A Letter Celebrating Romulus’ 10th anniversary

Hi Romulus family!

Today we turn 10 years old. I remember quite an intense experience setting Romulus up in the summer of 2008, but little did I know how much more was to come! Now I hope this is just the first of 10 decades I get to see of the journey.

I’ve now spent roughly a third of my life building this company. It has given me an immense amount of joy. In the process, I’ve learned a lot as an entrepreneur, as well as from the ~100 entrepreneurs with whom I’ve had the chance to meaningfully engage over that period of time.

People often ask me what my favorite part of the job at Romulus has been over the past decade. Near the top of the list has to be winning customers for our companies. Learning from and working with some of the smartest and most enterprising people in the world is right there too. The extended Romulus family – our team, the founders, our investors, friends, and family – are really the ones we owe everything to; this journey would not be nearly as satisfying without them.

I won’t spend this letter reflecting too much on specific events or on what has gone well vs poorly in our first decade. Rather, I want to use it as a way to abstract 3 interesting takeaways from my entrepreneurial journey thus far, and also take stock of where we are today and how all of you can play a role in the next 10 years.

3 interesting things I’ve learned about being an entrepreneur

You have to believe in yourself to an extreme. The world will try to pull you down, will criticize you – your vision, your ambition, your focus, your long hours, your little sleep. The sacrifices will be immense as you build the foundation. You will be rejected hundreds, thousands of times. Ultimately, I’ve always only had myself to fall back on. Do not let go of your blind belief in yourself, even if you acknowledge your many mistakes and pivots along the way. You will find a way. There is a positive narcissist gene and most successful founders have it.

Acknowledge when you have erred. While self-belief is critical, so is self-awareness. I have tried to surround myself with people who will tell me I’m wrong, and I’ve become very comfortable with saying “I’m sorry” or “my mistake”; if you have a tough time uttering those words, you create a dangerous environment internally and externally, and set yourself up to make company-ending mistakes.

Creativity is underrated, and you need to remain inspired to bring out your creativity. Yes, building a large technology company involves a lot of rational design and execution. But, some of the most powerful, value-additive company-building moments come from creative thinking and problem-solving, without letting the constraints of time, space, or anything else get in the way. I spend a lot of time trying to inspire myself to be the most creative version of me. Asking “why not?” has always been more interesting for me as a founder than “why?”

Where we are today

Technology is a misnomer as an industry label now; every industry is now developing and deploying innovative technology as a means to survive and grow. Thus, any great platform of my generation will have technology in its DNA.

As a platform, we have gained a great deal of experience building technology companies that

(a) engage with large, traditional industries (such as agriculture, construction, insurance, hospitality, real estate, retail) and/or

(b) are based on deep research at some of the world’s foremost institutions, including MIT, Harvard, Stanford, and Cambridge

We are very unique in that we now have a decade of experience helping build these kinds of companies (as well as a strong foundation for Romulus itself), and yet we still have decades left to give to this company. I believe that positions us well to navigate the opportunities ahead. I remain ever more inspired by the technology, research, and entrepreneurs around me, and more bullish on the opportunity in the areas defined above.

Our position today also means we could scale up what we offer to our companies. We are very involved with all of our core companies and help them across the board in ways we don’t see other VCs doing, but I’m confident that there’s potential to institutionally increase it by an order of magnitude without losing the entrepreneurial spark that defines us.

I look to all of you for your help as we start scaling our platform, thinking critically about what our team, operations, and vision need to look like to do so. The more transparency and feedback we get, the more likely I am to be writing something similar in 10 years. Rest assured that I will continue working every day as an entrepreneur first – someone who cares about the soundness of the enterprise being built, the consistency of the values inherent in it, and the vision being pursued by it more so than any short-term gains.

Yours truly,

Krishna K. Gupta