Meet a Member: Raghav Gupta

Sep 14, 2020·6 min read

In our next installment of our series on the members of TiE Boston, we spoke with TiE Boston Charter Member, Raghav Gupta, serial entrepreneur and investor, about his journey and what led him to TiE.

Raghav as a young child

Tell me a bit more about yourself and your background:

My story is one of a few continents.I was born in India in Kolkata and when I was 7 years old my family moved to just outside the Philadelphia area in the suburbs, and that’s where I grew up. I went to college nearby at Princeton and did my undergrad there. Professionally, I started off in New York. I was at a consulting firm where my first project was in the Bay Area, so I was going back and forth between the two coasts for a while. During the dot-com boom I ended up moving to the Bay Area and spent a number of years there. While there, I ended up running an internet radio company called Live365. In ‘04-’05 I came back to the east coast, first in New York and then in Boston. I was part of the early team at Brightcove, right when SaaS, cloud and digital media were starting to take off. It was a rocket ship and, after a couple of high growth years,, they moved me out to London to help open the UK and European markets. Originally, I was going to do that for six months and then go on to Tokyo, but I liked it so much I decided to stay and ended up being in London for 10 years. During that time I left Brightcove and joined one of our partner companies, first as a board member and then as the CCO. It was a company called Videoplaza, which was in the video ad tech space. They had just raised their Series B and were at an inflection point in trying to scale beyond their first few million in revenues. We were able to double revenues a year after I joined and, a year after, sell it to Telstra who were doing a roll up in video. I worked on the integration and stayed two years as a part of the acquisition. After that, I decided I wanted to do something different. My wife and I decided to make a move out of the UK. We chose Boston because we thought it would provide a professional platform for us. As I look at the coming decades, the technology and intellectual capital in Boston will only become more important. Once in Boston, I met Nilanjana two or three times, and she started telling me about TiE Boston and that’s how I got involved in TiE.

How has TiE Boston played a role in your entrepreneurial journey?

I’ve really appreciated the community that TiE has to offer. I’ve been heads down the last few years but have been able to have several touch points with the TiE ecosystem with the highlights being putting together the robotics panel for TiECON East and doing a session for Harvard’s Launch Lab X. I like to say that it’s a long term game and that’s about investing in relationships and giving back to the community. Some of the companies right now that I’m advising and investing in are TiE members, so I’ve really appreciated those connections. Actually right now, with one of the members who is a VC we may be looking at a company together and so all these touchpoints are really valuable. I’ve really enjoyed the social connections that have come from TiE Boston CM Socials and Galas — it’s so inspiring to meet such accomplished yet down to earth people. I’m really looking forward to more of that once people start getting back together in a normal way.

Raghav and his family

Have you faced any adversity in your entrepreneurial journey? If so, how did you overcome those challenges?

To the first question — how much time do you have?! The story of entrepreneurship is really a story of overcoming adversity and is like navigating a ship: you have a destination but you don’t quite know how you’re going to get there: You will need to tack to and fro, shelter to wait out a storm, or else open up the sails when it’s smooth sailing. I could go on. . I got a hands on MBA when I found myself early on in my career inheriting the running of an internet radio company. We were hemorrhaging cash, had no business model, low morale, our ISP even went dark a couple of times and turned us off. The dot com bust was like this nuclear winter; no one would take calls, no one was buying anything, it was just a total wasteland. There were a couple times I had to get in front of the company and tell everybody “I’m not sure if we can pay you the next payroll or two, and so coming to work is optional from now on because we didn’t have any cash in the bank”. Then there was the morning when we decided we’d officially file for Chapter 11 if we didn’t get any more funding. We were refreshing the browser of our bank account. In the 11th hour, the wire came, we stayed in business and were able to get it to profitability. It was a really formative experience for me early on in my career. You learn from your mistakes and learn what you would do differently. It’s honestly just part of the experience.

Any advice for entrepreneurs?

The first thing I would advise is taking care of one’s own psychology. Taking care of oneself and being able to get perspective is key. Some entrepreneurs don’t have the tools to deal with the inevitable ups and downs, especially during these days of social media when all your peers appear to be ‘killing it’. That’s just not true. Everyone has their own struggles; don’t fall for such theater. Second, piece of advice is to cultivate a few advisors or mentors that you trust that are outside the workplace. They can be a formal advisor to you or informal, but, beyond sounding boards, they should be able to call you out and help you cut through the noise to what is really meaningful. There are so many more resources and so much more content now than there was back then, like podcasts and forums. There are incredible resources out there, whether its communities like TiE, or the folks at First Round Capital, and they have all kinds of great advice. Finally, make time for your family and switch off. As unnatural as it may feel, it is really important to make the time to switch off and really enjoy the moments when you’re with your family or whatever your happy place is. It will make you a better entrepreneur. And then be focused in the moments when you are working on your business. What you don’t want to do is to try and do both at the same time and do neither of them well.

What are you looking forward to, especially during this time with the public health crisis?

There is so much misery and pain out there and it’s heartbreaking. Certainly for everybody it’s a time for reflection as well on the moment we’re in and what that means for us personally, for your family, but also a time for evaluating priorities as well. I’m an optimist and so I do think that this pandemic is going to ultimately be a net positive for mankind despite all the massive amount of pain that is there right now. Whether it’s going to be the acceleration of our digital infrastructure, investments in public health, to more investments in automation, there’s a lot that will be positive in the years to come. Even the ability to produce vaccines, which we were never really good at before, but now we’re developing a large amount of muscle around it.

Thank you to Raghav for sharing his story. To learn more about TiE Boston and how to get involved, check out tieboston.orgor reach out to info@boston.tie.org