Ashish Gupta is an outlier for many reasons. A gold medalist in computer science from IIT Kanpur, Gupta built a startup (Junglee) and sold it to Amazon, has been through several near-death experiences at his second startup (Tavant), and is now in the process of sunsetting his third entrepreneurial venture, Helion.

None of the above makes him an outlier though.

Over years, Ashish has found a way into some of India’s biggest and most valued startups as an angel investor. From MakeMyTrip to Flipkart and MuSigma, Gupta has been an early seed stage backer. It’s almost like getting a front row seat in a blockbuster movie, and also being able to help produce it.

There are very few investors who are as humble, intellectually honest and loved by the entrepreneurs.

How and why does he stay that way?

Please tune in to listen and read the full transcript below to find out more.

Hat-tip to Kanika Berry who helped transcribe the conversation, which is produced lightly edited below:

Pankaj: Welcome to Outliers and this is a Podcast with Outliers. I am actually excited with the hunts I have to make to sit down with Outliers and someday I will definitely share data on the average time taken to sit down with the Outliers I pursue. This Outlier in particular, you know, would join the club of, over a year chase. I am sitting down with Ashish Gupta. Ashish has many things that you know, we would remember him from building Junglee, being part of that team and selling it to Amazon and later building Helion. But, more importantly, when I go around the Indian entrepreneurial ecosystem, talk to entrepreneurs inside and outside, there is tremendous respect and love that I always hear about you, Ashish. So you know the reasons why I have been trying to sit down with you. Welcome to the podcast.

Ashish: Thank you so much and sorry that such a long time has been spent in this dance, so look forward to this chat.

Pankaj: So, let us start from the start. Where do you come from? I mean one of the things I always remembered meeting you for the first time is our conversation in shudh Hindi (pure Hindi). I was like, really enjoyed it. But tell me little bit about yourself, Ashish. Where do you come from?

Ashish: So, my father is from the armed forces and my mom while having a whole bunch of education, decided to sacrifice a career in favour of taking care of her kids. She did a lot of the heavy lifting. And I have a sister who is in Gurgaon, who is older to me. I spent some time bouncing around different parts of the country. Grew up in Hyderabad, Shillong, Mount Abu, Dehradun and then went to IIT Kanpur for an undergraduate degree. So, have just wonderful memories of growing up.

Pankaj: What was becoming an entrepreneur all about for you? How and why did it happen?

Ashish: I am an accidental entrepreneur. Actually, most of the things that I have done are more accidental than deliberate and I became an entrepreneur because I was dissatisfied with the day jobs that I was doing, so it was an exercise of running away from what was otherwise considered the normal thing to do as opposed to having the clarity that I wanted to be an entrepreneur.

I used to work for IBM research, had an absolutely wonderful boss, didn’t appreciate how good things were for me; so, left, joined Oracle, had another wonderful boss, still didn’t appreciate how good things were and then left and started Junglee. But it was mostly a quest driven, not by knowing what I want to do but knowing that I did not want to do something which was that I did not want to sit and work in these companies and then luckily and accidentally found that entrepreneurship was indeed what I enjoyed doing and since then to now, have been involved in starting three different companies, Junglee, Tavant and then Helion.

Pankaj: Before we move on, what is with the name ‘Junglee’?

Ashish: Oh, the name generally was… we had a Japanese investor and when we had originally five people had gotten together to start the company, the original idea was that of a gentleman called Dallan Quass. He seldom gets mentioned because the other four people were around when the company exited, Dallan had left the company, somewhere during the journey. So the five of us, when we started the company, the investor was a Japanese gentleman who was the Chairman of Sanyo Semiconductor. And we were playing this Shammi Kapoor song in the office, jo purana Junglee ka jo gana hai (the song from the old movie ‘Junglee’) and Yahoo was flying very high, this was 1996. Yahoo was all the rage, Netscape had just gone public and the biggest gorilla in the internet space was Yahoo and in that song ‘Yahooooo and Junglee’, both show up together as some of you might already know.

Pankaj: Of course.

Ashish: And that was the genesis and he said, ‘Well, you should name the company Junglee’, and we named the company Junglee. So a Japanese person who doesn’t understand the meaning of the word is responsible for the name.

Pankaj: Yeah, I can guess as much. Before we get to a mode wherein I, you know, take insights from you about the learnings you have had by watching entrepreneurs let us spend a little time on your entrepreneurial ventures and key learnings there. Take me through life and death of entrepreneurial dreams as you know, three old lens, across different things that you have built, capture some key lessons for us, Ashish.

Ashish: So clearly, we all take away very, very different lessons from this. People have different success formulas that work for them, so a lot also has to do with, who the person is? For example, if you look at founders across the board, there are people who like, Bill Gates who have a very different reputation than Steve Jobs but they are all enormously successful by conventional measures. So, take this with a large grain of salt. For me personally, what has worked well is, I have been blessed that I have got to work with some extraordinarily good people and I think in a team having multiple good people and my belief is that the founding team should be about three people, even though five started Helion. Actually, Helion, Tavant and Junglee were all started by five people. So, clearly, I am not standing by my own recommendation. Somewhere between three people, four people, I think is a good sweet spot because that allows some room for one person to fall off the bandwagon. Yet there are still more than one person left behind, of whom one will scale and one will potentially not scale, so you are still left with one or may be two people who can scale. That keeps the spirit of starting the journey with you.

And what do I mean by good? The traits that I have been blessed to find in several of my partners, there are two or three that really stand out. One is intellectual honesty and that allows one to see the facts for what they are as opposed to what one would like them to be. So for example, when we started Junglee, we thought we are starting a database company and we very quickly realised that the world doesn’t want another database, what they want is an application on top of the database, so we started building comparison shopping. Actually, we started first building a way to find jobs – it was a job hunting application and then we realised that actually Yahoo wanted a comparison shopping engine, so we built a comparison shopping engine after that. And this evolution happened to a response to accepting what the market wanted as opposed to necessarily being caught up in what we thought needs to be built. So, that intellectual honesty, and that also by the way is a fine line, you just can’t be jerked around by the market every morning. There is a fine line between being nimble and being fickle. So, that is one, intellectual honesty.

The other one that I have found very useful in pretty much in all my partners is the willingness to put the organisation ahead of themselves and that allows decisions to become, therefore, much easier and one is not caught up in whether the person is saying something because of the wrong intentions… therefore, one can move forward, much faster, so it is important to be aligned from a value system perspective, in my mind for that. There is the importance of just hard work because there are plenty of smart people out there. So, things don’t happen just because one is supposed to be smart or whatever, you got to work hard and even then you got to get lucky. One can’t take one’s luck too seriously and conflate it with one’s right. So, hard work, intellectual honesty and alignment of the value system are some of the things that I found to be interesting ingredients for at least what has worked for me.

Pankaj: I am a rookie entrepreneur, still learning from these conversations. But one of the questions I find from almost every entrepreneur I have met or even successful business people is that this question about should I continue doing it or not? Or, should I move on? Or, should I keep hanging in? And then we start defining people, ‘ok this person is not letting it go, this is a zombie startup’ or, on the other hand, someone stays in and it becomes a big thing. Help me understand: how do you approach such questions? And how have you approached this in your career as an entrepreneur?

Ashish: So, in my career as an entrepreneur, so Junglee, we got lucky. In that, we were at the right place at the right time, we were solving a problem that was interesting, somebody came along and said, ‘let’s buy you out’ and we sold. Now one can ask a question, ‘why did you not keep building?’ which is a proxy of what you were saying because walking away from something whether one walks away because the money was good or whether one walks away because one decided that the business is not going away, is not going forward, it is still walking away. So, at one level, it is the same kind of decision and then at Tavant, we had started a SaaS company which we then converted into a services company. This was circa 2000 and we realized that the SaaS business, it was very early for the SaaS business and also our idea was not at the right place at the right time. So, in that one, we actually walked away from the business and converted it into a regular old services company and the company is doing very well, thanks to the leadership of the CEO Sarvesh (Mahesh). So they were both examples of walking away and ironically Helion falls in that same category also. We are not raising any more money.

How do I look at this? I think there is no right answer, that is first and foremost because it is a judgment call and there is no way to build a parallel universe to figure out, what would it have been otherwise? So, I think the biggest thing is that one has to make sure that the people who are taking the call are bought into that decision and whether or not that decision is right or wrong, we will never know, so one has to be at peace with it. So, I know, several people have told me that, ‘Hey, you should have continued to build Junglee because it could have become a very large enterprise’. Maybe the answer is yes, maybe we could have gone to nothing, so I don’t know.

So, I am sorry, I don’t have a very good answer to your question other than the fact that believe your own answer, keeping in mind the trade-offs that you are willing to make because it is a very, very personal question. It is as personal as whether you should do a startup. Not everybody should do a startup, there are 99% of the world is happy not being an entrepreneur. It’s not because they are wrong and that 1% is right, it is different strokes for different folks and lot of things go into it. Can my family afford the continued price that a startup exacts? Whether it is time, whether it is money, whether it is attention away from kids, parents, whatever else it is. Very important factor, would I rather have some money in my bank, if we are talking of selling a company or would I rather play for larger stakes?

One of the people I worked with once told me that, I think small, I meaning me, I think small. Because I was telling him, ‘Hey, you’ll make a 100 million dollars’ and he said, ‘well, that’s not the reason I am in this game’. Whereas for me, it was a very logical thing to do which was to take that exit. So I think it is an intensely personal question. What I would say, however is that, one should listen to the people around you to ask, what would they do but more importantly, why would they do what they did because what would they do is very easy to say. The reasons behind why they would they do will give one material to then think about whether I have considered all the factors? So, if somebody tells me, ‘hey, I would exit this company’, that is not so interesting.

What is interesting is to find out, why would you exit this company, Pankaj? And if you tell me, because I think that you are going to get eaten up by Amazon and so on and so forth, now I have more material to factor into my judgment. I would talk to a bunch of people around me, not take their opinions on what they would do but rather factor in the reasons for why they would do what they would do (and) then take my own call.

Pankaj: I think I completely understand what you are saying and I think I agree with it because of the point you mentioned about the understanding ‘why’. Decision-making frameworks are different for different people. There is context.

Before I transition into your role as a bystander, why did you become an entrepreneur again? Is there something else that we discuss a lot, so-called ‘serial entrepreneurship’? I was like serial killer or something.

Ashish: Reasons are very similar.

Pankaj: So why did you become an entrepreneur again?

Ashish: So, clearly the decision to leave Amazon from a financial perspective was a stupid decision. And like I’d said right in the beginning, most of the things that I have done are not very deliberate. I ended up becoming an entrepreneur again because five of us were talking about this idea and we all liked it and we thought, ‘ok, so might as well go do it’. So, a combination of excitement, some measure of naivety, clearly it was not such a good idea, we figured out in months that it was a bad idea. So that excitement, naivety, also there is a different level of adrenaline that comes in the early journeys of a startup and I like that. And it is very important to acknowledge that it is being done for the fun of that portion because from a financial perspective, it might result in nothing. So I find that at least for me, if that problem is not exciting and Helion started for the same reason. I moved from the US to here and it took a bunch of time to raise money and there were four of us that were pounding the pavement to raise the money, so it was not easy. But then nothing is ever easy. But it was again for the same reason. The excitement of doing that thing was the primary reason.

Pankaj: That explains it.

Ashish: And there is some hope that excitement will be correlated to value but I would be incorrect if I told you that it was the potential value of the, what was being created, that was the fun. It was the excitement of trying to do that, which was the primary driver.

Pankaj: Let’s shift gears. Your role as an angel investor or a partner with entrepreneurs is equally fascinating if anyone were to look at the entrepreneurs or the entrepreneurial teams that you have been a part of. What I want to understand from you, Ashish, are a few things. What works and what doesn’t work, very broadly but in particular, so when you decide to work with an entrepreneur, what is that decision-making all about?

Ashish: So, some of it is looking at the people who are involved, coming to a conclusion whether these are people that I think and again time will tell us that are going to be able to pull off what they want to do. I am also particularly biased in favour of going after spaces that are somewhat early because there is room to make mistakes. There are people who are experts in spaces and they are comfortable going into spaces that are late because they understand spaces very deeply. I don’t understand too many spaces very deeply. So as a result, I am reluctant to go after ideas that are very narrowly focused because there is less room to make errors and there is more depth of knowledge required. I prefer ideas where the space is early, for example, Daksh was one of the first companies in the BPO space. There people who are strong on first principles, intellectual honesty, hard work, listening to the customers, can adapt to a market which is in itself very nascent. And, therefore, they are at par with anybody else. And, therefore, a good athlete has a good chance of winning that race. Whereas if you are looking for specialists, that is not something that is my sweet spot. So, I am biased, therefore, in that way.

And market size, of course. Now market size is a confusing thing especially in India because very few markets look like they will fundamentally be large. And that comes down to how much money you put in versus what is the size of exit you want to get and that is the problem with a lot of the size of investments in India. If you end up putting in 50 million dollars, getting a 100 million dollar exit doesn’t work. You fundamentally need much larger exits. If you had put in five, then getting a 100 million dollar exit is fantastic for everybody. So when I say size of the market, I mean the size of the market commensurate with investments that will come in. That is another thing that is interesting. In India therefore, I end up choosing not so much necessarily identifying the size of market but rather the amount of value creation vis-à-vis how hard will it be for somebody else to replicate and does it solve a real problem?

And then I am betting on the fact that the market will grow because the problem is interesting and it is hard for somebody else to just come in. So there the framework is slightly different as compared to a US company where you can indeed look at an existing market size which is large enough but that I personally find a harder exercise to do in India, so I go back one building block lower, that is it defensible and does it solve a real problem for somebody?

Pankaj: We also keep hearing, you know, idea maybe good or bad but entrepreneur matters; idea may fail, entrepreneur will always win. Also help us understand things through the India lens Ashish, right. So who is this quintessential Indian entrepreneur?

Ashish: The quintessential Indian entrepreneur, I don’t know because the whole space is evolving so quickly that the nature of the people in the business is changing very quickly also. So, I don’t think there is a quintessential Indian entrepreneur. I don’t know what else to say there. I can tell you what are some of the things that I think, make gear somebody up for success over others. Some of them are as I was talking about before, intellectual honesty, the ability to work hard, the ability to put the company ahead of themselves. Some other things that I would throw into the mix, one is outbound skills because somebody in the team needs to be able to sell the company to investors, sell the company to recruits, sell the company to customers, so there has to be somebody who has outbound skills. It is very essential whether it is an engineering product or whatever because sales is part of everything, recruiting, generation, revenue, bla, bla, bla. So one is outbound skills and that I think is very important.

Finding people who have grit in that, have they struggled through some adverse circumstances somewhere in the past because adverse circumstances are going to arrive, that is for sure. Matter is when, not if. And in India, particularly, I also end up looking for, do they have appreciation of cash. Now, that is a very dangerous one to call out because there are several companies in India that are highly valued precisely because they have no appreciation for cash. And I don’t, therefore, quite know, how to reconcile this last conundrum. And I think, there one way that I do reconcile it but I am not totally bought into my reconciliation is that, if someone has extraordinarily high fundraising skills, the market is, especially in ‘winner takes all’ kinds of categories. One can compensate for the inability to deal with cash, with the ability to raise large amounts of cash. Fundamentally, if you ask me, I am not at peace with that trade-off, so, therefore, I struggle with that last one and I still believe that somebody who has respect for cash and ability to make sure that they understand how much cash is getting spent is, somebody I am more naturally biased to. But like I said, I can argue against myself in (the) Indian context there.

Pankaj: One of the other things is, does one has to be really nasty to be successful?

Ashish: I think that is not at all the case.

Pankaj: And I am asking that question and this is the culture question. And I used to track the Infosyses, Wipros of the world, Murthys, Premjis and all that. And now, of course, it is the next generation. I keep picking these things. So the way you talk, internally and outside, so this thing of being cool and this thing of being nasty, there was this beautiful article someone wrote on about Virat Kohli and how he epitomises and he reflects this generational shift wherein great examples are about people who are nasty in that sense, right, and they are obscenely successful. How do you explain something like this to someone who is wanting to be a new entrepreneur and is looking around for examples? This is a little philosophical question but I have seen this percolate to the culture of organisations, is why I am asking this question.

Ashish: So, fortunately, if we just look around us in the Indian ecosystem, there are innumerable examples of individuals that I believe are very fine people and not just in my squishy thing but non-nasty. They are polite, they are respectful, they are not putting on a veneer. At the risk of naming names, you meet Deep Kalra, you meet Sanjeev Bikhchandani or Hitesh. They are as successful by any measure, as entrepreneurs can get and they are pleasures to be with. And I am not just saying this because we are friends but I hear this from, repeatedly, from the ecosystem also. And there are many, many, many, many more. So clearly one doesn’t need to be nasty to be successful. At least we have evidence that allows us to be non-philosophical about that assertion.

Why does this belief system get about, I really don’t know. I think sometimes being firm and direct gets conflated with being nasty and that is also sometimes, I think people who are firm and direct sometimes get branded as being nasty because we do have a challenge in our Indian cultural ethos where we have a lot of trouble saying ‘no’ and somebody who says no can sometimes be perceived as being nasty. So, I don’t know how much of this comes from mislabeling a behaviour which otherwise is not acceptable. I do believe that people have to be direct, they have to be firm and if that means they get labelled ‘nasty’, so be it.

But, truly being nasty for the heck of it, I don’t see why that would be a reason why people would succeed. I actually think that there are strong evidences, if you read Good to Great, for example, to the extent you can believe that research, they have a consistent theme that the people who come out ahead are people who are not nasty and by the way that is true of the guys who run Google, the guy who runs Amazon and the list goes on and on, so it is not about the domestic stuff. So I would actually urge folks to totally not take my word for it but do their homework. I would be surprised if they come to the conclusion. Are there examples who have succeeded by being nasty? There are examples of everything out there!

Why does this lack of nastiness, I think, work in the long run? People matter, when most people like to be treated well, I doubt anybody likes to be treated badly. So if one is actually respectful of people, I think you will build a longer set of folks who will speak well of you, who will do well by you, who will want to work with you and most companies at the end of the day are people. So I don’t see why it is a more complicated argument than just that. In individual sports, I can imagine, even there I struggle by the way. If I am let’s say, a tennis player or a golf player where the only person I have to deal with is a set of five people, maybe I can afford to be nastier. I don’t see how one can be an unreasonable person in the context of a cricket team, so one probably has to be exceptional to get over that handicap, is the way I would see it.

Pankaj: I give it to you. Final two questions Ashish, quick ones. One is, I mean, if we don’t talk Flipkart with you, it will not be complete – biggest exit. But I don’t want to focus on details and anything else. I just want to understand one thing from you, especially since you have been part of that journey or at least entered that journey much before, very early on. If you were to pick one or two signals that kind of explain this success that followed later, what would those things be?

Ashish: Got it. So, if I understand your question when I tagged along? I was brought into the deal by Subrata (Mitra) and Abhishek (Goyal) at Accel and I came along because both of those guys, I have a lot of respect for and when I met Sachin and Binny, they to me were very appealing because they fit a lot to the characteristics that I was talking about. If your question was, did I have a sense that it would become so big? The answer is absolutely not, I had no clue how big this is going to become. I seem to remember the discussions were, maybe this can become worth 100 million dollars. So, I don’t know if I have a good answer to your question. I had no clue.

Pankaj: Ok, not necessarily, whether it will become that big but in terms of what you saw and remember the most from this entrepreneurial team.

Ashish: Sure. So I think one of it was the team. I would also actually give a lot of credit to Lee (Fixel) of Tiger and this is my perspective by the way. Blind man and the elephant, each blind person sees only one part of the elephant and I was only peripherally involved, so I could have missed many parts of the elephant. The part of the elephant that I saw and I also would like to call out is, I think, credit to Sachin and Binny for buying into a very large vision and also a lot of credit to Lee for helping everybody around the table see a much larger dream than one started out and then backing it with a lot of money because large dreams often take a lot of resources. That was one of the lessons at least from that whole journey that came to me where he is one of the interesting examples in my mind, Lee, of when an investor can meaningfully change the size of dream and then credit to the rest of the people to say, ‘Ok, we will go for a big dream’, because it comes with more risk, it comes with more pain and so and so forth. So, that is one thing that stands out to me.

Pankaj: Yes, that is absolutely clear and I agree with you. Final thing, Ashish. This is philosophical. What does wealth mean to you?

Ashish: Oh my god. Ok, this is a very, very hard one. It is both an asset and liability. One of the things that it means is the ability to do what I would like to do. The hard part is figuring out what I like to do because I was doing it even when I didn’t have ‘wealth’. I left my job when our family income, together, my wife and I, was $60,000 per annum which doesn’t go that far. So that has not gotten in the way of doing stuff but that is indeed one of the things that I think wealth means to me, which is the ability to do what one wants as opposed to what one doesn’t. I think another part of it does mean and I don’t mean this in any altruistic sense because I don’t believe in altruism. I think, just the model of selfishness helps explain why one should do all kinds of things, including helping other people because one gets joy out of it and one doesn’t even know whether it will have good consequences for the other people like, mosquito nets in Africa, it ended up in people killing fish because they started fishing with those mosquito nets. So, altruism is a very dangerous thing which is why I would rather come from a selfish frame of reference.

Doing things that other people want to do, so not only what you want to do but enabling other people to do things what they want to do. So if somebody wants to start a company or if somebody wants to go do something, I think the fun of having some wealth is to be able to not only have your own journey but vicariously join other peoples’ journeys because the kind of energy that comes out of being party to doing things that people want to do, innately, that joy is just amazing. So, it is just the variant of the first one. Those are two things that come to me.

Pankaj: Final question. It’s infectious, every time I meet you and I don’t mean to question and you know and get the secret out  What does one of the things with wealth and everybody is seeking, happiness, right? So what is your definition and even the legacy question? What are these things? What do you think of these things?

Ashish: Legacy I don’t understand because I don’t think that big or that far, maybe. Wealth and joy, I think are totally un-correlated because if wealth was a reason for being happy, the data would be very different than what it is outside. People who commit suicide are more often people who are wealthy. There is plenty of evidence that they are uncorrelated. What to me it means is bringing down expectations and this is going to sound very whacky but I think the whole duality issue that one comes up within Hinduism is very powerful. They are all the same things by the way. I don’t think there are too many concepts, the number of concepts is very small. So being on this dual edge, so as an entrepreneur, you need to believe in yourself yet you have to be willing to replace yourself, you need to conserve cash yet you should spend cash on the right things, you should be very aggressive yet you should plan for the downside. These are all very contradictory but the fact is that is the job of an entrepreneur and I think it is no different than all of our jobs on a day-to-day life which is what I mean by the principles are all the same.

So, should we be trying and creating wealth? In my mind, the answer is no, we should try and create value because value then creates wealth. So, if I solve a problem that is in the logistics space and if it is important to somebody, money will come out of it whereas if I try and get money, the shortest path is to go and rob a bank. So, I think one needs to pursue value in cognisance of the fact that wealth will follow. So, if I am making sense at all…

Pankaj: Yes you are.

Ashish: And joy is also, I think, very similar where I don’t want to pursue joy because that is a destructive process in its own right, so something else needs to be pursued of which joy is a side effect. And one of them, like I said before is, what is a value creation exercise that I truly feel passionate about? If I pursue that, joy will come out as a side effect. So I think the quest is to figure out what can one do consciously and then all the rest is side effect. And if one can figure out what one can do consciously, so, for example, humility, I think one should not pursue humility because if you try and pursue humility, you destroy humility. A person who tries to pursue humility becomes artificially humble. Am I making sense?

Pankaj: Yes, you are.

Ashish: But instead if one tries to pursue intellectual honesty and one tries to pursue empathy, humility comes out as a side effect and those are two that you can actually pursue. I can make a conscious effort to listen to the other person, that is empathy. I can consciously try to make sure I accept all the facts and if I am listening to the world and I am accepting of reality, I will very quickly figure out that I have nothing to be proud about, it does not take too much and humility will come out as a logical consequence because what other choice does one have, if one accepts the rest of the fact? I am sorry I wandered off on a tangent but joy is another one of those things, I don’t think that can be pursued, consciously. Either what one can do is make a choice to look at the constructive part of what is going on and I am not able to do this all the time, lest I communicate the wrong, this is intellectual comprehension, execution is much poorer.

Pankaj: But, so beautifully put, Ashish, and one of the things I always believe in, conversations is what I also chase and focus on, stories are by-products as a journalist. So, I think the term what you used is not by-product but the consequence of it.

Ashish: But ‘by-product’ is a wonderful word also.

Pankaj: So great talking to you, Ashish, and godspeed with everything. Thank you.

Ashish: Same to you. Thank you.

(Kanika Berry has a Masters in Business Administration and has been a communications specialist for over eight years.)

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