Alumni Interviews – Deepak Ramachandran

DeepakDeepak Ramachandran is an entrepreneur and investor in the areas of software, clean technology and electronics. Most recently, he co-founded FundThrough, an online funding platform that helps small businesses manage their cash flow by using their invoices as collateral. He has worked with start-ups and bigger companies in Canada, the US, Europe, China and India.

Ramachandran earned his BA in philosophy and chemistry at U of T (1991), where he was active in student government at the Department of Philosophy, before completing his BPhil at Oxford (1994). At U of T, he was granted a Moss Scholarship, awarded to the best all around graduating student for outstanding academic performance as well as extracurricular leadership in a Faculty of Arts & Science program, and he served on the board of Victoria College.

In this interview with U of T’s Philosophy News, Deepak reflects on the ways in which his time in Toronto and his philosophical studies have shaped his career and worldview, and speculates about emerging trends in technology, democracy and global economies.


Philosophy News: Tell us about your time at U of T. Why did you choose Toronto and how did your time here shape your career?

DR: I was looking for a big university that was great at many things. Like many kids, I didn’t know what I wanted to study or do in the future. I took courses in pre-med sciences, pre-commerce accounting and—for fun—a couple of philosophy half-courses. Those were so much more lively than the others, philosophy quickly became my specialist. I chose philosophy because I loved the people I met in the classes (students and professors), the questions we asked, and the way we discussed them.

From an academic point of view, the most formative part of my education was getting engaged in small, seminar-type classes in which students spent a lot of time arguing out points of view as peers. My favourite professors would turn every class into a chance for students to talk to each other. I got to test and develop my thinking in a crucible, a bit the way we all develop our tennis strokes or basketball shots by playing with people of similar skill levels and a coach.

From a career-developing point of view, the most formative part of my education was getting involved in administration. I sat as a student rep on the Victoria College Board. Looking back, my initial questions about the budget and pension-fund investments must have been irritating and amateur; but over time, I think I became a productive colleague at Vic and in the philosophy department. The Philosophy Course Union back then was very activist, led by great students (now professors at other schools) such as Rebecca Kukla (now at Georgetown) and Valerie Tiberius (now at Minnesota).

We also had an amazing department chair in Wayne Sumner; he shepherded an inspiring program to ensure seven out of 10 faculty hires in the 1990s were women—and he did it by proactively recruiting the very best female graduate students from the top PhD programs, rather than just “preferring women” among whoever happened to apply. The results really changed the department and the University, including bringing in Cheryl Misak, Jennifer Whiting and Margaret Morrison. At Vic, I was equally inspired by Eva Kushner, Sandy Johnson, Roger Hutchinson and others. In Philosophy and at Vic, I helped out as we launched new courses and tried new experiments in the curriculum, some of which I see transmogrified into Vic One and parts of the philosophy calendar even today.

So my most inspiring role models at U of T were visionary academic administrators—they had a clear sense of the value of an education (see Northrop Frye’s Massey Lectures, The Educated Imagination [1962]); a long view of the University’s history and evolution; and a strong drive to experiment, evolve, push forward, never settle. I have tried to take a similarly long view and purpose-driven approach into my work.


PN: You studied both philosophy and chemistry at U of T. How did this combination influence your work?

DR: I am just naturally curious, and these were two subjects that let me dive relatively deep, relatively quickly. At the time, there was a great organic chemistry professor who taught characterization of large-chain molecules as a kind of detective work (before crystallography evolved; now we can just “take a picture”). His courses were fascinating.

Even though I wrote and sold software to earn money in high school and during university, I didn’t take any computer science or engineering courses at U of T. Now, with universal access to very prominent thinkers like Andrew Ng and Geoffrey Hinton pushing envelopes in AI, virtual reality, quantum computing and encryption, I’d probably be exploring those topics both academically and by tinkering. (By the way, I am in fact exploring those at work today!)


PN: As an investor and business advisor, you have specialized in technologies that reduce waste and use very few non-renewable resources. Why did you get interested in these technologies, and what do you think they have to offer?

DR: I wanted to “do well by doing good.” I asked myself how I could join the most important/inspiring cause while still using my skills and abilities. At the time I believed that our impact on the environment was our biggest issue as a species and an ecosphere. I still believe that.

I’ve learned a couple of things worth sharing. One, venture capital and angel investments in particular are much higher-risk and lower-impact on average (and in my portfolio) than I had hoped. My portfolio is actually doing better than the statistical averages financially; but it is probably similar to the average in that several investments I thought would be environmentally beneficial are probably only marginally impactful in the end. Two, participative democracy is in a crisis unlike anything since the 1930s; and without successful participative democracies, we are very unlikely to sustain any real improvement in our impact on the ecosphere. So while I continue to put some personal effort into the environment, I am shifting my focus to helping keep our democracies alive even as the world’s working-age population peaks and the (technological, economic, geopolitical, and natural) environment likely makes people hungrier and more likely to attack their neighbours.


PN: You think strategically about complex business challenges in creative and perhaps unconventional ways. How has your education in philosophy prepared you for this? What do you think the discipline of philosophy can offer emerging start-ups and businesses?

DR: My favourite part of philosophy was asking essentially unanswerable questions, and discovering that the same question can often be seen from several very different “cardinal” perspectives, each of which offers its own insights, but none of which is by itself comprehensive or definitive (e.g., ethics of rules vs. outcomes vs. character; or, free will vs. determinism). In the end, we get to choose which perspective to inhabit, and when; and this is a very powerful tool, to realize that the perspective I inhabit at this moment can be more or less useful, and I can choose an alternative perspective for a different purpose. So for instance, Janet Yellen as an individual presumably thinks she’s making a free choice when she chooses whether or not to buy a bigger house; but Janet Yellen as Chair of the Federal Reserve abstracts over all those free individual choices to a more deterministic/probabilistic view that rising interest rates will cause people to defer expenses.

So for me the most useful part of philosophy—for start-ups, mature businesses, government, non-profits, or anyone really—is to help us realize that our positions and preferences are somewhat arbitrary, and then to choose the perspectives and preferences that best serve our deeper values and goals at any time. It is much easier to create new things when you can simultaneously see what is relatively invariant and hard to change (the supposed “laws” of physical or human nature), and what is more readily available to choose again (our values, perspectives, preferences, goals) in any moment.


PN: What is the most interesting emerging trend in start-ups today? Is there a particular industry or type of business that you think is going to have a moment, and why?

DR: I suspect that artificial intelligence will likely change the world as much as or even more than the hype suggests. It’s not that we will certainly have sentient droids or Cylons living among us, though that is a non-trivial possibility in our lifetimes. But it’s already clear that AI will bring a new wave of automation and labour replacement. In only a handful of years, I suspect many jobs will be better done by machines than by humans—from driving trucks to micro-surgery. And while the surgeon will likely be fine, just able to treat many more people with this new tool, the truck driver and many white-collar workers will join yesteryear’s assembly-line worker in an even lower-paid and less secure future.

In a way, most of us in the richer countries are already living the leisure lives of the Jetsons compared to the relatively hard physical labour of even the 1950s (or in China or India, relative even to the 1980s). However, because we’re sharing the rewards so disproportionately among so few, most people are stuck doing whatever they can to “get by,” i.e. to survive emotionally, spiritually and economically, while a small group (including me to some degree) gets to choose what we do and works primarily for meaning or self-expression. AI will exacerbate that divide; and that divide threatens to destroy this fragile thing we call democracy.


PN: What advice would you give to students studying philosophy? Do you have any advice for philosophy graduates who want to pursue a similar career path to yours?

DR: For better or worse, I never really had a “career path” in mind, and still don’t. Studying philosophy was a very luxurious period in my life, and I’m very grateful for the opportunity to have spent time just thinking about things, surrounded by inspiring and enthralling students and professors (not to mention the great buildings, grounds, facilities!). I loved it, I cherish it, and it made me a lot of who I am today.

For my career path, I credit all those “extra-curricular” activities that were my passions before, during, and after university. For me, those were software, entrepreneurship, administration, leadership, innovation.

University is a great time to explore and to learn what makes you tick. Classes themselves for a philosophy student take ~15 hours per week. That leaves something like 100 hours per week for reading, talking, arguing, experimenting, falling in love, and all the other craziness of your age group. Budget a chunk of time to experiment with how you engage the world and make your mark. Get out there: talk, listen, volunteer with, work beside—engage people outside your age group and natural comfort zone. Find role models who seem to live the kind of life you aspire to, 20+ years ahead of you—ask them out for coffee. Then carve your own path to your own future, inspired and informed by those who have gone before.