Episode 150. Quit Story: Lessons from an Engineer who Became a Tech Co-founder & Entrepreneur (Shubham Kaushal)

This is a very exciting episode because it is the first of a brand new series we are doing on the show. It is called the Quit Story series.

The intention behind this series is to bring on really cool and interesting people that I‘ve met, who have a Quit Story of their own.

The most natural story that we might think of is quitting a career. But a Quit Story can also look like quitting a relationship that wasn’t working out, or quitting a lifestyle that wasn’t aligned with your values, or going on a sabbatical temporarily to rejuvenate. It can look like so many things.

But the common thread between the Quit Stories we’ll be hearing on this show, is that the individual has basically chosen not to fit themselves into a box and check all the boxes, which is what they might have done previously.

Now that they’re pursuing their own journeys, they are really choosing to define success or define what a successful life and career looks like on their terms. They also are choosing courage in times of uncertainty or difficulty. And they are also choosing to make decisions in accordance with their values and what matters to them. That is the essence of what a Quit Story is on this show.

The first person we’ve invited to the Quit Story series is Shubham Kaushal.

I first met Shubham at a local event discussing mental health for entrepreneurs. Shubham reached out to me after the event to ask me some questions about starting and growing a podcast, but the conversation then turned into me learning a lot more about Shubham’s career journey.

In just the short span of 75 minutes, I learned about his story, his values, and how he chose the unconventional over what was perceived to be stable, traditional, and expected.

At that moment, I realized that I MUST invite Shubham onto The Thought Leader Club Podcast and have him share his story and other candid stories on failure, self-doubt, and paving your own path.

We are recording this in-person. For those of you watching the video version, you will see that there’s the two of us on this video. And for those of you listening to the audio, you just have to tune in on YouTube to see the video version.

In This Episode:

How family, cultural and societal backgrounds played a role in Shubham’s career decisions and views on success
Shubham’s unexpected journey from a traditional path to becoming a co-founder
The romanticization of entrepreneurship: Advice to those who are questioning their current career situation and are deciding whether to make some changes
Fresh perspectives on failure, quitting and paving your own path
Music, Singapore and food: Making time for non-work interests and hobbies and being a life-long learner

How family, cultural and societal backgrounds played a role in Shubham’s career decisions and views on success

Cheryl:

Shubham and I met about a month and a half ago. We’re new friends. We met here in Singapore, we met at an event where it was focused on mental health and entrepreneurship. And we connected afterwards.

At first Shubham actually wanted to reach out to ask me some questions about podcasting. But it turned into a conversation about Shubham’s own career journey.

I realized that you’re a really interesting person that has a lot of viewpoints. And I just thought you were an incredible person that I really wanted to bring onto the show and really kind of poke into your brain. I think you are an encapsulation of the Quit Story, in my opinion. So I’m delighted to have you here with us.

With all that being said, I’m going to pass it on to Shubham. Could you please tell us a bit more about who you are and what you do?

Shubham:

Sure. Well, thank you for that kind introduction. But you know, it’s good to hear good things about yourself. So I’m Shubham and I am a co-founder at this startup called Airboxr. We do data automation for DTC (direct-to-consumer) brands. Specifically, if you have a Shopify store, if you’re running on Shopify, we can essentially help you understand all of your data to help you make better decisions. So that’s what I do. Yeah, Mr Entrepreneur, I guess.

Cheryl:

Yeah, and let’s start there. So entrepreneur is your job title, co-founder is your job title. I’m curious to know, is entrepreneur and co-founder the job titles that little you envisioned? Like was I even on your mind when you were like, let’s say, in your teenage years or even early 20s?

Shubham:

No, I don’t think so. I mean, I guess I didn’t even know what “founding” is. I thought maybe it’s the past tense of the word “find”. But that’s not true. I looked it up. “Found” is actually a word. I had no idea.

When I was younger, perhaps in my teenage years, I was kind of all over the place. Part of me wanted to be an astronaut, I guess. I did this one paper for NASA in my high school and designed, like I don’t know what it was, a search and rescue aircraft.

Cheryl:

Like you literally did this for NASA?

Shubham:

Yeah, there was a competition that NASA hosted. I think it was called the Aeronautics High School competition or something. And I was so excited to do that. I was like, “Wow, this could be my career. This could work out. What if NASA calls me and goes like, we need you.”

I was a little bit all over the place. I was always interested in computers and software. So I knew that that was one path for sure. I think a part of me also wanted to study music, which I did not, in the end. So yeah, I had no idea that I would be running a startup.

Cheryl:

So then, tell us more about how you, let’s say from high school onwards, like what was the path you took? Because you clearly took some detours at some point to end up here today. So could you give us a backstory about how you got from there to here?

Shubham:

From high school, I think, if I remember correctly, I was always a little bit of “I just wanted to do things differently.” I did not like studying for exams. In particular, I think there were some subjects that I absolutely loved. And depending on the teachers, I would take the appropriate amount of interest in them. But I was always kind of like a last minute person when it came to deadlines, or, you know, even the NASA paper I wrote in like three days or so just because it’s lazy, you know.

So I moved to Singapore for high school and then University. You’re here, you’re in a good high school, junior college, as they call it here. You do your stuff and work hard. And just like, slog it out.

But I don’t think I didn’t identify with that a lot. Yet, I think part of me was like, Oh, I have this opportunity. So I must see it through. I must not waste it. So there was a bit of that push and pull. And I think at the end of high school, when I got into NUS (National University of Singapore), I had to decide on a field of study, right?

So I was a little bit torn between studying computer science, computer engineering, to be specific, or music, which are like, worlds apart. Part of me wanted to do music, because I’ve just been very passionate about it throughout my life since young. It just seemed like this crazy thing to do as an Asian student.

Computer Engineering had all the security with it. Because it is usually a good career choice. I think back then perhaps it was not the most popular field of study. Today it is, for sure.

That was one of the turning points where I actually chose the safer path. I was like, Okay, let’s not take too many risks. You can always come back to music if you want to. Let’s build a solid career first.

Cheryl:

Okay. So now I think I’m really curious to know about your cultural background. Perhaps because the audience now heard that you’re currently in Singapore and you moved here for high school. Where were you from before?

Shubham:

I grew up in New Delhi, in India. That’s where I spent most of my schooling. My parents are actually from the mountains, from a state called Himachal. I specifically grew up in Delhi.

Cheryl:

I’m curious to know, from your own, whether it’s family or culture, how would you say that your family or culture had some sort of influence over that specific turning point where you were choosing between music and computer science? Did your family play a role in your decisions?

Shubham:

Absolutely. I think as a 19 year old Asian student, you’re still very much living under the shadow of your family.

Cheryl:

Yeah, that’s a great way to phrase it.

Shubham:

Yeah. I think it comes from a place of self preservation, right?

I come from a family where we grew up, I would say middle class at best. In fact, I think I remember that the first 12 years of my life, I was living in what you call a joint family. So here you have your immediate family, your parents, your siblings, but also your uncle’s family and your grandfather and your grandmother. So it was quite a basic sort of upbringing.

For my parents generation, their biggest and well deserved achievement was to find a stable, secure job that pays consistently. Something that can sort of help lift the family up. So that’s what I think is the kind of thinking they were trained in, is to not take too many risks and just follow a set path to your thing, do your hard work, and then work towards that.

When I was deciding what to study, that definitely factored in. I remember having my parents, honestly, were quite supportive of whatever I would choose to be.

But I had a hard conversation with my sister who believes that “You know what, I think you should do computer engineering, because it keeps the options open. You can do that first. And later on, if you want to do something else, that’s always the case. Whereas if you study music, it’s a tough life, for sure. Building a career there is not easy. Then if you want to switch your career back, it would be a lot more difficult.”

Honestly, I think back then it made sense. I was like, yeah, I can’t really argue with that. So that was, that was definitely a factor.

Cheryl:

This hits home for me a lot because I was born in the United States, and I grew up in North America primarily. My parents were immigrants there. I’ve always had this narrative inside my head that my parents worked so hard to give me the resources I have, and they work their hearts and asses off… So I’ve always had a story of like, I will give back through my career. I told my mom that not too long ago, she’s like, where did you get that story from? I’m just like, I don’t know where I got the story from, but it was something I internalized since young.

When I quit law school, I think it’s five years ago. My parents were furious at that point. Now they’re much more open to my not-so-traditional career decisions. But five years ago, that was not the case. When I quit, they couldn’t understand why I couldn’t just finish the degree first and at least have a degree.

When I quit, my mom actually said, you need to bring harmony back into the family. That’s when I realized how much for some of us, maybe for certain families or cultures, the career decisions we make, kind of influences the family dynamic, more than we can imagine.

I didn’t realize how much my family really were following along with what I do, and secretly hoping I will go this direction or that direction. And that came to light when I decided to quit law school. So that’s why I was really interested to hear what your family had to say.

Are there any particular experiences that you might be able to share when it comes to your family? Like, where else did they kind of plant the seeds such as to like “Oh, you should go down this career path” or “That’s not what we do.”

Shubham:

It’s an interesting question. I don’t actively remember such instances. But you’re absolutely right. When you said that, you were wondering when did this get imprinted on you that you’re supposed to give back through your career? It’s such a pervasive social programming that most people who are born and brought up in Asia go through.

Family is the most important thing growing up, right? Because they take care of you. Then the unset expectation is you’re supposed to give back and take care of them. Which I agree with. I think that’s also one of our strengths, as a culture, that we stand by each other and all that.

But it does take away the power of the individual a little bit, their potential as a human being a little bit. It takes away their options, right? It takes away their adventure, almost. Like sometimes you just want to try something crazy. It doesn’t have to make sense. But when you have bigger things to worry about, you limit yourself.

So I think the programming sort of happens, not just in your family, but just hanging around with similar people. It’s their own families who think the same way. You just observe that this is how life is supposed to be.

Cheryl:

This actually reminds me of a comedian named Ronny Chieng, I don’t know if you’re familiar with Ronny Chieng. I believe he said a joke once, and it was something along the lines of Asian parents wanting their kids to become doctors. Because in just one generation, they could turn it around.

And I was like, Oh, that’s a great way to put it.

Shubham:

Yeah. I think they were looking for that exponential growth through generations, you know, generations. Yeah. And they’ve done it right. The previous generation, like my grandfather, had real struggles, so to speak. The stories that I heard about him were that he built this home at night, because during the day, it was during the British Raj in India, and they would not let people build houses.

So he would just put himself through school, pull them up from his bootstraps, and he provided this safety for my father to grow up. And then my father followed on. So you’re always supposed to sort of keep going up. That is the expectation, almost. It’s interesting.

Cheryl:

I really resonate with that, because my father especially loves to imprint certain values in me by sharing stories of his own upbringing, and my grandparents stories as well. And hey, let me tell you it worked! They are deeply imprinted in my brain.

Shubham’s unexpected journey from a traditional path to becoming a co-founder

Cheryl:

But now let’s jump back to near-present day. So it’s University for you at NUS. From NUS to now, what happened?

Shubham:

I think choosing Computer Engineering was back then the right thing to do. I did that through the course. I quickly realized that I, again, do not like to follow a set path. I would just show up really late for my lectures, just skip them entirely. I was not the best student, I would say when it comes to NUS. They have this, it’s a boon and bane, the webcast of their lecture so that even if you don’t go, you can watch them later. And every semester, I found myself just putting it off until it was exam week. Then of course, you can’t go through them, even if you watch them at 2x. Of course not.

Academically, I did the bare minimum. But I also realized what it is that I actually like about school. I think in my course around the third year or so, it started to get a little bit more interesting. The focus was a little bit more on projects rather than examinations. So 50% of your score will be determined by the project. At that point, I started to take a little bit more interest in my education.

Then I started just picking up work, started with a few internships, went for this industrial attachment at Autodesk. And then found this program that NUS offers called NUS Overseas College, which is actually a program centered around entrepreneurship.

So you would get attached to a startup overseas, you would go there from six months to a year, whichever you want to choose. I applied for it and actually went and worked at a startup called CallApp, in Israel back then. That experience really opened up my worldview, because it was also the first time that I lived in a country that was neither India nor Singapore. So a little less Asian, in terms of individuation and risk taking.

I think that was one key turning point where I was like, this is a non set path of exploration. And I really enjoyed my work there. I was very inspired by the people that I was working with. Just a small team of eight people and making a huge impact. And I came back from that fourth year. Slowly and slowly, I started to realize, okay, I think this is the kind of work that I enjoy.

When I was about to graduate, I had two options, essentially, in terms of my first job.

One was to start my career at Citibank, in their software team, or whatever their technology team. Or join this obscure startup that I had never heard of, called Chaldal, which is essentially the RedMart of Bangladesh.

Now, back then, they were really small. I didn’t know what it was. I got to know about it through a friend. I had a quick in-person chat with one of the co-founders who was visiting. Surprisingly, this person had also gone to NUS. So there was some common thread there. The chat went great. He just sent me some take-home assignments. I got that job.

And I was like, which one? Should I? Which one should I take?

At this point, I’m old enough to make my own decision without consulting my family. And also both of them paid. So it wasn’t like I was breaking any rules. So I went with the crazier option back then and decided to join this startup. And just went ahead in that direction of a small company, trying to do more with less. I think that was probably one of the inflection points as well.

Cheryl:

So I’m really curious to know, from that point on, where’s that particular inflection point onwards till now? Today is November 3, 2023. During this timeframe, I’m sure you’ve also, maybe, dabbled in different startups or spaces. We can dive into that as well. I mean, now you’ve co-founded your own thing. But were there any points where you’re like, “Why did I go down this route?”

Shubham:

Oh, yeah, absolutely.

Cheryl:

Okay. Can you dive into that?

Shubham:

Sure. Happy to. I think there’s the way that I look at it is, at all of these junctures, these inflection points, you essentially have a binary choice.

One is to walk down a road that is very well lit up, very well paved, it seems safe, it seems predictable.

And then there’s a small alley, dark alley that you don’t really know where it leads. But it could be exciting. There’s some promise based on what other people have told you about, you’ve heard some rumors that this could be interesting. And that you might find something new there. So deciding to take that job at Chaldal was one of those points.

But it didn’t really end there. Now, the thing is if you take this path, as you’re walking through darkness, really, you’re filled with self doubt, all the time. Because I think most of your peers, especially in a place like Singapore, are not on that path. Right?

I think today, Singapore is a lot more supportive of new ventures and startups and it’s a hard thing these days. Back then not so much. I think back then even the big tech had not shown up in Singapore. The top players in the market were the big banks, even in computer science or engineering, those will be the highest paying jobs. So you look at your peers and you hear their stories and they sound like they have a good work life balance. everything’s taken, they get a bonus, you know, they get, they seem to have a bit of a balance.

And so you’re filled with self doubt throughout even working at a startup as an employee. But I really think that that’s a good thing. In a way, looking back at it, I had a bit of a quarter life crisis. As I went through it, I was like, you know what, I think this is what people go through in their midlife actually. If they have a very stable career. And if we follow every do everything, right, perhaps then you know, find a partner and have babies. And I think at some point, they must wonder why or is this it?

I think, in a way, I felt a little bit fortunate to find myself in that headspace at 25. Three years into working at Chaldal, at this point I had gained such a great experience working there. I got to build amazing software systems, I had a really good supervisor. I just absorbed everything like a sponge. And I was doing well, from all accounts. Then about three years and I was like, okay, but is this it? Now what?

Cheryl:

We were talking about did you ever, like at any point from NUS till now or when you got your first job? After graduating till now, did you ever look back and be like, why am I doing this?

Shubham:

Yeah, many times, many times during the job. After I went on a sabbatical… That was a good story. But that’s another story.

It’s something that we don’t usually openly talk about, especially in our culture. I think you don’t want to come off as someone who doesn’t know what they’re doing. There’s a bit of that saving face kind of thing there.

But even to this day, there are times when I’m like, Oh, am I doing it right? Is this the right thing to do?

Cheryl:

Yeah, I can imagine, for myself, whenever I open my LinkedIn app, and I see my friends, my classmates who are now medical doctors, they finished their PhD, unlike me, who quit after two years of her PhD. And because I come from a science background, so a lot of my friends back then are now like scientists or dentists, etc.

I‘m curious to know, even to this day, when you go on LinkedIn, do you ever still wonder like, huh, what if I went down another path?

Shubham:

Yeah, absolutely. It comes up. I don’t browse LinkedIn that much.

Cheryl:

That’s a good decision!

Shubham:

That’s a good decision. But yeah, it definitely comes up. I think all those paths not taken, it’s like, wow, this could have been me.

Cheryl:

And being an astronaut could have been you also.

Shubham:

Sure, you know, in some parallel universe, probably.

Cheryl:

What else did you consider? Okay, so we’ve got startup founder, we’ve got computer engineering, we’ve got astronaut, musician… Was there any other option we could have?

Shubham:

Well I could have taken that job at Citibank and had a very nice career, built a nice team and enjoyed my weekends.

Cheryl:

The city never sleeps though. That’s what I heard.

Shubham:

That’s true. I don’t know. Countless. I would say, countless. All those possibilities. That could have been. You wonder sometimes.In a good and a bad way, you know?

Cheryl:

Yeah, sometimes I still wonder. Oh, should I have gone to medical school? Take the MCAT (Medical College Admission Test) and go to medical school. Would I have even gotten in? I don’t know!

Okay, so, I really appreciate you for sharing openly about how even to this day, basically self doubt still clouds your head here and there, every day, or nowadays.

The romanticization of entrepreneurship: Advice to those who are questioning their current career situation and are deciding whether to make some changes

Cheryl:

So I want to kind of jump to present day and ask about, just because I think nowadays when our listeners think about entrepreneurs, whether it’s an entrepreneurship can look like so many different things nowadays, but I think the general image that people have of entrepreneurs is like, “Wow, they’ve so much grit, so much resilience, so much work ethic, it looks so cool, like, Silicon Valley.” I think there’s certain narratives that we now have.

Shubham:

The romanticization.

Cheryl:

Yes, the romanticization of entrepreneurship. If you were to talk to a fresh grad in 2023? How would you give them an honest depiction of entrepreneurship? What would you say?

Shubham:

That’s a really good question. I think you’re right, there is a certain image of founders out there. Part of it is keeping a brave front. Or, of course, you don’t want to share, like, the sad things, right? You only share the good things on social media. That’s the whole point of it, I guess, which I don’t get.

Entrepreneurship, especially more so than other career choices, is actually a graveyard of failures. There is so much more that you don’t see that is happening behind these 1% who are doing amazingly well, seemingly. I’m sure they have their own struggles that they don’t talk about. But it’s not cool to talk about that. Right. It’s cool to talk about tens or hundreds of millions of dollars that you’re raising, and cornering this market, and this and that.

So what could I say to a fresh grad, perhaps? It’s interesting, because just earlier this week, I was helping out my university by interviewing some people for the program that I mentioned, the NOC (NUS Overseas Colleges) program. It was really good to go back to that state of mind, because I also went through the interviews, and I was just remembering what kind of person I was back then.

During that time, you’re a bit of a clean slate. You’re ready for anything. Perhaps the people who apply for this program already have a little bit of that spark. I think what I would say to them is that this path is not glamorous at all, in my humble opinion. I’m sure that different people have different experiences. More so, I think in the entrepreneurship plane.

But this path for me has never been glamorous. It has been a path of self discovery, perhaps, of self actualization, of proving it to perhaps yourself, more importantly, than others, that you can do something big. That you’re capable of doing something big.

I think that’s how I would put it, that don’t do it for the success of it. That’s definitely something you want to aim for. You know, of course, you should be highly ambitious. And I am.

But the experience of it is something unique that will teach you so many things about yourself.

I don’t know if I’m making sense. And I don’t even know if that is a pitch, like if I could discourage them from doing this. I think that’s a good thing. If I can talk you out of it, that means that you should probably not do it.

Cheryl:

That’s a great way to put it. And I’m so glad you shared what you just shared, because even though I would say the majority of our audience are not fresh grads. I would say that, based on what I know about the listeners, most of them have worked for at least maybe like 5 years, 10 years, generally speaking. But many of them are curious about doing something of their own.

And that’s a very vague term right now. It might still be fuzzy in their heads, but there’s something in their heads they want to do. Whether it’s being a content creator, or maybe being a founder, or starting an online service-based business, it could be anything.

But they are at a point in their life. And that’s probably why they’re listening to this podcast. They’re at a point in their life where it’s kind of like a major crisis, or quarter life crisis. I mean, things are fine, but it could be better, or it could be different. And I think that’s a sentiment that a lot of the listeners share.

So with that being said, as someone who is a founder yourself, is there anything you would say to someone who might be, whether they’re older than yourself, or has more industry experience in yourself? But now they’re at their own crisis of sorts and they’re looking at your interview right now. What would you say to someone who isn’t a fresh grad, but is at a similar juncture? Mindset wise.

Shubham:

Yeah. And, you know, even for the fresh grad, I mean, I did say that if I can talk you out of it, you probably shouldn’t do it. But if that doesn’t discourage you, and you’re still on it, then I think that’s where the real conversation starts.

And this goes, like you said, for someone early in their career, or in the middle of it, or even looking for a career change, for that matter. I think if you still have that nagging feeling inside you that this is not it, or perhaps life could be different. Then you have to owe it to yourself to listen to it, and act on it.

I think what I would say is, look, everyone’s situation is different, right? In a way, I was fortunate that I was at a point in life where I didn’t have a lot of responsibilities. I was still early in my career. I didn’t have a very lavish lifestyle. I was never, I never got used to that.

So I was good at saving money. I saved some money from my first job. And I think that’s partly why I got this nagging feeling like yeah, I’m saving money, and it’s probably going to keep on going up. And then what? Is this it?

For someone in that position, I would say just go for it, take the risk, take the plunge, make sure that you’re able to sustain yourself through that. I’ve managed to last maybe two and a half years without a job. like I went on a sabbatical and it just never went to the company.

Because I had this sort of financial mattress that I built for myself to bounce back on. So if you don’t have a lot of responsibilities, absolutely take the plunge, see it through, stick it out to the end. And because you owe it to yourself. Absolutely.

For someone who, when people get older, they do accrue more responsibility, perhaps you have a partner, perhaps you have kids. In that case, I think it’s contextual. And I think in that case, you need to do a little bit of risk management. You don’t want to be too outlandish either. Perhaps you can start something on the side without quitting your job, or quit your job but find a way to earn money somehow, some basic amount right, like do consulting on the side.

Interestingly, when I started this company with my co-founder, Saps, we both started with the idea of actually bootstrapping it. We were like, you know what, we’ll just perhaps get a few, some contract work here in there. And we’ll keep exploring this as a hobby. Ideally, we never have to raise capital, and we can just take it off the ground.

Now, one thing led to another and as we were exploring the problem, we realized it’s a big problem which needs to be solved and people are trying. And then eventually, we decided to raise capital. When we started with that mindset, because we weren’t going to get some basic sustenance, money every month, just to make sure we were paying the bills and feeding ourselves. And then put the rest of our time into exploring this.

I think it depends where you’re at. I think you have to understand what you need on a daily basis, make sure that it’s covered, make sure that your survival is not in danger. And from there on out, everything else is a bonus.

Cheryl:

Yeah, I think what you just shared is particularly helpful for those who are not a fresh grad and they have more responsibilities, but also have more of a financial safety net as well. So a lot more factors to consider. But you can also probably buy yourself some time at this point.

Fresh perspectives on failure, quitting and paving your own path

Cheryl:

One profile of a person popped into my mind as you were sharing. So I have discovered that actually a number of our audience members of this show are holders of PhDs. Because I myself was in a PhD, so I think over the years, I have kind of accrued a bit of an audience base, who also are PhD students, or you’ve already gotten your PhD.

But one thing I’ve heard from some of our listeners who have PhDs, and I’m sure this applies to any tertiary degree holders, is that they feel like they’ve put so much into the darn PhD. And now they’re thinking, I don’t think being a professor or going down academia is for me.

So I know you weren’t in academia and you’re not a professor, but you’ve gone down something similar? I’m curious to know, like, what are your thoughts because it seems like you’ve had several junctures of your journey so far, where you have invested time, and energy and hard work into something. But at some point, you realize, “Oh, I don’t think there’s much of a future here anymore for me. How did you navigate the feelings of, but I’ve been here for like, three years. Now, I’ve done this for so long.”

Your identity is wrapped around that role, how did you unravel that identity?

Shubham:

That’s a really important question, I would say.

You’re absolutely right. I haven’t been into academia. But I have hung out, you know, or been around a lot of PhD people. I was part of this startup program called Entrepreneur First. And their Singapore chapter. It’s closed now. But back in the day, they were very deep tech focused. So almost 1/3 of the cohort were PhD students.

I made great friends there. But it was very interesting to observe how they think and how they approach the program. I think you’re right, when you do something like a PhD, it becomes such a big part of your identity.

For me, I can’t say that I’ve gone down that road, but I have at some points, like perhaps it was a passion project of mine that I tied myself towards. I was like, okay, this is it, I tried to solo found this company, and I worked on it for six months, day and night. I was like, just Yeah, just one person army, you can do it. And wrapping that up and saying that, okay, this is not going to work, was a difficult and emotionally difficult process.

How did I do it? How did I get around it? I think I sulked for a while. I started entertaining the idea that, okay, perhaps this is not really working out. And maybe we could make it work, maybe we could find a business partner. And really, you know, try and see it through. Do I want to do it? And do I feel excited about that prospect? Or does it feel like I am just sort of carrying this load on my back and seeing it through just because it’s a bit of a sunk cost fallacy, right? Absolutely just like that, just maybe a little bit more on the emotional level, because your entire identity has perhaps warped around it.

So it’s never an easy call. And I think there’s probably no combination of words that can convince you to take that leap. I think it’s your choice. It’s your job to decide for it.

But it’s important to remember looking back that no one thing can ever define you. Right. I mean, I think entrepreneurs really suffer from this because our startups, our ventures, are really like a big part of what we do. Our identities are tied up with it, intertwined with it.

But even in that situation like even today, if I’m four years into the startup, you know, we’ve made some pivots, I love it, I enjoy it. I hate it too, sometimes, like you should. It’s a mixed bag of feelings.

But even today, I think I try to remind myself that this is not the entire definition of me. I am a lot more than this. And so are you, right? As a PhD student, as a lawyer, as a politician, for that matter, you’re not defined by one, you’re not one dimensional.

So if you perhaps remind yourself of that, perhaps you’ll feel a little bit more at ease, entertaining the idea of closing this chapter down, or maybe just putting it on pause, and seeing what else is out there.

Cheryl:

I think that’s a great thing that really ties in with the theme of the Quit Story, the name of this series that we’re doing on the show. I really love how you talk about, we’re more than just our work, we’re more than just one facet of our lives.

I would love to take some time before this episode wraps up to talk more about the multi dimensional sides of you, I really want to dive into the music side, actually. But before we do that, I do have one more question I want to ask, related to, I guess you can call it quitting.

But I want to know more about your thoughts on failure in particular. I don’t know if any listeners right now are building something of their own and it’s just not working out. Whether it’s a side hustle, a business, a podcast, maybe you found a startup yourself, but it’s just not working out. What would you say to someone who might be at that crossroads?

Shubham:

It’s difficult to come to that realization or even that feeling that something’s not right. It’s a difficult feeling to confront. I think in the past, I did not have a good relationship with failure. I don’t think most of us do in this part of the region, in this part of the world. There’s feelings of shame associated with it.

When you entertain the idea of quitting this, you wonder how you’re going to answer people. People are going to ask you questions. “Oh, but you spent so much time on doing this, and now it’s over?” These are the thoughts that you play with. It’s not easy.

And I think the reason is that the fact that it’s not easy, is all the more reason that you need to face those feelings, you need to work through them, and you need to build a healthy relationship with failure.

So if you’re at that point, I think it’s really important to remember that the best person to make a judgment call on this, is you, especially if it’s your venture, right? You can take advice from people, you can hear them out. But you know this thing better than anyone else. You’re the one who’s put in the effort, you know exactly how much effort you’ve put, and you are the best person to measure the results of it as well.

It helps to have a bit of a wider perspective in the sense that measuring success is honestly a little bit overrated, I would say. Because we usually measure it, especially if it’s a venture with either how much money you made or how big of an impact you had, on the outside.

You almost never wonder what impact it had on you. What did you gain out of this experience? Perhaps you failed, but did you learn something? And the answer almost always is absolutely you did. You must have picked on so many things going through this experience. Just going through hardship in itself, it strengthens you in a way that you can’t really quantify.

I know for a fact today that regardless of whatever happens in my current career, I can always go back and work for a big company. And be better than most software engineers, probably really good, if I had to take a guess. And I would probably do it comfortably. You know why? Because I’ve been through shit here and that has hardened me.

So if you’re faced with that kind of difficult decision of labeling this venture as a failure, which I do think has a lot of negative connotations to it, maybe you want to pick a different term. Experience, or just failure. I think I’ve come to terms that it’s not a bad word. It’s not a bad word at all.

And if you’re faced with that kind of decision, it’s important to sit down and really, really understand what the experience has been like and what impact it had on you. If you can say that you’re walking away right now with something bigger than what you expected, or something that you can’t measure, then it’s worth it.

Cheryl:

This is exactly why I want you on this show. Precisely what you just shared right there, I think it really is. Even the word “quitting”, the word “failure”. It just has so much like… People just frown upon it, when they first hear it as like, oh, they quit. They gave up.

But honestly, it takes courage to even quit, or to acknowledge that you’ve failed it, that alone takes courage. And as you said, you must have learned something that will shape you for the years to come. You must have gone through something that will really influence what you do moving forward.

So it’s not like it’s wasted. But it’s how you look at it and the language you use to describe what happened. It’s like, okay, you went through this chapter of your life, how do you want to tell this chapter of your life?

Shubham:

Yeah. And, you know, just like, some thoughts that are coming to my mind right now.

This sort of feeling or this sort of unhealthy relationship with failure, I really do believe it’s largely cultural. It’s not you who has arrived at this confusion or this kind of feeling. It’s the family you grew up in the society that you grew up in.

Because you compare it to, let’s say, a country like America, right? And you see people there celebrate this iterated process. They’re like, okay, you’ve done some real shit. You know what you’re talking about. And it’s so bizarre almost, to see this being celebrated in especially the startup ecosystem. You hear about founders who quit college, who got into Stanford, and then they quit. And that’s like a badge of honor.

And it’s so interesting. I think there is actually an active program by the Thiel foundation. Peter Thiel and his foundation where they actually pay students to quit college.

Cheryl:

I heard about this!

Shubham:

Yeah, and just work on something that they want to work on. I feel like that is exactly the kind of encouragement or motivation you need to break the mold.

Support you need from the larger ecosystem that you’re part of, just so you build a healthy relationship with failure. So it’s important to remember that if you’re feeling this way, it’s probably your social programming, rather than there being a lot of substance in it.

Cheryl:

I love that. I love that. Speaking of culture and social programming, I’m just curious now, just kind of looping back to earlier in the conversation. So nowadays, I’m curious to know, how does your family view your current career?

Shubham:

Yeah. I have to say, I think they were supportive of my choices along the way. I don’t think they understood it. I think it was foreign to them. It was new to them. I come from a family who mostly played very safe. I do have an elder sister who’s been very rebellious and she always did her own thing. So I had a bit of like, precedence that way.

But I would have to say kudos to my parents, for never once like, doubting it. Doubting what I was doing. I think they had some genuine concerns at points which they presented in very respectful questions. And I answered them.

Today, I think they understand it a lot more. Also, I think I’m at a point where at least I can sustain myself. Perhaps I’m not earning as much as my peers. But I’m not out on the streets. I don’t need help. So they understand it a lot better now.

And having talked about it in length, from different perspectives, has also opened up their worldview about how the world works. Because they come from a very different world. Back then I think, specially in India, it was a lot more basic living getting by kind of an attitude.

And today, it has completely shifted. So I think they understand a lot better. They’re like, “Okay, we don’t really know exactly what you’re doing, or what it is that you’re building and what are people paying you for.” But they’re a lot more supportive, and they understand it from a distance.

Cheryl:

I love that. I think that reminds me a lot of my parents as well. I’m an only child. My parents still don’t really understand podcasting.

My dad, last year, last Christmas, actually, he said, so you just talk on the Internet, and you make money on the Internet? And I was like, Yeah, let’s just say that. Okay. That’s the extent of their understanding of podcasting, let’s just say.

Music, Singapore and food: Making time for non-work interests and hobbies and being a life-long learner

Cheryl:

So I think now that we’re starting to near the end of our conversation, there were so many helpful insights that you shared today.

I want to just make a little pivot and talk about music. Oh, because that was something that must have been a big part of your life at some point. What does music look like in your life today?

Shubham:

This is a little bit more recent, I think, a few months back, I made a very conscious effort of going back to music as a student. Back in India, I think when I was 13 or 14, I started learning music, very specifically, Indian classical music. And there was a great Institute for it called Gandharva in Delhi, and they had a great center there. So I just went for it.

Once again, I have to thank my parents for this push. In fact, they were the ones who encouraged me. They were like, yeah, studies are good and fine, but explore this side as well. So I think I studied it for about two years and I have very fond memories of those lessons.

They were almost a saving grace. Through what otherwise was a pretty shitty schooling experience, I would say. Because it’s just crazy, I think, the amount of competition you’re forced into, especially if you’re half good at studies. There’s suddenly so much expectations on you. Like this is your path, buddy, you gotta get those marks, gotta get those grades.

Music at that point was almost an escape from that craziness into something that was a lot more just an experience rather than a goal. So I have very fond memories of it and the only reason I stopped is because I ended up moving to Singapore. I was fortunate to get the scholarship to do my junior college here. And I had to put an end to my life back in Delhi. That was I don’t know how many years back.

And recently, and this is, I think, a bit of randomness as well. That happens in life. I was on Facebook, I don’t know. Don’t ask me why. I am not on Instagram, but I have a Facebook account. And I guess, you know, once in three months I check in to see what’s there. That’s the extent of my social media. I think that’s gonna be a joke later on…

So I went back on Facebook, and I saw an update from my music teacher back then he was like, I’m taking online classes, please reach out if you’re interested. And I was like, let me do that. So I reached out to him. We connected after so many years. And I was like, this is it. I’m just not not even going to think about it. I’m just going to do it. Just once a week. Music lesson. Going back to your roots, in some sense.

And I think that is the most active sort of musical part of my life these days. It’s once a week. I take this lesson, most of the other days I’m practicing. I’m trying to understand it better. Just being a student, again, is such a great feeling.

Otherwise, I like just actively participating in music in general. I ended up finding this group on Meetup, which is like a free jam, sort of thing. This dude who moved here from Hong Kong a few years back, he was like, I used to do this back in Hong Kong, I went to Hong Kong, I want to bring this concept to Singapore to get people together. You don’t have to do an amazing job. Just jam. And so I connected with them. I do that once in a while. And I think that’s pretty much the extent of music right now in my life.

Cheryl:

So does everyone play a different instrument? Yeah,

Shubham:

Yeah. So this is more of a traditional sort of a band setting, you’ve got like the instrumentalists and you can you can, you know, same or you can play things. You can switch around, it’s a very free sort of concept. I like it.

Cheryl:

I see. Yeah. Okay. So cool. Okay, so as we start to wrap up today, I’m just going to ask you a few miscellaneous, fun questions. And I’ll say, so besides classical Indian music, what, what do you listen to?

Shubham:

What do I listen to these days? Well, that’s a question that doesn’t have a straight answer.

Now I listen to I think all sorts of things. I don’t have a very specific taste in music. I enjoy everything from rock, to sometimes blues. I like a little bit of slow music here and there.

I can listen to Bollywood. That’s how I grew up. It’s familiar to me. I don’t, these days so much. But every once in a while, some of my friends would force me to listen to this song because it’s just so amazing. Like, yeah, that is really good.

So it’s a little bit all over the place. It depends on my mood, in the month, or in the year or where I’m at in life. I think there’s music for all sorts of emotions or occasions that find you.

Cheryl:

Awesome. I see. Okay. Rapid fire miscellaneous slash fun question number two. What was your biggest culture shock when you moved here to Singapore?

Shubham:

Wow. Culture shock. I think it was just so safe. Now, it’s shocking to me a lot.

Cheryl:

Yeah, I agree.

Shubham:

Like going out at night at 3am. No big deal. You just walk down the streets. No threats.

You know, leaving your wallet on the table. As you sit down and you eat, you leave your phone and wallet on the table.

Not leaving your door locked. Like, I should probably not be saying this on a public forum. No, I mean, I lock my doors sometimes.

But these kinds of things. Things I was like, This is crazy. How? Yeah, that’s the first thing that strikes me, which is a very positive and underrated thing about Singapore. I’ve had a love-hate relationship with this place, which has, I think eventually morphed into respect and love more than anything.

These are the kinds of things that are very rare around the world.

Cheryl:

I agree. I really resonate with that. Yeah. Okay, final question. I’m making these questions up on the spot. For the listeners. I’m literally making these questions up on the spot. And there’s no notes by the way.

Shubham:

So crazy. Cheryl, I was just gonna, I was thinking this, but I might just say this, because this is the most improv conversation that we’re having. I see you don’t have any notes on you. You didn’t send me any questions or thinking points. You’re like, we’re just gonna have a chat. And that is, I think, pretty cool. I think that kind of authenticity and approach is very unique.

Cheryl:

I really hope the audience can just feel the sincerity in your sharings and in your story. I am glad that we were able to do this so casually, without prompts or scripts or any notes. Like literally, there’s nothing. We’re just looking at the Zoom video right now. I really hope the audience can feel the sincerity in the question and in your sharing as well.

Okay. Final question. Favorite place to eat in Singapore. I’m asking for myself, by the way.

Shubham:

That’s a tough one. I must admit that I am not a foodie. So take my recommendation with a pinch of salt. I recently went to this place called Herbivore, which is a vegetarian Japanese restaurant.

Cheryl:

Okay.

Shubham:

That is very ironic. I know. Yeah. But I think they do an amazing job of it. They’re actually quite nearby at Fortune Centre. And I just had a very spiritual experience eating there. The food was so good. I overate. Which I usually don’t. By the end of it, I was just like, this is it. I could die right here.

Cheryl:

Okay, so dish that you would recommend me to order when I go. And I’m going to message you after I go.

Shubham:

Sure. I had the life changing dish for me there was these bacon wraps. Obviously it’s not real bacon because it’s a vegetarian place. But I’ve heard a lot about bacon from my meat eating friends, they like it. You see the face of God when you eat bacon. I don’t know, either, because I’ve never tried it. And I don’t know if it’s clearly not bacon, but it tasted so good. It really was great. So I’m just gonna say that one for now.

Cheryl:

Okay, well, you will probably hear from me soon after I go eat those bacon wraps.

Shubham:

Veggie bacon wraps.

Cheryl:

With that, Shubham, we are at the end of our conversation for today. So before we wrap up, I know you don’t have social media, you’re not active on social media. But two questions.

Number one, where can people find you? After they listen to the show and they want to connect with you? How can they get in touch with you?

And could you tell us a bit more about how people can potentially work with you?

Shubham:

Yeah. So yeah, that’s true. I’m not really big on social media, not really out there. But in general, you can find me on LinkedIn, by my name. And just drop a message in the connection request, I’d be happy to connect with you.

Cheryl:

It’ll be in the show notes people. Yeah.

Shubham:

I think I should do a better job of this though. Like, in the future. I’ll think about it. Thanks for planting that seed in my head.

How could I work with people?

So one thing that I want to do more of is, if you’re early in your career, you’re thinking about a lot of things, especially if you’re in tech, because that’s the field that I know best. And if you want to just talk through it, talk about career or what you want to do, I’d be more than happy to have a chat with you and just think it through with you, be your sounding board. That’s something that I think I’ve been meaning to do a lot more of. So I would be happy to help there.

Oh, one more thing. If by chance you happen to run a Shopify store, we’re here to help. That’s Airboxr for you. We can help you understand your data in a way that would probably take you two to three data analysts to get the hang of.

So if you’re anything in e-commerce, Shopify, feel free to reach out to me. We’ve got tons of things that you could just take with you.

Cheryl:

Great. That was exactly what my question was. Awesome. So all the relevant links and information will be in the show notes below. Whether you’re listening on a podcast platform or on YouTube, you will find all the necessary links below.

With that, Shubham, thank you. Thank you. Thank you. Thank you for being the first guest ever on this brand new series. It was a delightful conversation. I am so grateful that you’re here.

I’m so grateful that we crossed paths and that we were able to get to know each other a little bit more. And I got to know more about your story, your perspective. And now we’re here. So I’m so grateful for that. Thank you so much.

Shubham:

And thank you for having me. I think I really enjoyed this conversation. Thanks a lot.

Cheryl:

So with that, everyone, thank you so much for listening, and I’ll see you in the next one. Bye, everyone.

P.S. And if you loved this episode, you can 1️) Leave a 5-star rating and an awesome review, and 2️) Share the episode on your social media.

About Shubham

Shubham is the CTO/Co-founder at Airboxr – A data automation platform for DTC brands. He loves to build software systems and applications following the lean methodology. Outside of work, he’s micro-ambitious about many things – music, travelling, writing, chess, psychology, philosophy.