Rajiv Vinnakota ’93

"Go and try something stupendously crazy."

Rajiv Vinnakota '93, is the Executive Vice President of the Youth & Engagement division at The Aspen Institute, a new venture focusing on youth leadership development, civic engagement, and social justice. Prior to the Aspen Institute, Raj was the co-founder and CEO of The SEED Foundation, the nation’s first network of public, college-preparatory boarding schools for underserved children. Raj is a former trustee and executive committee member for Princeton University, former national chair of its annual giving committee, and former executive committee member for its Aspire capital campaign. In 2009, he received the Woodrow Wilson Award, the highest honor that Princeton bestows on an undergraduate alumnus. 

Read and watch to learn about Rajiv's journey from consulting to co-founding the SEED Foundation to the Aspen Institute, how he got on important people's schedules with no time on their hands, and why your Princeton education gives you a responsibility to try something crazy. 

1. Tell me about your path since graduation.
My path since graduation has been a really simple one. I graduated with a major in molecular biology and a certificate at the Woodrow Wilson School. I was completely burned out by school, even though I wanted to go get an MD-PhD, so instead I went into management consulting, because I thought that's what everyone did coming out of Princeton. I did that for three years, loved it, but didn't want to do it for the rest of my life, and also decided I didn’t want to go back to school. A group of my friends and I came up with this idea to start a college prep boarding school for inner city kids. In 1997 I started that with my business partner and did it for 18½ years. I just recently moved over to the Aspen Institute to help lead the start of a new division focused on youth leadership development, civic engagement, and social justice. 

2. Was shifting from management consulting to starting a school really that linear?

Looking back on life things look very linear, but you have those moments in time that are really the inflection points. One of them was at Tower Club at my reunion. I loved management consulting, but I knew it wasn't what I wanted to do with my life. A group of my friends and I started talking about what we wanted to do. The conversation quickly gravitated toward urban education, because even though this was 20-plus years ago it was an issue. We started talking about how we thought we might be able to change the dynamics. One of my close friends said, “There are boarding schools for rich kids. Why aren’t there boarding schools for poor kids?” For the next couple of years I kept that idea in the back of my head. I talked to a few people about it, and finally decided that if I really wanted to do more research on this that I would need to take some time off.

Fast-forward a couple of years. I then took a leave of absence and traveled around the country for two months basically saying, ”You can't tell me five of us drinking a beer were the first ones to think of this idea. Has it been tried? How has it worked? What is the financial model? What's the programmatic model?” I was able to get in front of a lot of very important people who had no time on their hands, but made time for me. I was able to build a plan. During those two months of travel I also met a guy named Eric Adler. The second time we met we decided to go into business together to start SEED.

3. How were you “Able to get in front of a lot of very important people who had no time on their hands”?
I think the most important thing was that I called them. But the other thing was that I really utilized my Princeton network. One of the things that is amazing about being part of this network is that people will return your calls; people will make the time for you. And they did. I learned so much about education, but also about public policy from these folks. I'm so thankful for it that the only way that I believe I can give it back is to pay it forward. So when people call me I try my darndest to make the time for them the same way that people did for me 25 years ago.

4. You ultimately moved on from consulting, but you mentioned that you loved it. What did you love about it?
There were a few things I loved about management consulting. Number one is the idea that a 21-year-old is working with Fortune 500 companies on issues of real importance to them. Strategic issues, operational issues, marketing communications, some really heady stuff. You learn new things every single day. There's an immense network of folks that you can learn from. I learned so much about business planning, and it was fundamental to being able to be successful and to starting the SEED schools. In addition, it's just another way in which you get to be introduced to this amazing new network of people of the elite of the top 1% of the top 1% of the top 1%. This was an opportunity to meet top folks coming out of Penn and Dartmouth, University of North Carolina and Chicago, and so on and so forth. Just getting really excited with this new oxygen and being able to meet such folks. Third, it teaches you a new language, a new way to think. I walk into a fast food restaurant that's not operating efficiently and say, “What are the things that should be moving around so that they could do that better?” Or I walk into Whole Foods and say, “Wow, they have their shopping carts set up in the wrong place for them to be efficient,” things like that. It's weird, but you never think the same.

5. You really enjoyed it, eh?
I mean management consulting isn't all heady great stuff. You work really hard. At its core, you’re helping big companies make more money and that has consequences both on the revenue side, but also on the expense side. So you might be cutting jobs and so on. So it's not that management consulting is all perfect, but as a 21-year-old there are very few places where you can learn so much and get such an introduction into a whole new network of folks who are important.

6. Are you continuing to work at SEED while in your new role at the Aspen Institute?
So this transition from SEED to the Aspen Institute is taking a while. When you're running an organization you co-founded for eighteen years, you can't just transition like that. Especially because I made a number of commitments to the institution and to the board, I'm still basically in an eighteen-month transition process. My day job is now at the Aspen Institute, and the exciting thing there is that I was approached by the CEO to help start this whole new division. The Aspen Institute's board and the CEO, Walter Isaacson, recognized that in order to maintain relevance and also in order to expand not only the diversity of the work that we're doing, but also who we are serving and working with, we needed to get engaged with youth. That idea and concept is what was handed to me. So my small merry band of colleagues and I are trying to figure out what we are actually going to do. So it's in this fun ideation stage where we have a few projects we're already doing, a lot of thinking, and a ton of people approaching us wanting to partner with us both internally here at the Aspen Institute, but also other entities. It's this fun time where we get to decide what we want to do, why do we want to do it, where, how, and so on. And then I’m still working through a transition at SEED.

7. It sounds like you have just a few things on your plate.
I haven't even mentioned the most important thing, which is family. I have a 10-year old-daughter. She's in fourth grade and I want to make sure that I spend as much time with her as possible. She still holds my hand when we walk to school and I know that's going to go away at some point soon. I’m making sure that I literally structure the time to be able to be with my daughter and my wife.

8. Why education?

Well the reason I chose education is because education chose me. I am the grandson of a rice farmer in India in the poorest state in India called Andhra Pradesh. He earned 30 rupees a month, he had six children, and he spent 24 of those 30 rupees to pay for his children's education. All of them ended up getting advanced degrees. They all moved to the United States, doctors and engineers, and they're all doing great.

I never met my grandfather, he passed away a few months before I was born, but I got his name. The story of my grandfather and the sacrifices that he made in the name of education as the lever to ensure that his children were effective, was something that was very much in my DNA. And then I have two parents who are educators. My mom was a second grade teacher in the Milwaukee Public Schools and my dad was a professor at Marquette University. So education is really in my blood. Even though I didn't have an explicit expectation that I would go into education when I went to Princeton, it ended up being where I went. I think it’s in large part because of both the stories that I was taught, as well as looking at the role models, my parents, and the work that they did.

9. Do you have an advanced degree?
I do not have an advanced degree. I am the black sheep of my family. My wife has three masters and a PhD. My sister, who went to Princeton, has a PhD and a veterinary degree. My brother-in-law who is married to my sister has a PhD. My parents are wondering when I'm actually going to do something with myself.

10. Think back to when you first graduated. What would surprise you most about your path?
There are two things when I look back between now and 1993 with some level of knowledge but also with surprise. My father when I was growing up was really great at saying, “I've had two jobs, Raj. You're going to have multiple jobs and it may not even be connected with what you major in.” And he was right. I mean I'm a molecular biologist by training. I haven't used the core content of what I did literally since the day I started in the work world, but I've used all the skills in just a multitude of ways, from thinking about things from a scientific perspective, to having an analytical mind, and so on and so forth. The education that I got in Princeton was incredible. I just used it in a fundamentally different way than I'd assumed.

The second surprise, as I mentioned earlier, is the depth and breadth of the Princeton network and the love that Princeton's network has not only for the institution but also for the network itself. The reason I'm late here is because I had breakfast with someone from the class of ‘69 that ran over. He also happened to be the first person who joined my SEED board when I started SEED in 1997. So you think about the arc of all of these connections and they just continue every day and every month. I'm amazed with the way in which people interact with each other.

11. What strengths and personal qualities make you effective at your role?

I get asked often, “What are the characteristics that you needed to have in order to be successful with SEED?”  Eric Adler, the other founder, and I talk about it often. The two that we point out, remember I was 25 when I started SEED, are that we were naive and we were stubborn. We were naive in that we didn’t know what we were getting ourselves into. We needed that, because anyone who actually knew what we were getting ourselves into would have said, “We’re not doing it.” And then we were stubborn. Whenever people said, “No, you can't get legislation passed in congress,” and “No, you can't change funding laws in the District of Columbia and get Marion Barry to support you. No you won't be able to find a site and negotiate a lease here in the district that's longer than five years. No you won't be able to get dept financing. No you won't be able to convince families in Anacostia that you should have their children during the week living with you while you're starting school" we just kind of took it all in and said, “We’re gonna do it.” So being naive and stubborn was exactly what we needed at that time.

So now I'm 45 so it’s a little bit different. I still think I’m naive and stubborn, and if you ask my colleagues they would say, “Definitely stubborn, maybe not naive,” but there are other characteristics. One is to be incredibly empathetic. Empathy is the ability to be in another person's shoes and understand how they're coming at issues. Being able to understand what motivates other folks is incredibly important to be able to get the ball across any finish line. The other thing that is the single most important characteristic or capability is to be able to listen well. I think that listening is a lost art. If you want to do it well it requires 100% of your effort. You can't be trying to also write a text, you can't be listening to music in the background, you can't be trying to write an email, if you want to listen and if you want to do it well, and if you want to do it in a way that you're actually capturing the information, you have to use 100% of your brain.

12. Have you ever received feedback about your leadership that surprised you?
I get feedback on my leadership all the time. In fact, I look for it often. There are two things about me that I know quite well, but I always need feedback on. One is that I'm the eternal optimist. That's great when you're trying to do impossible things, because you have to have a belief in yourself and in your idea. I'm also the eternal optimist who says, “Yeah, I have a breakfast at Georgetown from 7:30 a.m. until 8:30 a.m. and at 8:28 a.m. I can walk out of that breakfast and get to the Aspen Institute by 8:30 a.m.” Frankly, unless you're bending light you're not going to make that happened. So there are some practical levels of optimism that I need to be able to understand. And I don’t mean that as the only example. Therefore, I do need to have around me people who are also realists. One of the things I've learned is how you need to create a team that balances all of these capabilities. I love strategy. I love big ideas. So I need to make sure that I have a few people around me who can execute around those ideas and who can be the operational focus to actually get things done.

I think the other part of what I've learned is that I am incredibly bad at being able to say no. That can be everything from when people want to have meetings with me, to the number of things that I want to take on at any point in time for myself and the organizations with which I'm engaged. Being able to do that well is a skill and talent that's required. I know I'm not good at it, so I have to force myself to think through and make sure that I have people around me who can help me think through that. The other part of being able to say no is just to do it for my own fundamental ability to live, my physical sustainability. It really helps to be married to someone who is very good at being able to say no for you. So I get all this feedback. I understand I've gotten better at it, but I've also gotten better at knowing who to put around me as part of my team so that I do these things better than I can on my own.

13.  Have you ever been faced with a situation where your values clashed with those of an organization for whom you worked? How did you handle this?
I've been lucky enough to be working in institutions where my values and the institutions values were aligned. However, I certainly have come upon situations where there is a values clash. Where you have to decide that you’re going to trade-off value A versus value B. I think the place that I experienced this the most is the question of breadth and depth. How many people do you want to work with effectively, and how deeply versus the pure quantity of people that you can impact? To me, that's one of the most important values clashes that I run across all the time. I certainly ran across it at SEED, because we believe in the depth. We said, “We want to work with a group of people who are going to be most successful if they're in a boarding school,” where the cost per student is anywhere from three to five times as much as a cost of a regular school. To me that was important, because there is a group of kids whose success capability is going to be so much lower unless you make a very heavy investment.

Princeton believes in some ways exactly the same thing. Make a heavy investment in a few people and decide that they have the capability to be the leaders who then will have a greater impact on society. There are other people who think the best thing to do is to start programs that can help a multitude of youth. An afterschool program that costs much less could help many more youth, but maybe not help them as deeply. To me that's one of the values challenges that I'm engaged in when I think about what role I should be playing in education reform. So it's not a values clash in the sense of, “Oh my gosh, I can't work here.” It’s a values clash in terms of asking, “What do I think is the greatest value of time and resources?”

14. Tell me about the role that failure has played in your career development.
The only way to be successful professionally is to have failures. To me the failure of a big project blowing up or a business not working is not the real failure that I want to focus on. What I want to focus on is that only through constant learning do you actually become successful. One of the things hopefully that my colleagues will tell you is they get a lot of feedback from me. A lot of that feedback is, “Hey this went well. Here are ways to improve,” and so on and so forth. My view is that's hopefully how everyone with whom I interact works, both ways, because the only way you're going to get better is by getting feedback. I don't call that failure. What I call that is learning experiences that hopefully make you better over time.

One has to come into that environment with an understanding that they're not anywhere close to perfect and that learning is the best way to get better. If one were to come into that environment saying, ‘I'm the greatest thing since sliced bread,’ and by the way it may not even be that person's fault, but it may be the fault of the whole culture around him that says, ‘You have to be perfect,’ then you're going to have a problem. Because we're not going to be successful with that kind of person and that person’s not going to be successful, because there's no job that exists that allows you to live in a cocoon. Even being a caterpillar allows you to live in a cocoon only for a short while. Then hopefully you become a butterfly.

15. We’ve been talking a lot about the myth of "effortless perfection” here at Princeton.

So this idea of effortless work is a myth in our society that's actually really troubling to me. It's troubling to me on two levels. Number one, it's not true. Number two, when I look back at my experience at Princeton I was part of that. I was the guy who worked really hard, did two majors, I wrote two senior theses, also was on a team, also was in a fraternity, and also drank too much. It was the ethos of work hard, party hard, sleep two hours, and you can get it done all the time. I appreciated that that's part of the ethos. I fell into it, it's easy to fall into it, but it's not what life is really like.

The messy part behind it was, well you know, when I got that 33 on my first exam in chemistry 203, and the amount of work that I really needed to do to make up for that. Or when I got my first Junior Paper back and it had more red than black on it. But all that was covered by a veneer of, “Hey everything's gonna be ok,” and “I'm doing well.” I think that the long-term consequences of telling myself that I could do all of it has been well, fewer brain cells from drinking way too much in college. Less time spent on the things that looking back I wish that I did. Princeton has so many resources, conversations, other places to meet people, and so part of it is about trying to get all of us to understand that the experience itself is the single most valuable thing at Princeton, as opposed to achieving X, Y, and Z.

16. Who do you hire?
I really look at four things in deciding whether or not someone should be part of my team. Number one, are they oriented to the mission of whatever institution I am engaged with. In the end I want to know that they have a heart and what motivates them is to do the work really well. Second, I want to make sure they understand what excellence is, because we all need to shoot towards excellence as our goal.  Quick asterisk, you need to shoot for excellence, but you're not always going to get it. This is the learning part of the work that we do. It is perfectly fine not to achieve excellence. It is not fine to not understand what excellence looks like and to be able to learn from your experience.

Third, and in some ways this is the most difficult, is I want to be able to work with people that I really enjoy. People with whom I come into the office saying, “I'm really looking forward to spending time with this person. I really enjoy my time.” There is no other person besides hopefully your spouse and your children that you’ll be spending more time with for your life, so you better darn well enjoy. They have to be a joy to be with. Fourth and finally, there's got to be an actual fit, in the sense of, OK, does this fit with the job. But it's really those first three characteristics that, to me, end up being the differentiating factor that define who do I want to work with.

17. You’ve stayed very connected to Princeton. Tell me about how and why.
So I love Princeton. I was involved in Princeton Project’ 93, which I did as a senior. Then I got involved with Annual Giving coming out of Princeton for five years and helped to lead that. Then I was on the board from 2004 to 2009. Then I was national chair of Annual Giving for the next two years, and also on the executive committee of the Aspire campaign, the last campaign for Princeton.

Look, Princeton did a number of things for me for which I will be eternally grateful. I could never actually pay back. It gave me a wonderful education, a wonderful liberal arts education as well as a science education that I use in countless ways. Secondly, it introduced me to a network of people who have a similar love for the institution and appreciation for the network and a willingness to be as helpful as possible in any way possible. Third, it introduced me to my wife. So that was pretty important as well. Fourth, I am incredibly proud of the ways in which Princeton University thinks about using its assets. To me, my proudest day as a Princetonian was when we decided to do away with loans and decided to go to a grant policy. To me, that was a fundamental placement of how we thought about our values and using our resources in such a way so that we ensured that every graduate would be able to do anything that they wanted and use their talents the best way possible, rather than thinking about, “How am I going to meet my loans?” That was, in a microcosm, exactly the kind of values an institution would hold with which I want to be affiliated.

18. Who do you look up to as a prime example of living a good life?
Well it's funny that you should say living a “good life”, because I’m here at the Aspen Institute, which is really based around certain seminal texts and ideas, one of which is Aristotelian in the idea of, “What is the good life and how do you live it?” People I look up to as “living the good life,” are people who fundamentally define what they do as giving back to society.

People like Wendy Kopp will always be somewhere near the top of my list, because of the idea that she had, the stubbornness that she had in developing it, and looking at how, now, Teach For America, has fundamentally driven much of the education reform that's happened in this country in the last 20 years. I mean that's an amazing pursuit. So that's one type of person. The other is what I'll call your “regular Princeton alum,” in my case someone I looked up to from the classes of the sixties and seventies. Princeton does something around the idea of giving back and making sure that everyone has not only a responsibility to do well, but also to give back to the University, to be involved on boards, to be a contributor both in time and in money to the work that they do. I'm always amazed with meeting so many folks who are incredibly philanthropic.

I'll give you two examples. One is Jack Laporte, who unfortunately passed away, but is from the class of 1967. He was the founding chair of the SEED school in Maryland. Incredibly quiet person, unbelievably intelligent, worked at T. Rowe Price for 25 years, just did so well financially, but did even more well spiritually. He was the soul of the SEED school in Maryland and led our institution until unfortunately, he passed away. When you get to be around those kinds of people you really take away a lot. The second person is actually a person who is one year older than I am. His name is David Ball ‘92 and we were friends in college. David now is the Principal of the Milton Academy up in Massachusetts. One of the things that I always appreciated about David is that he was Phi Beta Kappa, he had amazing jobs, but he always viewed that the most important thing that he could do was to teach. To me to be able to see people like that go back into teaching to give back, and to think of that not only as part of their ethic, but as their raison d’etre, to me is the ultimate aspect of how you can use a Princeton education. And he’s someone I always looked up to.

 19. What does service mean to you?

Service is an incredibly broad concept. But to me, it requires that you are giving something that is important to you to others. If time is important to you, then you better be giving some of your time. If your money is important to you, then you should give some of your money. If your network is important to you, then you should be using your network to give to others. If something doesn't have value and you're giving it then to me that's not service. The idea is to give something that you yourself feel has great value and you're giving it to greater society.

Let me give you an example. One of the things that my wife and I talk about is that by far the most important thing in our lives is our time. But we have tremendous experience in nonprofits, and starting nonprofits, and talking about them, and experiences around fundraising and so on. So one of the things that we have done is make a commitment between the two of us that one of us serves on a nonprofit board, usually a startup board, so that we can give what we have learned back. So we're giving time, which is probably the single most important thing of which we don't have enough. And we're giving the expertise that we've built over twenty-plus years in the work that we have done, to organizations and people that don't necessarily have it yet, but have a tremendous idea. That's how I define service.

20. So time is most important to you?
So time to me is the single most important thing, for me, because I feel like I am triple booked all the time. Also, because it is the one thing that you can ask for that goes in a linear sense. You either use it effectively or it is gone. As opposed to money, where if you save it maybe you'll have another opportunity to use it, or your network so you're developing you can still use it in the future. Once time is gone it's gone, so make sure that you use it incredibly effectively, or you don't.

21. Any secret passions?
I have two incredibly important, incredibly not secret passions. One, I am a complete sports nuts. I love every sport. You want to talk cricket, we’ll talk cricket. I'll talk NCAA basketball, I'll talk hockey. I have to be very honest that I am not very good at curling. I haven't really followed curling, but I'm generally a sports nut. I think the other thing that might be surprising to people is just how much I love reading newspapers. If I if I could have wiped away the world to do anything I wanted on a Sunday, I would take a copy of the New York Times Sunday section. I would go with a huge pot of tea, and go read it for six hours. To me that would be the single most enjoyable way I could spend my Sunday.

22. What does success mean to you?
I don't mean to sound flippant when I think about success, but to me the single most important thing right now is that I know that my daughter looks at me and says, “Hey, you know what? My dad is doing incredibly valuable things.” Then there's the other part of how do I wake up every morning thinking whether or not I'm successful? For me, it's the idea of giving back. Am I doing something that is truly giving back? I use this phrase often, which is “What is a social footprint that I'm leaving in this world?” To me, success is going to be determined by whether or not I left both a multitude and large enough footprint, social footprints, in giving back to others all that I have been blessed to get.

23. If time and money weren’t a factor, what would you do with your life?
If time and money weren't a factor what would I do with my life? Well, I hope that the answer would be, “Not that much different than what I'm doing with my life.” The opportunity here at the Aspen Institute is to start a whole new division focused around a population that we haven't focused on in an explicit way. The platform of the Aspen Institute is tremendous. The leverage here of the name, the leaders, the board, the assets available, the financial resources, really gives us an ability to do amazing things. And I want to be able to do amazing things. Now having said that, remember that the question is, “If time and money weren’t in any way a constraint upon what I want to do,” then I actually would say I’d want to be a philanthropist of a major way. I’d be more engaged in making sure that the money was going to high-risk ventures where I'm not afraid of failure, but have really big potential for changing society. I would engage with them not only with my money, but also with my experience.

24. Career and life advice to college grads?

What do I tell a college graduate? I tell them two things. Number one is go and try something really stupendously crazy, because it's a time to do it, and because the education you've gotten actually gives you that opportunity to do it. It's something that you have to be willing to do, and in fact in some ways you have a responsibility to try something crazy. The other part of it is to make sure that you have a general plan for what you want to do, but also be willing to scrap it at any moment in time because of new data. So you know I went into management consulting without having any thought of going into management consulting until I walked in the Career Center in September of my senior year and said, ‘oh my gosh, maybe I should apply for this.’ That's where I went and it fundamentally changed my life. Then when an opportunity for SEED came up because of work that I did, I kind of toggled again and did that for a number of years. Then I was approached by the CEO here at the Aspen Institute who said, “Will you take this job?” and I said, “Ok, let's do it.” You have to be willing to look at the opportunities and to make the right turns that allow you to continue to enjoy life.

25. Any other wisdom you’d like to share?
So you asked me whether or not I could share some wisdom. I'd be loath to say that I've developed wisdom yet. Maybe I've got a few points of experience that I can share. I would really go back to how to think about one's life coming out of college. Take risks and experience new things, especially at an early age. To me management consulting was that risk, as weird as it sounds, but it fundamentally changed my life and my way of thinking. Secondly, is to appreciate Princeton for what it is while you're there, but also when you're gone and what it gives back. The third thing is, I have done this incredibly poorly, but when I've had the opportunity to do it it's been amazing, is to stop and to smell the roses. We're in a society and then we are self-selected in a Princeton world that really always talks about scaling the next mountain as opposed to appreciating the mountains that we've already scaled. To celebrate those things and then every once in awhile to just look around us. For me, the greatest single event that allowed me to do that was to become a father. It constantly reminds me to do that. I wish I had done it more often throughout my life.

This interview was conducted and condensed by Lisa Einstein '13. 

Career & Life Vision Conversations is an interview series by Princeton Career Services highlighting lessons learned by inspiring Princetonians. For the whole series visit: https://careerservices.princeton.edu/node/2191