My name is Shubham Gupta.
By any measure, I had a good life.
A dream job at a top-tier investment bank in Singapore.
A blessed life with every material comfort that I could possibly aspire for.
A wonderful family and amazing friends.
But there was something missing.
A nagging sense of void that left me feeling unfulfilled.
That is when I started my “double” life.
It started small. A quick fling here, a brief dalliance there. During commute hours, after office hours. One stint followed another until it became all-consuming. Then it gradually took over my entire life.
Before you start fantasizing that this was some nefarious clandestine activity, let me make it clear that what I am referring to was angel investing!
Making small investments as an early believer backing founders of seed-stage startups.
At this point, I must confess that I always wanted to be a founder myself.
Around a decade back, I discovered that many of my college mates were launching startups and becoming founders. As I watched their journeys, I felt that it was not just my calling but my destiny to become a founder. I reached out to a few friends and brainstormed a bunch of ideas but we didn’t eventually start up as we could not zero in on one that we were passionate about.
I was happy with my professional career but I wanted to be part of the India startup world too. So I went for the second best thing to becoming a founder — partner with founders and work with them in some meaningful way.
I quickly learnt that the only way founders will talk to you is if you have some skin in the game — if you put money into their company. That’s how my angel investing journey started.
The money part, though, was the least interesting part about angel investing. It was never about financial returns. It was always about talking to founders, about supporting them, about doing something for them. It was the adrenaline rush of chasing an impossible dream, of taking on unbeatable challenges, of shaping the world in your own vision. All this is of course what founders did — I was happy that they gave me a chance to join them on these adventures and witness their journeys first-hand at close quarters. It was a heady feeling, almost like being a “mini founder”.
But getting this chance to be an angel investor didn’t as come easily as one might believe. From the outside, investing, even as an angel, might often come across as an easy and even glamorous thing to do but I was a nobody, working in a bank in Singapore. Founders rightly asked why they should take money from me. And it is not even that I had a lot of money to invest. I could at best write cheques for $5,000 or thereabouts — money that I had originally saved towards funding my MBA (which never happened)!
Instead of being defensive about my small cheque, I decided to make it my calling card. I told founders that I will give them what that other “logo” angel investors cannot offer — time and commitment. I told them I will be with them on their journey, at every step. I will be the guy they can call and speak to for anything that they need. At any time of the day. I also made it clear that I was not an expert by any means but I mean well and that I will learn alongside them by investing my time as much as by investing money.
Founders were truly receptive — I had figured out my initial go-to-market! Since I invested only $5,000, the founders knew that I was doing it for the right reasons. On top of this, I was very proactive when it came to winning tough angel deals — when I started, it was almost unheard of for angel investors, much less one sitting in Singapore, to approach founders in India with investment offers.
I would work on my day job till 7 pm. On the long commute back home, I would work with portfolio founders in any aspect where I could lend assistance and proactively reach out to founders that I wanted to work with. Despite being tired from working the entire day, the infectious energy from founders made it easy for me to spend 8 pm — 11 pm working with founders.
Doing angel investing enabled me to learn two new skills over the course of six years. Connections and Counsel.
I am known as an “enabler” in the industry and that goes back to this time in my life. One meaningful way I could help a founder was by opening doors for them. I had founders asking me to help them get a customer in Southeast Asia or China or the US, or help them with a key hire. While many in the industry do introductions and networking connections, my focus was on making quality connections that would truly open doors.
The reason founders reach out to me and the reason I make connections that work is because I work hard at building authentic relationships. This has been possible, I realise in hindsight, because I am with the founders during their low times. Many founders who have gone to raise various funding rounds still call me when they need to talk something out or when they want non-judgemental feedback and suggestions. Sometimes they need help with co-founder relationships or with support while communicating a tough decision to the Board. I have been there with them through such tough calls.
By 2016–17, I had realised that this is my calling; I want to do this full time — interacting with founders, hearing new business ideas, helping founders and enjoying the journey with them.
That meant joining the venture capital world. Being a non-MBA, non-McKinsey person was not helpful and I got many rejections. I was fortunate to have an offer, but the VC fund wanted me to move back to India. I couldn’t do that as my then-girlfriend-and-now-wife was in Singapore. Sometimes in life you need to take crucial decisions and anchor yourself. I prioritised a family over my ambition and it has truly been a decision that I have zero regrets about.
Despite the VC rejections, I continued to work with founders passionately as ever as an angel investor.
In due course, I got married and in 2019 I decided to try again and reached out to Avnish Bajaj, Founding Partner at Matrix Partners. Avnish agreed to give me a seat at the VC table at Matrix. Even though she thought it was a crazy move, my wife was supportive to make the big shift back to India so I could join Matrix. I am very grateful to Matrix for giving me that break and my wife to support me in this big step.
But while my stint at Matrix was great, it still left me short of one step — I was a VC but not a founder.
In August 2020, I got a call that changed my life again.
Girish Mathrubootham and Manav Garg called me to broach the idea of Together Fund and invited me to join them.
While they said they liked the work I have done, what stood out for me was their assessment that I was in venture capital for the right reasons — to work with founders and help them. To be fair, I am an ambitious guy as well, but that ambition is tied to my passion to support founders.
When I got that call, I knew this was it.
Personally, Together has enabled me to become both a VC and a founder at the same time — the best of both worlds and the best outcome that I could dream of. What started as a hobby many years back has now become the most fulfilling thing in my life — a journey from banker to angel investor to not just a VC but also a founder. A chance to create something everlasting.