In this interview, I explore experiences in business leadership, ethical dilemmas, philosophical applications, and personal growth strategies with an insightful industry professional.

Can you share an experience where active listening and open-ended questions helped you understand a complex issue more deeply?

After moving to America (from India), I worked roughly a dozen blue-collar jobs alongside my parents. This is important to put in context because while this was going on, my peers, both in India and the US, were saying things like, “I just got a job at Goldman Sachs!” and “Just got back from a shopping trip to Dubai!” - while both my parents and I were working minimum wage jobs to pay rent and put food on the table. My active listening and questioning skills were molded by necessity rather than born out of curiosity.

In parallel, I struggled through university and finally lucked my way into a job at one of the big companies, Shell! But there was a catch: I was to show up at the oil refinery every day at 5 AM. This meant I had to wake up at 3, since it was at the very opposite edge of the city, at the Port of Houston. This also meant I had to change how I spent my free time, stop going out the night before, etc. - but I was ready to give this opportunity my all.

At this “big boy white collar job at the refinery”, like all newcomers, I was given tedious tasks nobody wanted. I measured stairs for compliance, installed whiteboards that nobody ever used, and made reports that got the messenger shot, the usual. I did my best and was soon promoted to bean counter: I had to match the amount of oil we had on hand with what the computer said we had. In other words, inventory reconciliation.

I remember actively listening and asking (way too many) open-ended questions that some were supportive of but most just found annoying. I was often mockingly called “the scribe”, for example, for asking questions and noting down the answers in my notebook (reminds me of notes-shaming on Twitter, lol!). But this process has its upside: by repeatedly doing this, I eventually understood how the entire place worked! And not just on paper, I knew the mechanics and dynamics of each machine, which person did what, what problems each department had, which problems were unique to the refinery, and which ones were commonplace in the industry, you name it. It was like learning to speak a second language; it sounds like gibberish and one day you catch yourself speaking it - as long as you really listen and ask naive questions.

How do you approach decision-making in uncertain business environments?

When the path is uncertain, the approach becomes risk-based. There are a few things to keep in mind:

  1. Kelly criterion: optimal size of bet an investor (or gambler) should place to maximize expected value - developed by John Larry Kelly Jr., a researcher at Bell Labs, in 1956. In other words, split your resources into asymmetric fractals across time and space. “Hedge your bets” but dynamically.

  2. Path dependence: your path is not the sum of all paths. Maybe I’ll expand on this one in a future post but for now, I’ll leave it at this.

  3. Simpson’s paradox: individuals and groups may have opposite characteristics at their respective scales.

My personal experience of Simpson’s Paradox: weirdly, I benefitted from the FTX crash. Path dependence: the group has a different path than the individual, which have different paths from each other.

Can you provide an example of a challenging ethical dilemma you faced as a business leader and how you resolved it?

While doing oil inventory, I noticed this was an industry-wide problem - that inventory never matched the numbers in the computer. This was an ethical dilemma because it meant millions, potentially billions of dollars worth of accounts were being misreported. That had massive ramifications.

I resolved it by working on the problem until I fully understood it more than anyone else (to my knowledge), and making others aware of why it was such a big deal. This took infinite debates and conversations, but this was what got me funded to go fix it, and fix it I did! With AI before it was cool, in 2018. But then it got taken over by McKinsey people and the like, so now I work on other things. Feels good that I conquered it, though.

Can you share an experience where philosophical principles, such as existentialism or stoicism, helped you navigate a challenging situation?

Without knowing anything about it prior, I joined a DecafQuest class out of curiosity the day after quitting my job - seemed like the right time to look into the big questions, which I had never done before. I’m glad I did because I now have a basic working knowledge of a lot of Philosophy and Physics. It’s a great experience and the learning aspect is real - it’s surely one of the best investments I made.

The situation of purposefully quitting my job was quite challenging for me, but in retrospect, I prepared well and was lucky via circumstance to learn from everyone I looked up to and mimicked in my professional life. I owe big thanks to Joe Norman, Nassim Taleb, and Sahil Lavingia for amazing insights that are lifelong lessons worth their weight in gold.

How do you foster a growth mindset and encourage continuous learning among your team members?

Decentralize ownership and move it to the edges. Let everyone be their own boss as much as possible. This includes “letting them fail.” I learned this at Apple but applied it best at Shell.

Can you provide an example of a time when your team successfully adapted to a significant change?

When McKinsey people took over the oil inventory project I mentioned, which was near and dear to my heart, it felt like a significant change. It was like having a “professional CEO” given to a founder (something I only later learned was commonplace). Me and my team were being told it was an upgrade but everything about it felt like a downgrade.

We discussed it internally and came up with a weird strategy; we managed this change by open-sourcing our project. In other words, instead of hiding information, code, and subject matter expertise, we put it all out in public for anyone and everyone to use. This worked out because all the engineers I led went on to get amazing next jobs and the McKinsey consultants got to have their victory laps. Win-win. Best of both worlds. I managed this transition for about 6 or so months and announced that I will leave once the handover was finished. I even got to play VC for a bit, which maybe was their way of making me want to stay, but I thought it was incredibly boring and zero-sum so I left to do other things.

Later that year, while attending Real World Risk Institute, I learned that this experience of a nifty innovation being taken over by “professionals” was not a special case, but it’s how innovation has worked throughout history - and it’s the outcome new, useful things almost always face.

You can hear the more detailed audio version of this interview here: