offices around the world. Like companies have offices in Argentina, Poland, India, China, of course, Israel, where you can hire more people and retain them for a lot longer. And I think that it’s the reality of our current times, right? You have to work with remote teams, and it is challenging. But, lots of collaboration tools now, which makes it somewhat easier. But it still involved late nights and early mornings. And it is what it is. But the good thing is like the team in Israel was really strong, and people remained in the company for a long, long time. So, they were very loyal. The attrition rates were very low, and that enabled us to actually get a lot accomplished very quickly.

Rohit: Yeah. I have a feeling there is going to be a Fundbox mafia soon. [inaudible 00:35:05] one company, and I feel like others will also soon start another. So, you worked at Fundbox and then you came to Lightspeed directly after that. How did you decide to make that transition? And why did you decide to make that transition?

Raviraj: Yeah, so that’s an important question. I feel like moving from operating to venture is a pretty big decision. And the way I got to-- I wasn’t really actively looking to move to venture. Nakul Mandan was also a partner at Lightspeed for many years, and he reached out to me and he said like, “You should explore talking to us and see if there is a fit for you to join Lightspeed.” and at that time, I was like it seems like an interesting place and I had a chance to talk to the partnership at Lightspeed. And I amazed by the work ethic there and then you know, the hunger and desire to actually succeed. If you talk to some of our portfolio companies and everyone spoke very highly of the firm. So, I felt like if I wanted to go to venture, I think, this is the place and now is the time. Because into venture is hard, in general. It’s even harder for someone like us, right? We’re not like, from the Bay Area, we don’t have any natural networks to begin with. So, it’s just super hard to get in. So, for us-- for me, it was very important to actually figure out that venture is what I want to do. Because if I did, this was a great opportunity. Probably, as good as it gets. And I spent time talking to a lot of my other investor friends and I spent time thinking about it. I realised that look, I love working with startups, I love working in cutting edge of technology, and venture gives me the opportunity to actually work with a lot of high-quality cutting-edge technology companies at the same time. I’ll play a small role in their success, and I feel like that to me, as I thought more about it, was very, very satisfying. And that’s how I make decisions. It’s not as much about money or success. It’s about done I feel excited about the day-to-day because that’s what matters, right? If you are spending like 50, 60, 70 hours a week doing something, you better enjoy doing it and feel satisfied doing it. If you can’t, nothing else can match up for it. So, for me, it was extremely important. The more I spent time, the more I thought about that, it felt that this was what I wanted to do, and I decided to join Lightspeed.

Rohit: I actually remember this. After you joined Lightspeed, I think I met you for coffee a few months after that. And you were like, “Dude I haven’t worked this hard in my life.” And you had been to IIT, you had been to Harvard, and you had done other things, and you first comment was that it was a pretty tough job. You have to be super interested like to do this otherwise you’re going to give up.

Raviraj: You have to be extremely driven, right? Because it is highly ambiguous. Nobody is watching behind your back. Nobody is looking at, “Oh, are you doing your job or not?” You have to be extremely self-driven. You need to figure out your way to get in front of the right companies, help them, and actually build reputation such that people would want to work for you. Because, it’s a tough industry, right? Like, the best entrepreneurs have a lot of choices. And I think in the end, for you to be picked as a trusted partner, that entrepreneur you want to work with long-term is not that easy. And I think-- so it’s a very, very hard job. It’s a lot harder than I ever thought. It’s also very, very satisfying as I mentioned. So, it’s totally worth it.

Rohit: Awesome. The second thing you mentioned that I want to touch upon is building networks. So, you said you knew Nakul for a really long time, and you had never sort of considered going into venture. How do you think about building networks? Someone coming for outside the US doesn’t have a natural network in the US through undergrad, through other channels like family, friends and whatnot. So as people think about moving to the US, whether it’s venture or whether it’s startup or tech or anything else, do you have any thoughts on how people should think about building a network?

Raviraj: Yeah. So, I think — and this may not be a very popular opinion — I don’t think you should a network. It feels to me that that’s a very transactional way of approaching things. I’m an introvert, so I am not like someone who’s trying to get to know 200 people. It just doesn’t come naturally to me. I’m all about like, finding a few people I connect very well with, and just building a very good relationship with them. I think, to me, that’s what matters. Even now as an investor, it’s like, well, I meet a lot of people, but it’s about a few people that you really get to know well and build deep relationships with. And that’ll just be helpful to anyone and everyone you meet, right, in any small way. And I think to that extent, if you do that, I think generally, people are nice. And if you are a good person, you’re adding value and you generally care about other people, I think it works out by itself. You don’t really have to think about “Oh I need to build a network.” I think, if you start thinking that way, it becomes very transactional and it shows, right? I think nobody wants to connect with someone who is transactional. My personal way was always when I meet with anyone, it was never with an intention of “Oh I will” -- when I met Nakul, it was not with the intention of “Oh, I want to get a job at Lightspeed.” Right? It was like, he was very smart, he’s extremely driven, I love my conversations and brainstorming different ideas with him, and that was what I was looking for. Right? And I think, everything else comes in. So, I think it’s a function of-- be generally curious about people, be ready to help to the extent that you can, and yeah, the things take care of itself.

Rohit: I totally agree. I think building honest relationships with people you like is highly underrated in today’s world. And generally, those are the people in those relationships help in the long run. Other side of the question or thought is if you don’t-- let’s say we’re not thinking about building a network, mentors is another thing that, I think, anyone who is either in the venture or tech world-- having mentors just helps you improve faster in a way, and that’s a super honest relationship with someone and that goes on for years. Do you have any mentor? Did you find any mentor? Do you consider people-- some people as your mentor? And how did that come about?

Raviraj: I think that’s-- that actually is a very important point. I never understood the importance of it till a few years back. My first mentor is Parikrama, who is also one of the senior PMs at LinkedIn.

Rohit: Parakram Chandpur?

Raviraj: Yeah. So, he’s just been very helpful throughout my product journey because he was a few years ahead of me. He would always advise me on how to think about product management that helped me a lot as I went through my journey in product. And I think for now in the venture space, Nakul continues to be my mentor. He’s a friend, but also an important mentor. He’s been in the industry for much longer. He’s had a pretty amazing portfolio. And there’s a lot of learning I have. So, he is someone I reach out to all the time. And to your point, mentors can help accelerate your growth, and I think finding a mentor is an extremely important thing that everyone should do.

Rohit: And is there any specific thing you’ll mention in terms of who is a good mentor, who is not a good mentor, or how you should think about having a mentor? It’s like how deep of a relationship and stuff like that.

Raviraj: I think it’s hard for me to say because I haven’t had very many mentors. But I think what I would say is like find someone who has been on a similar journey as you, but they are a few years ahead of you. And I think that actually is a big deal. Like for example, at some point, I would look up to Prashant for example — like, similar journey; was ahead of me by like a decent 10 years in product management, right? Parikrama, like, five years in product. And that ways, you actually know the choices they made, and they feel that they should have done things differently, you can at least learn from that. To me, that’s generally the framework that I use, which is like find someone who had a similar trajectory as you, but just five years ahead of you, and learn from that person. That’s how Nakul is very similar, Parikrama is similar, as well as Prashant. But, in the end, that’s the framework I use. There may be many other flavours to it that could work as well.

Rohit: Yeah, totally. And the person’s relationship and understanding of your background is important.

Raviraj: And I think you need to find someone who is generally invested in you. And I think it doesn’t happen in 

first go, but I think you really need to-- again, no relationship should be transactional. It doesn’t really result in anything great otherwise. So, I think I have a very close relationship with PK as well as Nakul, so I can learn a lot from them.

Rohit: I am not sure if PK introduced us--

Raviraj: He’s the man who introduced us.

Rohit: Yeah. So, just as a side note on Parakram, I got introduced to him through his wife because of some reason, I met her somewhere. And PK actually helped me think about Stilt and business a lot. And that’s very early on. And he never-- so one of those like where Parakram generally helped me think about things. Never sort of asked for anything. Like the non-transactional part. And he was trying to put himself in my shoes and giving me advice and like, “I haven’t thought about it this way.” So Parakram — PK, as he is called — is one of those people who is absolutely smart. I think he has like IIT rank 30 or something and is very knowledgeable about product and also investing.

Raviraj: As you said, he is very authentic in terms of helping people, and that was actually very helpful to me.

Rohit: He introduced me to you. He introduced me to a lot of other people also, who have been super helpful.

Raviraj: Cool.

Rohit: Yeah. Awesome. Cool. Yeah, Shantanu, PK — I didn’t know that before. So now you’re at Lightspeed and you’re on this venture path. For a lot of people who are still very early in their journey, what would you advise people if they are either thinking about coming to the Bay Area or getting into tech or getting into venture? Some learning that you had along the way.

Raviraj: I think that’s somewhat broad as a question. If you are moving from India to the States, I think it is generally doing a master’s and building some tangible skill sets is definitely helpful. I think it is much harder now with all the visa situations to actually transition from India to States right away. I think going for Masters — I mean that’s no surprises — is definitely a great way to do it. I do think there is a lot of value, as expensive as the Valley is-- there’s a lot of value in actually spending time in the Valley. It’s just a different place. It’s like nothing else in the world. It’s amazing. The amount of like innovation, energy in this 30-mile radius from here is just phenomenal. I think if you want to be in tech, I think there is a value in spending a few years here at the very least. Just learning and absorbing from people around you and the ecosystem. So, I think definitely, I strongly recommend-- like a lot of times we make the decision based on “Hey, it’s very expensive to live in New York-- in San Francisco. I should live in some other city and save more money.” But I think that’s fine. You have to think really long-term. I think there’s really value in being here, getting to know a lot of people because the concentration of very smart people is very, very high. So, you get to know a lot of really smart and driven people in a very short period of time. I think it’s a very valuable thing to do. So, I strongly recommend that even though it may seem like a costly proposition. I also think, in terms of moving to tech, when I joined LinkedIn, I was little sceptical about joining a big company being an entrepreneur all the while. But I feel like there’s a lot of value in joining a bigger company early on in your career because you need to understand and learn how organisations function at scale. The second thing that’s really valuable about joining a big company is there are [inaudible 00:48:22] and they are kind of like training, in some sense that is available. So as a PM at LinkedIn, you can learn from like, the Director of Product or VP of Product and there are formal ways within the organisation where you can get mentorship and learnings from other senior leaders. And I think that kind of stuff you don’t necessarily get in a startup. So, there is value in actually spending a few years in a big company before you venture into startups. But at the same time, I would say if you are in tech, and I think if you can afford it, you should definitely explore working for a startup, or starting a company if you can. I think that’s where the real excitement comes from and you really see the impact of your work in a very, very tangible way. So I feel like if you have to think about your tech career, the ideal path would probably be to start with working for a bigger tech company, learning the ropes of both the function as well as the organisation, and then transition into taking a higher risk position in a startup and making a real impact and making [inaudible 00:49:35] doing that. I think that’s typically what I would recommend. I think venture capital is very different, just because it’s a very tiny industry and very, very few people actually join venture firms. And I think you need to be very careful which venture firm you join because some firms actually drive a lot of returns; a lot of them don’t. You need to be careful about the firm you join and the people you learn from. I think the three things that mattered to me when I thought about venture and Lightspeed was am I working at a firm which has a strong track record and reputation? I think that matters a lot in this business. Am I working with a firm that has people I can learn from, who have deep experiences and consistently investing in high quality companies that Lightspeed is definitely doing? Third is that am I working with a group of people who are invested in my development? Because I was not an experience investor. So, for me, the job was also-- a large part of that was learning as well from other people. You know, venture capital can be a situation where everyone is like just doing their work and nobody cares about your development. That’s not a great place to be. And I felt like at Lightspeed, a lot of folks in the leadership were really-- it felt like they were invested in my development and progress in the firm. And that has been true since I joined. I think that’s another thing because it’s kind of like a business where you learn by apprenticeship, right? So, I think you need someone to coach you. And I think that was the other thing that was extremely valuable. So, you have to think through all these things, and you think about all those and there are a hundred other filters which makes venture capital just like a very hard place to grow. I think the best way to join a venture capital firm is when the venture capital firm wants you to join them and you want to join them. And I think the best way to position yourself such that the venture firm wants you to join them is to either start a company and make it successful or join a high growth company early on and make a substantial contribution to that. I think that’s the most common-- I think that’s the best way to join, but there are other ways. And you know, there are journalists who became successful venture capitalists, lawyers that became venture capitalists. So, I think people move to this industry. So, by no means, that’s the only recipe. If you feel very strongly about it, you should go for it. But I think in my mind, the best path is probably that.

Rohit: Yeah. That’s absolutely true. That’s what’s the most common path that I’ve seen too, and it’s not an easy path. Just keep that in mind, it gets harder as you go to the industry. Now time for my favourite question that I’ve been waiting. What do you look for in founders and teams before investing?

Raviraj: I think I believe in this simple principle that the gradient of your life is more important than your altitude. By that what I mean is how much have you progressed in life and not where you are right now. Because the rate of your progress or improvement determines where you can be. So, I feel like, I like entrepreneurs who have shown that, who have shown that they’ve been able to improve themselves in many ways; in a very, very short time, they’ve grown very fast. Examples of that could be you know, someone who came out of nowhere and build themselves somewhere, or someone who grew within a company very fast, or someone who actually established themselves an expert in the space where you quickly-- someone who hustled their way into doing things which does not seem very obvious to a lot of people; like people who can walk through walls, right? That’s the kind of people I feel like make great founders. That’s not the only kind. So that’s what I really look for in founders. And you know it much, much better than I do which is like, it’s a hard job, right? And nine out of 10 days, you doubt yourself. The one out of 10 days where things go well, it’s totally worth it. But you should have that persistence, you should have that hustle to actually go through those nine days to get to the tenth. And I think that’s what we try to measure. The second thing we also particularly like founders who have very product mindset. Like, gone are the days where you can just build a product and sell it to customers at the strength of your sales team. On the enterprise side, I think what you need is now, you need to have a strong sales team, but you also have to have an amazing product that the users love, right? And I think we have seen a lot of companies that have this. So, I feel like having a product mindset is extremely valuable in a founder. So that’s another thing that I look for. The third thing is like a deep-- you need technical insight and that’s more relevant to my deep-tech firm portfolio like computer vision, like self-driving cars. Because you’re in a very small subset of people who have a differentiated insight and an edge over others in terms of their development of the technology or a nuanced view of the technology, and those are founders-- those are the third set of founders I look for. Anyone can be a combination of these three or anyone can be outside of that. I’ve learnt one thing that there is no rule. There are entrepreneurs who become very successful and they all look very different from each other. So, I think in the end it’s about-- it’s a lot of more softer aspects of it, like getting to know the person, understanding their vision, drive, and making a decision. That’s what makes venture capital such a hard business because there’s no formula. But if I have to pick, those three would be the right subset.

Rohit: Yeah. Awesome. So, thanks for talking to us.

Raviraj: Thanks a lot for inviting me.

Rohit: Yeah. It was one of my favourite interviews. Thank you.

Raviraj: Alright. Thank you.

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