Shashank Singh
Here for the Long Game

29 Oct 2018



"I'm in here for a long term. I'm a very long-term vision person actually. I don't care about short-term things like if I survive. If I live, I'm here ... for the long game."

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Show Notes

Topics: Ad Tech, Career Advancement, Career Responsibility, Case Studies, Failure and Learning, Founding/Startups, Managing Engineers, MBA, Product Development, Social Apps, Team Leadership, Virtual Reality

Companies and Organizations

Introduction A veteran founder of multiple app-based startups and an experienced engineer, Shashank Singh finds himself embarking on a new chapter as CTO of New York-based startup Datamarx. There he can establish an engineering culture and draw on his engineering experience, startup lessons learned and MBA training in entrepreneurship from NYU Stern. Singh looks back to reflect on what he has learned about building apps, growing a product by delighting and retaining users rather than relying on social hacks, and why social apps are meaningful to us as social animals. And he looks ahead into the future, asking himself about the purpose and meaning of his work and why he works on what he does. He also discusses what he learned about ownership and responsibility at the large and disciplined organization Goldman Sachs, the differences between working at large organizations and startups, and how engineers can maintain a healthy career track by learning more about business and pursuing varied technical work. Singh doesn’t shy away from either ambition or sincerity. Why are we doing what we’re doing? Should we be doing something else?

Guest Bio

Shashank is currently CTO at Datamarx and is helping build a unique data marketplace by connecting brands directly with the users. Prior to joining Datamarx, Shashank was VP of Engineering at Publicis Media, where he helped lead the development of their proprietary Data Management Platform (DMP) and built their data pipelines. As one of the first employees of the Flurry’s Ad team, Shashank helped launch one of the world’s first mobile-centric RTB exchanges. After Yahoo’s acquisition of Flurry, Shashank worked on the integration of the Flurry’s platform with Yahoo’s AdServer technologies and also helped integrate BrightRoll into Yahoo’s platform. Prior to Flurry, he was a Lead Technical Engineer at Goldman Sachs, where he led a team of developers in architecting and developing the firm’s OTC derivatives trade flow systems. In his free-time he also co-founded three mobile start-ups: Truffle, Steams and Majikal. He has an MBA in Entrepreneurship & Finance from NYU Stern and B.E. in Computer Science & Engineering from MMMUT, Gorakhpur, UP, India.

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Transcript

Host
Hello and welcome to “Using Reflection”, a podcast about humans engineering and we’re here today with Shashank Singh. We’re going to talk to him about some of the entrepreneurial things he’s been doing, different startups, some of them with a social angle and, I also wanted to talk to him about the fact that he’s both a talented engineer with a lot of track record as a contributor and manager, but also a graduate of the MBA program at NYU Stern with a degree in entrepreneurship. I wanted to talk to you about the difference between running startups, trying to start startups and learning about how to do that. But why don’t you go ahead and give yourself an introduction, tell the audience a little about yourself and then we’ll get into the conversation.

Shashank Singh
Thanks Mark for the introduction. I’m Shashank Singh. I’m currently CTO of Datamarx, a New York-based startup, and in my past life I have done a lot of startups. Like I have started three of my own startups. I’ve worked for startups like Flurry, which was acquired by Yahoo. I worked for an RUN Ads, which was acquired by Publicis. Yeah, I’m a technologist, and I also did my MBA. It has helped me quite a bit to understand the business side of things.

Host
So maybe let’s start there. Why did you feel the need to get deeper knowledge on the business side and how do you think it’s changed your trajectory or point of view or had an impact on you since then?

Shashank Singh
Being an engineer, you always wanted to build something new. Most of the jobs I was doing before pre-Mba and my past life was like, you join a company, you have a product already there or it’s half-way there. They’re really some green green projects. You wanted to be entrepreneur because I wanted to make from scratch, so yeah, I decided to get my business degree just because after doing my stuff, like I tried building my own small … like I ran, some blogs, also news blogs. Being a technologist is OK, you can build a product, but how do you actually take it out to the market? How do you actually think about what’s the need of the market? How do you study the market, how do you do the first sales kind of things and learn all those kinds of soft skills and even hard skills of understanding the financials of a compan? When you’re running a company, you need to understand the financials. You need to understand a lot of things. You are wearing multiple hats every day, every hour. I think. So kind of MBA gave me that rounded knowledge around things where I can understand things. I can know what people are talking about and not be siloed along the technology. Because I’ve seen engineers getting deep into the technology stuff and they are doing. I mean, it’s good for everything that getting deeper and deeper into technology, but they sometimes lose the vision of why actually they are doing something. It’s my personal opinion that we … as an engineer we are just an enabler of a business. Like we enable, we solve a problem which is mostly a business problem or some kind of problem. Or if you make a business out of that, like Facebook or anything like technology is an enabler. You find the problem and you use technology as a tool to solve that problem.

Host
So it sounds like you became more interested in the context and more interested in trying to understand what problems need to be solved. Right.

Shashank Singh
That’s definitely there. I mean I had the skill set of building things. I was very confident that I can build but I was not very confident about like if I go out in the market, I want to be a leader, I want to be an entrepreneur, then what should I do? So doing an MBA was kind of a way of taking a shortcut maybe to learn things. And I can get more deeper details into that. Like one of the examples would be like you do a lot of case studies in [an] MBA [program], and what do you do in case studies is that you study all the companies which have failed, which have a success based on certain scenarios and all those things. And you’d discuss among the friends like what do you think worked for that company and what didn’t work for that company. You learn a lot from their experiences with those case studies and then you have a certain set of tools in your … It’s in your brain like OK, what might work and what might not work. So if you do enough case studies of like 20 companies or 30 companies, then you can definitely get into the habit of thinking critically. Like right now I have right now the reputation of like when somebody comes with an idea I most most likely kill it. I would say “No, it’s not solving a big problem.” Because I have failed myself multiple times. I’ve done my MBA where we have studied a lot of companies [and] why they have failed. When you come to me, I would most likely kill it. If you are still having that urge you want to develop after talking to me, then I would definitely say go for it.

Host
So I noticed all of the things you listed at the top of your LinkedIn are all of these startup things, right?

Shashank Singh
Yeah. Like I would say the startup bug actually started from 2008 or something, when the whole Apple ecosystem didn’t even come up. Actually it was coming up in 2008 and I started working on a … I got into IOS APIs and all those things and that made me very curious about like let’s build some system. And I was working with one of my cousin actually we were trying to make something. That’s where all the entrepreneurial bug started biting me actually. [Laughs] And we’re thinking about all the crazy kind of small ideas which we can actually work on your own and launch it. But then I got into finance, Goldman Sachs, which is very demanding the working there. I was there was there for four years and also did my MBA there, [so] I couldn’t give too much effort to my entrepreneurial efforts. But later on, like a, I developed an app called Magical along with a few of my friends and it was collecting all the events all around your city or your location. It was a a location-based social events app. So when you open the app, you can see what’s happening in and around your city, you can search by keywords and all those kinds of things. You can save that event, invite your friends and all those kinds of social aspects, were built inside it. And our long-term goal in that case was like, I wanted to be Google of events, actually. I wanted to cover all the events going on in the world. And we are pretty good at it. We were collecting a lot of events based on different types. Like there were Meetups, EventBrite, there were all the ticketing sites, all the concerts and everything. We were indexing it properly and it was working good. It’s just that like I’m more of an engineer than a marketing genius or something like after a few years of keeping it up and running, my partner’s got distracted in their life and everything happened there. So that kind of stayed there and I had to shut down a year back. Then there were other things like Steams. Steams is a social network, anonymous social network. There are tons of them [now], but when I started working on it there were none. [Laughs] But by the time I launched it, we had Whisper in the market, we had Secret in the market and we had … later on came YikYak and I was like, “Oh crap, this is like … this market is now too crowded actually.” And again, my marketing skills were not good enough to actually market it out to a large group of people.

Host
That market was both crowded and had a lot of controversy around it.

Shashank Singh
I mean, you can still see … we still have Steams up and running. I actually don’t spend too much time on it, but it’s working actually. It’s there, people download, do some crazy stuff there. I won’t want to get into details of what people do there because it’s anonymous. You can imagine what happens there. [Laughs] It has kind of become a dark alley of the web, of the app site.

Host
That’s awesome. You created your own little dark web. You should be proud. Right?

Shashank Singh
[Laughs] And keeping up is not that expensive. So it’s like spending less than 100 bucks [per month] to just keep it up and running because I really want to get back on it sometime when I have some more time and have some ideas over there. So I’m just keeping it for now.

Host
Where does that benefit from what you learned in school and where did … how far did it take you and then where did you hit the wall and you have to learn completely new skills that you need when you’re actually starting your own company?

Shashank Singh
Yeah, I mean, all the case studies … like one thing I can say like doing it by yourself is a different ballgame altogether. Like when you do it like you realize that you don’t have … you have … if you have not raised money, or even if you have raised money it’s a different story, but if you don’t have money then how do you actually market yourself? Or what tricks or hacks can you do to actually get your name out there on a dollar budget, for example? Like you don’t have that much money then what you do? So I can give you an example like for Magical when we launched that I didn’t have any marketing budget. Like I didn’t have much actually. So I didn’t do any marketing. It was more leveraging my current social network I have. And I decided doing little bit of ASO, studied how Apple search works. I mean believe it or not without doing any kind of advertisement or any kind of even posting on Twitter or Facebook or anything, I was getting like 40 to 50 downloads a day without doing anything. And I have worked with legit companies which have a marketing budget and they are not able to hit that number.

Host
So that was all through trying to optimize your results in Apple App Store search?

Shashank Singh
Yeah. Yeah. That is one of the things. And then you try to build the app in such a way where you can actually have some social aspect that tries to spread itself without being spammy, for sure. What people forget in life is that you get too involved in technology and you forget that that technology is an enabler of business. Technology is enabler to make you happier than actually getting too involved in that.

Host
My general attitude toward this is that, you know, we, what’s meaningful to us as people is how we affect other people, how we interact with other people. You know, the emotional truth of our experiences and, even in such an analytical profession, I think that all those aspects are still really important and that also we do engineering because like you’ve been describing, you believe it has an impact on the world, not just as an abstraction. So returning to the social idea. It is something I really wanted to talk to you about because I noticed several of your businesses have a social aspect and you just talking about how social marketing, I guess you could say, you were able to organically grow the usage of this app. So what, you know, do you think that that’s essential really to any, sort of a consumer startup these days or you know, how important do you think social is? Do you think it’s just table stakes and then do you do it just because it’s helpful to market or is there something inherently interesting to you about social, you know, when you want to do social products because they’re interesting.

Shashank Singh
That’s what we were taught in biology actually like humans are social animals and it’s very ingrained into our DNA that we actually talk to people, we interact, and we have some kind of social experience. So it’s a very natural actually that social network is playing such an important role right now. I mean I have other thoughts about current social network things. If you’re on the consumer side, you need to think about like how socially beneficial your app is, what problem actually you’re solving or what … how you’re helping people to actually communicate more or do something meaningful, or even having a fun app. Actually, it’s, that’s, that’s also fine actually if you’re making a fun based app actually, but then you are solving a problem of like when somebody is bored or doing something and you’re adding some kind of fun in his or her life. Going back to the social aspect of it, I think that’s how I came up with all the ideas like I have. Does he like to meet people and like to talk to them? So what do you do with your friends and family? You actually plan out things and you plan or things as like, let’s go to that event. Most of the time it happens you I come to know of an event when it has already happened. That’s where Magical can in. Like I wanted to make something and the name Magical was more about let’s create some magical moments with your friends. Most of the magical moments are when you’re at the concert or you’re at an event or something. I don’t think you can, you can think of an app which is not social anymore actually. Like you have to have some kind of social aspect to it. Not just for the essential, for your growth. I mean that’s one of the things, like you will probably not grow if your app is just siloed.

Host
So what about when you’re in a crowded space or a space with really established deep-pocketed incumbents? Like Truffle? Maybe tell just to give a little context, could tell people what Truffle did and maybe what were some of the challenges there with some of the competitors.

Shashank Singh
So Truffle is an app where you can actually share your best restaurant with your friends and you can plan out and you can go and have a chat, and chat is built inside it, but it’s all about sharing your favorite restaurant to your friends. The problem was like when you go to Yelp, you see all those ratings and you don’t know how good those ratings are or not. You don’t even know what that person likes actually or dislikes because everybody’s taste is different. But you know, your friends like whom you hang out with like what kind of food they like and what kind of things. So you can kind of rely and trust on that friend. Or like if you’re going to a new city. I traveled to San Francisco and I know a friend who has been there or they lived there. I can just ask them and they can answer there. You don’t have to experiment anymore. You don’t have to actually go to Yelp or Google Maps and look at the star ratings which can be hacked and which has its own downsides. Well, so many people are actually asking like, “Hey, I’m traveling to this place and do you have any recommendations?” That’s the problem we tried to solve and have a place where you can actually store your list. You can save on you add your things. So automatically I feel like I’ve added my favorite restaurants in New York and a friend who was visiting New York, he doesn’t even have to ask. Like if he opens the app and then New York and then he will see all my listings there. They’re right there.

Host
I see. So the idea is … you’re not as focused on mass scale but rather much more high quality recommendations because they’re coming from a known network

Shashank Singh
Yeah it was a little challenging also, like the network effects as everybody knows, like the experience … we still are kind of a little bit struggling with the experience of a single user. Like when you, if you join us as a single user and you will have no friends in the app, then the app becomes a little … I will say … like we have featured places and all those things we built around that, but it’s not as useful as when you have like say 20 friends. 20 friends is good enough actually and you can have really good experience in Truffle. That’s the thing we are working on and that’s what we want to solve. It’s not an easy problem to solve. We are very conscious about not being spammy and we are like, there was so many opportunities. We have so many ideas we could have kind of spammed people or something, but we are … I mean we are very ehtical on that side like we don’t want to actually spam people without their permissions or like, like … when you join Truffle, you have to give access to your Facebook or contact list or something. But a lot of companies have been built on hacking those things. Like getting the list of people and doing all those crazy stuff. You would have heard about them and we said, no, either we do it in the proper way or we don’t do it. It will be fine to close down the company but not go that route.

Host
Right. So this is interesting because you brought up this idea several times and there’s such a focus, you know, I did some other interviews where this came up, like I interviewed someone who had … Andrew Marsh who’s CTO at interviewing.io now, but he previously worked on Facebook games, for example, and a lot in the gaming industry. And he talked about how that whole industry became really focused on optimizing to capture and retain peoples’ attention. And that’s a nice way of putting it, you know, I mean, the not as nice way to put it as just to call it addiction mechanics, which is what it’s called in the industry. So it sounds like you’re very conscious of the value of what you’re delivering to people and that it’s … you’ve mentioned that, you mentioned that it’s actually solving a problem for people and you mentioned that you’re judicious, careful about sort of how much pressure you put on people, right, to you to use the app. So why are those things important to you and do you think that you can still succeed in scale and like be a good citizen?

Shashank Singh
I mean for me being a good citizen is the first and foremost thing. Like a lot of people actually do it going away … like “Let’s do the hack for now,” don’t tell anyone about it, and then get discovered, “Oh we are very sorry about this,” and you have seen … I don’t want to name the companies, but you can go …

Host
You can go down the route of it’s better to ask for forgiveness than permission. Right?

Shashank Singh
I have heard it so many times an I would be like “No, I’m not going to allow that.” Yeah. So I mean yeah it’s a life choice as you do actually, like I want to sleep better at night. And so that’s one of the things …

Host
Right and I think, you know, you may maybe early in this, but, Like if look at advertising online advertising, which is an industry both of us are familiar with, we worked together briefly in that industr, you can see the big, big shift in the last several years of awareness in the big advertisers of some of the issues with quality, a much greater demand for, you know, better quality, better ethics reall, you could even say, and I think you’re also seeing a lot of backlash since the election and so on about some of the, you know, maybe less beneficial to society aspects of social media. Right? You know, what happens with technologies I think is that we get more … we learn to live with them better. We learn how to use them better. You know, in the beginning you’re hitting yourself on the thumb with a hammer a lot. And I think the next generation or two as they grow up with mobile and social, you know, learn to use it in more beneficial ways more of the time they’re using it. And so maybe you know, you’re just, things will catch up to you to people like you are making that decision consciously now.

Shashank Singh
I’m in here for a long term actually. I’m a very long-term vision person actually. Like I don’t care about short-term things like I don’t want to succeed in like three months and then die down. If I survive, if I live, I’m here, I’m here for the long, long, long game actually.

Host
Okay, that’s interesting. So then do you have like deeper values or like a larger arc that you see yourself traveling on with what you’re doing with these companies and you know, what you’re pursuing professionally?

Shashank Singh
A lot of times I think, “Well what are we actually doing in life?” And then think about like is this necessarily to do or not. So I always have that battle inside me going on where I’m thinking like, “What are we doing, actually?” So … [laughs]

Host
Yeah. But that’s the same question you were asking about the apps really, right?

Shashank Singh
Yeah, exactly. So that’s, that’s the question I keep on asking myself. Like is this like what you were … you really want to do actually in [the] long term? So Truffle I definitely want to do it long term, like we are in a long game. Same goes with Magical. Like I had to shut it down because of various reasons, but I believe once I have a little more time I will actually revive it back because I still don’t see a product which actually solves that problem.

Host
The challenge there that that problem may be more most easily solved by, I don’t know, a Google, like someone was very big … ability to build big data sets over the whole Internet. Right?

Shashank Singh
Yeah. Definitely like when I was thinking about it and … now I have a different approach of doing … I would take a different approach to do that thing, because technology has evolved. Like you talk about NLP, you talk about AI, you talk about machine learning stuff. I definitely want to add those kind of things inside my … all my previous efforts, because I see that is one thing which was lacking there and now if I add that thin it might be actually really useful.

Host
Sure. But I guess the contrast I was drawing was something like Truffle, you actually are taking advantage of the fact that it’s starting out with a more boutique idea. You’re like, the value of the product is in the actual direct relationships between the participants, right? So, so that’s, you know, in a certain sense it’s not an opportunity big enough at the start for a huge company to go in and get, and you have all … you can do it at that scale and the advantage you have is that you’re actually delivering something really valuable to passionate users.

Shashank Singh
That’s my life-learning also, like what I have learned from all my efforts is like we worry too much about growth and if somebody asked me like how to grow, I think you’re asking the wrong question. Like a startup should never worry about how to grow, in my opinion, the first to be the first phase of their life. Actually, they should never worry about how to grow. They should worry only about one thing which is very critical, is retention. Like how do you retain the … if you get one download, how do you retain that guy? Or that girl? How do you retain? How do you actually make the time they spend in your app very valuable so that they come back again. That’s the key. That’s the holy grail of actually any any APP, any idea, anything you are making. If you can do something like that, once you nail that down, you know your audience, you know what they need and you get them hooked into your app. Not in a bad way but in a positive way. You’re adding some positivity in their life by doing something, not making them addicted, but if they think about it, for example, like for Truffle, like if they think about restaurants and they think about friends, Truffle should come in first thing in their mind instead of Yelp or anything else. Once you get that thing nailed down, that’s when the growth comes into the picture and the full growth. If you have a very active set of users or even if it’s like a hundred users actually and they are very hooked. They’re using your app and they value it a lot. That’s when you start thinking about adding those growth features into the app. First nail down the first thing and then growth can happen.

Host
So does that connect back to the social media marketing? Like how do you … how do you add growth features that then help it go viral?

Shashank Singh
Make it very easy to share things, so there are a lot of things there like sharing and chatting is definitely there. You can actually build chat inside your things, or if not, then make sure it plays very well with the currehnt chat services, Messenger or iMessage. Make sure your links when you’re sharing that links have enough information and it has a preview and all those kinds of things. Make it very easy to share. When you share on Facebook, it adds some value there. Don’t rush into things. I would say take one thing at a time and nail it, and then we’ll do the next thing. A lot of startup founders they do is they want to build the Titanic on the first day and they get lost. They take years and years to develop that thing and then by the time they launch … I have done it personally. So speaking from experience, you’re late into the market, or the need has gone, or you added so many things that you cannot manage it. Like you cannot manage all the features because you’re cash strapped, strapped from developers, you are … you don’t have that many resources to actually manage things, so you are buying a bigger bite than you can chew. [Laughs]

Host
Right. And in fact this goes right back to what you just said previously, like if you’re always focused on what is the essence of this thing that will move users, then you’re building the right things or trying to anyway, rather than building so many different things. Like you’re building less and you’re building the right things. That seems to be the target to aim at and that’s hard to hit.

Shashank Singh
Yeah that’s very hard to hit. Yeah I think another thing that I would like to add is that sometimes, or I would say most of the time, founders always over-estimate the problem because it’s there bias – they think it’s a huge problem.

Host
Right which … because it got them excited enough to get started with it. Right.

Shashank Singh
Yeah, so bias that I see that you over-estimated the market, even if it’s a small market or a very niche market, you think this is gonna solve a problem for humanity and the fact is that only few people care about it, [Mark laughs]. Or people are not thinking that far sometimes, actually so …

Host
Right. I mean it can be that they might care, but it’s hard to understand. Like I’ve been at those kinds of companies too.

Shashank Singh
Yeah. I mean if you look, a very good example is Foursquare. The founder I mean, he launched a couple of apps before having Foursqure as a success, and when he launched the location-based stuff, like he was way too ahead of his time actually. So that can also happen like you were thinking about something which probably people don’t care, they might care after like a year or two. So …

Host
That’s actually an interesting example of a lot of what you’re talking about because even though when it first came out, a lot of people were sort of saying “What is this thing?” There were people who were passionate about and using it early. And that was well before it was kind of understood maybe the more broadly what the utility was and even whether there was ever going to be a business there and what that would be.

Shashank Singh
Yeah.

Host
But he stuck with what you’re saying, which is let’s make this something that these people love and that finding value from.

Shashank Singh
Yeah, exactly. You see now like they have been so many products, like you’re in ad tech so we both know like what kind of products they have made and it’s …

Host
Yeah, they’re actually public customer of my current employer. So it’s, I can even just say that we, you know, we help them directly now and you know, we help them leverage all that data that they’ve built up to use on the advertising side. So …

Shashank Singh
Yeah, I mean, Foursquare is one of the examples, there’s so many of them actually. Like even if you look at current VR and AR, virtual reality and augmented reality … I’m not taking any credit for it, but my, one of my friends, my cousin and I was actually, he founded the company for VR, and I was like “You think this is the right time to actually do it? And he was very excited about it, rightfully so. He built some cool stuff. He bought those bulky headsets and everything and I was like, I’d look at the demo, I was pretty impressed with it and I said, but do you know how many people are going to have … wear this headset,

Host
This is my take on VR too, but, but it’s like I’m just in the camp of people who don’t get it. You rightly said there’s a passionate small group of early adopters. Right. And that’s …

Shashank Singh
But there will become people who would stick, they will stick with VR, they will figure out, figure out a use case and they will nail it and they will survive, but 99% of the companies will actually close down and shut down because they cannot … they will give up.

Host
Right. I wanted to also talk to you about, you know, some of your more, I guess quote unquote traditional roles in, in bigger companies. The fact that you both can compare that to being … starting your own thing and also that you can compare kind of different roles within teams, right? Team leadership, technical leadership, architect, individual contributor. So maybe speak a little to both of those. Maybe let’s start with kind of what are … what are some differences between, you know, working at like say an early stage company, a later stage company and on your own and you know, maybe things you’ve learned in each of those situations.

Shashank Singh
Yeah, I think like working for a startup is awesome, actually an awesome experience. It’s not for everyone for sure, but what you get is actually you wear multiple hats. You decide on things, you’d talk about it and you start doing it in on the same day actually most of the time. Like you talk about things and you start doing it. Like I’ve worked for financial banks in New York and you talk about it …

Host
[Laughs] … and talk about it …

Shashank Singh
… years pass by and you’re still talking about it. Yeah. So …

Host
… emailing about it.

Shashank Singh
Yeah, emaling about it, and there will be like higher ups in the bureacracy come in and they would be like, “Yeah, I’ve been thinking about this. Let’s set up some meeting for this.” Yeah, I was, I was in Goldman Sachs for like four-and-a-half years. I mean I did pretty interesting stuff there. And they’re, of course … everyone has their own story about what you wanted to do and what you ended up doing there. So working in the startup is actually that exciting, but working for yourself actually trying make a startup is like, like really different than anything else you would have to think about. So first of all, like you have to believe in the idea. Second, you have to start selling your idea if you need help because you can do few things … well a lot of things, but you definitely need help if you’re thinking big. You cannot make one huge life-changing application. I mean everybody knows the technology … you need somebody who can do back end, who can do front end, who can build the app, and if you’re doing everything then instead of that thing taking a month or two months to do a prototype or something, you will take years to do that. So. So you have to sell to your friends or people you like or people you think you can work with. So you have to start selling that idea and make sure to sell enough and that they start believing and it becomes their idea. That’s the key thing. Like it has to become their idea that only the startup and only then you can actually build out the product. Otherwise they will say, most of the time you’re going to end up hearing is like, “Oh, it’s a good idea. Oh yeah, I can do something.” And then they might contribute a little bit, but it’s not that passionate, as passionate as you are. And then you will start feeling that frustration because if the passion was not at the same level then you might just seem like you’re dragging me down.

Host
So it’s like what you said, where you as the founder have so much bias toward loving the idea and now you’ve got … you’ve got to incite that passion in other people so you can get help.

Shashank Singh
Remember this, if you’re looking for a partner out there, make sure it’s no longer just your idea. It becomes their idea too. They’re not helping you, they’re dreaming along with you. So if you cannot get that kind of vibe or something, I think it’s not worth making them as a cofounder. Then maybe they can help you … get assigned some tasks and get some help and done.

Host
What about, you know, managing engineers and building teams. Probably something you’re thinking about, you know, as you look at the current startups and hoping you get the opportunity opportunity to do that with them.

Shashank Singh
Right even here … that’s why I joined Datamarx. It’s a very early-stage startup and I’m the CTO there so I have to build the culture and this will be my opportunity to actually instill the culture which I love and which I want to actually … and of course with, with the blessing of the founders. What I personally believe in is the team should be something like where like people say, but I genuinely believe in it, like everyone should be equal irrespective of you come with the 20 years of experience or two years of experience. Like people should feel equal and you having more experience should have a duty about like actually teaching people that rather than having an attitude about, “OK, I have experience. so you’ve got to respect me.” You don’t demand respect. You get respect by doing things actually. And it should come naturally from people. As far as managing the team is … like the best way to manage is like don’t manage them. Let them manage themselves. Everyone is a grown up. They need to understand, they really need to understand. Everyone needs to understand that you’re doing something for us, enabling the business or something. And if you’re not contributing enough. And I mean, if you have to always come back and give a feedback to somebody, then they’re not the right person. Find a way to let them go or, give them a good talk about like what you’re trying to do here. And if they are still not performing, they should go. Yeah. we should not be wasting our time in managing. One thing I learned from Goldman, a lot of good things I learned from Goldman. One thing was like, you take ownership. You start giving ownership to people and they should actually take ownership. There should be a good accountability of things. Like if you own a certain things like things go strong, somebody should not come to us and this is wrong. And you have to step up and do something. Once you build a product, you own it. You have to actually take care of is as your baby, actually.

Host
Right. I think of it like, at least from the engineering side, like we are the caretakers, you know?

Shashank Singh
Yep. So you know that that’s where like if somebody is not owning up their own shit actually the I think that’s a red flag and you need to have a conversation. I’m not rude when I talk to people. I try to be very polite and I try to sell them like why they need to step up and why this is not expected or what is expected of you.

Host
Do you think that changes as the size of the company changes or do you think that … like in other words, at a very early stage communication is very fluid. Everyone has the same context very easily. And you know the goals are very clear. And so that expectation of everyone owning, I think it’s totally realistic because of those things, because of the context and the goals are all very clear and the same to everyone. And the communication is easy. Do you think that changes as the size of the business scales?

Shashank Singh
Definitely yes, I think so. But I think what you can do is you can end up … it’s not easily done. I, hopefully I can do it … that’s what I think I’ve tried to do … is you create small teams as a startup in itself actually. So if you have that team and they have independence, then you don’t have to have a very big hierarchy also. Like you have a team which actually works as a startup, as an independent unit, and they can try to have that kind of culture inside what we’re talking about in a small team actually. So you’ve tried to build that kind of culture inside a larger company. I tried that in the companies, but of course if you’re management is not being supportive enough, then you cannot probably. You can do a little but … yeah, you can see … But larger companies, yeah, I’ve seen so much bureaucracy coming in the picture. I mean that aspect is like people start … people are very hungry for recognition, so people will try to grab all that engine they can and that’s where they start stepping on somebody’s toes, and that’s where the friction starts, and over a period of months and years like that friction can be clearly seen and walls build up. You try to build up walls and yeah, I mean people are trying to protect themselves actually. And it’s a very toxic culture actually. And I’ve been running away from those companies for all my life. [Laughs]

Host
[Laughs] Yeah, me too. Probably everyone listening also. [Both laugh]

Shashank Singh
Yeah, if you see that … Like another thing is like what I believe in is like try to change the culture. If you cannot, and if you think like it’s not worth actually putting that effort, then run away from that place. There’s no point in wasting your time and bitching about it and having negativity in your life. If any of my friends actually comes and bitch about their work to me I say “Change the job, and if you cannot change the job, try to change the place, change the culture there. And if you cannot do both of them then there’s something wrong.”

Host
Then just leave. Right. I think when I was less experienced, I’ve had a, I had experiences where identified so personally and deeply with the struggle of wherever I was and was so, you know, angry even is the word – passionate would be, you know, understating it. And all the things that were so wrong and … and that is very unhealthy. You have your ideas of what, how the company could be effective, right? And then you try to foster that and nspur that and if you can’t then you know, you can’t take that on as your own personal struggle. You yourself, one person is not going to change a whole company.

Shashank Singh
I think you can. I still believe in that, but you should give it a shot before you leave. In my opinion you should give it a shot to try and change it before you leave.

Host
Okay, that’s fair. Maybe I’m being too negative. And, and you definitely … like at smaller companies that are more open, you can definitely have a huge impact.

Shashank Singh
Don’t give up, in my opinion, never give up without trying. Try it. There’s no harm in that. Worst-case scenario, you’ll get fired. That’s a blessing in disguise most likely.

Host
Well, I mean also you’ll learn from that experience I think, you know, and going all the way back to things you said earlier, you’ll be true to your own values, right? And you’ll be doing things for the right reason, with the right intention. And you know, we’re still, I think we’re very lucky that there’s plenty of employment opportunity for engineers right now. So the way I actually look at this then too, is there’s a large opportunity cost in staying at a place that’s not working for you.

Shashank Singh
That’s true actually. And also when you move … like I’m not encouraging the culture of job hopping every now and then …

Host
I’m not saying that either. I’m just saying staying in a miserable situation and making it your own personal struggle when there’s all this other opportunity out there, that makes no sense.

Shashank Singh
And also as an engineer I see when I’m in the company for long enough. I’m doing the same thing every day and there’s no change. Then also I think you need to think … give a hard think. Is this, what do you want to do or do you want to learn something new or not? Because the technology is rapidly changing. If you’re not keeping up believe it or not within a few years will be totally outdated, and then you will be … it will be very difficult to catch up.

Host
Yeah, definitely. Like when we worked together at RUN, the reason I was there was really, I had been for several years like in leadership roles and not individual contributor roles, and I felt like wow, the cloud just happened all around me and if I don’t get back to an individual contributor role and build things in the cloud, I’m going to be totally irrelevant. Like what am I going to manage people I’ve never built stuff the way they’re building it. Like that doesn’t make any sense.

Shashank Singh
I was interviewing somebody in RUN. He was a very senior guy, worked for an FX, like foreign exchange, and very senior guy, probably 20, 25 years of experience in the industry, and he was kind of a CTO in an FX company. And he was there for an interview at Run, for a similar position I had, and I gave him the same advice actually. “You have been in finance for long, have been seeing a certain kind of industry. You have not worked on AWS, you have not worked on the cloud part of things. Most of the things you have done is your own proprietary stuff. I would say blindly accept this job because even for long term, if, if it works out very well … if it doesn’t work out you, you are here for six months to a year. You will never get [another] opportunity [like this]. If they are offering you a job, then take it.” And that guy joined. He was there for more than a year I think, and right now he’s working for Microsoft AI.

Host
There you go. That’s perfect.

Shashank Singh
Yeah. When he was leaving, I was telling him aren’t you glad now that you joined and I was kind of pushing you to join. Because he was kind of taking a step down. But sometimes you have to take a couple of steps back to take a long jump, right?