Don’t Underestimate the Power of Serendipity


When asking successful investors or entrepreneurs the reason for their success, the answers might be all over the place – skill, team, execution, strategy, IP…but few will mention what is often the key or at least big catalyst for the outcome – luck! It’s basically being at the right place at the right time. The inverse is also true – wrong place at the wrong time can turn what looks like a billion dollar outcome into a write off (yours truly has been through that roller coaster as well). But, my better half has a “glass half full” approach to thinking about the above. Her thought is that people make their own luck or bring about positive circumstances. That is the crux of this article. I am starting to become a believer in the notion that people can influence their own good fortune, in their personal and professional lives. Let me ‘splain.

I thought I would dedicate this article describing my own professional journey which has less to do with thoughtful planning and preparation and much more to do with sheer serendipity — being in a unique situation when an opportunity presented itself, and then having the courage or naivete to say “yes”. Let me rewind a bit and take you through my life story. About 35 years, having arrived in the US in the early ‘80’s, and after going through a very challenging first few months, the family settled in Southern California. I went to a high school that had the highest teenage pregnancy rate in the state, low graduation rate and where no one in the decades long history of the school had ever applied to MIT. I was lucky to have a counselor who, in passing, encouraged me to apply as a “really long shot”. I got lucky and that long shot worked. Ironically, I got rejected by UC Davis, my sure-shot school (although, again ironically, the UC Regents gave me a full scholarship. So, the right hand (admissions office) was not speaking with the left hand (UC Regents)). As I approached my four years, and was seeking a dream job as an Aerospace Engineer either at Boeing or NASA (both of which offered me a fantastic $25k/yr and a $32k/yr gig, respectively in 1991), my thesis advisor got a small grant from NASA for some research. The day before I had to make a job decision among my two top prospects, Prof. Martinez-Sanchez basically persuaded me to stay and do my Masters with a fully paid fellowship. Life would have been very different after another 48 hours, had I picked a traditional aerospace career.

Fast forward to 1995. On a whim and slight nudging by a friend, I ended up going to an open house for UCLA Anderson School of Management in Boston. I wasn’t really interested but she said “what the heck. It can’t hurt”. I ended up speaking with the Dean at length at that event. Sure enough, the “it can’t hurt” turned into an Anderson MBA. In 1997, I did not know what I was going to do for the summer between the two years of business school. I didn’t want to work for a big company, but wasn’t really sure of how to connect with small ones or startups. I happened to stop by the career center at the school to browse. In those 5-10 minutes, started a conversation with a senior executive from Epson who had had a last minute cancellation, so he had 45 minutes to spare. A slight chit-chat/water cooler conversation turned into a summer internship helping Epson figure out its online strategy. Upon graduation, again, I knew that I did not want to go down the route of consulting, investment banking etc. During a conversation over a drink with another classmate, he asked if I had ever considered Mattel, the toy company. I said, “of course not”. It’s a big company and I really want to focus on a smaller company. He said “what the heck. It can’t hurt” as he spoke with me about a small group of MIT folks at Mattel whose charter was to find technologies that could be embedded in toys of the future. I thought it was an interesting job description. That nudge from Rob led to a one-year stint at Mattel. While there, I got a cold call from Guy Kawasaki (the prolific speaker/author and one time Chief Evangelist at Apple). It turned out that one of my business school classmates had become pen-pals with Guy, and right out of business school joined Garage.com, a boutique investment bank Guy he had co-founded in Silicon Valley. Guy asked if I might be interested in learning about Garage. The phrase “what the heck. It can’t hurt” went through my mind yet again. That led to my departure from Mattel and joining Garage.com in 1999, and a series of roller coasters over the next eight years, that led to Garage.com pivoting from an investment bank into Garage Technology Ventures, a seed stage venture firm. Overnight, I became an accidental Venture Capitalist. In 2006, I happened to be in India looking for potential investors for Garage’s second fund. As part of that trip, I was asked to come and speak at the Indian School of Business in Hyderabad. At a business plan judging competition, I happened to sit next to Raj Atluru who, at that time, was a Partner at DFJ. I had known Raj for close to a decade and was surprised to see him in Hyderabad. He mentioned that DFJ had been investing remotely in India and was now looking for a partner to set up their India operation. That chance conversation on a panel half a world away led to my joining DFJ in 2007, moving to Bangalore and starting a really interesting next nine year stint as an early stage global VC. India threw a bunch of googlies (or curve ball, to use a baseball analogy), as it usually does, but I ended up spending five years in Bangalore, which were amazing, both personally and professionally.

Fast forward to 2015 when I started thinking about a move from DFJ as the firm’s focus had shifted from being global to completely local. I got an outreach from my now partner, Anand Prasanna. Anand had been contemplating a fund like Iron Pillar and was looking for someone who had been an investor in the US and India. I was one of a very few that fit that profile. We spent a day together in Bangalore, and I was sold on the thesis/approach. We spent 2015 putting the team together and in early 2016, officially launched Iron Pillar. While early, it’s been a great entrepreneurial ride, with a first time team and first time fund. I have experienced the challenge and exhilaration of fundraising for Iron Pillar 1.

I love helping entrepreneurs and I often say, “I am in the business of putting good people together”. Which is true. I recently got a call from someone who basically indicated that I had changed his life. He is now a senior exec in London with an investment firm. And apparently some advice that I had given him 15 years ago at Garage changed the trajectory of his life. To be honest, I did not remember the gentleman, nor the context. Similarly, I remember years ago, sitting at a law firm listening to women entrepreneurs pitch their ideas. I started a conversation with the gentleman sitting next to me, who happened to be the then CTO of Mozilla. We followed up to connect in some more depth, and he connected me with a gentleman named Daniel Epstein, of the Unreasonable Institute (based in Boulder, CO). The group effectively helps social entrepreneurs instill best practices and access to capital through global mentors and advisors. It’s truly a do-good, do-well organization. I have had the privilege of being involved with them as a mentor/advisor for almost seven years – all because of a brief seemingly random conversation at a small gathering.

The reason for giving you the painful detail above is to drive home a few points. One, that life-altering events happen more often not through careful planning and immaculate execution, but rather through happenstance meetings and random conversations. Two, more often than not, we choose not to speak with the person sitting or standing next to us (on a plane, at an event, in line at the grocery store or wherever). I am also not saying that one should go around interrupting nice family meals at restaurants, but when in an environment where a brief conversation is not intrusive, have a chat and get to know a bit about the individual next to you. Sure 90% of the time, there may be little or no overlap in background or interests. But in 10% of cases, remarkably, you will find some connection that binds you with that individual in either subtle or not so subtle ways. Finally, just give. If you can, give your time, your advice, your connections to the extent they can be helpful to others, without expecting anything in return. A random note of gratitude years from now from someone you may not even remember, will make your day, week, month or year.

All too often, people in the investment and entrepreneurial business are too busy or pre-occupied with the fires that need to be fought on a day-to-day basis. I think it’s important for all of us to take our heads out from the weeds and zoom out a bit every now and then. There is no better way to receive than by giving. As I think about what makes Silicon Valley so unique, I think the above is a big chunk of it. That random conversations lead to significant events and milestones, and that people are fairly open to helping. At Iron Pillar, the team subscribes to that mantra. Live to the fullest. Give to the fullest. Because, it all has a way of coming full circle.