Ep350: Roshan Cariappa – Being Pragmatic Will Save You From Startup Failure

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Quick take

BIO: Roshan Cariappa has over 12 years of experience as an entrepreneur and operator at early and growth-stage startups, specializing in going from zero to one and setting up cross-functional teams. Currently, he heads Marketing at Vymo, one of the fastest-growing SaaS startups in India.

STORY: Roshan started his business in 2012, offering marketing services to startups and small businesses. He then pivoted to offering digital assets when digital marketing hit. The business was quite a success. In 2015, there was a vast consumer internet boom in India, and so Roshan thought he’d take advantage of this and pivot his business to offering tech products. He created an app to connect families. This was a huge change that worked against his company. In a few short years, the business failed.

LEARNING: Pivoting is about making small changes, not huge ones. Do not go all in; make room for risk and probability and always have a plan B.


“You can be super optimistic about your vision, but be a little pragmatic, or even slightly pessimistic about your execution.”

Roshan Cariappa


Guest profile

Roshan Cariappa has over 12 years of experience as an entrepreneur and operator at early and growth-stage startups, specializing in going from zero to one and setting up cross-functional teams.

Currently, he heads Marketing at Vymo, one of the fastest-growing SaaS startups in India, and also runs Bharatvaarta podcast (Politics, Policy, & Culture focused on India) and The Startup Operator podcast (wisdom from Indian founders, operators, and investors).

Worst investment ever

In 2012, Roshan started a business offering marketing services to startups and small businesses. The business then pivoted to building digital assets. Roshan and his team realized that digital was becoming the front and center of business, and people didn’t really have a focal point for all marketing activities. So they took advantage of this and pivoted the business.

For a couple of years, the business was doing well and making good money.

Pivoting a second time

In 2015, the team had an itch to pivot again. This time they decided that they were done with services and decided to build products. They settled on creating an app to connect families.

Going all in

At the time, there was this colossal consumer internet boom in India. There were a lot of new users on the internet, and every app business was getting funded. So there was a lot of optimism in the air. Roshan decided to go all in. He believed they could build the app successfully just as they had done with their previous offerings, the digital assets.

It was not as easy as it seems

Roshan and his team grossly underestimated the time, effort, resources, money, patience, and skills required to build a consumer app.

Roshan soon found out that App Store discovery is quite hard, and an app has to either go viral or spend a ton of money on acquisition. And once you’ve acquired these consumers, you still have to retain them and then make money out of them, which is not a trivial thing.

Having to wind up

Roshan had to wind up after a couple of years of trying to make the app a success. This was quite humiliating for him as he had to let go of people he had hired and nurtured.

The failure of the app drained all of Roshan’s self-confidence. He hit a real low point after this venture.

Lessons learned

Do not go all in make room for risk and probability

While it is good to be optimistic about the outcome of your new idea, it helps to be a little pessimistic about your execution. Before you go all in, think about risk and probability. Consider that things might fail; what will you do in that eventuality? It is always better to be prepared for such an outcome than for it to hit you by surprise.

Always have a plan B

It may sound like a cliche but always have a plan B. There is a lot of survivorship bias, especially when starting a business, so it’s going to take a lot out of you, and it’s good to have a solid plan B.

Andrew’s takeaways

Pivoting is not about making big moves but about small changes

A lot of times, when entrepreneurs want to pivot, they make big changes. But the fact is that a pivot is just a small change. Pivoting from a service to a product or a product to a service is a huge change, and you are no longer pivoting but starting a new business.

Actionable advice

Be deliberate about your choices. It is also imperative to be pragmatic about the present.

No. 1 goal for the next 12 months

Roshan’s number one goal for the next 12 months is to stay healthy and happy and keep his family happy.

Parting words


“I think we underestimate how much success can be had by not doing dumb stuff like, in my case, put everything on the line without a plan.”

Roshan Cariappa


Read full transcript

Andrew Stotz 00:03
Hello fellow risk takers and welcome to my worst investment ever stories of loss to keep you winning. In our community. We know that to win in investing, you must take risks but to win big, you've got to reduce it. And I bet you're exposed to investment risk right now. To reduce it, go to my worst investment ever.com and download the risk reduction checklist I made specifically for you my podcast listeners based on the lessons I've learned from all of my guests. Fellow risk takers, this is your worst podcast host Andrew Stotz from a Stotz Academy, and I'm here with Russian curry Yapa.

Roshan Cariappa 00:44
You got that right.

Andrew Stotz 00:45
Russian. Please take a minute and fill in any further tidbits about your life.

Roshan Cariappa 00:51
Yeah, that sounds about right, Andrew, excited to be here. And you got the pronunciation right. Perfect.

Andrew Stotz 00:59
Well, let me introduce you to the audience. rashaan has over 12 years experience as an entrepreneur and operator at early and growth stage startups specializing in going from zero to one, and setting up cross functional teams. Currently, he heads marking at VMO, one of the fastest growing SaaS startups in India, and also runs Bharat writer, podcast, which is about politics policy and culture focused on India. And if it's not enough to already do one podcast, he does another one called the startup operator, podcast. It's wisdom from Indian founders, operators and investors, you can connect with him on Twitter at rashaan cariappa. And you'll have all that in the show notes that you can go to but Roshan, take a moment and tell us a little bit about your fascinating life.

Roshan Cariappa 01:56
Thank you so much, Andrew, you make me seem, you know, like a porcelain vase without any cracks. But I'm happy to talk about the cracks as we go through the podcast. And I think that is what is super interesting about what you're trying to do. Because I am reminded of this, Steve Jobs quote, something to the effect of, you know, everything around you was built by people no smarter than yourself. Right. And great, I think. Yeah. And I think what you do in these podcasts is to unravel the human element of everyone around you, and get people to talk about their failures, which I think is an admirable thing. So Fantastic.

Andrew Stotz 02:34
Thank you. And that's, you know, it's what makes this podcast so fun, because this podcast is real. And how many podcasts you know, are you on where, you know, you listen to or you're on that you're basically feel like the person's kind of putting on a brave face of who they are and amazing things that they do. And here, it's like, I, we already it's already taken as a given that you've done all those things, and you've got all those things, I mean, but then to come on here and speak in real terms. So I think with that, as a leader, now it's time to share your worst investment ever. And since no one ever goes into their worst investment thinking will be. Tell us a bit about the circumstances leading up to it, then tell us your story.

Roshan Cariappa 03:19
Sure. So up until the point where I've made this mistake, I had done plenty of dumb things in my life, right? You could think about silly things like investing in retail MLM schemes, or, you know, buying that stupid heating belt that burns your belly fat and things to that effect, right. And something so which, you know, a lot more impactful, a lot more larger mistakes as well. But you know, none of them compared to the cost that this particular incident had on my sanity, right. So the story starts in 2012, I started a business. Up until then I had worked for about four years in an early stage startup, and was fairly cross functional, didn't find an interesting job. I mean, the growth function, as it stands today had not been invented. And I didn't really want to sort of pigeonhole myself into sales, Product Marketing, I want to overlap meaningfully on all functions. So I kind of invented one, you know. So we start off offering marketing services, to startups and small businesses, and then pivoted to building digital assets. what we realized was, digital was becoming front and center. And people didn't really have a focal point for all of the marketing activities. So we set out to build these apps and so on, right, and this was 2012 2013. And about a couple of years and we're making reasonable money, you know, no complaints. It's not going gangbusters or something, but it's a living, you know, with being able to pay for ourselves. And then some, you know, and then we had this Ah to pivot again. And, you know, you know what's coming up, right? So, so this time, we decided that, you know, we're done with services, and we decided to build products, right, which is, it's not a bad choice by itself, if you look at it, you know, products are a lot more scalable. You know, unlike services, where more money means more people, products are a lot more scalable. And really, you know, the services business, it requires an enormous amount of patience, and there is a certain temperament that you have to sort of develop. And, you know, no, you know, no disrespect to whoever's in services, but it really sucks the passion out of building things. Because you really have to be hands off. And you might have to build the 14th ecommerce site or the 25th social app after this, right and beyond a point, it just gets jaded. And you don't really want to do that. And this was also during 2014 2015, when there was this huge consumer internet, boom in India. So literally, every app business was getting funded. You know, you could just take an example like, you know, your name app.com. And it would get funded, right. So there was a lot of optimism in the air, and a lot of new users on the internet and so on. So we decided to go all in, you know, and to be fair, before that, we did try to hive teams off, but it didn't really work out. Right. So we said, you know, let's do this cold turkey. And, you know, I remember meeting my clients around that time and talking about this, and they thought I was just seriously nuts, you know? Because here is this kid who is actually, you know, persuaded me to part with my money. And then he's coming back and saying, No, I don't want it anymore. You know? I mean, I can't imagine what they thought, right? I mean, so they probably thought I got a concussion over the weekend or something of that sort. Yeah. So but I went about it. stridently. It hurt. It really hurts to say no to cash. I mean, you would agree, right? And we decided to build and, you know, what did we want to build? We had to pick a market. And that's about the only deliberate choice that we made, right, picking a market. And we thought, you know, tech for families, specifically, because people had started building apps for dating and apps for professionals, and so on and so forth. But we thought that, you know, families were kind of getting more remote and distributed and nuclear in some sense. And we thought that we could build this app to connect families, right? It was called tribe, tr, IV. And, yeah, we want to connect families. Great name. Yeah. Thank you. And all of that sounds, it sounds good. So far, right? I mean, it's normal, even, right. But the grossly grossly underestimated the time, effort, resources, money, patience, skills. And you could probably add another 20 things in there required to build a consumer app, right. And App Store, discovery is hard. One thing that I realized, you either go viral, or you have to spend a ton of money on acquisition, right, so more dollars, more users, and so on. And once you've acquired these consumers, there's the other business of having to retain them and then having to make money out of them. Right, which is, again, not a trivial thing as well, you know, 80% of the people who download an app, don't use an app after three days, you know, and a further 40% of them actually delete the app. Right? So I lie. Exactly. Right. So you can see how the odds are really stacked against you.

Andrew Stotz 08:58
And as you're telling this story, the listeners and myself are all thinking about apps that we've downloaded any night, how many we you know, didn't do anything with but then there's the other ones that have Why did it? Why is it that that one grab me? So yeah, this is great.

Roshan Cariappa 09:14
Yeah. So when you look at it, right? I mean, we we have this sort of survivorship bias in some sense. I mean, when you look at the apps that you use, you don't think about the apps that you don't use, or you probably download and then deleted or you didn't even bother downloading, right. So again, huge respect for anyone who's made it in the app business. I mean, it kind of looks easy from the outside, but, man, it is super difficult, right? super difficult to do it. And, yeah, that's really what we realized, you know, that execution is super hard. And we learned that through many, many, many different heartbreaks that we got along the way. And, you know, long story short, we had to wind up after about a couple of years is trying And this involved, you know, unfortunately, this involves letting go of people that had hired and nurtured, you know, I hadn't taken a salary for something like about eight or nine months was pretty broke by then. And, you know, it didn't have that self confidence to do anything really. So I hit a real low point around then. But yeah, I've since Of course, recovered. splendidly thank God, and, you know, reflect upon us.

Andrew Stotz 10:30
Can you remember? One day, that was like, the lowest time whether that was dealing with your employees, or whether that was you come into the realization, holy crap, I just wasted all this time. And I, I lost, you know, time and money. And here I am.

Roshan Cariappa 10:46
Yeah. So the realization cannot dawns on you, right. But then I mean, you don't act upon it. There are the hints, right? And, you know, other startup founders who are listening can talk about this as well. A startup is something like a baby, you kind of give birth to it, you nurture it, and then you know, to say that you're going to let it go is perhaps one of the most difficult choices one has to do. Right. And you know, that things aren't going right. But then to actually take that decision is, I think it was many months in the making. And it took, it took a lot of a lot out of me, you know, and I can remember many different days, when, you know, I was probably short of cash. And, you know, I was literally hungry, or, you know, I had probably a friend's marriage coming up. And, you know, I didn't really have anything to offer as a gift, or, you know, plenty of these embarrassing social situations. So, but really, what really stung was not being able to live up to that potential, you know, we were running a successful business, but then there's pivoting to do something else, and then realizing that this isn't going anywhere, that kind of hits you and faces, and yeah, many, many different moments along the way.

Andrew Stotz 12:07
So tell me, what were the lessons that you learned from it?

Roshan Cariappa 12:12
Well, the one overriding lesson that I learned from this was to not go all in, you know, we're often peddled this nonsense that, you know, you should follow our passions. And, you know, oftentimes, I mean, there's this So Mark Twain quote, I still think it's Mark, Mark Twain, although I mean, he's often misquoted right, throw off the bowlines, sail away from the Safe Harbor, catch the trade winds and all of that romantic stuff. And I think there's value in that, right. I don't think I mean, you should confine yourself to doing something mediocre. But then, obviously, there is a halfway mark. Right? You don't really have to throw off the bowlines in, in the literal sense of it. Right. So one thing and, you know, we spoke about this earlier, was the element of risk and probability. I wish I understood that a little better. I wish I had discovered Nassim Taleb a little better. And I wish I had read fooled by randomness a little better. Because, you know, oftentimes, we kind of model risk and probability in real life, as he says, as six plague six people playing Russian roulette. You know, the difference between six people playing Russian roulette and you playing Russian roulette six times right? Now, the condom, I mean, you know, you think about it, and it's so obvious, but then you make these, you make these choices every day, and you catch yourself doing it, right. Because, you know, you playing Russian roulette six times is destined to fail, right? I mean, there may not be a third, fourth or fifth time, you know? And, yeah, always have a plan B, I would say, you know, it's not fashionable, you know, and you won't, you won't, you won't hear of this from all of the, you know, quote unquote, successful people. But you know, that there's a lot of survivorship bias as well, especially if you're starting a business, so it's going to take a lot out of you. And it's good to have like a solid plan be.

Andrew Stotz 14:16
Great. Well, maybe I'll share a few things. First of all, I want to highlight an episode 265 with rivella Roy, also from India, who, you know, explain how he when his startup that he was involved in failed, he had to get on a plane and go back to his home. State, I guess in India and or province, and you know, just tears You know, on that plane as he was flying home and the pain of loss, the pain of failure is just so real. There's, a few things that I would talk about. The first one is you reminded me I like to say that you know, when you think about if you remember when we're in school, we use a compass. If you put a point down And then you can draw a circle with that. compass is a good example of the idea of pivoting. Because when you draw a circle properly, you keep the sharp end down on a piece of paper, and then you pivot the pencil around in a circle. And the key thing about that is that that sharpen is set to the ground. And it's same thing about pivoting. A lot of times we look at pivoting, and we make big changes. But the fact is a pivot is just a small change. And like a pivot from a service to a product or a product or service, these are huge changes. And that's the first thing that I really made me remind me, it's out myself that if you hear the word pivot, Stop, wait a minute, are we talking about changing the business? Are we talking about a little pivot? If we're talking about changing the business is not a pivot? It's a new business.

Roshan Cariappa 15:52
And it's absolutely, yeah, that's a very important point. I think you need something to revolve around, right? You need that central fulcrum to revolve around, I think what we were doing was not a pivot, I mean, we were hopping around, you know, we were really doing a jump, I would say, right.

Andrew Stotz 16:13
Now, it also reminded me of my worst investment ever, which was with a friend of mine, and we decided to make an app. And you know, he was the driving force and a, you know, really smart guy. And he had a really great idea. But after spending a lot of money in developing this, there came a point where I had this realization that just like you, we were going to bring an app or software or a website out into the big world, to compete globally, because that's ultimately what you're doing nowadays. And I just realized, you know, we need $5 million to do this, you know, we're gonna go up against the best out there, we need 5 million bucks now, to have the marketing budget to have the programmers to have everything, you just can't do it out of your garage anymore, unless you've just got something absolutely amazing. And it was at that point that I just realized, nope, that we were not ready for that. And I'm not comfortable going out and raising capital from friends and family or others to do that. And that's when that idea, sadly, had to die. And so there's this, where you go from the idea of the excitement of an idea and all that to the reality of global competition. And then it really is a matter of, you know, if we had gone in, we would have been like a 16 year old, you know, skinny kid going into the ring with Mike Tyson, you know, boom, one punch, and we would have been out. Luckily, we didn't do that. Now, I want to highlight another thing, which is survivorship bias, which you mentioned a few times. And that's really, as I talk in the world of investing, in fact, I was just advising one of my clients on the business that they have. And we've done, I've done a lot of the back office, academic work on the investment methodology of this. And basically, I, you know, they're talking about, you know, all these other people talking about their great investment returns, and I'm like, it's all survivorship bias. It's all winners, they're talking about their winners, but they're not talking about their losers. And that's the beauty of this podcast is that this is there's no survivorship bias. We are we are, you know, talking about our losses, so that come to us, if you want to talk about getting rid of survivorship bias, this is a place where we can really honestly do that. And survivorship bias can be so, so dangerous, because it can pull you into things. Now, there's one last thing that I want to talk about, and that is about revenue. You know, we oftentimes say that revenue is proof of concept. And as a finance guy, I like to say and profit is proof of competence. And the idea that I've learned from one of my businesses here, which is coffee works, we're a coffee roasting company, is that my new goal when I meet anybody who says their startup, I mean, unless it's like something amazing. But even Amazon, you can say, got a lot of resistance in the beginning, just about any startup, my whole thing is, when can you get to three to $5 million in revenue, you must have three to five millions of dollars of revenue to support the infrastructure, you need to run a business without killing yourself. You know, you've got to have a human resource team, you've got a head of head of sales you've got to have ahead of you can't do it all. And so many people listening to this podcast and otherwise, are messing around with $300,000 in revenue and this and that, you have got to move to 3 million as fast as possible. Otherwise, you're gonna burn yourself out. And so I never thought about the fact that you really need to hit that number to get the resources to have the infrastructure to really run the business without burning yourself out. Those are all the things I Took away from yours anything you would add?

Roshan Cariappa 20:03
No, those are all great points, you know, really great points and see, in the end, I think you have to be deliberate about your choices. And you know, I think founders often fall into this trap of trying to find a problem to solve, you really have to abstract yourself away from the problem and look at the market in itself, right? Are there enough people who would really pay you to solve this problem? And is that something that you are uniquely qualified to solve, and how much time effort and resources it's going to take? And that's something that I've noticed, you know, over the last year that I've been doing the startup operator podcast, the amount of savviness that founders have, at this point of time is amazing. You know, I would say about 10 years back, we were just like, you know, kids trying to, you know, solve a problem, really went into a goal without understanding any of these things. But people today are a lot more deliberate about it. And yeah, that's, that's something to be optimistic about. I feel,

Andrew Stotz 21:03
yeah, I mean, someone like yourself is such a valuable resource, because you've been through it. And the idea of minimum viable product, and that type of stuff is out there. You know, it's great knowledge. But when you've actually been, you know, struggling in that space, you really know the value of it. So yeah, let me ask you, based on what you learned from this story, and what you continue to learn, what one action would you recommend our listeners take to avoid suffering the same fate?

Roshan Cariappa 21:29
Well, really, I think, just be deliberate about your choices. You know, that's a great job, by the way.

Andrew Stotz 21:36
One and a half. milliliters. Wow, okay, probably drink a lot of water with a little lemon in it.

Roshan Cariappa 21:44
Right. So yeah, make deliberate choices. You know, you can certainly be optimistic about the future. I'm not saying that, you know, you should start off saying that the sun will cause skin cancer and things to that effect, you don't have to be overly pessimistic, you should be optimistic about the future, you know, you can think that we will solve climate change at some point, so on and so forth. You can see how the vaccine has happened, right, for instance, less than a year, and we have a vaccine out in the out in the market. But it's also extremely important to be pragmatic about the president present. You know, when I say the President, I mean, you could also sort of extrapolate it to the midterm as well be extremely pragmatic about it. In some sense, I would say, you know, be a little pessimistic. Also, if possible about your execution, you can be super optimistic about your vision, but be a little pragmatic, or even slightly pessimistic about your execution, understand, you know, what things will fail, and you know, what you will do in that eventuality? Because, when you do, or if you do meet that fate or circumstance, I mean, you're just better prepared for it, you know, even if you have just thought about it, right? So, play a part of your, what if scenarios a little better, I would say because, you know, founders tend to get carried away with all of the joy that comes with ideating, and, you know, printing and stuff like that. But it's, it's useful to say stay grounded, you know, and, and it serves the business, it serves a business way better. You know, an old boss of mine used to say, Morphe was an optimist. You know, that's a good one to think about. When you're executing, you know, and also, there's a quote by Louis Gerstner, right? Only the Paranoid survive. Yeah, so not fashionable. Again, you know, we tend to think of these as relics of any age gone by, but, you know, it's, it's important to kind of keep this at, at some point in the, in your, in your memory, you know, I

Andrew Stotz 23:44
mean, it's, it's important, I would say, be pragmatic about the present. And what matters is a good phrase that we use in America was when the rubber hits the road, you know, like, the wheel spinning and all that. So exciting. But Whoa, we can get out of control real fast. So that's great. Fantastic. All right. Well, last question. What's your number one goal for the next 12

Roshan Cariappa 24:07
months? Um, well, I'd like to stay healthy and happy. First of all, I'd like to keep my family happy as well. And as everyone should. Well, it's remarkable times, as I mentioned, you know, we have a vaccine out in the market, and we'll be out of this soon. I'm really looking forward to meeting people, you know, not not really, you know, being pensive or skeptical about that. But otherwise, from a professional standpoint, interesting things happening at y Mo. And, you know, we're scaling very rapidly across the world. And this year, the US and Japan markets look super interesting for us. And I'd love to scale. I'd love to help my team scale. And, of course, the couple of podcasts as well. Both of these, you know, started very organically. We didn't have any grand design as such, but we've done about, I would say 200 plus podcasts On the both of them combined and really hope to build a better audience, bigger audience and, you know, have better engagement on that. Yeah.

Andrew Stotz 25:08
Fantastic. Fantastic. Well, for the listeners out there who want to understand what's going on in India, and in the startup scene, what a great, you know, opportunity to the startup podcast. All right, the start up operator. And now, and it's good that you mentioned operator in the podcast, because that's really where the rubber hits the road, right. So listeners, there you have it another story of laws to keep you winning. And my number one goal for the next 12 months is to help you my listening to reduce your risk in your life. So go to my worst investment ever.com right now and download the risk reduction checklist and see how you measure up. As we conclude, Roshan, I want to thank you again for coming on the show. And on behalf of Ace Dance Academy, I hereby award you alumni status returning your worst investment ever. Yes, indeed, your best teaching moment. Do you have any parting words for the audience?

Roshan Cariappa 26:09
Thank you so much, Andrew, this was certainly an interesting experience. And again, you've been doing a fantastic job. I think it's not easy to talk about failures, but you make it you know, you make it seem so simple. And yeah, I think we, you know, just a parting note, I think we underestimate how much success can be had by not doing dumb stuff. You know, things like don't do hard drugs, commit crime, go to prison, or, you know, like, in my case, put everything on the line without a plan. Right. And yeah, I mean, think things through, you know, so that's,

Andrew Stotz 26:42
that's beautiful. And that's a wrap on another great story to help us create, grow and protect our well fellow risk takers. This is your worst podcast host Andrew Stotz saying I'll see you on the upside.


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About the show & host, Andrew Stotz

Welcome to My Worst Investment Ever podcast hosted by Your Worst Podcast Host, Andrew Stotz, where you will hear stories of loss to keep you winning. In our community, we know that to win in investing you must take the risk, but to win big, you’ve got to reduce it.

Your Worst Podcast Host, Andrew Stotz, Ph.D., CFA, is also the CEO of A. Stotz Investment Research and A. Stotz Academy, which helps people create, grow, measure, and protect their wealth.

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