Serial Entrepreneur, Prolific Investor and Partner Emeritus Prime VP Ashish Gupta on Entrepreneurship and Investing in India

Ashish Gupta, Serial Entrepreneur chats with Amit Somani, Managing Partner Prime Venture Partners.

Ashish Gupta is a well-known and highly respected figure both in the Indian startup ecosystem and in Silicon Valley. He is a Kauffman Fellow, holds a Ph.D. in Computer Science from Stanford University, and a BTech from IIT Kanpur where he received the President’s Gold medal and is on its list of 50 illustrious alumni. His first entrepreneurial venture, Junglee (a price-comparison platform) was acquired by Amazon in 1998 following which he founded Tavant Technologies in the year 2000. Known for being a prolific investor, Gupta has been an early investor in startups that went on to have very successful exits, such as Flipkart and MuSigma. Ashish is the co-founder of Helion Venture Partners and serves on several boards including Ezetap, Pubmatic, Simplilearn, SMSGupshup and Naukri. Some of his past investments include Qwikcilver (acquired by Pinelabs), Daksh (acquired by IBM), MakeMyTrip, Upwork, Perfios, and Redbus.

Listen to the episode to learn about:

3:07 Angel investments and VCs: myths vs. realities

5:18 FOMO mentality in the private world

6:23 Difference in Indian and US markets in terms of investing

11:27 What makes a great company?

16:23 What’s more important than team for a company’s success

19:41 Importance of timing when it comes to trends

22:57 Thoughts on exits

25:37 Thoughts on selling a company

26:42 Why companies are choosing to stay private

31:20 Tips for young entrepreneurs

33:07 Joining the Prime VP team

Read the full transcript below

Amit Somani 1:02

Welcome to the Prime Venture Partners podcast. Today we have with us a special guest and a dear friend, Ashish Gupta. While Ashish needs no introduction, he is a well known technocrat serial entrepreneur and been an investor both at an individual level and as a VC for many years. Welcome to the show, Ashish.

Ashish Gupta 1:21

Thank you very much Amit.

Amit Somani 1:24

Ashish you’ve done a lot of different things, you and I started careers together at IBM Research many moons ago. You started with your first company Junglee and sold it to Amazon in the early days. Can you talk a little bit about the various things that you have been up to? And some of the stories from the various things and you’ve first stint in India as well?

Ashish Gupta 1:44

I guess, not knowing what I’m doing is probably the hallmark of my career. As a result, I bounced around in a lot of different jobs and IBM, as you remember, we had a wonderful boss who I didn’t appreciate enough but over the years, I regret having left too early. So I ended up at Junglee and then left Amazon to start another company, which became a service company called Tavant. Tavant is what brought me to India really the first time because we opened two offices, one in Gurgaon and one in Bangalore. And as a result, I stayed in India for close to a year, at that time, HSR layout had practically no homes in it, and finding an office used to be hard. So it was an interesting time, and then spent eight years in India with Helion, which is a venture fund that I started along with four other folks. And now I’ve been back in the US for about five years.

Amit Somani 2:37

Wonderful, Ashish, and many of the listeners may know that Ashish’s recently joined us as partner emeritus at Prime. So we’ll talk a lot about his journey as an investor on this podcast. So Ashish, you have also done a lot of angel investing and professional VC investing. So can you talk to our listeners about some of the lessons that you’ve learned over the last 10 years and in particular, let me start with what are things about angel investing or for that matter VCs that people believe or have myths versus realities, but may not be true.

Ashish Gupta 3:07

So one of the myths that I have heard from a lot of folks, especially those who are not in investing is that somehow angel investing is a way to make money. I found that angel investing is more a way to exercise one’s passion, and it costs a lot of money. So it is probably more expensive than golf or tennis as a way to keep yourself entertained. And once in a while when one gets lucky, which forms the apocryphal stories as to what draws rest of the flies only to get fried on the flames of angel investing. But that is that is one.

The other one which I find as an investor is that one can become a good investor by learning what works for others. And probably Warren Buffett is an interesting example. He’s written more about investing than most other investors. So by that token, we should all have become Warren Buffett by now. But man, is that story, a sad ending for most of us who have tried to emulate. So it comes down to discipline of execution. It’s very easy to read but like everything else in life, we all play a certain stroke. And just by watching Nadal, I can’t change my backhand to the way he plays his backhand, and we regress back to the stuff that we know.

So one of the things that I find is the myth that a lot of people believe in, that I found it very hard to practice is that talking to folks and learning what others do one can become an investor. That is what I found. It is more like finding what works for you. Because all one needs are three good deals in an entire lifetime. And one is done. And that is out of hundreds of millions of deals. And it’s discovering what is that special something about how you play the game that I think is the hard part.

Amit Somani 4:43

Yeah, since you mentioned Buffett, one of the things that he also says is you need to be right five or six times in your entire life, to have sort of an extraordinary outcome. And yet, even in the venture community, one of the things that I see is, there’s a lot of FOMO and a lot of this zero sum kind of mentality. Whereas you don’t see that in public market investors. Public Market investors, you could invest in value, you could invest in growth, you could do that, any kind of thoughts on why that is or is it that India has classically been a little shallow as a market in terms of market depth and therefore, there are only going to be so many few companies. So, what do you think about that?

Ashish Gupta 5:18

I would agree with you that there is FOMO in the private world, and that comes I think because of a scarce resource, because there is only one seat on this motorcycle, the motorcycle being any startup that is leaving at any point in time and they will take only one rider on the pillion with them, whereas the public market investing looks like a bus, as many people can climb into it as they want. It is still equally hard as to which bus to climb. But that perception of a bus versus a motorcycle exacerbates the sense of FOMO in venture investing. Incorrectly so in both cases. In India, as you correctly pointed out, even more so, because there are only so many motorcycles out there. Whereas, in the US, there is an entire kafilla of motorcycles that one could ride. So it’s a more mature space. But I think it’s more this motorcycle versus bus. Given the number of investors you can count, it does lead to it.

Amit Somani 6:12

So since you’ve also invested in the US and you were also a Kauffman fellow earlier, do you see that landscape differently? I mean, obviously, it’s a deeper market, no question. They have a much larger economy. But in terms of just investing itself?

Ashish Gupta 6:23

It’s significantly different. If you think of investment banking, circa 1970s, there would be one investment banker who did everything and then over time it got specialized. There were tech, healthcare, etc. within tech, they became internet bankers within internet bankers there are advertising bankers and so forth. So the US is much further along on this journey. And as a result, the market is significantly more specialized, even starting 2006 if you look at Helion’s journey or some of the others, we all did everything. As the Indian market has gotten more depth, people have become more specialized. So that is one.

Two, I think it’s the same thing as in the venture business, the startup industry, the US had HP going back to the late 50s, early 60s. So, there is 60 years of startup tradition, your neighbor is the VP of engineering, the guy backdoor is the VP of Marketing and so forth. Whereas in India, you’ve got to hunt the experienced people down to get guidance. So the whole maturity curve is very different, the depth of the market is very different. The fact that there are exits on a regular basis, makes the market very different also. And it reflects in the mentality in how many people that are of each type practitioners that is, and how specialized any of these areas get, you can find VP of engineering recruiters that specialize only in back end and performance oriented companies.

Whereas I think finding an executive level recruiter in India right now who specializes only in VP of engineering is still a way to go and this is nothing good or bad. It’s a matter of growing up as the market is growing up and the India market is growing at a much faster pace than the time that it took the US.

Amit Somani 8:05

Another thing that you shared with me earlier is this whole notion of investing behind trends. So what do you think about riding the next wave? 2015 was all hyper local and now suddenly edtech and healthcare is all the rage and AI. Any thoughts on that?

Ashish Gupta 8:20

So I think trends are very dangerous, because most of them turn out to be misleading and venture is a micro business. If you find the right micro in the right macro, then you do make a lot of money, but picking the right macro, but missing the right micro, you just end up in trouble. And a lot of macros turn out to be the wrong macros, ATM networks, a whole bunch of the telecom infra stuff, as soon as it was getting hot, it died out. Security turns out to be an off repeated macro theme, hyperlocal and so on and so forth.

So I think, one needs to focus on the specific company that one is talking about, and then see whether it is in a market that is large, there is room to make mistakes, as opposed to picking the right trend, but then getting the company wrong. Some trends, by the way, do turn out to be more valuable than other trends. But most trends turn out to be wrong.

So for example, if you look at ecommerce investing in India, in the 2008 to 2012 timeframe, dozens of ecommerce companies got money, pretty much one is left standing, Flipkart. And I was an unfortunate investor in several of the others. So by no means is this claim of having picked the right one, we missed the right ones at Helion. But just as evidence, that right trend, and a whole bunch of other stuff got mixed into that a lot of it was getting access to capital, which was the bigger driver than the trend itself. So I find a trend based investing a very dangerous way to go about trying to make money.

Amit Somani 9:58

So Ashish if I want to unpack the micro trend or picking the micro in the macro? Is that just a bet on a team? Or is that a particular niche that you’re going after? Or is that just luck? Like what does that micro mean if you can elaborate.

Ashish Gupta 10:12

Indeed, the team makes a huge difference within that micro. Because in a new trend, the big advantage is you can make mistakes, because presumably it is whitespace. And then the person who can make those mistakes and fix those mistakes, turns out to be a much higher probability winner in a new trend. There are very few rules to follow. That is one. Let’s continue to take ecommerce as the example in that particular trend, fundraising skills would have been a huge differentiator for the people who would win versus the people who would lose and then the luck portion comes in, as you called out, the person who had access to deep pockets or a deep pocketed investor early in the game had a much higher odd of winning that game because it turned out that money was a huge determinant of success. And luck, by the way, is just an overriding theme across the board. So let us just remove that out because over that, we have no constraint. So therefore, I would reduce it down to the team, the team’s ability to be intellectually honest, learn, correct their mistakes within a trend.

Amit Somani 11:21

What makes a great team? What makes a great investable company in your mind?

Ashish Gupta 11:27

So the team actually is a very interesting one. And by the way, about 18,20 years ago, the two of us, a guy who’s a senior executive at Facebook today and I, we were both Kauffman fellows, so we went and interviewed a dozen of the who’s who in the venture industry, David Morgenthaler, Tony sun, Lynn Baker, and the list goes on. And believe it or not, we did not walk away with one not even one agreed upon set of principles on which they all invest. And these are all ridiculously successful investors. So with that caveat, I will tell you what I end up looking for. I mean, of course, one, is that people should be smart, people should be honest. But I’m talking about stuff that goes beyond the basics.

So the stuff that I end up finding works for me in a team is, one is intellectual honesty. By intellectual honesty, I mean, the ability to face the fact for those of you especially given that most of our audience is in India, a lot of the stuff that the Gita talks about. So being able to look at facts, I think, is extremely important, especially when they’re unpleasant. Outbound skills is another one. In some cases, that manifests itself as marketing. In other cases, as sales but it always manifests itself in the ability to sell the company to investors, to potential recruits, to other team members, and so on and so forth.

The ability to think big but execute small because if one doesn’t think big, one ends up building a rinky dink company, if one only thinks big but doesn’t execute small at all, then one is trying to climb Everest, but one is stuck with analysis paralysis at Basecamp. And last but not least, is adaptability. One thing is for sure that whatever you thought is going to be wrong. So how does one keep changing as the game plays out? These are four of things that I end up looking for. And then there are table stakes, they have to be intelligent, you got to be honest, by the way, lots of people make money with people who are dishonest. So there is nothing wrong. It’s just something that doesn’t work for me. I don’t mean that as a left handed remark, there are folks who get away with that, and power to them, but those are some of the things that you have to choose which are in the value system portion, and not the skill set part.

Amit Somani 13:39

If I may interrupt for a second, so these are hard things to assess in terms of intellectual honesty, maybe some are more skill oriented like this, sales marketing, outbound or adaptability. How would you figure that out when you’re investing in a team and you don’t have all day and all night and certainly not months and years to make that decision?

Ashish Gupta 14:00

Some are easier than others. So actually, intellectual honesty turns out to be somewhat easier, because you can actually pick arguments and fights with founders, on belief systems that you are actually antithetically inclined to, but you can still pick a contrary position to find out and especially in the course of a debate, you find out whether people are willing to change their minds. So one very interesting thing that Michael Dell used to do, he used to interview people for 12 hours straight. I don’t know whether he still does that or not, they would join him for breakfast at 7am and they would stay with him till dinner. And part of the thinking was that how long can a person keep up a pretense, sooner or later that veneer is going to fall off, you will discover who the true person is..

And some of it does work for entrepreneurs also if one spends enough time you begin to find out whether people do believe what they’re saying. Outbound skills and marketing, you also kind of figure out. Adaptability is much harder because it’s a much smaller area. Some folks actually Rishi Navani, who founded matrix, once told me a very interesting thing, he would pick people who had dealt with adversity in their lives. That would give him a sense of the fact that whether or not they were adaptable. So looking for historical stuff, reference checks, I find is pretty much the only reliable way of getting data because I find I’m fairly easy to fool.

So talking to people who have worked with folks in the past is I think, a necessary precondition. Thinking big executing small is extremely hard, especially for first time entrepreneurs just comes to you with an idea and I have often gotten clobbered there. So agree with you Amit, that they are on different dimensions, in terms of hardness, in terms of evaluating and some element of risk is indeed very much there. And one thing that you do is you don’t put up more money if you figured out that you’ve invested with the wrong set of people, which by the way, is a mistake that we as institutional investors often make because we fall in love. We don’t give up hope and we keep putting more money behind some of those companies, so some of these lessons actually carry over to round two of investing not just round one.

Amit Somani 16:06

Very fascinating. Switching gears Ashish, from teams to companies. Teams obviously are a critical part of the company. But there’s also market, timing, there may be other things. We talked a little bit about trends earlier. So what would take a company to a great outcome of success beyond the team, any thoughts on that?

Ashish Gupta 16:23

That’s a hard one, and while I am sharing some of these things. There is an overriding theme, which is that all startups are an exercise in managing schizophrenia in my mind, you tell people to be cash conscious, but they should spend on the right things. They should believe in themselves, but they should be willing to replace the folks with the right team members. They should listen to the market, but often the market doesn’t necessarily know what it wants. So it’s a series of these schizophrenia calls, which is why judgment turns out to be such an important ingredient of what companies succeed or not. So with that caveat, please take all of this with a large grain of salt, because it is that situational judgment which makes the difference between right call and wrong call.

To your point, what makes companies interesting, I think the companies that turned out to be, in my mind more successful than others, the CEO has a huge, disproportionate impact on successful companies versus not. While the founding team is important, the CEO turns out to be disproportionately important as time goes on. Which by the way, really pisses off people like me, who have never been CEOs, and who have been VPs of engineering or head of product or stuff like that. But the reality is that the CEO has a disproportionate impact on the success or failure of a company. And that begins to sort itself out relatively quickly. Also, people say this, in many words, culture, and I find the elements of culture are more along the lines of, does the company do what it says is the single biggest element of culture and that includes implementing its own culture.

When a company says, we believe in honesty, the question comes down to do you do what you say? Do we believe in humility? Do you do what you say? Or do you keep that arrogant developer around? Because Oh my god, she’s the best. So I think the single biggest determinant, in my experience to the company, is do what they say. That way they plan but then the question is, do they implement the plan that they talk about? So if you ask me, that turns out to be the single biggest determinant in my experience, and that is the company moving forward. And if a company is not moving forward, they are only going to make progress by moving forward. Even if it’s in the wrong direction, then you fix it, and you move into a different direction. So I would probably come back to this one thing, Amit, which is, does the company keep doing what they say.

Amit Somani 18:46

Understood. How about timing Ashish? I often think about the fact that and not necessarily completely as a determining thing, but if you just happen to be in the right place at the right time, just catching a demand curve, like we’re going through this COVID pandemic right now. Digitization is happening like there’s no tomorrow, education is happening online like there’s no tomorrow and you obviously can’t plan for this but it could be some other trends. Jio nobody could have predicted in India would lead to 500 million daily active mobile internet users five, six years ago, it took a while to get that. But our partner, Sanjay Swami, likes to say that when the company is born is a big determinant of what it will end up being. If you’re born in 2016, you don’t know of a world before 500 million internet users but if you’re born in 2010, people would laugh when we launched mobile at MakeMyTrip saying what’s going to happen you will do 10 transactions a day. How important is timing in that?

Ashish Gupta 19:41

Yeah, very much. So Amit, as you pointed out, being too early or being too late, are often equally fatal. And being too early often is even worse because one doesn’t give up hope and keeps waiting and in the process burns hundreds of millions of dollars. And then the luck element that you were talking about. I don’t think any one of us could have determined when Mukesh bhai is going to go ahead and put Jio in place. So he isn’t listening to any one of us.

So some of this stuff, one will just get totally lucky. The same idea, at a different time, turns out to be less successful or more successful because stuff is mature. So timing is very important. And there are some things that people are able to do, which is once they’ve started playing the game, they figure out that it’s the wrong time, and they can adjust. But I really don’t know what is the practical way to deal with this timing issue, given that the luck element and so much of it is out of control, but that I can only stop it saying yes, it is very important, but I wish I had something more pragmatic to offer. Okay, so what do you do about it? Other than suffer its consequences?

Amit Somani 20:46

So there is one sort of, lining around this cloud, which is that if you constantly keep at it, there’s a fine line between stubbornness and persistence at some point you may want to throw in the towel. And obviously entrepreneurs are entrepreneurs because they’re supremely optimistic and willing to take that leap of faith and willing to take that risk. How do you figure that out? And when do you know when to hold and when to fold? Because you could keep at it. Cost of creating a company, marketing, etc, notwithstanding has actually come down quite a bit. Are there some kind of lessons learned from your various investments in your journey?

Ashish Gupta 21:27

Yeah, I wish I had any lessons here. Because the line between persistence and stubbornness or madness, and genius, is only post facto, in my experience. So I know people who have, of course, there are some things that you have to do. If you find that one is too early, one needs to cut burn, one needs to extend the runway so that you keep diluting. So I’m assuming that stuff you and I are taking for granted, which is how to prolong life. Let’s leave the how out.

It is when and why should one continue to persist? I don’t have good answers Amit. That is where I think several of the founders have to follow their own conviction. And they do follow their own conviction. And then history declares them as geniuses or history doesn’t talk about them at all. But I have not found any markers. Other than these practical how ones which is that if you think you’re too early, for sure, cut, burn, get rid of people, bring it down to a small set of people, not for cost reasons alone, but because then you need believers to be trudging through the desert with you in the hope of an oasis. So don’t carry a whole lot of people. Those tools, I have better answers for whether or not you should do it at all. I don’t know.

Amit Somani 22:45

Make sense. One of the options is to fold and a constructively positive option is to take an exit. How should one think about exits, either from a founder point of view or from an investor point of view?

Ashish Gupta 22:57

So all of us as investors love to talk about the fact that we are all on the same side of the table and stuff like that, which I find is a little bit of the lie because we are often on the same side of the table. But sometimes you’re on different sides of the table. And exit is one such thing. So if somebody as a venture fund has got $150, $200 million that they have raised, unless they get meaningful exits being at least a third of the fund or half of the fund, it doesn’t really move the needle. But for founders, it does often make sense to get out early. And that is one disconnect that does end up plaguing companies once in a while.

The reverse works also where I have found funders to believe that no, no, no, we have to keep going. Whereas my experience has taught me that we should not keep going. So ironically, we find ourselves often on the other side of the equation also where I’m trying to convince somebody that they should exit the company, but they believe that they should keep going. And by the way, again, only time will tell who’s right. So please don’t get me wrong. I’m not by any means implying that I’m right. But our judgments leave us in two very different places.

I think exits have to be constantly orchestrated many years in advance. And one of the things that I have found allows you to create exit opportunities is creating serendipity. And this sounds like an oxymoron. But by that, I mean, the CEO needs to constantly build relationships with all kinds of people in an ecosystem, so that serendipity has a chance to strike the company, because a lot of acquisitions happen, because people know you people have heard of you, and so on and so forth.

So building a steady stream of relationships, just like a CEO builds a steady stream of investor relationships, I have found to have meaningfully positive correlation with acquisition options going forward. So that is one recommendation that I would make to CEOs but this is an area that gets totally ignored. And I would do that for years, three, four years, and keep building these relationships with potential partners, acquirers, competitors and so forth.

Amit Somani 25:03

I completely agree with that response, speaking to Jyoti Bansal, well before he sold out, like, 12 hours before his IPO. And he said, every year I would talk to anybody who wanted to acquire me with no intent to ever sell until he eventually did. I think Cisco had been talking to them for six, seven years, like offering him every year, and helped him convert. And of course, he was doing well all along the journey, but he had cultivated several such people should the need arise. So I like that notion of creating exit opportunities, even at least as an option value.

Ashish Gupta 25:37

Yeah. And the caution there being that one needs to approach these conversations exactly, as you pointed out, with zero expectation and we are back to the Gita. So one should literally be having these conversations with the view that this is not because I want to sell the company because that often makes the conversations very awkward, but rather the belief in the fact that a larger network will be of some use to the company and do it from that first principles. But indeed, as you were mentioning, Jyoti I’ve not heard this before, but makes a lot of sense. Six years is a long time to have maintained a relationship which results in this but not uncommon at all.

Amit Somani 26:13

Yeah, not only six years, I mean, of a company that was growing at some crazy triple digit, you know, 50 million, hundred million, 200 million kind of revenue growth rate and still maintaining those relationships. That was definitely one big lesson learned. Continuing along those lines Ashish, you were an investor at MakeMyTrip and Helion was as well. We went public in 2010. But a lot of companies are choosing to stay private, longer and longer. What does that mean? What are the implications of it?

Ashish Gupta 26:42

I understand very little of this, but the little that I do understand, leads to a fairly interesting set of, I think, existential crisis around the notion of markets, one of the reasons people went public is because that was a source of capital. While most of us think of going public, as a path to exit, it actually, the single biggest thing that it does is gives the company access to capital, it gives it legitimacy. And it gives it access to cheaper capital, you can borrow more easily, and so on and so forth.

And I think a lot of this money that got printed in 2008, 2009, and which is now getting printed, again, has created private pools of capital, that make the public market somewhat less relevant. And companies therefore, keep relying on private folks. So what it tells us in my mind is that there is now a huge market outside of the public markets, where you can discover price and get access to massive pools of capital till the company has become massively big. I think if, and correct me Amit, you always notice stuff way better than I do. The Amazons of the world went public at sub billion dollar valuations, is that correct?

Amit Somani 27:49

Even lesser. I think that Amazon only raised about $8 or $10 million pre IPO.

Ashish Gupta 27:56

And look at the points at which the Ubers of the world are going public. I mean, how many orders of magnitude of. So it tells us that, at one level, most of the value capture is happening in the private markets and the public market is more and more for the suckers, which is not very good for the retail investor or for the vast majority of mankind in general and just points more towards the fact that wealth concentration is getting more exacerbated. And the private markets are one indicator of that.

Amit Somani 28:29

Very interesting Ashish, we could go on for hours, but maybe just a couple of questions before we wrap up here. Can you talk about things that you wish people knew, both entrepreneurs and investors that they don’t or perhaps are sort of left by the wayside?

Ashish Gupta 28:46

I guess one was just this notion of this exit planning that I mentioned, and the other one that, honestly is probably more indicative of the fact that I’m getting old and should go to pasture than anything else. I find that more and more folks are coming off the view that good guys don’t win, and that one has to be a jerk in order to do well. And it’s amazing how founders that had a reputation of being nasty used to find it hard to get funded where it is today. They wear it as a badge of honor. That is one thing that I struggled with, I’m not sure I can put it in the category of knowledge that is secret. It is, I guess, belief systems that are changing. I can’t think of what else Amit.

Amit Somani 29:35

One of the things you were telling me earlier was that money is a kind of side effect of creating value. So you don’t create companies for making money. I mean, that’s the outcome. That’s not an input.

Ashish Gupta 29:46

Yeah, I do firmly believe that to be the case. And that is also another one that is changing. But indeed, if I were to abstract it out at the level of outcome versus process, I think we can only focus on process and outcomes will be what they will, you can eat right, you can eat salad and the times will figure out whether or not my genetics over in my diet and I still ended up with a heart attack. But the process is what I can focus on. And that is extraordinarily true about companies.

One very interesting symptom of that is. Do you focus on competition? Or do you focus on your customer, as you will find that companies do a whole bunch of things driven by competition, whereas you have no control. Your competitors CEO might not know what he or she is doing themselves, but as I’m trying to figure out what they are doing so talk of extrapolating into the ether. But yes, I will reaffirm what you said that building a company is all about focusing on delivering value, and then maybe one will make money out of it or maybe one will not and being an investor makes it harder because as an investor, we have no control. And one is only talking about money, and yet I’m suggesting that don’t focus on making money, that sounds totally crazy. But I do mean that try to find companies that are creating value and money will follow.

Amit Somani 31:06

Absolutely. One last question, Ashish, what are any kind of tips or dos or don’ts for young entrepreneurs that are perhaps starting out today? Or in the last 6-12 months? Just one or two tips of what they should think about early in their journeys?

Ashish Gupta 31:20

A few different things. One is to pay attention to cash. It’s the single biggest reason companies die. And that sounds funny and tautological and obvious, but you’d be amazed how little attention people pay to cash. The other one is be empathetic, you will find that empathy actually increases the odds of success and empathy towards the customers, empathy towards your team, increases the odds of success. And last but not least, is a while this sounds very trendy, and my earlier comment about trends become spiritual, you’ll find that having no ego is a fantastic way to succeed, because then you listen to customers, you listen to teams, and you make the right decisions. And I would submit to you that whether it is Einstein or whether it is Warren Buffett or Bezos or Bill Gates, one of the things that you will find as a recurring theme and there are counter examples, by the way, is that self is trumped by fact and market. And these are all signs of having no ego. So these are the three things that I would call out cash, empathy, and try and get rid of your ego and be spiritual.

Amit Somani 32:34

That is a very profound note to end on. So we’ll, we’ll try and make it a little lighter for the user but some real deep and insightful thoughts there Ashish, since you’ve recently just joined us at Prime as Partner Emeritus and all of us have known each other for a long time. We often joke and feel honored and privileged and lucky that we were able to kind of get you to affiliate with us, maybe just some things about how you got to know us over the years. I know Shripathi and you were together at grad school. So maybe just something to say about Prime or any of the folks at Prime.

Ashish Gupta 33:07

First thank you for inviting me along the journey. This is an intensely personal journey. And I know that the chemistry between all the existing team members at Prime is like a family then anything else and a family which is pretty honest with each other, as I’ve also witnessed some of those arguments over the years so and really both grateful and honored that you all would have me along.

I know Raj for close to 32 years. I met him as a grad student, when I was a grad student, and he’s been a mentor to me for that long. He was already a very successful entrepreneur and I bumped into him. And Shripathi and I, of course, were at Stanford together as grad students figuring out how to share a beer because nobody had any cash. And then you and I shared a boss at IBM, you were smart enough to know that he was among the most amazing guys when I was not, so I quit and went to Oracle.

And Sanjay tried his best to get me involved in rotary. But I could never quite figure out why I should spend my Sunday evening when I could spend it on a badminton court why woud I sit around with a bunch of guys trying to do good. That’s how I ended up meeting Sanjay. So I have wonderful memories by the way, even more of eating food at each one of your homes, eating all that the dahi in Sanjay’s house and eating all the chutney at Shripathi’s house. So I have a bunch of wonderful memories. I’m looking forward to this journey.

Amit Somani 34:38

Absolutely, Ashish. We are equally excited. And I still can’t forget how you kicked my ass in badminton every time we would go play in San Mateo or wherever you would take me on weeknights whenever we visit the valley. But it’s truly an honor and privilege to have you and I’m sure our readers will enjoy listening to this podcast. So thanks again for being on the Prime Ventures Partners podcast. It was really good to have you.

Ashish Gupta 34:58

Thanks Amit.

Enjoyed the podcast? Please consider leaving a review on Apple Podcasts and subscribe wherever you are listening to this.

Follow Prime Venture Partners:

Twitter: https://twitter.com/Primevp_in

LinkedIn: https://www.linkedin.com/company/primevp/

Let us know what you
think about this episode

If you believe you are building the next big thing, let’s make it happen.