Krishna K. Gupta is the founder of Romulus Capital, an early-stage venture capital firm based in Boston that focuses on innovative technology companies disrupting longstanding industries. Krishna founded Romulus while an undergraduate at MIT in 2008. Over the years, he has grown the firm from an initial fund of $850K to $150M in assets under management.
Krishna Gupta
What does entrepreneurship mean to you? What underlying characteristics do you see in successful entrepreneurs?
Krishna: Successful entrepreneurship is the act of creating something from nothing, of ignoring what others wish you to be and following your instincts. It’s embracing risk while also seeking to cut it wherever you can, of dreaming larger than anything you can tangibly envision, of staying authentic even with people acting in "bad faith" all around you. It means staying focused on building something large and enduring rather than on the monetary gains associated with the same, staying disciplined and sweating the small stuff, and sacrificing sleep 7 days a week for many years!
What are you most proud of having accomplished? If you could change something from your past, what would it be?
Krishna: I am proud that we have built an established firm from scratch, in an era where doing so was highly contrarian. I’m proud too that we have not taken any shortcuts in our journey -- we've stayed focused on the fundamentals and done so in a manner that is authentic to our DNA of “building rather than betting.” I am proud that the innovative companies with which we have partnered at such an early stage have gone on to become real enablers of value for so many large enterprises across so many industries, and that we have shown ourselves repeatedly capable of both being contrarian and of convincing entrepreneurs to partner with us over other firms.
I wish I would have raised more capital in the earliest years -- we could have taken even greater advantage of our first-mover positioning and could have grown more quickly.
Tell us about an instance when you went against the flow to achieve your goal.
Krishna: Everyone told me I was crazy to start a venture firm in 2008, immediately after the financial crash, when I was just 21 years old and still in college at MIT. College VC’s didn't exist then. Everyone told me I was crazy to raise a $50M fund as I set out to do the same in 2011. Several of our investments have been made in companies where no other investors were interested. But we simply don’t care what others say in an absolute sense -- "going against the flow" based on our own conviction has been firmly ensconced in our DNA from day one. If I had cared more about “the flow,” Romulus would not be the firm it is today.
What drives you? How do you measure success for yourself?
Krishna: I really love to come up with new ideas, to bring these ideas to life, and to build rather than bet. I have always been motivated by building something massive and enduring. And I am a deep contrarian -- I hate doing what everyone else does, and I've learned to block out most of the noise around me. I measure success by looking at my growth rate relative to time, and by examining the health of our foundation: are we growing quickly enough and are we staying true to the fundamentals?
You invest seed money in mostly first time entrepreneurs. How do you vet founders and startups?
Krishna: Since we founded Romulus from scratch and continue to build it, I look for the same hunger and passion in founders that I have in building Romulus every day. It's not a distant memory -- I can relate to their exact sentiments in the present. I look at their backgrounds and seek a story -- I am a big fan of storytelling, and every founder must have a coherent and compelling narrative arc that leads him or her to this point. I look at market -- is there really a large business to be built here, and is there enough space to maneuver, to take a random walk, as is often required at this stage? And finally, I look at “the spots on the horse” -- is there something really differentiated that will make this horse run more quickly, not just now, but even 5 years from now -- than others who enter the maidan?
What advice would you give to your 22 year old self? What do you know now that you wish you knew back then?
Krishna: My 22-year-old self was traveling the world after having founded Romulus. I sometimes re-read the journal I kept for 6 months, and I see some angst. I would tell him to dream even bigger and to embrace every moment of rejection and uncertainty as a differentiated and valuable life lesson.
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