What were you doing in college? Most answers to this question would look pretty similar: going to class, spending some time in the library and hitting up a few parties here and there.
But if you’re Krishna Gupta (below), your undergraduate experience was centered around one thing — founding a venture capital firm out of your MIT dorm room. 
Prior to founding Romulus, Gupta spent time at McKinsey & Company and JPMorgan, executing billion-dollar deals in technology, media and telecom. He also spent time conducting physical chemistry research at the University of Chicago and the Weizmann Institute in Israel, produced a film on ancient history in England.
While Gupta was pursuing dual degrees in materials science and engineering and management science at MIT, he knew he wanted to start a business. Eventually, Romulus Capital would grow into a successful early-stage venture capital firm with over $150 million in assets and a portfolio of companies like Ginger.io, Placester, Humanyze and Cohealo.
Why Romulus Capital? We caught up with the founder and general partner to find out.
Why did you start Romulus Capital?
I was an undergrad at MIT and I came there to start a company. My friends and I were coming up with ideas but we found that there was no one there to really help build these companies. We felt like MIT companies were underperforming. We have the best human capital in the world but if you look at the successful ones they often don’t become really, really big, they just kind of settle. So I found myself helping some of my friends build their companies and thought, ‘I see a problem. Why don’t I solve this and turn it into a business?’ Angel investors and venture capitalists didn’t have a middle layer. It took me one and a half years to fundraise, which I did out of my MIT dorm room.
What kind of startups do you back?
We like companies that end up being B2B vertical software plays or fairly high technology plays. We’ve backed several out of the MIT Media Lab that used AI and machine learning to solve a variety of problems. We’ve also worked with companies like Placester, which has become the leading software provider to the real estate industry. We also work with E La Carte, a leading provider of analytics for restaurant industry. We’re all about building companies where we get really involved, roll up our sleeves and work with the entrepreneur.
Why B2B?
In seed stage, B2C is like roulette; it’s gambling. You’re betting on a team and hope they figure out how to get traction and even great teams sometimes never get consumer traction. We got phenomenally lucky with Class Pass, a B2C company based in New York but we found we can add more value to B2B guys.
What’s the story behind the name ‘Romulus Capital?’
I’ve always been a big fan of the classics of the Roman empire in particular. I appreciate entities that can stand the test of time and the Roman empire continues to impact us today. I thought if I’m going to make an impact on these companies, Romulus, the founder of Rome, made a great name.
How have your varied experiences affected you as an investor?
To be a successful businessman or investor, the more experience and the more things you touch and learn, the better off you’ll be because it will all feed into how you see the world. I’ve done a lot of math in my days and I have a big perspective on history and art and that all comes together. I’ve been to many countries in the past few years and it all plays into how you build something that is great and lasting.
We all think this is the golden age of startups but big and great things have been built for thousands of years so it is good to have varied perspectives on how to build things. I have a deep conviction about being a nonconformist. I don’t care what anyone says or thinks if I have a deep conviction. I’ve seen so much in a short period of time and I’m always looking to learn more; that’s the great thing about being in Boston.
What do you look for before investing in a company?
I look for a team with founders who also want to build something really big and lasting. The second thing I look for is market size. A lot of companies are constrained by their market if it’s only so big. Placester, for example, sees a massive market ahead of it, which is the real estate industry. We’re closing a deal in the agriculture space right now, which is a very global market. The third thing I look for is whether the company has a sustainable competitive advantage. Even if it is the first horse, there’s no guarantee that someone else won’t come out of the woodwork and have raised twice or thrice as much as you so what is it about your horse, what spots does it have that allows it to continue to run faster. It could be as simple as having a better team or a special set of customer relationships or something very deep about the technology.
How has being located in Boston affected you as an investor?
I think what I love about Boston is this mix of entrepreneurial and intellectual culture, which you really don’t get anywhere else. The Bay Area is more entrepreneurial and here, entrepreneurs are a little more rational but not any less aspirational. There’s a great talent pool here, which is not a new theme. But now the question is, how do we keep the talent here versus letting it go out west?
Photos via social media
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