Share on:

Angel investor Kunal Chowdhry on his philosophy and the biggest problem in the world today

The CEO of Apollo Investments reflects on the start-ups he's invested in and why failure is an important metric.

Kunal Chowdhry can tell you the names of almost every song on the last three Ariane Grande albums. It’s quite the feat considering Chowdhry is 42 and runs Apollo Singapore Investments, a multi-asset-oriented family office. He jokingly blames his impressive musical knowledge on his teenage daughter.

“I have been married for almost 20 years to my college sweetheart and have three kids and three dogs, so every day is filled with excitement and drama of one sort or another. I’m sure all parents reading this can relate!” says Chowdhry.

We chat with the angel investor on his investing journey, his philosophy and the most pressing problem in the world today.

(Related: How the Amarasuriyas run Singapore’s oldest family business, BP de Silva)


“I realised that we are all so conditioned to accepting only success that failure hits even harder. Most start-ups fail, so it was probably only a matter of time before I became acquainted with this metric! Failures are a necessary and often valuable rite of passage that makes us value success and all that it brings.”

Angel investor Kunal Chowdhry explains why failure is necessary for success

Tell me a bit about yourself.

I come from an entrepreneurial family. My father founded one of India’s largest IT companies, HCL and I spent my formative years in Singapore while my dad was setting up the South-East Asian division of his company called Far East Computers. I returned to India to complete high school but have since lived in London, Spain and the US before finally coming full circle and returning to Singapore in 2010 after completing my MBA at Harvard University. The entire world was in the middle of the Great Financial Crisis back then and I was of the firm belief that the decade ahead would be Asia’s time to shine, so it was a straightforward decision for me to return here. Singapore is also a great place to raise a family, which made my decision to return even more appealing.

I am passionate about start-ups and the energy and ideas these entrepreneurs bring. I have been an angel investor for over 10 years.

When you invest in a start-up, what do you look for?

I look for a couple of things. First, the idea needs to make sense to me and be scalable. Ironically, the simpler the idea, the more appealing it is to me. If you think about it, most of the well-known start-ups of the past decade solve basic human needs – Uber (transport), Airbnb (accommodation) and Tinder (companionship).

The founding team is very important as well. I spend a lot of time trying to understand the motivations of the CEO and their team. How did they come up with the idea? What drives them personally? I think it’s important to have a long-term vision in mind. The CEO also needs to be open to being mentored.

My family office has an investment committee, which vets every investment decision. And yes, sometimes the committee has made me change my mind about a particular investment! It is super important to have a system of checks and balances in place while investing, otherwise you end up inadvertently reinforcing subconscious biases.

Which are some of the more successful start-ups that you’ve invested in that you’re proudest of?

There are a couple of start-ups that I am very proud of. The first significant investment I made was in Gusto, an HR Tech company that deals with payroll and benefits for SMEs in the United States. Its latest round valued the company at $9.5 billion. Impress.ai, a Singapore-based start-up uses AI-based chatbots for recruitment. Its technology allows companies to automate the hiring process and find the right candidates faster. TrustSphere, a relationship analytics company, was the subject of a Harvard Business School case study and has developed technology which allows you to measure the level of diversity and inclusion in an organisation. It’s easier to measure diversity, but inclusion?

One of my more left-field (at least for me!) start-up investments has been a company in the UK that I set up with a friend from Cambridge called Cafe Torelli. We partnered with the son of the Costa Coffee founder to set up a series of retro-futuristic vans all over London selling gourmet coffees, gelatos and panini. If anyone reading this is planning on making a trip out to London, please drop by our airstream outside Paddington Station in London and let me know what you think of our coffee and gelatos!

Kunal Chowdhry has lived in London, Spain and the US before finally returning to Singapore after completing his MBA at Harvard University.

Kunal Chowdhry has lived in London, Spain and the US before finally returning to Singapore after completing his MBA at Harvard University.

What enormous problems of the world are you personally passionate about that you’d like to solve?

I am always disheartened by the sacrifice that working women have to make in balancing their role as mothers and career women. While many have been able to bridge this divide successfully with the help of a very committed support system, quite a few others haven’t been as fortunate and have had to leave the workforce to focus on child-rearing during the most important working periods of their lives.

When they return, they are subconsciously marked as ‘part-time workers’ or uncommitted workers because they want to go back home and put their kids down to bed at night. This is sexism. From a purely economic point of view, the global economy loses highly intelligent and capable women if they leave the workforce.

At Apollo, at least 50 per cent of my analysts are working from home (WFH) full-time mothers. I started this practice back in 2015, well before WFH became the default mode during the pandemic. I believe that as long as the work gets done and meets deadlines, I don’t care where it is done and what time my employee works on it.

I would like to see companies around the world create policies that are more working mother-friendly – working from home, job sharing, flexible hours. The pandemic has shown that the global economy did not collapse with people working from home!

Could you share with me some of your failures?

I have invested in several companies that didn’t make it despite the best intentions and efforts from their leadership and investors. One company whose failure surprised me was a UK-based start-up that created an app to pull critical data from a person’s LinkedIn profile and put it into the form of a crib-sheet for meeting preparation.

Similarly, a deep tech company in the US I invested in was purportedly the first company to offer Fully Homomorphic Encryption (FHE) as a service. Sadly, it didn’t take off. These things are part and parcel of an investor’s journey.

In fact, there was a period a couple of years ago when three of my portfolio companies went belly-up all within three months of each other. I spent a considerable amount of time questioning myself. I realised that we are all so conditioned to accepting only success that failure hits even harder.

Most start-ups fail, so it was probably only a matter of time before I became acquainted with this metric! Failures are a necessary and often valuable rite of passage that makes us value success and all that it brings.

(Related: Leadership lessons with Ruchdi Hajjar, partner at SGMC Capital)

What lessons have you learned from these failures?

Never assume that I am the ideal customer for any product or service being offered by a company. Just because I think it sounds amazing or terrible, doesn’t mean the rest of the target market feels the same. I made this mistake earlier on in my career and it is what led me to set up an investment committee within my family office to vet all investments on their individual merits.

Many have asked me whether I would ever invest in a company started by someone whose previous start-up failed. The answer is – it depends. If I feel the founders have learned from their mistakes and know exactly what went wrong the previous time, I would have no hesitation in investing in them. In addition, if they made mistakes on someone else’s dime, all the better! It means that they will be even more careful with my investment. Failure on its own isn’t bad. It’s the refusal to learn from that failed experience that irks.