HUBweek Change Maker: Krishna K. Gupta

Founder, Romulus Capital

Krishna K. Gupta is the founder of Romulus Capital, a Boston-based venture capital firm that focuses on building, not betting on, technology-enabled businesses that have the capability to transform entire industries. Krishna founded Romulus while an undergraduate at MIT, and over the years has led the firm to regularly be the first institutional investor of seed-stage companies. Most days you can find Krishna at Romulus Capital HQ doing calls with founders and potential customers or partners.

As the founder of Romulus Capital, what problem are you hoping to solve? We at Romulus are partnering with entrepreneurs with the intention of building differentiated, forward-looking companies that stand on solid foundations and on making meaningful impact in their respective industries for years to come. Our highly entrepreneurial, partnership-driven, “building rather than betting” approach is difficult to find in the venture capital industry.

What impact (personally or collectively) do you hope to have? I would love to help build hundreds of great companies, create thousands of jobs, and help our portfolio companies’ respective industries and ecosystems embrace the future. To that effect, I would like to build Romulus into a group that stands the test of time, into a group that is built to last.

What’s the biggest challenge you’ve faced in your career? Growing our firm from $1M to $50M at age 25 was an immense challenge for me. There were several instances when I felt Romulus would not succeed, but I refused to give up. The challenge went beyond simply raising capital; I had to lead the firm into a new era of growth and scale, which was a massive challenge. There will inevitably be even larger challenges coming my (and our) way.

We’ve read you love exploring conflict zones. How have your experiences in Nepal as the 10-year civil war was ending, in Kashmir amongst violence and strikes, and in Israel during the evacuation of Gaza (to name a few) affected how you run your business? Conflict zones are full of opportunity — they breed chaos, complexity, and constraints. When you are in a conflict zone, you are on the frontier, trying to find solutions to intractable problems. You have to be agile and audacious, you have to embrace a problem-solving approach, and you have to be authentic in your interactions with others in order to engender trust. There were times in Assam and Kashmir, for example, when I was flying by the seat of my pants and had no idea if I would make it out; there were other times when I felt elated at having made progress in some small way toward creating impact by bringing opposing sides together, and by involving the youth more in a participatory process.

These are all the same values and traits that represent how Romulus conducts our business. On some days, we have no idea whether a certain portfolio company will survive, and on others, we watch that same company win massive customer contracts and feel they are still very much on the journey on which we embarked together.

Ultimately, all of these problems require people-oriented solutions. Effectively engaging with people significantly increases the probability of success, whether in a conflict zone or in a deal room.

One thing people might find surprising about you or what you do? I once took an interpretive dance class at MIT.

3 things you wish you knew when you first started out?

  1. It takes a long time to win large customers.
  2. Entrepreneurs don’t know everything, even about their own industries, and firmly pushing their thinking can create massive value for the company.
  3. Markets can become overheated and overcapitalized quickly.

Best and worst piece of advice you’ve ever received?

  • Best advice: Don’t hesitate to reach out to someone even if you don’t know him or her; there is often mutual benefit in a conversation.
  • Worst advice: “Just screw him over” — short-term thinking is always terrible advice!

What’s next? We plan to go heads down and continue to grow aggressively and sustainably. There is tremendous current opportunity for a well-positioned, emerging platform like Romulus.

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The HUBweek Change Maker series showcases the most innovative minds in art, science, and technology making an impact in Boston and around the world.