Insights Into Investment Journey of an Angel Investor

Preeti Karna Preeti Karna
May 27, 2022 11 min read
Insights Into Investment Journey of an Angel Investor
StartupTalky interviewed Kunal Chowdhry, Global Angel Investor to know about his investment mantras, investment methodology, and how he judges founders and startups to make an investment decision. Get insights into his journey of Investment in Startups.

Tell us about your background and how you got to where you are today. What keeps you motivated at whatever you do?

I was born in India and spent the formative years of my life in Singapore. I graduated from the University of Cambridge and returned to Singapore after completing my MBA at Harvard University. I have worked in both consulting and the financial services industries and now run Apollo Singapore Investments, a multi-asset-oriented family office. Apollo invests in a range of different asset classes including startups in India and South-East Asia, particularly SaaS companies in the areas of HR Technology and Blockchain.

I come from an entrepreneurial family, with my father being one of the founders of the HCL group so I have lived and breathed the ups and downs of an entrepreneurial journey since I was young with exposure to new technologies as they were being developed.

I am married with three kids - a girl and two boys. I love keeping abreast of new trends and enjoy interacting with young people because they generally have their pulse on the ground and are able to offer a fresh perspective. Keeping this in mind, I believe in a mentorship-based model of investment, whereby I make mentoring a key component of my investment methodology. I also mentor University kids from the perspective of both career and life advice and I have to say that I find them very inspiring. The desire to constantly learn and refresh myself intellectually is what truly motivates me. For example, I spent the first year of the pandemic educating myself about crypto, an area I knew nothing about previously. I am inspired by a number of entrepreneurs who started companies in areas of business they knew nothing about but were able to learn on the job and ended up creating products and services that changed the world. You don’t have to look beyond Elon Musk as an example of such a visionary.

I am passionate about travelling and collecting art. My wife and I have travelled to almost 45 countries and we usually pick up art pieces/souvenirs which are representative of the country. One of my favourite pieces is a small statue made of lapis lazuli, which is emblematic of the large statues on Easter Island, Chile. I also love tennis and you can usually find me at a Grand Slam tournament with my daughter as she is also a fan of the sport. Thanks to my kids, I am also a big fan of K-pop and have seen BTS, EXO and Blackpink in concert!

How did you start your professional journey and what do you do now?

I started my career as a consultant with Accenture in London and even spent a year in Spain which has been one of the highlights of my life thus far! I love Madrid and even learned Spanish during my time there as my entire team was Spanish and I had no choice!! After graduating from Harvard, I moved to Singapore to work directly for the CEO of DBS Bank on special projects in Singapore and around South-East Asia.

I now run my family office from Singapore. As a full-time investor, I am responsible for obtaining good returns from all our investments across a range of asset classes and geographies. This allows me to take a macro view. It feels great doing what I do because I simply love to join the dots between macro events, politics and their impact on investing.

Share any story on a tough day at work and how you pushed through.

A tough day for me would be waking up to see that my portfolio returns have dropped significantly due to a major market event. I am currently living through this as we speak, as the combination of war in Ukraine, high inflation globally and monetary tightening by central banks globally has made things really tenuous from the point of view of an investor.

The one and the only thing to do in such a situation is to stay calm. It’s important as an investor to plan for contingencies but you can’t always plan for 'black swan' events such as Covid. While it’s important to stick to a plan, it is also imperative to be able to pivot should the key assumptions underlying your strategy turns out to be invalid in a new market scenario.

If one day I wake up and be you, what are the things that I will do?

If you were to one day wake up and be me, you might have a bit of a shock as I am usually woken up by 3 large Labradors every morning who seem to know when my alarm is just about to go off! I generally wake up at 7 am to see my kids off the school. I spend the next several hours reviewing global news and responding to emails and reviewing business pitches and investor updates. I work out at least 3-4 times a week before lunch and generally schedule meetings post-lunch until early evening. I tend not to work between 7-9 PM as I eat dinner with my family and enjoy putting my kids down to bed. Post-dinner, I spend a couple of hours on calls with Europe/US before unwinding by watching Netflix before bed!

How and when did you start your Investing Journey?

I am passionate about startups, given my entrepreneurial upbringing and always knew that I would be part of the startup ecosystem. I have worked as an intern in start-ups while I was an undergrad in the UK and also during my MBA in the US but I always felt that my forte lay in investing. I have been an angel investor since my late 20s so almost 15 years now! When the Indian Angel network was first founded, I had the opportunity to join and it ended up becoming my first exposure to the world of startup investing. Since then, I have invested in close to 50 start-ups in India and South-East Asia. I am always on the lookout for new business opportunities and most recently invested in a coffee cart business in London.

What kind of startup do you invest in? Are you a sector or geographic agnostic? What is your typical investment horizon, return expectation, and timeline?

I am always on the lookout for that one idea than fulfils the need of any big community as a whole. An idea that can better the lives of many because of its practicality or its use. I primarily focus on HR tech and blockchain start-ups. However, that said, I also invest in other industries such as FinTech, Consumer retail, Internet, and deep-tech analytics. My typical investment horizon would be 5-7 years. My return expectation is to always aim for 3-4 times my initial investment but that’s easier said than done as an early-stage seed investor!

What is your investment mantra? Please share the metrics you track and why those are key according to you. What do you look for in a founder?

My investment mantra is simple - know the founders’ purpose and understand their motivations. Also, it matters to me whether the business philosophy can be easily explained to any layperson. As such, I don’t tend to invest in overly complicated businesses such as biotech as I don’t have a background in this industry. I would, however, not be opposed to investing in a biotech fund, run by experts who understand the space well.

I have five metrics that I usually go by:

  • customer growth
  • top-line revenue
  • core operating expenses/cash burn
  • runway
  • alignment with the founders’ strategic vision.

What and how do you judge the Founding team before writing a cheque? What are the key challenges you face as an investor before you sign the cheque?

I love founders who are confident, focused, clear, strategic, and yet versatile enough to turn things around or pivot when their ideas are not working. Not just the founders, but the founding team is also very important. I look at the entire team to examine the competencies of senior leadership. As such, I always insist on meeting not just the founder but also the entire team before making any investment decision.

What are a few signs which make you trust a founder and find him/her Competent? What are the signs? How much does a degree from Tier I college matter?

Education is not as important as vision. Education definitely opens the door, but at the end of the day, it’s the founder’ innate strengths and vision which carry the day.

I love founders who put their own money into their start-ups, no matter how small the amount is. This shows that the founders believe in themselves, which is a key criterion for success in my book!

What is a warning sign for you when investing in a startup?

Some red flags would be inflated expectations of performance without evidence to back it up. For example, a financial projection of $100M in revenue by Year 3 when the company is making $100,000 in Y1! And yes, I have seen many pitches with these numbers!


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Apart from Investment, how do you help startups?

I believe in a mentorship-based model of investment, where I meet with the founding team on a monthly basis to review key metrics and discuss strategic decisions. I have often been asked to help vet potential candidates for senior leadership positions in some of my portfolio companies. Also, I have developed a strong network over my two decades of professional experience so I am able to make connections and warm introductions to other investors, potential customers or even potential partners in other markets.

Please share a couple of learnings which make your professional life easy and productive.

Learning from experience, I find things are easier if we just go directly to the top and not waste time with middle management. For example, earlier in my career, I would try and connect to someone at my level in a company so as to “not go over anyone’s head”. However, I have since found out that decisions are rarely taken by anyone in middle management and sometimes the message just gets lost in translation.

This is especially relevant in the Asian context, where words from senior management carry more weight and gain more attention. If you can get a message sent down by the CEO, you’d be amazed how quickly action is taken!

Another life hack which I learned a long time ago is to just ask because the worst that can happen is that you will be told “no”. But if you never ask, the answer will always be “no”. I learned this as a teenager whenever I would ask the check-in manager at the airport for an upgrade from economy to business class. Most of the time it wouldn’t work, but I did end up having a success ratio of almost 20% which is pretty good, especially as one of them was on a 17-hour flight from Santiago to London! This is equally valid in the business world. e.g. asking for more time to pay or asking for an additional discount.

When do you think it is the right time to raise investment for a startup?

In my experience, the fund-raising runway takes about 6 to 9 months. The best time to raise funds is when you have at least one year's of runway left. In my opinion, if you leave it too close, you may end up securing financing at too high a cost – in terms of interest, equity or even loss of control of your company.

How can we support/ enable entrepreneurs in Tier II and Tier III cities?

We are seeing more and more startups from Tier II/III cities but they need the right platform to showcase their capabilities. We can tap into our collective networks and link them up to investors, customers and markets not just in India, but across the world.

Some specific actions that can be taken include:

  1. Mentoring the founders thereby enabling them to better their businesses
  2. Organising pitch sessions for the startups to market their ideas to VC and angel investors
  3. Working with Govt bodies and private foundations with a vested interest in entrepreneurship to private grants to startups.

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What are the things that can help the founder retain maximum equity while negotiating with an investor?

I would suggest that in the early stages, particularly for seed rounds, founders should take investments in the form of convertible notes, rather than direct equity. This ensures that founders retain control for as long as possible, as usually in the later stages of funding, founders would have to give up a percentage of their equity stake.

What is one thing you wish Indian founders and VCs understand which will make the Indian startup ecosystem a much better place for startups?

I have seen inflated valuations in the ecosystem for some time, particularly in the last 5 years. Founders’ valuation expectations have become unrealistic. They are too eager to have a $ 20 million valuation based on 4 pages of a PowerPoint deck but there are insufficient revenue and customer numbers to back the valuation. I am of course referring to brand new startups which sometimes don’t even have an MVP (Minimal Viable Product) yet are asking for a $20 Million valuation!

One learning that you would like to share with founders who are looking to raise funds?

Raising funds in an economically volatile market is challenging. Investors are more cautious with where they put their funds and usually impose more stringent terms and conditions, compared to a bull market where financing is more readily available with fewer strings attached. Adverse economic conditions will have an impact on fund-raising initiatives. It not only takes longer but also entails several rounds of negotiations.

What are a few sectors you think would be hot in the upcoming year?

Web3 incorporating Metaverse, gaming and blockchain are some interesting sectors not only for the upcoming year but also for the next 3-5 years.

How do you keep track of what you have to do? What are you currently reading, or what do you recommend?

I like to stay abreast of current events because they provide crucial information for all my investment decisions. I read not only more traditional publications such as The Wall Street Journal, Financial Times and the Economist but also spend a lot of time on Twitter as it gives me access to information across a range of my areas of interest – from crypto analyst research to movie box office numbers, from macro data on the economy to the latest events in sports. I truly believe that the world of investing is very interconnected with lessons that can be drawn from a range of industries. And sometimes, it’s fascinating to realise that hype doesn’t always result in good business performance. Take a look at Netflix for example – just 8 months ago or so, everyone was talking about the TV show “Squid Game” and how it was proof that Netflix’s high-cost content acquisition strategy was working. But here we are a few months later and the share price is down 70%.

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