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The ability of a leader to bring everyone to a common goal determines the winner of any approach. People are at the centre of digital experiences, no matter how vast they have gotten. In this episode of The xMonks Drive podcast we discussed with Raj De Datta about how the lines between digital and real life become entangled.

Here is an edited transcript of the conversation with Raj.

On Accidental Entrepreneurship

Gaurav: Raj, you started, as I mentioned, you started your entrepreneurship

journey at the age of 22. I mean, were you clear about that, that you wanted to get into

entrepreneurship? Did it just happen to you? Very curious to know.

Raj: I’m not even sure I could spell entrepreneurship at 22. It was so far afield from what I had been an electrical engineer at Princeton, worked in a research lab, I had studied public policy. I knew nothing about business really. And I found myself after a short stint as a researcher as well as an engineer, I decided to spend two years on Wall Street. And how I became an entrepreneur is 100% accidental. I was working at a Wall Street firm in New York. I’d completed two years. I decided I would go back to school, go back to business school and get a graduate degree, having received admission from Harvard at that time and accepted admission to go. 

And it was about May of that year, I remember it well. And really, my boss’s boss’s boss was saying, Hey, you know, I’m looking at potentially making an investment and starting a telecommunications company in Europe, Raj, since you have the summer before you start school, can you help me put together this business plan? And I said, Sure. So I started to get into it. And then I should have known better. But I got so passionate about what that project was about, that by the time August came around, it was becoming real. The idea was to actually start a telecommunications business in Europe, I was living in New York, my investors and co-founders were living in New York as well and had families. So they said, We can’t move to Europe, Raj, would you be interested in moving to Europe and setting up this business and I had literally never been to Europe.

I was processing this information, I had spent summer on this business plan. And I just could not leave it. You know, I could not imagine leaving it and going back to school. So I tried to get a deferral from Harvard to say, Hey, I’ll come back in two years or one year? And they said, No. So then I was faced with the choice where I turned down the admission and continue this then do this crazy entrepreneurial project, or do I go back to school, and you can imagine it would have been a popular choice with my parents and others will also have no business experience, by the way, given their backgrounds. They were like, Why would you do this instead of you know, going to Harvard. But I turned down the admission and picked up and moved to Europe and and you know, the rest is history.

Raj De Datta today vs Raj at 22

Gaurav: So what difference do you see in Raj De Datta at 22 and Raj today?

Raj : Today? Yeah, I’m 46 years old. So it’s been a long time. I think, I think in many ways. Many of those core attributes are the same, the stubbornness, the pursuit of desire, all those things are all the same, the curiosity, what’s different, I think, is I know a lot more now. And so therefore, and just as prepared to make big bets, but I’m more thoughtful about those bets, to think through the downstream consequences of choice, whatever that those choices are. I am much more cognizant. At the time, I would say I thought entrepreneurship was about brilliant ideas. 

Now I realize entrepreneurship is much less about brilliant ideas, and much more about persistence, the team around you, the culture and the environment, all of the other things that make those ideas have any shot of coming to fruition. And, you know, I think there at that time, I viewed it as something that was just fun. You know, now I see, I actually do see the impact that it has on people on the world on so many aspects of our life. So, my perspective is perhaps broadened a little bit. But a lot is the same. And I try hard to retain that because I think of youthful naivete and optimism. When you lose, you stop creating, you lose life. You lose life, you lose the desire to create and if you look at the rods of 22 barring the niceness that you spoke about the curiosity, the stubbornness that you spoke about, and the willingness and the grit with which you would continue and the persistence that you spoke about, what do you think? 

I think what I miss the most is the freedom that comes from lack of responsibility. You know, in those days, you know, I was the first person starting that venture, I recruited some friends, we traveled around Europe, we went here, we went there, we tried this, we tried that there was just a, a serendipity to which much happened. And you know, I’m in a different position today. And I appreciate the position that I’m in today as well, but it’s different. Now I’m responsible for quite a large company that powers billions of dollars of transactions around the world with great aspirations and huge amounts of investors who have bet behind it. My responsibilities are much different. My actions and my actions, and my words have much greater consequences than they ever did at that time. And if I miss something, I miss the freedom of not having those responsibilities.

About The Speaker: Raj De Datta

Raj De Datta is the Co-Founder and CEO of Bloomreach, the leading digital experience platform for e-commerce that powers 25% of retail e-commerce in the United States and the United Kingdom. Before creating Bloomreach, he worked as an entrepreneur-in-residence at Mohr-Davidow Ventures, as Cisco’s head of product marketing, and as a member of the founding team of telecom business FirstMark Communications. He also worked at Lazard Freres in technology investment banking. Raj is a Founder Partner at seed-stage venture capital firm Founder Collective and an individual investor in over 20 Silicon Valley startups. He also serves on the US Tennis Association’s Council for Player Development.

Raj is the author of the upcoming book from Columbia University Press, “The Digital Seeker” which is a guide for digital teams to build winning experiences. He holds a BS in Electrical Engineering with a certificate in Public Policy and International affairs from Princeton University and an MBA with distinction from Harvard Business School.

Raj de Datta can be found speaking at The xMonks Drive podcast available to you here. 

Frequently Asked Questions

How does the ability of a leader determine a winner?

Any approach’s winner is determined by a leader’s ability to bring everyone to a single goal. People are at the centre of digital experiences, regardless of how large they have become.

Who is Raj De Datta?

Raj De Datta is the Co-Founder and CEO of Bloomreach, the largest digital experience platform for e-commerce in the United States and the United Kingdom, which powers 25% of retail e-commerce. He was an entrepreneur-in-residence at Mohr-Davidow Ventures, Cisco’s head of product marketing, and a member of the founding team of telecom company FirstMark Communications before starting Bloomreach.

How did Raj De Dutta become an entrepreneur?

Raj De Dutta became an entrepreneur was 100% accidental. His boss’s boss was potentially making an investment and starting a telecommunications company in Europe for which he made a business plan.

what is entrepreneurship about?

Entrepreneurship is less about fantastic ideas and more about perseverance, the people you surround yourself with, the culture and atmosphere, and everything else that makes those ideas a possibility.

What is The Digital Seeker?

Raj is the author of “The Digital Seeker,” a handbook for digital teams to create successful experiences, which will be published by Columbia University Press.