Siddhartha Gunti


I was sent to boarding school at my 8th standard. Not the fancy boarding school you see in a Karan Johar movie. The one in a remote village where my clothes were stolen on day 1.

It's been 17 years on the run now. Over these 17 years, life has always been a cycle of two phases.

First phase is when a big change moves me from a city.

Sometimes for education. Sometimes for work. Whatever the reason, what is constant is that I get homesick. And when I get homesick, I am the worst cry-baby. The pop-culture reference would be Sheldon in The Big Bang Theory. Physically, it is me crying, ranting and throwing tantrums. Emotionally, the homesickness and anxiety made me question if something was wrong with me.

Before I went to the boarding school, I was a topper from a remote village. On day 1 at the new school, I realized I was no more the first ranker. I also got bullied. Reporting the bullies to the headmaster isn't as much the correct answer as I thought it would be. It just made things worse.

The second time was when I took my first flight to Canada for an internship. I landed at the doorstep of a Facebook friend to save rental money. Only to realize the "friends" I made were 10-15 years older to me. And the "room" I rented was the floor of their fireplace. 

The third time was when I joined Goldman Sachs as a quant analyst in Bangalore. Just out of college. Reporting to someone, reporting on time, and maintaining decorum were too new and too sudden. Walter-mitty-ing during work was a real thing. "work" life felt like an alien concept. What's worse was no one talked about how alien it is. I wondered if I could ever "work" the way others did.

The fourth time was when I went to Singapore to start up. Before I realized what was happening, I was sprinting a startup, failing spectacularly and living an unhealthy lifestyle. Looking at all the success stories on Twitter, I used to question- How is everyone else doing it so easily? How are they not running to their homes and cuddling up in their mother's embrace? Which is exactly what I did, by the way.

It's not that every change is bad.

Almost every change that I made was well-calculated and self-inflicted.

I moved to a boarding school because I had outgrown the teachers of my village school. It’s highly likely that my teachers prayed a lot to humble my ego. (Needless to say, their wishes were granted quite generously). Seeing me upset, my parents offered me the option to return to my village school. Despite the bullying, I chose to stay because the new teachers were really that good.

I got the Canada internship by sending personalized emails to 100s of professors around the world. The thought of entering a new country without money, phone or fear didn't cross my overly curious mind. That is, until I saw my Facebook friend's impressively generous fireplace.

And there are changes that are temporary.

I knew Goldman's life wasn't for me half a year in. But I kept that life going until I figured out what next to do in life. It took four dating-app like startup failures over 6 months to decide my next step. I finally joined an early-stage startup to build my startup toolkit.

I recently got married and moved to Singapore (yet again). 2 months in, and I knew Singapore was not the place for us. But internalizing that decision and wrapping it up took 6 months.

Through it all, what I found beautiful is the second phase of the cycle—going from homesick to finding a home.

Each time I went through a change, I learned more about myself. But importantly, I found more of my people. People that get me.

Finding my people made me realize there's nothing wrong with me. They also helped me amplify what I am good at.

Going through a shitty boarding school made me realize I love math. I still remember waking up at 4 AM to go through a few more problems. None of it was required for my exams. It was just something I love(d) doing.

The internship in Canada gave me a flavor of research. The experience living in another country made me realize how small my view and perception of the world were.

Getting out of the trading world at Goldman made me join Headout as the first engineer. It gave me a chance to learn and love product building (the side benefit is I found my wife there).

Sustaining startup life in Singapore pushed me to find a co-founder and build a long-term startup. Now I am co-founder of a 5-year-old successful bootstrapped SaaS startup.

Change is scary. Change makes me anxious. But change is also what is constant in life. The current change got me (back) to Delhi, India. :D Here's to hoping I survive Delhi winters.

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