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Interview: Silicon Valley investor busts myths about risk-taking

Silicon Valley author and investor Sukhinder Singh Cassidy breaks down career risk-taking, negotiating, workplace biases and why her marriage is sometimes a negotiation, in an interview with Moneycontrol

Mumbai / September 03, 2021 / 08:17 AM IST
Sukhinder Singh Cassidy

Sukhinder Singh Cassidy


Even by Silicon Valley’s unique standards for career oddities and absurdities- for pivots, shifts and turns for a successful one- Sukhinder Singh Cassidy’s career stands out. She has left large tech companies like Amazon and Google when if she had stuck out, she would be sitting on generational wealth. She has started companies, folded them up after years of trying and yet remained steadfastly committed to taking risk- or in her words- ‘Choose Possibility’- at every turn.

Now a board member at tech lending platform Upstart (among other things), she has written a book about how risk-taking in your career is awfully misunderstood, why everyone should constantly take some risk, and what does risk even mean. The book tangentially raises questions about everything from what does changing jobs really mean, to Silicon Valley’s revered but hard-charging culture, to figuring out your career when everything seems up in smoke (that too during a pandemic).

In an interview with Moneycontrol’s M. Sriram, Cassidy spoke about company biases, offered career-planning tips and tricks and took aim at Silicon Valley’s culture.

Edited excerpts.

Sukhinder, tell me, what got you to this idea? Was there a certain point where you realized that your experiences merited a book?

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I think I’ve been wanting to write this the last six or seven years, maybe even longer. I've long wanted to write a book about risk taking, because I believe that lots of people suffer from this kind of myth that surrounds Silicon Valley that surrounds entrepreneurship, that successful people must be the mightiest risk takers.

So people are generally lost and a little scared of making new choices. I feel like when people ask me for advice on what it takes to be successful, they give me so much credit, as if I was so wise. And, I wanted to say, look, I just kept choosing possibilities. I just kept choosing my way, making new choices that were sometimes for learning, sometimes for discovery, sometimes for ambition, but I want to stress that there was no magical moment. It's the process of just committing yourself to choosing, choosing through successes, failures, to keep aiming for impact.

I really want to debunk this myth that risk taking and success is only for a certain class of people or a certain class of risk taker. It is much more of a process than an event.

The timing of the book is also interesting, because the concept of work and the concept of well, everything has already been upended by the pandemic. Do you think the concept of risk has also been upended? You know, if you say, to compare your book pre pandemic post pandemic, how do you look at it?

The irony is that I sold the book (to a publisher) before COVID-19. But, it was written during the first wave. There are a couple of COVID-19-related perspectives. Sometimes we take risks and when we're facing the threat of further harm or danger, often that's when we're at our most agile. If you look at the agility of people, of families, of companies over COVID-19, it would be hard to overestimate how much agility people showed right? Overnight people had to adjust the way they work . Overnight, I had to manage (ticketing platform) StubHub, from a $5 billion business to one that needed to survive.

So in the face of a crisis, we are at our most agile and able to make rapid decisions and new choices and take risks when we fear the threat of harm. People struggle to take risks when times are good. And, they have all this time to overthink what might go wrong.

But, COVID-19 has also provided tailwinds to so many new spaces, and given many people flexibility, to work from home, etc. People are rethinking their own work choices.

That’s fair. When you also address the concept of risk, and how we're supposed to perceive it, what advice would you give to someone who took a massive risk, and it didn't work? Someone who has to pick up the pieces after an epic failure.

I've had to pick up pieces of things that failed. So, I know this well. Number one, just take time to retrench and recover. When failures are massive, no matter what anyone says to you, we often all need to just hide and lick our wounds a little bit. Just to like, emotionally take a beat, take a minute, do whatever makes you feel good or safe.

But, once you're able to look back, take the learning. When we fail, the first thing we want to know is why we fail, as opposed to just condemning ourselves for being poor at execution or what have you. Take stock of the kind of the decisions you made, re-examine it and say, what was it? Was it the people I was with? Was it my own goals or ability to drive impact?

Also take a moment and just list the accomplishments. Even if you didn't put together the whole puzzle, identify and take credit for the pieces you did put together. I think that's really important. For example when I failed at Polyvore (social shopping platform), I was out in six months, and I had no impact. I had no impact, that's a particularly painful kind of failure. At (video shopping network) Joyus, I ran a company for seven years that was way too early in the space of video commerce.

And, although it failed, I took some heart in all the things we were able to accomplish. I felt that my six years had some impact in terms of creating a new product, accelerating the careers of the people who worked with me, creating something as a beautiful new consumer experience.

So, ultimately, after any failure, you have to choose again, right? That is part of the cycle of choosing possibilities. I think too often when we fail, we sort of doom ourselves and we get into a circular loop

We tend to think we didn't get the reward we originally aimed for, and all is lost. And, throughout my career, even when I failed I got credit for the impact I was able to have because I specifically looked for that.

Right. When you also just look at your book in the larger context, do you think it's a reaction to Silicon Valley culture? The Valley’s culture has come to be known as cultish, aggressive, and very homogenous. Is your book an attempt to re-contextualise that?

Absolutely. Yes, I believe Silicon Valley creates a lot of myths for people about how and what risk taking must be and what looks glorious. The whole reason I wrote the book is I want to dispel this myth that Silicon Valley has some magical aura and people are somehow more special than they are anywhere else in the world. That's not true.

What is true is that in Silicon Valley, companies have been trained to iterate and pivot. Pivoting is a philosophy. Yet in our own careers, we don't do that. So, there is an acceptance in Silicon Valley of this idea of pivoting, iterating, reinventing, not moving one degree at a time for 365 days, and you'll be completely right, a full cycle away from where you are. You will have done a complete revolution.

At the career level, all we do in Silicon Valley is risk taking, but the people celebrating these gigantic stories of risk taking are forgetting that most of the people who you see taking a very big risk are very calculated choice makers. They've made 10, 100, 1000 choices to become a good risk taker.

Correct. Your career is also interesting, because when I look at the vast majority of very successful tech executives, they have largely similar careers, not moving jobs every few years. You have on the other hand, worked in many companies, served on many boards, etc. I could argue that if you had just stayed at Google for 20 years (she worked there from 2003-09), you may have got to do what you want. Was it really necessary for you to go to all the places that you did?

I think it's a great question. It's not one that people have asked me. If you recall in the book, I said that there are many ways to get to the place you want to go. I could imagine 10 different paths I could have taken and still ended up as the CEO of a large tech company like StubHub. To your point, I could have stayed at Google and maybe 10 years after I'd been at Google. They ended up with CEOs of divisions. Like, Susan Wojcicki is CEO of YouTube.

But, I think moving away from Google was a seminal move, because what Google could never give me is to be the ultimate CEO. To let you live by and die by, ultimately my own actions and be accountable. Google would have let me reinvent my career 10 times, but I was never going to get the absolute top job.

I knew very early on that Google really didn't put business people in the top job. And, so, even if you look at Google today, it has an amazing, extraordinary number of divisions. And, I could have found variety in my work. I could have found equal amounts of wealth or even more. But, I think that my own goal and ambition for as long as I can remember was to build, scale and lead my own company.

And, those things happened in different ways. I got to found and build Yodlee (which aggregated financial data), but I did not get to be the ultimate leader. At StubHub, I got to be the leader, but I wasn't the ultimate builder. Right. And, so yes, I could have stayed at Google and probably had a fantastic career. But, I will say that if I think about the agility and confidence I had as a leader, it is only because I've had a diverse set of experiences that Google could never give me.

Frankly, even if I had stayed at Amazon, I could have had a great career. I hope that what people take away from the book is there are people who have stellar careers, pivoting 10 times inside a company.

To me, that's still a risk. I just wanted to take a different kind of risk.

One of the things you mentioned in your book is about avoiding biases. The exact line is- bias and prejudice are the greatest enemies of impact. But, I wonder whether that's possible, because we're all a product of our life experiences. And, our experiences automatically factor in some bias and prejudice right?

Biases create unequal distribution of possibility. There is a systematic lack of access for some people and more access for others, right? But, even if you're in a system where opportunity is abundant, bias creates the problem that it might not be equally distributed.

But, if you’re working at a place where the organization’s value system is aligned to your own, you will be much more comfortable even calling out bias. Even to be able to speak those words and take the risk to call us biased requires you to feel like you're in an environment of trust.

So, I don't think bias can ever be avoided. But, what you want is a set of people who collectively can identify it and what to mitigate it together. And that's only possible when there's an underlying value system that you feel is shared.

Workplace biases also affect women more often than men. Do you think it’s harder for a woman to choose possibilities? Simply because more is expected from them- managing family, career, etc. How do they overcome something like that?

I've looked at a lot of the research on gender and risk taking. And there is a meta-analysis of like 150 different research studies on gender and risk taking, that does support the finding that women are more risk averse than men, on at least 14 of these 16 dimensions that were measured in that analysis.

By the way, one of the reasons women take less risk than men is simply because there is a perception that women are less risk takers, and they act in accordance with that perception. Like, when there is a negative bias, then you are more likely to actually even check your own behavior in favor of that bias.

To answer your question, what can women do? First of all, one of the things that we don't encourage women to do often enough is really to put their ambition on the table and negotiate for what they need to make it so, and I mean, negotiate at home and negotiate at work.

As you said, there is an expectation put upon you that the sacrifice is all yours.

We have to encourage women in organizations to speak up and for what they want, and also to learn to negotiate for what they want. And I would say the same thing to women at home. I know, it's not a particularly romantic view of marriage.

But, my marriage is a negotiation. I mean, in order for us to make it work, my husband and I have had conversations every time I make a career change about what our family needs, what does he need? What do I need? And so, I think that it is more difficult for women when the perception is that they are risk averse. But, I think the counter to that is that as leaders, we need to support both their larger ambitions, and vocalize what they need to make it work, and learn to negotiate for what it takes for them to make the choices.

And so, I do think that women inherently have more put upon them. Like during the pandemic, women are the primary caregivers. So you can say, well, how can I take a risk when I also have this at home? And my only rebuttal to that is you're right, it is harder. And so, unfortunately, the burden is also on women to vocalize what they need and what they need to be willing to negotiate in order to make choices for themselves and in favor of some of their ambitions also.

I see a lot of women who just assume it won't work, because they don't ask.

Correct. You just also preempted my next question. How do you take risks when you don't have the ability to take risks? If you're having a hand to mouth existence, if you're barely making ends meet, how do you take risks there?

When we are in difficult situations, it is important to take the smallest of actions, which I call a minimum viable choice or micro risk towards the things that give us energy in our next possibility. So yes, maybe you can’t quit your job today because you can’t live without a job tomorrow.

But, it's also true that if you want to make any kind of change, there has to be the most micro of actions today. That small feedback loop and a reinforcement of the direction in which you want to head might be just enough to encourage you to take another small step tomorrow. So, I don't think the book is meant to say, hey, take a big and glorious risk, even if you can't afford to.

Start with researching a new job when your children are in bed. It may take you five months of sending out your resume to 50 different places to unlock a new opportunity. Each of those things is still a micro risk of your time and energy towards a new possibility.

But, then you also think risk taking is inherently a function of privilege, that the more privileged you are, the more risk you can take?

Well yes that’s true, but there is more to it. People who have the most wealth and choice deal with a different set of risks. People who have little choice are literally dealing with financial risks, like, literally can I put food on the table, if I make a new choice, right? People who you would think have a lot of privilege-and they do- they are actually trapped by a completely different fear. It's an ego risk. That I am on this perch. And if a change makes me fall off this perch, how will people look at me?

It's interesting that as people gain more privilege and more ability to make choices, their fear of failure doesn't go away. In some cases, it's just a different kind of a fear. It absolutely is a privilege to have abundant choices and to have abundant choices and make none to me is a waste.

You also say that you should distribute the possibility. That’s interesting because lots of people feel it is a competitive world and only so much possibility. You have said, no there’s enough to go around. Why do you say that?

Possibility is not evenly distributed. And that's where I think we all have to do work. Risk may not bring you your ideal life, but it brings agility and agency and I think the minute you feel agency in your own life to anticipate or respond, you realize you can generate more possibility.

You feel empowered. I know, I can anticipate, I can try something new. So yes, creating it for others multiplies your impact a thousand fold.

How much of the book would you say is based on your life experience? Because while that runs as a common thread, you also referenced a lot of your friends, your colleagues, people in the industry?

This is not an academic book. This is a practitioner’s book. So, I think you should presume a vast majority of the theories in this book are based on my life experience, but researched and validated by looking at the experiences of those around me. That’s why the voice of the book is personal.

I'll give you a scenario, just sort of talk me through how you would make a decision. If you have a job offer from a hot startup and from a large conglomerate, how will you decide which one to go for?

If I want to take the smartest risk, I want to figure out what it is that I want to learn? And what is the effect I want to have? What is my goal? And you might say, okay, at Disney, I'm going to learn large company management. And at the startup, I'm going to learn I'm making a product management from scratch.

And I’d say, okay, I want you to read both of these choices against your goal. What's your goal? If you say your goal is to be a CEO of a large company, I'd be like, okay, well, for that goal, maybe a large company is the place you want to go to really learn management chops, right. Number two, what group am I entering? Who am I working with? What can I learn from them? How will they accelerate my own journey?

And I would rate the two. Number three, I would look at the division I was joining one versus a company- what are the tailwinds in this situation? What is the momentum? What is the thing that will accelerate my opportunity for success?

And if there's a headwind in this situation, if the startups needs funding in six months, what is my opportunity? Is my opportunity going to be that I get to run a bigger group than I would otherwise get? Is my opportunity that somebody can give me more responsibility, because it's hard to hire?

And then I would rate these jobs against my superpowers and strength. Where will my values strength align nicely with what's needed? And, I can be at the center of the action. Because if me at my best it can be an accelerant there then I know I'm going to have along with those other factors that you had great experience.

Lastly, I would look at my last few choices and see whether they have worked out or not. If you’ve taken five risks and they’ve all failed, I would never counsel them to take another one. Can you take a sixth failure? They should diversify their risk profile.

By the way, if you've had five failures in a row, I would say diversify your risk my friend. It may be time for you to go to a more stable environment, particularly if those five failures have been in startups. And go get some wins under your belt, because ultimately, win rate does matter.

A lot of your book, somewhat tangentially, is also about just how to make it big, how to join the big companies, what are companies looking for? Amid today’s war for talent, the equation has flipped. How do startups attract and retain talent in this market?

My belief is startups attract talent by offering people the opportunity for accelerated impact. If you're going to go to a startup, you're going to go because you think you can learn and have the impact at a greater rate than you can in a large business where you're constrained by the role in the box in which you're put.

So ultimately, I believe that people flow from large companies to startups because they're yearning for more impact, and more learning both. They're learning, yearning for both of those rewards. And sometimes they're yearning for the financial reward that you and I both know, that may or may not come. These days, it comes rather quickly at startups, too. But, that's because we're in a complete boom cycle. But, they've been many times in which people have gone to startups and they failed.

And lastly, flexibility. Not just in pandemic terms of working remotely, but what all can you do? At every startup I've ever run, I've always said to people like what you're going to learn at an accelerated rate. You're going to be able to look back one day and have an impact that you can't believe you had in a condensed time frame.

I was competing against the Googles of the world so they could offer more money but I could offer more learning, impact and flexibility.

The way you've sort of structured your career, it's almost easy to imagine that you've played all your cards right. Although I'm sure that's not the case. When you look back, you feel like there are things you would have done differently?

Oh sure. A harsh critic could say I left Google too early. I took a risk and went to Polyvore. It didn't work out, I took another risk and started Joyus. It also didn't work out. I spent a good eight years taking lots of risks that didn't work out. Now I can tell you all the things that I believe I gained from that that ultimately led me to run StubHub, and that's all true. But, it's all about how you tell the narrative, right? When I think about the things that didn't work out the way I expected, there are many days I wake up and think, gosh, maybe I gave up on Joyus too early. At year six, I couldn't find anyone to fund it. And we sold the company for a small sum.

If I had stuck it out, if I had maybe figured out a way to get it funded for another year, I would have entered a period in which video commerce startups that were reborn and have the exact same number as my startup- they're unicorns right now.

I think about that a lot in a world where timing is everything. And sometimes it's just about staying long enough for the tailwind to arrive. So, I think about that a lot. I think about the choices I made to go to environments where they were, where my values didn't fit. Maybe I should have tried getting one more investor for Joyus. I have regrets over risks not taken.

What are your overall reflections on Silicon Valley and its culture? Because the narrative is changing from the hotbed of innovation to an era of reckoning, too much power, toxic cultures, etc. How do you think the scene is poised?

So I continue to believe it's a place of possibility, else I wouldn't still be here. However, I think the valley is very insular and very obsessed with itself. And some of the things you're talking about are now the repercussions, and a reckoning of a system that's so in love with what it does right, that it fails to see what it does wrong.

People at Google and Facebook aren’t necessarily malevolent. I've worked with many of them. But, the culture is- well, if we can build it, we should. Nobody said why it should not be built

Just because you can quash a competitor in another vertical by simply building that service yourself, doesn’t mean you should. Just because you can be a monopoly, doesn’t mean you should be one. You say you're a place of meritocracy. Yet, bias and discrimination exist. And so, I think one of the reasons that the valley gets a bad reputation is because when you don't question yourself and others start to question you and the day of reckoning comes, you don't have that many friends, right?

People are like, yeah I told you so. And look, the Valley needs to take it and learn from those lessons. And look, I'm somebody who loves meritocracy. I love aggression. I love ambition, and I hate entitlement. I hate it. And so, the entitled part of the Valley needs a reckoning, and you can’t hide from these things.

The Valley is a great place but needs to have its eyes wide open on its effects on the world. And do some serious soul searching.

Correct. Your book is also inherently for people who are ambitious. People who want to make career changes, people who want to get somewhere. But, there are a lot of people who are just not that ambitious. What would you tell them? Should they be ambitious or just do what makes them happy?

I would say a hybrid of it. I want to give people the tools to lean in, but if people don't want to lean in and they're happy, who am I to tell somebody not to be happy?

But, if you think that risk will not find its way to you in your career, that's a naive point of view. Because even if you want to stay still and not really let's say take a risk, risk will come find you- in the form of a pandemic event or just because of everybody competing around you.

So at least have strategies to anticipate and respond to the risks that come your way. Even if you say I don't want to embrace risk taking, you will still need to deal with risk within your lifetime at work.
M. Sriram
first published: Sep 3, 2021 08:17 am

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