Interview with Sukhinder Singh Cassidy

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Lee Kennedy: Hi, this is Lee Kennedy. I'm the CEO of Bolder Search and a board member for the National Center for Women & Information Technology or NCWIT. This is part of a series of interviews that we are having with fabulous entrepreneurs. They're women who have started IT companies in a variety of sectors, all of whom have just fabulous stories to tell us about being entrepreneurs. With me today is Larry Nelson from w3w3.com. Hey, Larry.
Larry Nelson: Hey, I'm excited about this interview, certainly a person with a tremendous amount of experience. Wow, I can't wait to get into this and we know we have lot of firm executives and young people that are looking into becoming an entrepreneur and getting into the high tech arena who are listeners. So, I'm really looking forward to this interview.
Lee: Super. So, today we are interviewing Sukhinder Singh Cassidy. She is a leading Internet and media executive with a touch over 18 years of leadership in working with early stage companies including Google, Amazon, Yodlee and Polyvore, which is a leading global fashion community site. So, why don't I go ahead and interview Sukhinder. We are so happy to have you today.
Sukhinder Singh Cassidy: Thank you.
Lee: Larry, I think we'll just jump into things.
Larry: All right. I'm going to ask you a question that Lucy Sanders always likes us to ask and that is how did you first get involved in the technology business and what technologies do you think are cool today?
Sukhinder: I actually first got involved in the technology business probably 13 or 14 years ago in 1997, actually, late '96, early '97. Prior to that, I had been working in New York, in London in media and that investment banking. I stayed in Merrill Lynch for several years and then I went on to market BSkyB, which is the leading satellite broadcast at that time. So, actually, kind of a technology company but more of a media company. I moved to the Bay area on fundamentally I guess on thesis that I wanted to be close to entrepreneurs and one day be an entrepreneur myself. I did not know what I wanted to do but I did know there were smart motivated people in the Bay area. I had traveled out to San Francisco to visit friends and fell in love with the Bay area. So, I took a leap of faith. I moved from London, sold everything I had in London. Bought a car for $10, 000 in LA and drove up the Coast to San Francisco and found my first job.
Larry: Wow.
Lee: I have to say it is not too dissimilar to my background. I moved out to the Bay area and it's kind of hard not to get into technology.
Sukhinder: Absolutely. So, I did not want to be an entrepreneur. But it was that classic, I didn't have an idea. So I thought the next best thing was to put myself close to smart people, working on interesting problems and being entrepreneurs themselves, somehow that path would be a positive one.
Larry: Of all the different things that you've been involved with the technology, which ones do you think are cool today?
Sukhinder: There are some I had been lucky enough to be involved with and some less so that I just admire from afar a bit. Probably, two of my favorites I'll say as consumer there's something you got to see these businesses built at Google. One, I mean the technology I just to love today, are anything that you would of think as geo or location based. So, my first job at Google was helping to launch Google maps and Google logo and the idea that your location is a pretty important indicator. Where you are relative to your friends in the case of Foursquare or where you are on a map and where you are trying to get to go and having driving directions on your iPhone, forgoing the traditional, heavy-duty MAPS systems that are sitting in cars or something; lightweight but just as revolutionary. So, I love anything geo where as a user my location has something to do and some relevance to play in what I want to do next. And I think we see geo now as a layer on top of many technologies. The second thing I love is of course cloud-based applications. For me, it is actually very simple. As a consumer, the idea that I no longer have to be stuck to one PC to access my contact list, to access my emails, to access documents. I mean today we have apps of every kind based on the cloud; business apps, enterprise apps, consumer apps. But I think of Google really as introducing that concept in a pretty revolutionary way with Gmail and now of course its very standard. I just love cloud based apps because they truly make me mobile. And the last thing, it's hard not to love the iPhone, now the iPad but if you think about the iPhone as just an incredible tool but more importantly an incredible statement instead of just ability to use that hardware and software. To have a pretty revolutionary consumer design and that the integration of hardware and software still matters. And owning both, which was Apple's proprietary focus and goal. And long after people forgot about hardware, Apple believed that innovation was still possible in hardware, right? And the group did this to all by fundamentally changing the way we communicate with the iPhone.
Lee: I'll have to have an offline discussion about the iPhone versus Android GP and you being a former Google employee.
Sukhinder: Yes and it means like I said like the Android OS and then the non proprietary system and that is amazing being able to boot application development to many different phone and the fundamental thesis for Google creating an OS and then integrating with third party hardware and redesigning hardware. Instead of working a new age phone that showcase the power software. So, I guess my point is that long after people have forgotten about hard ware and all the software, lo and behold Apple app and hardware.
Lee: I know that's the jobs.
Sukhinder: Application development layer and in Droid continues on that screen stream. 
Larry: Well, I just want to let you know that I have something in common with you. We moved from Copenhagen to the Bay area a number of years ago.
Lee: Are you trying to warn me up Larry? OK. All that said about your background and the technologies you think are cool. Tell us why entrepreneurship turns you on? What are you an entrepreneur?
Sukhinder: I think there are probably three things I just love about it. Number one is obviously the building that create an author and that is every level. Yes, you are creating a business model on a product but also to go and author your team. Who you get to work with, how you want to work, the culture you want to create. I think that there are people who love to build stuff. I happen to love to build stuff. I think authorship and creation except for some people is a drag and I think I really enjoy the process. I think the second think is I'm sort of a gratification junkie. I like to put in work and get back feedback quickly and then iterate like progress to me is best measure in those increments and that is also how I motivate myself and I think entrepreneurship is really suited to this iteration cycles, right? You get to put out something out there, see the results, see what works, see what doesn't, try it, try something else. And I think that fast cycle times really feels and considers me and probably my own kind of cycle which I work and I think that is fundamentally one of the reasons that it gives me so much excitement. So, I think authorship and the ability to create the kind of quick iteration and feedback loop in entrepreneurship those are things that resonates really, really highly with me.
Larry: Sukhinder, with all the things that you done in the different organizations, it's really phenomenal. But let me ask you this, along the way, who supported you in your career path or your role model or your mentor?
Sukhinder: Well, first of all, it is interesting. I don't believe in a single role model. I feel like for different parts of my career, depending on the things I have to learn, there were different mentors to me and role models along the way. First and foremost, my father. He was a doctor and loves to be a doctor. He loves running the practice like the business of running the practice. My first job was doing tax returns when I was 15 years old. My father taught me balance sheets and income statements because he was fascinated and he was thinking of different ways to optimize his business and he share the same with me. My second job was in his office as secretary but he was clearly passionate about the job he was doing. The content of his job which was medicine and also entrepreneurship and running the business. He was from very young age clears want to work for yourself. I would say more recently, I think my role models and mentors have really been at some point of time very relevant to what I have to learn to ramp sure ramp, Google and obviously very notable angel come valley. Before that was the CEO of Jungly, my first copy in the Valley that was acquired by Amazon and I had a pleasure to work with the man. And he was an investor in Yodeli, the company that I joined as a co-founder and then ultimately was also involved with Google where I joined next. From Rome, I learned great skills and I also just learned how important it is to match a great business team with a great product team and Rome as an angel has been very successful in helping to find and integrate entrepreneurs. Rome was certainly one. I think Henry Ryan, one of the founders of Jungali, first company that I joined in the Valley. He is a serial entrepreneur. He is in a company five and he has calm, stability, successful exit, diversity and experience and it turned operating CEO so when I have current issues, I call him and I think about my route in Google. Certainly my boss Kurt Estani who was the chief revenue officer at Google and he was probably employed 13 or something like that build Google's revenue from zero to 23 billion. For me, certainly, I just add what I learn, the skill associated with being a great relationship daughter and a great manager not to say I was but I think I learned from him the important of their skills and he is just the ultimate consistent builder and relationship manager. And also, someday he was able to hire greatly skilled people and let them run. Stan Standberg is now running Facebook, Armstrong is running AOL. These people are on the team and I give credit for figuring out how to hire us, mentor us, harness us and still let us run and build. So, I think the different people are the different points of my career to some of them.
Lee: Sukhinder, you have been super fortunate at least from my viewpoint to have such phenomenal mentors. That is really exciting.
Sukhinder: Yeah, I certainly felt privilege to get to work with these people. So, I guess my point is it is not just one mentor but there are people you learn different skills and I think at different point of my career, I feel like I had the opportunity to work with these people and certainly some of them go and instilled to them. I go for different type of advice when I think there is something they have to offer me.
Lee: So, on to something a little more tough, what is the toughest thing you've had to do in your career?
Sukhinder: I think of very tough business challenges, but then I think of the challenges that take their toll on you emotionally. This is often a question I ask others when I'm interviewing them, when I'm interviewing executives to join my team. I often just say, "What's the biggest career mistake you've made?" Which is another way of asking the same question. But I think the things that take the hardest emotional toll on you are not the decision or strategy vantage point perspective you called wrong, because you can two or three or four different paths in a different strategy, and maybe you chose the wrong path, but smart people can have different answers. But the ones that're really tough, honestly, are the ones that surround people, right? Awful, making a decision that someone's not a fit. I think those are the most personally taxing and tough things to do in my career. You know, at Yodelly, certainly, we went through to Boston , we had to lay off people, and it was my first time laying off people. You dissolve a relationship with people, you feel a huge amount of responsibility for people's career and career choices when you bring them into a company, I do.
Lee: Yeah.
Larry: Oh, sure.
Sukhinder: Some of that was recession-driven, but there're other times where it's actually not a function of the recession. Often in cases outside of those extraordinary circumstances, like the Boston 2002, the Internet dark days. It's really actually just about culture set, because the people you hire are, by and large, exceptionally competent. It's whether or not they're a fit with the organization, and it's a place that allows them to thrive. When you see that for whatever reason it's not working, learning to make that decision or call quickly or expediently, expeditiously, is important. Because the cost of not doing it well or quickly is high for everyone. It's high for the organization, it's hard for the person who feels like they're, for whatever reason, not able to get it done. They're feeling frustrated. But it's very hard to bring that conversation to a head, and I've been on both sides of it, right? I've certainly had to make the call when someone wasn't a fit, so I just think that whenever you have people decisions, your own decision to move on from something, or managing someone for whom you need to negotiate whether or not they're going to move on. Those are always the most difficult decisions, because they involve people's lives and careers and you want to do them with the right amount of diligence and care and conscientiousness, but also in a way that is expeditious for everyone. So everybody can move on.
Larry: All right, well let's move on, and we're going to lighten this one up a little bit. Let's pretend, right now, you are sitting at your desk or around a table. You had a young person who thinking about becoming an entrepreneur. What advice would you give them?
Sukhinder: Well let's see, I think there're tons of bits of advice you can give to young entrepreneurs, and I'm sure you have, in all of these interviews you've done, many greater nuggets than what I have to offer, but...I think if there were two things, and one may be obvious but I don't know if people truly accept it. So clearly one of the key things is to iterate in very quick cycles. I think a lot of times I spent, like, perfecting the business idea in PowerPoint. But the reality is, it's not substitute for customer feedback. As quickly as possible, and as cheaply as possible. So I think before you go out and raise money or create too many PowerPoints, you want to find a quick way to test and iterate on your idea at low cost. And keep trying until you find the nugget that seems to resonate with the consumer. Particularly true in Internet business, right? We're consumer Internet businesses. We can't quite predict how the online consumer is going to react, and what they're going to love, and what they're not going to love. It's not always just rational, right? Some of the web stuff companies weren't built of rational need. They just were launched and tested and iterated on, and they found some resonance with the consumer. So that's one, and it's probably fairly obvious. I think the second one, I think a lot of people say they're self-aware. But honestly, I think as an entrepreneur, you have to become incredible self-aware, and I think that's for a couple reasons. First of all, I think self-awareness revolves around understanding what's your own trademark strength, and what do you excel at, right? And part of building a great company, obviously, is figuring out how you fit and how to do what you're great at. If you can build an entire company around it, around your trademark strength, that's amazing. But quite often, building a great company is bringing into the building and, bringing in a diverse set of experiences. Often that means self-awareness about what you're also not great at, right? Where can you attract and surround yourself with people who have other strong skills that are complementary to your own. If you really want to win, and you really want to grow a company of some scale, I think it starts with self-awareness. Playing to your own trademark strength, and then being very quick. I would say in some ways open to building a company of great, strong, diverse talent that helps complement the skills you have. But it takes both parts, right? Playing to your own strengths, but also being, being pretty clear on your weaknesses, and certainly if you want to scale a company beyond a certain size. It is about recruiting incredible talent to your vision, but with complementary skills.
Lee: I have to totally agree with you on that.
Larry: Mm-hmm.
Lee: I'm going to follow along and ask you, what do you excel at that's made you a fabulous entrepreneur?
Sukhinder: Well I think first of all, I think most people who know me would consider me high energy and intensity. I think an entrepreneur for many years, it's about being your own best evangelist, right? Not for you, but for your company's vision. I think that requires a lot of energy. Then you have to be able to do that, and have a surplus of energy, if possible, to give to your team, right? To motivate and bolster them, and let them know it's possible. Again, most entrepreneurs, there's not always a rational need for what they're doing. They're often thinking to where the market is going, right. That requires evangelism. It requires a certain energy and intensity to come to work every day, and when the market's not yet there, or investors don't believe, that you believe, and you're able to convey that belief and conviction to others, with energy. So I think that's one piece. You know, I know how to sell. I spent most of my early career in sales. My college jobs, were summer jobs, were in sales. Then when I arrived in the valley, my functional specialty, if you could call it that, was business development. Business development in every company I've ever worked at correlated with sales. It was revenue-producing. As an entrepreneur, you kind of have to sell. And so I think having core skills that are functional set in sales and being very comfortable with that, has been helpful. And then roughly, I mean, I would circle back to the self-awareness piece. I'm certainly very, very flawed. But I think over the years, being in a variety of leadership situations and having to scale through both successful and failed experiences, I have the benefit of a lot of feedback. And I know what I'm good at and I know what I'm not good at. While I work at what I'm not good at, I try to play to my strengths and find a place where they can be accelerants, to a business or a team, and where they're not, I don't, I guess, pretend to believe that I'm going to become perfect. But I think I'm pretty clear on the areas I need to surround myself with to actually have a fully embodied and diverse team that's capable of getting it done. And so I think years and years, instead of repeated feedback on the same issues has yielded a lot of self-awareness. I think at this stage that what am I good at, and where is it that I need to bring in a strong and talented team to really create, and as I said, some things a team together can win.
Larry: Well I like that. Let me throw a little curve ball at you. Now, with all that stuff that you're doing, you've mentioned everything from high-energy and intensity, how to sell, being self-aware, and everything else, how do you bring balance into your personal and professional lives?
Sukhinder: Well, first of all, I guess let me start by saying I'm not a believer in balance in the typical way that people talk about it, which is just this ... I have this thesis that people imagine this perfect day, right, where you wake up at six, and you work out for an hour, and then you play with your kids. And then you have a great breakfast filled with protein and carbs, and you work perfectly from nine to six, and you come home and you feed your children and you have wonderful family time, and then you do two hours of email, and you get ... early, this is thesis of what balance looks like and I just don't believe it. I don't believe it, at least for me. I think balance has to be measured in cycles that are far longer than a day, often months and years. Because I think that to do anything well requires a certain amount of energy and focus. To be a great parent requires energy and focus and intensity. To be a great manager requires it, to be great manager requires it. To be a great entrepreneur. To be great at sports. And so, when you think about trying to do things well simultaneously, I'm a believer that kind of the best it gets is that there are going to be periods of your life which are all about work. There are going to be periods which may be all about family. And I measure balance in my life by cycles, there are cycles of time, often measured in months or years, where I know I'm going to have to give a lot of focus or priority to something. And then the best you can do in that situation, is really trying to manage very clearly expectations, which I think of as the multiple shareholders in your life, right. Your husband expects something from you. Your children expect something from you. Your team expects something from you. Inside constituencies. Boards you serve on expect something from you. And the most you can do is actually manage expectations very clearly, like hey, I'm going into a period that's going to require a lot of travel. What are we going to do about it. In the case of managing expectations, what I would say instead of negotiating with your family. There would be other times that you negotiate with work. And you say I'm about to have my third child. I'm going out on maternity leave, but I know we're trying to close a big deal. How are we going to get it done. And so, I guess I don't believe in balance, as by the standard definition. I believe instead, of cycles in your life. And managing expectations with an increasing number of constituencies as your life goes on. And hoping that when you look back on your life, as measured in months or years, maybe it was equally divided between all the things that are important to you, or at least divided between the one or two things that are important to you, in a way that you feel good about. But it's measured in a much longer cycle. And in between, you manage expectations, and you learn to live with a lot of guilt.
Lee: Well, thank you for that honest answer. Suhkinder, it's clear you've achieved a lot. And we have thoroughly enjoyed hearing your answers to our questions, and last but not least, we're curious what's next for you.
Sukhinder: It's a good question. I don't know. I mean, I think in the spirit of what we chatted about, which is, you want to play to your trademark strengths. For me, it's about working with great teams at high intensity and high RPMs, and feeling honestly that I could move to a place where I could make my maximum impact, and that's about finding a place where my skills are a great fit. And I think it could be pure entrepreneurship, and founding something, or it could be operating at significant scale and complexity. But where the trajectory for a company is high, and navigating it with a smart group of people is important. Both to them and to me.
Lee: Well, we wish you great success in your next.
Larry: Yes, and we're going to follow up on you too.
Lee: So thank you so much for spending this time with us.
Larry: You listeners out there, pass this interview along to others that you know would be interested, you can listen to it at w3.w3.com and ncwit.org 24/7, look at our blog, it will be in our podcast directory too.
Lee: Thank you so much.
Series: Entrepreneurial HeroesInterviewee: Sukhinder Singh CassidyInterview Summary: 

Sukhinder Singh Cassidy has worked at companies large and small in their early stages, including Google, News Corp., Amazon, Polyvore, and Yodlee. But before she got into the tech industry, she did the taxes for her father, a doctor. In this interview she gives some great advice about the energy and intensity she thinks are vital to being a successful entrepreneur, as well as the importance of knowing how to sell, and how to be self-aware.

Release Date: January 30, 2011Interview Subject: Sukhinder Singh CassidyInterviewer(s): Larry Nelson, Lee KennedyDuration: 22:10