Season 1 | Episode 2 

10X Founder. Author. Investor. Meet Rajat Bhargava, an industry legend and the CEO & Co-Founder of JumpCloud. Rajat has founded 10 companies with eight exits, including two IPOs and six trade sales. In this episode of The Tech Icon, he shares his many adventures and learnings including attending two high schools, taking on Microsoft, and dealing with pressure.

Show Transcript

Chitra: Welcome to the second episode of The Tech Icon. Hi, my name is Chitra.

Aditya: Hello, my name is Aditya, and we're going to be your hosts for today.

Chitra: Our guest today is an industry legend, Rajat Bhargava. Rajat is an investor, author, and a serial entrepreneur. He's founded not one, not two, but 10 different companies with eight exits, including two IPOs and six trade sales.

He's currently the CEO and co-founder of JumpCloud, the leading open directory platform provider. His company has raised $425 million in venture capital and commands a valuation of $2.65 billion USD. Today, JumpCloud has been used by more than 200,000 organizations. Yes, you heard that right. We’re talking north of 200,000 customers.

Rajat strives to strike the perfect balance between personal and professional lives. He graduated from the very prestigious Massachusetts Institute of Technology and has co-authored The Startup Playbook. The book has a 4.7 star rating on Amazon and it is a must-read for all startup founders. We are beyond delighted to have him on the show. Rajat, you are a technology icon! Welcome.

Aditya: Welcome to the show!

Rajat: Thanks. Thanks for having me. Wow, that's a crazy introduction! Thank you so much. Very nice.

Chitra: Awesome. So while we focus on your journey in today's episode, let's begin by learning about JumpCloud. So what is your vision for the company?

Rajat: Yeah, you know, our vision for the company is we want people to be productive with technology. So ultimately, how do you get people productive with technology? Well, you have to connect them to that technology. And we know now that we need to safely connect people to technology with all of the threats and cyber attacks and things like that.

So ultimately, our vision has been for people to do what we call: “make work happen.” So in a business setting, we want to see organizations be productive. And we want to do that as easily and safely as possible for end users, making sure that they can connect to whatever IT resources they need and make sure that they can be productive in their jobs.

Chitra: Cool. So make work happen, it is! Now from the TechCrunch Disrupt Battlefield in 2013 to more than 200,000 organizations having used JumpCloud today, you’ve clearly come a long way. And you even got customers without writing a single line of code. How?

Rajat: You know, very early on, we wanted to test whether people would be interested in what we wanted to go build and what we wanted to go sell. So the way we did that was we created landing pages and ads and we brought people in. Then what happened is we said, you know, if we built this, would you be interested? Would you want to buy? So ultimately, we were able to find a few people who said, yes, please build this. We will buy. And so that's how we got our first customers. But I think it's really important.

You want to test your ideas with real live customers, not just your friends. Obviously, we talk to our friends, we talk to our colleagues, we talk to people that we know. But you really want to test with people you don't know, who basically don't have that relationship with you and are maybe being a little bit too kind or nice to you for your idea. But you want to get out in the real world and figure out whether it's going to survive being in the market. So we were very fortunate that people wanted to buy what we wanted to build, and then we went off and built it.

Chitra: Very cool. Now, how are you and your company really transforming human lives through secure frictionless access?

Rajat: I think all of us want to be productive at work. So I think all of us want to be impactful in our lives, whatever we do—whether that's personal or professional. But from a professional context, which is where we focus as a company, I think we all want to make an impact. We all want to be valuable. We all want to be able to be successful in our roles.

Well, a lot of that depends on, do you have access to the right tools? Do you have access to the right technology? And so, if we can make that access much easier, much safer, much quicker, we think you're going to have a more fulfilling experience at work. We think you're going to be more successful. We think you're going to be more productive. And hopefully that organization benefits and then you benefit as well. But I think ultimately all of us want to make an impact in whatever career or role that we're in. Obviously, we can't replace the human effort that somebody puts in but we can make that a lot easier by giving them access to technology.

Chitra: Absolutely. Now for the next section, let's take a walk down the memory lane to celebrate your journey and inspire the world through your story of courage and conviction. I'm going to hand this over to Adi.

Aditya: Yeah. So childhood experiences play such an important role in our lives. And with that being said, let's get to know a bit about your early years. So how would you describe your childhood?

Rajat: How would I describe it? That's a great question.

So I think it was pretty fun. You know, I grew up in Michigan, grew up in a great community and we had great friends. Obviously, it was a long time ago. But I'd say it was a time when we could be out playing in the streets pretty easily. We could go to friends' houses, we would ride our bikes around. So it was probably just a different era than things are now. But it was a fun, easy childhood experience.

It was a really warm, welcoming community. There were a lot of tight-knit relationships in the community. We didn't live in a really big city. But it was big enough where it wasn't like you knew every single person in the community. But you were able to build really nice relationships and friendships. I was able to play a lot of sports, which I really enjoyed. It was competitive, so you had some of that push to get better at your sport. Then academically, we had some great schools that were in my community, and I was able to take advantage of that. And that's really important, too.

Aditya: Yeah, totally. Sounds like the childhood experience was really fun. May I ask, like, how was it growing up in USA being of Indian origin?

Rajat: Yeah, well, I mean, I was one of the few Indian people in my community. So, you know, obviously, that is somewhat challenging sometimes. But you also think it's unique. You feel you're unique and you're special and you have a different, maybe, perspective or point of view. I think as you get older and as you go through life a little bit more, you appreciate that unique experience. Everybody's unique and you try and find different ways to make it special for yourself and kind of what you want to do. And I think, you know, being of Indian descent, that ended up being unique for me and something that was quite special.

Aditya: Yeah, that's a really cool way to look at it. Okay, what did you want to become growing up? Did you have a dream?

Rajat: Well, I probably wanted to be a professional athlete, to be honest with you, but I absolved myself of that pretty quickly. You know, I think I wanted to be an engineer, an aerospace engineer for a long, long time. That's what I actually went to school for initially, I was going to do aerospace engineering. But it was a time in the world where aerospace engineering wasn't as dynamic as it is now. So I changed over to electrical engineering and computer science, but what I was sort of really was very interested in was aerospace engineering.

Aditya: Cool. Are you able to share what your parents did and what kind of a value system you believed in as a family?

Rajat: Yeah. My father worked in IT. It's an interesting sort of parallel because I ended up working in IT in a lot of ways. My mom was at home taking care of the family.

I think it was a very tight knit family and a family that really believed in education and doing your best always, trying really hard, having really strong values around honesty, integrity. Those things were really important. But I would say the thing that probably stands out the most was just making sure that we always did our best and we always tried our hardest. So as long as we did that, everything was good. I think a pretty important theme in my life is continuing to always push and try and do your best always. Sometimes you're successful, sometimes you're not and that's okay.

Aditya: Yeah, yeah. Looks like your family really pushed you to work hard and I guess IT runs in the genes, huh?

Rajat: Yeah, exactly.

Aditya: All right, that's cool. Next, let's dive into your educational journey and get some advice for students out there. So which high school did you attend?

Rajat: So I actually attended two high schools. So I had a very unique high school experience and we were very fortunate that in my hometown, they built what is called a magnet school. So they built a school just focused on science and math. And that was funded by the pharmaceutical company that was headquartered in our hometown, which was really amazing that they did that.

I was one of the first classes that went through that high school. So we split half our days doing math and science at this school. And then we would go to the regular public high school. So I had two different high schools, which was, again, another unique experience. There's not too many people who got to experience that. It was great because I got a world class education, I think, from a math and science perspective. And then I had a great education from the public school on, you know, kind of, let's call it humanities. So I got kind of both experiences in there.

Aditya: And you were, like, attending these schools at the same time, right? The public school and then the special school for math and science.

Rajat: Exactly. So I'd spend half the day at the math and science school and then half the day at the regular high school. The math and science school didn't have any real extracurricular activities. So sports and everything were done through the public school. But you had a very focused academic experience that was really accelerated. So it was a very fast-paced, intense high school, math and science high school, which I think ended up preparing me pretty well for college.

Aditya: Yeah, that's awesome. And then, of course, you went to MIT, one of the top universities in the world. Were there any challenges you had to face either at school or college?

Rajat: Yeah, of course. I mean, MIT is a great school and there's a lot of great schools in the world, of course. I would say, the first thing is, I think in college, it's completely what you make of it. So it doesn't really matter, I think, what college you go to at some level. I think what really matters is whether you take advantage of that experience.

Aditya: Yeah. Were you a good student? And according to you, what is the definition of a good student? Is it like your personal mindset like you talked about?

Rajat: Yeah, I think that's the right question. What does being a good student really mean? I think, unfortunately, there's a lot of focus on, well, a good student equates to you had a good GPA or you had good grades, or you took the right major or you took the right classes or whatever that may be. I think over time you realize that's not really the definition, I think, of a good student. I would say everybody has their own definition and that's fine.

But I think for me, maybe the definition is more about, did I learn the material and did I learn how to work? Did I learn how to prioritize? Did I learn how to get through a lot of work very quickly? I mean, one of the things that they do at MIT is they give you so much work that you actually can't finish it, right? Because they don't want you to finish all the work. What they want you to do is, they want you to prioritize based on what's important to you.

You realize that you cannot get through everything that you've been given. So you have to very quickly understand that you're not going to solve every single problem. You're not going to learn every single piece of material. So you better prioritize. You better understand what's important and what's not important. I think that's a little bit more of what the intent is. Then they're trying to prepare you for what is life going to be like when you work in the real world and you have all of these different challenges. Any day at JumpCloud, I can't finish every single thing that I've been asked to do. Neither can the company. So you have to prioritize.

Aditya: Yeah. It's really about these life skills. Not necessarily memorizing this material and then doing well on a test, but what you take into the future.

Rajat: That's right.

Aditya: Yeah.

Rajat: Ultimately, I think the memorization is not going to work long-term because you're going to forget that, and that's not really going to help you in the future. But I think if you can figure out a mechanism for you to learn that material and have it stick with you, or you can come back and relearn that material very quickly, then I think then you've been successful, right?

Aditya: Yeah, totally. Okay, would you call yourself an introvert or an extrovert?

Rajat: Introvert for sure.

Aditya: Yeah, I feel the same. And what is your advice to students who find themselves drowning in parental expectations, peer pressure, and crazy competition these days?

Rajat: Yeah, it's very hard, right? I mean, as I think about me trying to go to MIT today, I don't think that I would be able to go to MIT today, right? I think it's so competitive, so difficult to get into, and the pressure is very, very high. But ultimately, I think the college experience and the high school experience is what you make of it.

So if you can flip it from the pressure of grades, the pressure of everything else to being... I really want to learn this material because if I learn this material, I'm going to learn how to learn, I'm going to learn how to problem solve, I'm going to learn how to be successful. That might end up relieving some of the pressure, and then truthfully, you may actually do better because you basically figured out a mechanism to learn. And if you can really learn quickly, you can learn accurately, then you probably end up doing a lot better.

Aditya: Yeah, I feel like that's really valuable. Do you have any advice for the parents of these stressed students?

Rajat: Yeah, of course, but I think obviously every family unit is different. But I always thought more about how can we focus on what is the core outcome we're looking for. And that's to learn to be able to problem solve, to be resilient, and be able to ultimately be successful in the real world. So if you can do that, that's more important than I think honestly what school you go to, the grades that you got, whether you had this or that award or whatever it might be. I think all of those things are nice, but they aren't necessarily determinants of whether someone is going to be successful in the way that they want to be successful.

Aditya: Yeah, those are good tips. I hope students and parents are listening. Okay, now I'll pass it over to my co-host to cover the next segment: Entrepreneurship, the segment you've all been waiting for.

Chitra: Thanks, Adi. Rajat, those are some really great points. There were three things that stood out to me; I was taking notes on the side: work your hardest, relentless prioritization, and really learn as much as you can. That's so deep and so awesome. Thank you. Now on to entrepreneurship. So what was your first job out of college?

Rajat: Well, my first job was my first company. So I didn't really have a job at another company. We started our first company when I was a senior in college. So I didn't really maybe get the same experience that everybody else got, which was to go work at a company, learn how companies operate, and then go start your own company after that. I was thrown into it where we just started our own company, and we didn't really know what we were doing, but we had a vision for what we wanted to build.

Now, I did go to work for Intel during my summers at MIT. So I was able to get a little bit of corporate experience, but being a summer intern versus being kind of a full employee are probably two very different things. So I don't want to say that I really understood how to work in a company and all that, because I never had that experience.

Chitra: Cool. And which was your first company, if I may ask?

Rajat: It was a company called NetGenesis. We were basically building website usage analysis. So when you think of who came into your website, what they did, how they got there. Now that is a pretty sophisticated category. But back when we started our company, we were one of the first people to ever come up with that product. So very, very early on in the lifetime of the web.

Chitra: Something similar to GA?

Rajat: Yeah. Think of it as a very, very early precursor to Google Analytics, like probably one of the first analytics tools around websites ever.

Chitra: Very cool. And then you went on to found company after company. You are a 10-time entrepreneur. How did it all happen? Did you always want to become one?

Rajat: Well, I think I wanted to always have an impact, kind of like what we talked about before, where obviously I wanted to work. I wanted to do things. I wanted to contribute, but I wanted to have an impact and I wanted to be able to do things that were interesting and have real ability to learn and grow and the responsibility. So ultimately, I figured out if I wanted to have that kind of responsibility and impact, the path for me would end up being entrepreneurship and building our own company because at that point, you are responsible for the whole thing. So that really appealed to me because it really said, I have to be really good at what I do and I have to learn quickly. I have to be able to adapt and be able to be successful because there's a whole group of people that are relying on me to do that along with my co-founders.

Chitra: Sure. What did the initial years look like?

Rajat: Well, the initial years were a lot of just learning and navigating all over the place because we were learning not only about the business that we wanted to build. We were also learning how to just be founders and entrepreneurs and how to basically run and operate a company. We didn't know how to do that.

All of my co-founders and I were all in college. We didn't have any real-world experience. But we were able to figure it out. We were able to build products and we were able to sell the products and then ultimately grow the company. But I would say it was a lot of learning trial by fire every single day because it was uncharted territory for all of us. Although many people had built companies before, we just didn't have that experience in the group.

Chitra: Wow. I think that's a great segue into my next one, which is about the rejections and conflicts and heartbreaks. I'm sure you experienced some of that. How did you navigate that?

Rajat: Well, I think as an entrepreneur, you experience that almost every day. I think you have to become pretty resilient pretty quickly. I thought about it as ultimately, when you start out, you take things very personally: a customer that doesn't want to buy or an investor that doesn't want to invest. Or you have something go wrong, you were trying to recruit a candidate and they decided not to choose to come to your company and work.

All of this stuff is all around you every single day. What I think happens is people get very up and down. It is manic because when you have something successful, you get really high and you're excited and you think everything's great. Then when something goes wrong, you get really low and it's like, okay, everything's broken. The truth is neither one of those are the reality. It's probably more in the middle. I think over time, you learn that rejection is going to happen every day, but then you're going to have a success almost every day too. Just knowing that you're going to face those things and getting comfortable with that makes a big difference.

As a leader running a company or a leadership team running a company, I think you want to be very careful about the highs and lows too because that ripples through the organization. If you don't have something to be successful, I think it's important to be resilient like okay, that was a setback here. How do we move beyond that setback? Then of course, when you have something to be successful, I think you want to be careful about saying, well, oh gosh, everything is working great, and we're super successful, and then you lose sight of the issues that need to be solved. From my perspective, rejections and the challenges that we have are a normal part of every single company. It's a normal part of every single day. As long as you understand that, then you can work through that.

Chitra: I absolutely love that. And how you describe the highs and the lows reminds me of some of the most famous sportspeople. Now, you found JumpCloud about 10 years back. You decide to compete with Microsoft's Active Directory head-on. You take a share of the marke and you make a dent in this identity management space. Now, that's huge. Where did that courage and conviction come from?

Rajat: Well, the courage and conviction came maybe because we didn't actually understand the market completely. It wasn't like I was an identity person at the start of the company. We just had a vision of how things could be done differently. I think maybe that having that little bit of naive perspective is a good thing because we didn't really understand why everybody had to be tied to this thing called Active Directory and everybody used it.

We said if we created something different and better, then we thought that customers would be interested in that. Ultimately, there's a lot of reasons why I think that played out, but it was really just this belief that we thought we could do something better for customers. And something that was more open, gave people freedom, gave people choice, was more cost-effective. All of these things were important to us and we were able to make that happen.

Chitra: Cool. Now, what is your advice for startup founders and builders who are struggling in different phases of their startup journeys?

Rajat: Well, it depends a little bit on what phase they're in. But I think the one thing I would say maybe that cuts across all the phases is making sure that whatever you're working on, you're incredibly passionate about and you believe in. You have to be deeply committed and the only way I think you can be deeply committed is if you truly believe in it, you're passionate about what you're working on. I think that cuts across all phases, but as long as you’re constantly checking in with yourself and your team that this is really what we believe in, then I think you have a chance of being successful.

Chitra: Awesome. For more tips, they can get a copy of the Startup Playbook.

Rajat: For sure.

Chitra: With that, I am going to pass it back to Adi for some fun stuff.

Aditya: Yeah, let's talk about some fun stuff now. What are your hobbies?

Rajat: So, what are my hobbies? Well, I enjoy working a lot. So I work a lot, but I'd say my biggest hobby is probably, I enjoy playing tennis. That's the one that I probably will gravitate to most outside of being with family and friends and working.

Aditya: Nice. You believe in achieving the right balance between personal and professional life. How can one do that?

Rajat: Well, I think that one thing is the balance is different for everybody. I think we talk about work-life balance, but I don't know if that may be the right way to talk about it because it really is a very personal thing. I do enjoy working a lot and I do work a lot, but that amount of time that I work is the right thing for me. But it may not be right for somebody else. In fact, it's probably not right for everybody else. It's really important that you think about it. What's best for you, maybe not what's best from an external perspective or how maybe the world thinks about it.

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But as long as you're happy with the choices that you make and how much time you spend in different pockets of your life, then I think that works best because that's going to make sure that you're happy. It doesn't really matter if other people think that those are the right choices for you because those are very personal choices. As long as you feel like whatever balance is right for you, wherever you are on the spectrum of how much you work and how much you maybe don't work, then that's what's most important. It is really figuring out what's right for you.

Aditya: Yeah, totally. It varies from person to person. Your family deeply supports you in your endeavors. What does it take on their part to make you thrive?

Rajat: Yeah. Obviously, I think with anything, it's not just you doing it, it's a group of people around you too. A large part of that that often gets overlooked is your family. Especially as an entrepreneur, it does take a toll on your family because you are working quite a bit, you are traveling quite a bit, there's a lot of pressure, all of those things are there. You have to make sure that you have a family unit that I think is supportive of that. If you don't, I think it gets very hard to make that work. It's hard at home with your family and then it's hard at work because you are torn.

We talk a little bit about this in the book, it's just making sure that you are checking in with your family and making sure that the things that are important to you and your family are being taken care of. And that you are spending the time in the right way: meaningful time doing the things that you and your family want to do. As long as you do those things, then I think that gives you energy to go do that. Then your family also feels very supported and then they can support you and your endeavors at work as well.

Aditya: Yeah, that's awesome. All right. Finally, would you like to share: maybe a little secret or a fun fact that very few people know about?

Rajat: Oh gosh. I get asked this every once in a while. I have no idea how to answer it. But I think that maybe we talked a little bit about it. I think a pretty important experience for me was that I did go to two high schools, right? I went to a high school that was very focused on math and science, which I really enjoyed. And then I was at a public high school. So I got two different experiences, very, very different experiences. That's maybe not something that a lot of people know. But I think that probably did shape me in a really positive way because I got these really unique experiences.

Chitra: Yep.

Aditya: All right. Thank you for sharing about your personal side. We're now nearing the end of the episode of The Tech Icon, and we'd love to get some final thoughts in this final segment. So back at you, co-host.

Chitra: All right. Let's end this final segment on a note of celebration. So Rajat, what would you say to your younger self? Is there anything you would do differently?

Rajat: I mean, it's hard to say that you would do things differently, right? Because if you do things differently, you may not end up in the same spot. It could be better, it could be worse, it could be different. I mean, who knows, right? So maybe the answer to the question is, for me at least, maybe just enjoy the journey a little bit more. I was pretty focused on the work that I wanted to do and probably didn't enjoy the process as much as I could have. But over time, you learn that. You'll learn that the process is a part of the joy of what you're trying to do. And I think over time, you come to terms with that.

Chitra: Sure. Now, when you were growing up, did you know that one day you will build this unicorn that is used by more than 200,000 organizations, that is valued at $2.65 billion, a company that competes with Microsoft. Your family must be so, so proud. What do they say?

Rajat: Well, I mean, we don't really talk about it a lot. Truthfully, that's a part of who I am, but it's not completely who I am too, right? So, I think it's actually a good thing that we don't necessarily talk about it all the time, because it does give you kind of a more holistic perspective, that what we do at work isn't really completely who we are. We have a life outside of work, we have friends, we have family, we have other things, other interests, and making sure that those get prioritized too. I think everybody's proud of each other, right? So, I'm very proud of my family, of what they've accomplished and what they've done, and who they are as people. And hopefully, they're proud of me for what I've accomplished and who I am as a person, which probably matters a lot more than what I've accomplished, or again, whatever we've done at work.

Chitra: Wow. It's awesome how you all support each other. Any parting thoughts or pearls of wisdom?

Rajat: I don't know if I have any, but this has been great. So, thank you for having me. And I loved the set of questions and talking a little bit about all kinds of different things. But I think maybe just the last thing is because hopefully there's going to be a lot of kids who end up hearing this: just really follow your passion, find something you're really passionate about. Even for adults, at any time, find something that you're passionate about. And if you're passionate about it, then more likely, you're going to enjoy it more, you're going to end up being more successful, or at least you're going to be happier working on those things that you're passionate about. And I think that makes a big difference.

Chitra: So, follow your passion, it is. And on that note, we want to thank you very, very much for joining us in our mission of giving back, and inspiring not just the two of us, but so many students and entrepreneurs out there. We wish you all the best.

Rajat: Thank you. Thanks for having me.