So why don’t we start from the very beginning. Tell me about your early years and where you come from.

Okay. Well I was born in New Delhi almost 50 years ago. I grew up in Delhi, went to school in Delhi, went to college in Delhi— pretty much stayed with my parents until I left home. I left roughly 25 years ago to come to America. The reason I wanted to come to America was very simple. I wanted to be a journalist in a big market and it was a weird idea that I could be. A lot of it was also inspired by my early brush with online communications through CompuServe and reading a lot about ARPANET and the information superhighway. A part of me said perhaps that was going to be the biggest story of my life, and I should figure out a way to write about it.

I had no idea why that thought clicked in my head, and I still don’t know, but I think deep down I’ve always understood that communications are a fundamental human need, and the networks were essentially fulfilling that. But I wasn’t really clear as to why I was thinking like that. It just was something which went “click-click” and there it was. That was about 25 years ago so I’ve lived in America half my life and I’ve lived in India half my life. I traveled a bunch before I got here. I went to England, I went to parts of Europe and here I am. That’s my story in a TL;DR version, though growing up in India was interesting.

I come from middle-class family. The middle class in India is very different now than it was when I was growing up. Middle class India then was very different than middle class in America now or in fact what it was back then. My mom, dad, and my grandfather all worked to make sure that there was food on the table and clothes on our back. We all lived in a very small house. That included my father’s sisters and my aunts, me, my mom, my dad, and eventually my sister and my brother, my grandmother, my grandfather. The house was about 70 square meters. It’s a tiny place—but I think our parents will call it big. We still live in the same house back home, like we haven’t moved. And still— whenever I go back I sleep in the same bed I slept in as a kid and it’s cold in the winter.

I went to what we call private schools in America—equivalent of that but not quite because—it wasn’t really the top private school or anything of that sort. It was just one of the schools you had to pay to attend. Public schools there, like public schools here, are free and but they’re like public schools everywhere. My mom was a teacher in a public school, but I went to a private

school, and then I went to a college called Saint Stephen’s College, which is one of the better colleges in our country. It’s around 200 years old so it has some history behind it. I never really wanted to be there, to be candid. I just felt I was going to college because that’s what everybody does and that’s what my parents expected from me.

I really wanted to be a journalist. I knew that a long time ago. I was almost fourteen years old when I knew I wanted to be a journalist. I just didn’t have the right phrases for it, but intuitively you know what matters. I had no guidance on how to go about doing things. My whole life has been a bit self directed in that I have made decisions, and figured out what to do after making those decisions. More or less, it’s worked out. It’s okay. That’s life.

When were the earliest moments where you knew that you were interested in tech?

I learned how to program in India back when I was like 19 or 20 years old. It was like BASIC, etc. mostly because my mom said, “Yeah, it would be good for you. You should just study this rather than trying to figure out a career.” So I did, and I wanted to be an engineer at one point. Then I realized I don’t want to be an engineer. The thing which I absolutely loved was writing and through writing, I got a chance to meet a lot of interesting people.

Around age 20 is the first time I understood that I liked tech. I was writing about fashion and movies and sports and I was all over the place. The thing I loved the most to write about was Formula One. Unfortunately there was no Formula One in India at that time, so I just had to read about it more than anything else. I was pretty nerdy about that stuff. It has been about 27 years now since the first time I wrote about tech. It was about local companies in India who were doing tech, like ATN etc. It was pretty basic at that time. The world is very different today.

Walk me through some of the early years. What was the impetus that brought you to the States and into the blogging world in American tech?

As I said, I was very intrigued by the whole idea of ARPANET and the information superhighway and CompuServe. This idea of of online communication. Part of me intuitively knew that it was going to be something important, and it also dovetailed with my idea of, “What if I just move to the US? This would be a good thing to write about.” I also wanted to live here because I always felt that I needed a bigger playground. I have these goals I set and it’s like, “Okay, I’ve met this, now what? What do I do next?”

Most people like to have traditional things like family and kids, and all those things don’t intuitively make sense to me. Spending more time on things I like to spend time on was very important for me. I think it was all in my head. All of it was reading. I used to read a lot, and I still read a lot. The more I read, the more I learn how things are, and so that was my path. I came here and after I moved, I was like, “Oh my God, this is not going to be that easy.” It wasn’t that easy. You make a decision, you’re here, and you’re kind of stuck with that decision for a while.

How did your family feel about you leaving for the States? What plans did they have for you and what did they want you to be growing up?

My mom and dad would have been very happy if I became either a doctor or an engineer. And I don’t really know what I would have been if I stayed there, but I knew I wanted to be a journalist a long time ago. I wasn’t very clear how to go about doing it. I always had an opinion about something. This was always the case with me.

Yeah. So, let’s talk about the earlier years of your journalism career like tech blogging in the 90s.

I didn’t start blogging in the 90s, I started tech blogging on December 13, 2001. Specific date. Before that, I used to write for Forbes. Before that I was doing a lot of shit work for three years or so—doing a lot of freelance. From there I went to Forbes.com. From Forbes.com I went to Red Herring. From Red Herring to Business 2.0. When I was at Red Herring in 2001, after September 11th happened, I wanted to move back to New York. When I moved back to New York I realized that I was working for a monthly magazine and I had a lot of time and a lot of information which I wasn’t really doing anything with.

At that time the internet start-up ecosystem had collapsed and so there was very little technology coverage. I had been reading and collecting my pieces on my personal website. I used to occasionally write a newsletter or opinion pieces except they were were not really blogs because they were just long pieces. I would write them and publish them as an email, and then put them back on my website as an archive. So it wasn’t really a blog but I just tried Blogger and the like until 2001 when I went all-in. I started linking to whatever I found interesting and commenting on it. So that’s how my tech blogging career started.

In doing so I may have sparked something in a sense. I was the first guy who started reporting on original tech stuff, new stuff without really realizing that I was the first guy to do so. But I started writing—about 95% of what I did on a daily basis had no takers because the magazine could only publish one or two stories a month and about 95% of the stuff fell on the floor. I just started putting it on my website and that’s how it started and slowly grew from there.

Yeah. Walk me through what, in the 14 years since that happened— what have been some of the most exciting moments of your work? What are the things about it that really activated you and what were the things that you were proudest of?

I don’t know if there is any specific moment that I can say that was special. I just say the whole thing has been special. I think from the day I started until today that I might have found my art form, right? It was not traditional journalism, it was not writing news. It was a little bit of opinion. I think my whole past was building up to me being a blogger. Because when I was a younger guy, I worked at an Indian newspaper— magazine called The Sun. It was a teenage magazine and they published a lot of pop music news and Hollywood news and my job would be to read 100 or so Hollywood magazines and pop music magazines and listen to music charts from short-wave radio and figure out a way to write about it. Essentially, it was not really reporting, it was like rewriting a lot of the stuff which was done and putting it in a little bit of context, so it was essentially a form of blogging.

Then I worked at Forbes, where they teach you to write succinctly, very short. The biggest lessons in the 90s from Forbes was if you write 1000 words, you can write it in 500. If you write 500, you can write 200. You start to look at it and you’re just like, “Okay.” You’re trained to rewrite, trained to write tight, and trained to ask tough questions as a reporter. All of these things came together as a blog format for me, in a sense. I found that that was my form. There are very few people who I think do this, natural-born bloggers. Dave Winer is one, I think Michael Arrington is definitely one  That’s why he was so popular. Most people don’t quite understand that. To some extent, M.G. Siegler is one of those people, and I was one of those people. Arianna Huffington is one of those people. Even though she has some news, she likes it in a way which has got opinion in it, has a lot of context with it.

My past brought me to my form, which is why I have struggled to write a book, mostly because I feel, this is how I like to write. I don’t know how to write a book. I like to read a book, and I find myself saying, “Get to it, guy. Why are you taking so long?” 85% of books are so badly written. I like the idea of not having finality to what I have written. Most people, their books are very final. It’s like, “Okay, this is it.” Things change. You look at a guy like John Legere—the guy who’s running T-Mobile now—his past is pretty colorful if you go back to his Global Crossing days, and who he was, and who he is. Not the same person, and yet, the same person. But if he was a hustler trying to get money out of big companies then, and now he’s getting interviewed from individual investors— the objectives are different, the thinking is different. So for me, I think this was my forum. And I don’t have any specific moment. I have things I’m proud about.

I was proud to say goodbye to Steve Jobs in public. I was very proud to write about Skype being acquired by Microsoft because I spent ten years writing about Skype. I finally got my big story on Skype. They were always going to bigger publications. I like the fact that the thing which made blogging and my independent life as a writer/founder great was that we would do stories which we’d notice before everybody else. We were talking about the “Cloud” on my blog in like 2005 and now it’s all mainstream. Same as with data— data was something we were writing about in 2006. When GigaOM came about, we wrote about future of work and online video. I’m proud of the fact that we were always ahead of the curve on everything, but I can’t pick a single story. I’m very proud of all the people who came together. I think that is the lesser known topic on the history of GigaOm, the amazing talent who came together.

I think we were all people who got better because they worked with each other. I think a lot of places have star reporters and star writers and I think we were the star team. Each person made the other person 10x better. That is what I’m proud of. Soon it will all be forgotten, but in my heart, that’s what I think. We were a team that worked together for a very long time. The core team was pretty tight editorially. For me, that was the biggest, proudest part of my blogging per year, as we went from individual to a team. We had a lot of content. I heard a lot of stories. I interviewed a bunch of people. I wondered what was going to happen in the future. Even I’ve stopped doing aggressive writing like I’ve used to, mostly because my day job now is not being a blogger; it’s something else. I don’t know if I answered your question. It was a big ramble.

You’re doing great. What’s it been like transitioning from journalism and blogging to VC?

Very different, right? Take a blogger and a journalist and no matter how much access you have, you’re still outside looking in. Inside looking out is very different. I think it is a much tougher realization I had when I became full-time VC. When I was I was part-time, it didn’t really matter as much, because I was traveling the two worlds and so it was pretty easy.  But now, being full time makes it much, much more explicit. Being an investor is a different kind of work and different kind of stress, as in it needs a different kind of mindset.

Do the same things that excite and activate you as a journalist, excite and activate you as a VC?

Yes. The core of why I’m drawn to it is technology and change. I think the motivations are different. Motivation as a writer are to tell a great story and then move on, and it’s like a motivation. It’s like having a flame, whereas investing is more like being in a relationship. You are with the company for a very long time, so you actually have to be very certain to commit when you make an investment in a company. Because it’s not an investment in a company, you’re investing in a relationship with the founders, you’re investing your time, you’re investing your emotional energy into something. And that leaves a very little time for all the other stuff, because that is the vector with which you look at your investment, whereas the  journalism world is a little easier. You don’t have to worry about running out of money. You don’t have to worry about having a tough conversation with the founder, trying to tell them that they’re screwing up or et cetera, et cetera, et cetera. You know what I mean? That is what I find is different. It’s definitely different kind of challenges. I have no problem with both. I still like to write. I want to write more, but I want to invest and find more companies as well. I think the challenge is that if you’re a journalism you can be more empathetic and more kind to people making mistakes and if you’re an investor, you have to be very direct with them. A lot of people don’t like it when you’re too direct. I made so many mistakes and I learned a lot from one of my board members who’s also my partner now, is John Callahan. It’s like, you can be direct and yet be human. So I aspire for that now. That’s like my way of dealing with it. It’s definitely an interesting tradition.

How do you think the culmination of your life experience, like growing up and all the years that you spent in journalism and blogging, how do you think that affects the way that you approach your work now, and makes you unique as an investor?

I think because I grew up the way I did, I’m grateful more often than most people around here. Because my first was equivalent of 13 dollars in a month, so for me this is like I won the lottery of life. I feel that gives me a little bit more— I take a more philosophical view of everything. I think that’s been my approach, and I think a lot of it is because of my boss. I don’t have time to play games and all those things. You know what? If your aspiration in life is to only make money, then you can do that. I have a different aspiration. My view is that I think technology and change are important to society, and we should be thinking about that. I look at things which are important. I look at science, I look at technology, and not look at opportunistic pointless things to try and make a difference. Everybody says  if you want to invest by making a difference, and it’s like, I don’t know. I mean, like, I like to think about it from a more philosophical standpoint. Like, are we really making a difference? Because most people think of it as a deal. I think of it as an opportunity. I think that’s — like, if you had to just sum it up, that’s… I look for opportunities, people look for deals. That’s my way of putting it.

I love that. Let’s see, you’ve seen tech go through a couple of cycles now. I’m so curious how you’ve seen it change for better and for worse, and particularly culturally, and how you feel about the state of tech in 2016.

That’s a pretty broad question, so you’ll have to slice it.

Let’s slice it then. How have you seen tech change as a culture since 2001?

I think technology is now at the heart of everything. I kind of joke about this, but I think Silicon Valley has become the Babylon of the twenty-first century. And are we doing things right or wrong? I’ll let other people be the judge of that. I think we have a moral responsibility now I don’t think Tech ever had to think about it before. Like 2014 onwards I’ve been writing consistently about this. I think our moral obligation to society at large— society that can make decision based on what the future is right now. I think that is something that we need to be thinking about. Whether it is Facebook, Twitter, whomever— that’s the most important thing. I think Apple is standing there on it’s own and making a statement around privacy. And they’re not saying there’s privacy in encryption. It’s bad for business. And maybe it is and maybe it’s not, but I think it’s bad for humanity. Like if you are— if there are microphones and cameras in our homes all the time, do we even have a modicum of privacy? Are we human then? Aren’t we all living in a zoo at that point? It’s like, what’s the point? And I think there is a moral imperative to all technology, and I think it is time we better start talking about it and acting on it, right? That’s how I think about technology right now. That is the most important change. 2000, 2001—it was all about big companies and a few thing here and there accessing information on your website. Now we are squirrelly. Everything is happening because of tech now. The guys in the Middle East is fighting with the west though Twitter devices. You have spying happening through the Internet. There is a story on the US hacking into Iran’s infrastructure incase there was something weird going on. All those things tell you that every step you take, you use a phone to call in an order, you use a phone to order stuff from Amazon. There is very few things you do now which are not technology. Right? And so there is a moral imperative. I think that’s the biggest change. I think I wrote a piece in 2003 about Redheaded magazine shutting down and pointing to technology becoming completely consumer and pervasive in every way and that was the future and that future is here now. That’s technology today.  I think that’s where we are, right. And so I think it’s cool to be part of it but it’s important to be thinking about the larger, moral impact of what we’re doing here.

With that in mind, how do you feel about the current tech ecosystem right now?

Well, I don’t know about tech ecosystem. I feel like there is many, many ecosystems and there are some parts of the ecosystem which are somewhat unsettling and disturbing because we’ve never— I don’t know. I think there are some parts of it that I don’t like. I think— I’m trying to figure out how to describe this.

Take your time.

There is a cultural aspect of it. And we don’t think before we speak. I think culturally, we’ve come to a point where we shoot before we ask questions and I think there’s a little bit of a Wild West mentality in the ecosystem. I think there needs to be a little bit more thoughtfulness. I think we also have challenges around intellectual leadership. There is guidance which takes into account the moral and societal obligations of technology. There’s a lot of talk about diversity in the Valley. And my view is not just as diversity. It’s diversity by race, diversity by gender, diversity by economic strata. Everybody just talks about their point of view without thinking that each thing has an impact on the other. And we’re talking about these things without a larger context of where our plan it is headed. It is good that we’re talking about diversity, and it’s good that we’re trying to— Numbers are only like half the story. It’s like, we’ve got to think about this bigger—just can’t be about the numbers, because we need to be about systematic change. I like what folks at Facebook are trying to do. They’re not talking about, “Let’s fix this problem.” It’s not an engineering hard fix. This is like, “Let’s develop a new system which is more open to the ideas from more people. And I think that is a longer process. It needs patience. It needs consistent education on all sides. More importantly, it needs action, not reaction, right? I’m very proud of the fact that my favorite part of GigaOM was that we had a huge number of employees who were women. And they were all— I then listened to all of them because they were just smarter than I was. Collectively we got better because of it as a team. It was not because I was playing some game of, “we should have more people.” It was just we should have more great people and they just happen to be of a different religion, or a different color, or a different gender, or a different race. And I think that diversity in the ecosystem is very important. It makes the ecosystem more resilient. It’s a scientifically proven fact that we need more varied people in the system. I don’t know, I look at myself as an example and it’s like, “I shouldn’t be here, but I am.” And I definitely am different than most people I know here. I know that, I have my own way of looking at the universe. I’m okay, but that’s how I see. That’s the ecosystem needs to evolve from better things— to be looking inward looking to a more outward looking ecosystem.

You know one of the things which I actually, what my mother is responsible for, is she worked very hard to put me through college— through school and college. Just like my dad, but my mom worked extra hard. She did tuition and stuff like that and took her own extra money to put the kids through college. And I think for me that has had a much more of a lasting impact. It was like she’s no Sheryl Sandberg in terms of being famous and everything, but I find her more inspirational than Sheryl Sandberg just for that reason. She lived with in a society which had very little room for women who worked and stuff like that and she managed to put me where I am. I think that’s very important for me. It had a way longer— like that’s what I mean the long term it that I saw her do all those things and I realized, “Well, you know, she’s actually pretty smart.” That’s why I am here, right? If she hadn’t pushed me to study, then pushed me to go to a better school and a better college and paid for it, I wouldn’t be here. That kind of tells you everything, right? That’s how you should be thinking, because she was very different than my father. My father was not that person. As a child, you learn a lot about your people from your parents. And I think, similarly, when I came here, more editors I encountered who were open to me, the more open I am to other people because of that. You only learn from people. When I say we have to take the long-term, let’s not focus just purely on numbers, but focus on actually inspiring people to think about the subsequent generations. In my case, it was my editors. I got some really great editors. They couldn’t give a shit how funny my accent is. As long as I got them the story which mattered. There were always positive. And I think there’s a lot of people who would not, and I remembered that. And I remembered to avoid that mistake. Half like New York establishment— I never got a job offer from any of the big publications. Forget job offer, I never even got a call back from any of the big publications. Even today. For me, the path has been on my own. And that’s the challenge of our ecosystem. Is that most of the thing we will need to do is to inspire people to make right decisions five years from now. And we had to start a systematic change, not just numbers but also make people think different.

Where do I want to take it from here? I’m curious to know what your priorities are in 2016 and what you’re working on either for for work or for yourself.

Work things, I’m focused entirely on finding some interesting new companies to work with. I’m interested in writing more regularly. I promised myself that I would write every day and so far I’ve written— it’s 50 days into the new year and I’ve only written 30 times, so I’m falling behind on that [chuckles]. That’s it. Then I have a personal project called PI.CO, which is where I interview interesting people. I want to interview 25 interesting people this year. So far, so good. I’m on top of it for that.

What, as a VC right now, what are are you looking for—it could just be conceptually—in a company that you’d want to invest in in a year like this?

I don’t care what the market is doing, I look for companies which are using technology to solve a great problem. And my preference is for companies with technologies which are more behind the scenes—sort of like networks, and sensors, and stuff like that—but nothing has changed for me. Last year I made only three investments and in the year before it was two. So I’m not rushing out to spend a lot of money. I am looking for a company that I would like to work with. I look for opportunities— and my personal belief is that there is going to be need for software which helps us live better. Because as humans, we are soon going to come to the limit of our ability to live with the world around us because of data and technology. So we will need another layer— just like Google helped us figure out how to find things on the Web, and Facebook figured out how to rearrange our relationships,  there will be new software which will allow us to just exist smartly in the universe and I’m interested in that aspect of technology. People are talking about artificial intelligence and stuff and my view is before we get to the Skynet, we will get to augmented intelligence where we need the software to help us make better decisions. So that’s where my focus is right now.

And then, as far as Pi.co, what kind of people do you gravitate towards the interview?

Well, a lot of photographers. I think photography, visual culture is going through change. I’m going to talk to a bunch of scientists in this year. I’m interested in talking to more in a smaller fashion people, trends, like you know, people— I just did the piece on this young blogger called Julie Zerbo, she runs the Fashion Law and she writes about fast fashion and stuff like that. So I’m interested in that, maybe I’ll interview some economist and stuff like that. I mean, I’m just looking for people who are at the nexus of today and tomorrow, people who are predicting the change. That’s what is very interesting to me.

And I don’t know, for some odd reason, I like talking to photographers. I might start a Twitter feed just linking some of my favorite photography oriented articles and stuff I read. I read a lot about photography. And I don’t think of photography as just photography, but more as what other possibles of camera sensors everywhere.

Okay, last question. What advice or major lessons would you have to share with someone who has a similar background to you and is hoping to get into tech. What advice would you have for them based on what you’ve learned about yourself?

I think every time somebody said no to me, I tried to figure out why did they say no. No is fine, rejections are fine, but you use the no to calibrate why. That means having to take no graciously. I think it’s pretty painful to say no to somebody, as much as it is to take a no.

The advice i have for anyone, whoever they are. If you believe in something, you’ve got to go for it. Don’t worry about the consequences. Don’t worry about the financial outcome, or how famous you’re gonna get, or how poor you will be. If you believe and you can’t seem to do anything other than think about something, you’ve just got to keep doing it. I think the universe has to follow. What’s the point of living if you don’t chase what’s important to you? That’s how I see it.