Transcript: Sukhinder Singh Cassidy



The transcript from this week’s, MiB: Sukhinder Singh Cassidy, is below.

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BARRY RITHOLTZ, HOST, MASTERS IN BUSINESS: This week on the podcast, I have an extra special guest. Her name is Sukhinder Singh Cassidy and she has had a fascinating career in technology, starting as an analyst in the investment banking group at Merrill Lynch before going west to join a company that ends up getting purchased by Amazon and she stays at Amazon for a while before leaving to join another startup then ends up doing well. She eventually takes a couple of roles at Google, Google Maps, and then running a couple of other projects, Google International Commerce. And from there, ends up launching a couple of more startups, all of which that have done very, very well.

She talks about the process of risk-taking and decision-making and why you can’t think about the risk reward calculus in terms of one big win or lose choice. You have to think about a series of smaller incremental steps that all involve risk and eventually determine the path you take. It’s a good framework for both technology and finance. I thought this conversation was quite fascinating and I found her book to be intriguing as well, “Choose Possibility.”

With no further ado, my conversation with Sukhinder Singh Cassidy.

VOICEOVER: This is Masters in business with Barry Ritholtz on Bloomberg Radio.

SUKHINDER SINGH CASSIDY, PRESIDENT, STUBHUB: My special guest this week is Sukhinder Singh Cassidy. She is a technology executive and serial entrepreneur. Previously, she was president of StubHub, her new book is “Choose Possibility: Take risks and Thrive (Even When You Fail). Sukhinder Singh Cassidy, welcome to Bloomberg.

CASSIDY: Thank you so much for having me. Excited to be here.

RITHOLTZ: So, let’s talk about your career which is really so interesting. It covers everything from finance and investing banking to technology. Let’s begin at the beginning. You started at Merrill Lynch in the early ’90s, a great time to start in investment banking. What motivated that decision to go into finance?

CASSIDY: Well, a couple of things. Number one, I’d say the most more intelligently reason was because I wanted, sort of a base in financial literacy and financial analysis which I thought would be great for any career I had. And then the more emotional reason, honestly, I was at a top undergraduate business school in Canada and all my friends were doing it.


CASSIDY: I was like, well, if they’re doing it, I should be doing it too. So, in some ways I call it — I call it a couple cat goal. I’m sure there are many ways I could’ve gotten financial literacy but I was bound and determined to keep pace with my rather competitive colleagues to get a job n Wall Street.

RITHOLTZ: So, you head to New York, you start at Merrill Lynch. Any formative experiences stay with you years later, what do you most remember from that era?

CASSIDY: Well, the first is, honestly, just the struggle to get the job, believe it or not. And I say that to people because often, when you look back on the careers of others, that they’re — they look so pretty from the outside. But from the inside, it took me a good year plus to get that job. I was rejected by a number of banks. Merrill didn’t even come to Canada to recruit. And they offered me one of those polite informational letters which said something like if you’re ever in New York City, we’d be happy to give you 15 — a 15-minute informational interview.

And I remember saying to my father, I’m like, well, look at that. They just rejected me and he said, well, why don’t you take a train to get it, down to New York. You’ll never know. And I was at the end of my rope. I’d been searching for jobs for over a year. I said — as I said, determined to get this job and not successful and I took that train ride and 15 minutes turned into a three-hour interview.


CASSIDY: And then they accelerated me to the final process, which is for investment, it’s very competitive. I came down on a weekend and competed with all the sort of Ivy League American kids who had been through rounds of interviews, undoubtedly. And I got the job. So, it was a pretty sweet — it’s a pretty sweet success after a year and a half of trying. But it was very formative for me because it really informed and, I guess, my view of how often you have to choose keep choosing in order to get to the goal you want.

RITHOLTZ: Keep banging away. So, what — what did you do for Merrill when you — when you get the job, what was it that they had you do? What were your responsibilities and what was the job like?

CASSIDY: Well, and I think this is probably the second formative experience I had at Merrill. So, my role was financial analyst. Anybody who maybe has studied finance know that that’s really a job where you create pitchbooks.


CASSIDY: The books with facts and details about different industries. I was in the financial services industry. And that was the entry (ph) that I was assigned to and you really create those books or what’s called managing directors who go out and pitch large companies on using their services, M&A services, IPO services, what have you.

And so, the average analyst is spending, you know, days and nights, often through the night, toiling to create these perfect pitchbooks. So, I certainly had that experience but I ended up working for a pretty eclectic young managing director called Henry Michaels and Henry was, as detailed as they could get, pipe smoking, definitely capable of driving others crazy but he took a really deep and really interest in just teaching me about, believe it or not, the savings and loan industry.

And I think he found me to be maybe a rough (ph) student and, I freely admit, after taking a year to get that job, I was bound and determined to be successful at it. So, I would, very inquisitive, very curious. And as a result, Henry kept stuffing me and putting me, I would say on the — on jobs with increasing responsibility. And so, pretty early on, I was going to meetings with CEOs that he would — he would set up and let me attend. Of course, I was carrying the pitchbook, but that didn’t really matter to me, the exposure did.

And as a result, I ended up working on an IPO early, the Long Island Savings Bank. Henry kept giving me more and more responsibility. And in my second year, Merrill sent me to London which was unusual as well to send somebody that early and I got to go work on banking in the — in the European banking industry and had just an amazing experience.

So, I give Henry Michaels a lot of credit. Henry, definitely, skipped a bunch of layers to teach me and I, as I said, maybe my best contribution was I was a rough (ph) student but the result was that, an experience where I’ve got a lot of exposure very quickly to kind of senior executive.

RITHOLTZ: Really interesting. I have a specific recollection of the Long Island Savings Bank going IPO in the early, I want to say mid ’90s and eventually …

CASSIDY: That was me. I was the analyst.

RITHOLTZ: And eventually, it got acquired and then that company got acquired. And in a certain point, you just lose track. But this leads to an obvious question, all of your background is finance related, how did you transition to tech and what made you decide to leave the East Coast and the world of finance for the West Coast which has more of a technology bend?

CASSIDY: Well, I — so, ironically, I made my way to the West Coast, not from the East Coast but via London because if you recall, Merrill sent me to London. And when I was in London, I had spent, maybe two years with the bank and its classic length of each program for two years and then they expect you, actually, to move on. So, analyst programs are two years in investment banks.

So, I spent two years. They offered me a third and I really want to be, quote-unquote, “in industry.” Now, I had no idea what that meant but I wanted to work for one company.


CASSIDY: And so, I was able to secure a role with the CFO at a company called British Sky Broadcasting, one of the biggest satellite broadcasters in the world. If you recall, this is part of the News Corporation, its kind of empire. And luckily, for me, I parted with my job in finance to a job in finance inside of a company at BSkyB and then I was promoted to working for the CEO and the COO there.

So, actually, it’s probably a more dramatic story. I was promoted. I was working on the top floor for the — one of the two top bosses and I’d been there, I’ve been at BSkyB for only a year and I walked into my bosses’ office and I told them I quit. And he was shocked. And I said, two things are true, David. Number one, I have this epic promotion. I sit down the hallway from you, I get — I get lunch every day, I’m on the — I’m on the executive floor, I’m like but you don’t really use me. It’s true. My boss is very used to sort of operating like lone wolf as that as sort of effectively president of the company. And I said, number two, I think I want to head back to North America. I’ve been there for two and a half years and a girlfriend of mine, a very dear friend from Stanford Business School, I had visited her the year early — earlier and I fell in love with the weather in the Bay Area and this kind of sense of entrepreneurship. That’s true.

I mean, for a girl who comes from Ontario, Canada, where it gets pretty darn cold, once you visit California, you sort of realize that it’s possible to live in good weather all year long.


CASSIDY: But the other — but the other truth is I wanted to be an entrepreneur. My father, loves running some business. I had no idea how. I love the Bay Area for the weather and I sense that it was, that there were a lot of people starting companies. So I quit my job, I went skiing for three months and Whistler, and I moved to the — I moved to California and bought a car, drove up the coast from L.A. to San Francisco. Luckily, those friends of mine, their parents put me up at their very nice house in California until I found the job and I started over.

RITHOLTZ: And how did you end up at Junglee?

CASSIDY: If you can’t tell already, I was a fairly impatient young woman because, I moved a fair amount in that first six years of my career. I, as I said, I was looking for a job in the Valley. I found, what, unfortunately, the job I found was not nearly as positive experience as I’d hope. As you — as we just talked about, I actually had a really good experience with Merrill. I even had a good experience with BSkyB, if you look at the fact that I got responsibility, I was promoted.

And I got to this, I found a startup end in Silicon Valley that was in interactive television which is we somewhat related to what I’ve just got in at Sky, which is a TV industry. And on second day on the job, my boss told me I was scaring the secretaries and I was like, what — what do you mean?

RITHOLTZ: What does that mean?

CASSIDY: What do you mean? Yes, what do you mean? I’m like I just come from two industries that are highly male dominated, nobody ever told me I was scary. And that began a rapid decline in our relationship. I felt like I wasn’t getting a lot of responsibility. He kept telling me I was the rookie that needed to be coached. And I quit six months later. Actually, fairly deflated, because I was, like, if this is what it means to be in Silicon Valley, I must be this meritocracy. I’m supposed to be having the time of my life. Maybe I’m not meant for this place.

Luckily for me, I started thinking about getting another job and a recruiter called and pitched this idea of a company started by four Stanford Ph.Ds. in — who have this very cool technology. I took the interview I didn’t really understand fully the technology but I loved that. They were smart, they were thunderous. And so I switched, and luckily for me, I made the switch, Junglee ended up building a whole engine for shopping, for comparing prices across the Internet and Amazon bought the company six months later and that was the really the start of my career in Silicon Valley. Just a great experience. But following a very poor one.

RITHOLTZ: Really — well, everything can’t all be wine and roses. Sometimes, they’re going to miss. Tell us a little bit about what it was like working for Amazon in ’98 and how closely did you work with Bezos back then?

CASSIDY: Well, believe it or not, back then, it was a pretty small company. There was about 1,200 people. We were public. So, everybody got exposure to Jeff, myself included. And so, what are some of those early year — those early times like at Amazon? Well, first of all, as I said, everybody was — it was a small enough company that you could sit most of Amazon in one or two buildings, so we made a couple of moves where — we were all in the same building.

Number two, we all had to work in the warehouse including like the very top executives at Amazon. Jeff and Rick Dalzell, like everybody had shifts over Christmas. You had no day job. You literally all had shifts in the warehouse which was a pretty amazing cultural feel. And by the way, that included, like overnight shifts. You work taking and packing books and music — books, CDs, and videos. That’s true.

Jeff had bought the company because he, believe it or not, in 1998 still had this vision of a day where Amazon show you every product on the Internet whether or not they had it in stocks, so this early vision of marketplace. But Amazon at the time was just building out its own verticals. So, what was sit like? He was really the main champion of this acquisition of buying us for our technology. He used it to start version one of Amazon marketplace which he shut down several years later.

So, he’s made many attempts at marketplace before he got the one that worked. And by the way, before the world was ready for it. So, it was pretty — it was a pretty neat look into how sort of visionary he was even early on, of course, not nearly as sort of daunting a presence as he might be now. Just like very accessible, pretty goofy, actually pretty quirky sense of humor. And I got to work with him specifically because I was one of the people selling new merchants, like people like Macy’s and others on the idea of putting their products on the Amazon’s website. So, I got to pitch a few different retailers with Jeff which was really cool (ph).

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RITHOLTZ: So, I know this is going to be a very fanboy question, but I have to ask because there’s a broader component about understanding or not the future, in the late ’90s, in the early 2000s, did you have any indication that Amazon would become the juggernaut that it became or was — that was early days. Hey, we think we’re going to be successful, we could be a real solid company, like, what was the view like from back then?

CASSIDY: The view was not that we were going to become the juggernaut we are today as defined by Amazon’s not just a retailer but it’s like a dominant movie studio. It’s not just a movie studio, it owns a grocer. It’s not just a grocer, but it happens to own the largest infrastructure, backbone of the web called Amazon Web Services and other merchants, like no way was that obviously. As I said, like, literally, the days where we’re selling books, music, and video and launching new categories. And, Jeff, as I said, like, he was impressive but he was also a very accessible, funny, young, like, he’s only a few years older than I am, at best.

And so no, I don’t, I mean, all the people that you think of now who’s quite famous, there was no indication. As I said, now, you might and I might say, wow, buying a company in 1998 to launch Amazon marketplace, certainly there were early inklings that he has a vision to sell a lot of stuff. As we say, hey, should I see this company becoming one of the larger retailers, sure? But it’s defined by what Amazon is today, yes, no way to connect it.

RITHOLTZ: Quite fascinating. That’s quite fascinating. So, let’s talk about your transition from Amazon to your next venture, you co-founded a startup, tell us a little bit about Yodlee and what made you decide to say, well, this Amazon company is kind of fund, but let me see what I can build on my own.

CASSIDY: Well, remember we were chatting about that rather restless and impatient young woman. I don’t think any of that dissolved when I was at Amazon, it was a great experience, by the way, and remember, I had never gone intending to be in Amazon, I had gone to a startup, right, which got buy — bought. And while Amazon was a great company, that’s in Seattle, it was now public and so there is me thinking, gosh, when am I going to get the chance to start my own company and I know many people listening to this podcast would be like, really, you left Amazon to start your own company? Is that a really smart decision?

But in some ways, Amazon to me, still at the time, felt very big and I want to get there. So, I’m at Amazon, and remember, many of the founders of Junglee, you know, has made a lot of wealth. They’re certainly mentors of mine. They are even today. And they start angel investing in a number of companies in the valley.

And knowing that I have this ambition, I’ve been at Amazon about a year and I get into the — I get a call one weekend that sort of said, hey, there’s this professor from UCSD who’s a computer science professor and he built this really cool technology that goes out of across the web and it gets all your financial information behind all of those sites with passwords and it puts them in one place. You can have an aggregated view of your financial life.

And by the way, the technology is not the same as Junglee but it has some analogy. And they’re like, and they’re lucky for a business cofounder. They have all these engineers that they need someday to establish but there’s this model, raise the money. And so I got one of those inbound calls and through that network of angel investors who’s — who were the founders of Junglee. I flew down from Seattle to San Francisco for a weekend. I took one look at the technology and I’m suitably impressed. I was like, wow. You just grabbed all my credit balances and my bank balance and my brokerage balance in one place and gave me this aggregated view. Nobody can do that. It’s pretty revolutionary technology at the time.

And they offered me the opportunity, at 29 years old, to become what’s called a cofounder of the company and the first business executive. And I just jumped at the chance. I love the technology, I love the fact that I would be with — they were engineers that this company do, again, very similar to Junglee but now, I was going to get a seat at the table as literally one of the executive team at such a young age and get to raise the money for venture capitalists, make the business plan. So, I said yes.

RITHOLTZ: So they were really very early stage.

CASSIDY: Yes. Yes, yes. I mean, it was 12 engineers in a room and as I said, I was the — I was effectively the first business leader to be hired at the company.

RITHOLTZ: And so, I gave my notice at Amazon maybe a month later and moved right into Junglee and we raised $15 million from venture capitalists within a month of that and we were off to the raises. And thus, began kind of the six-year journey to build what today many would consider the pioneer in really aggregate your financial information. I’m really proud of the fact that Yodlee really did create a whole industry of companies that were able to access financial information using our services and our kind of technology backbone and build many of the financial outfit people use today.

So, Yodlee, Yodlee had a 15-year run before it became public and I was there for the first five of those years.

RITHOLTZ: So, let’s work our way through this chronology a little bit. You ended up at Junglee which gets acquired by Amazon in ’98. From ’98 to …

CASSIDY: Ninety-nine, I’m at Amazon.

RITHOLTZ: And then when do you leave ’90 — when do you leave Amazon …

CASSIDY: Mid ’99.

RITHOLTZ: So you were only — OK. Got you.

CASSIDY: Yes. I was there a year, I mean. It was a year.

RITHOLTZ: And you stayed — did you stay with Yodlee until they were acquired by Envestnet?

CASSIDY: No. I stayed with Yodlee for five years and that time, I had every job under the son. I was predominantly responsible for the executives for not just raising the money, we’ve raised about a 100 million in the time I was there in several rounds of financing but I was — I was just responsible for sales and business development, selling our technology to all the banks and brokerage companies.

And so, I stayed until in 2004. I (inaudible) our CEO at 2000 and he wasn’t going anywhere, by the way. So I always say the people tapped out of my own startup, like, literally I’d had every job. I’ve done sales, I’ve done marketing, I’ve done PR. I was our spokesperson, I raised money. And I — an in many ways, I was partnered very closed with the CEO and we had a great relationship.

And in 2004, I was like, OK, now, what’s my next horizon? Like I’ve been here five years and I’ve done all of these roles but there’s like the company’s not growing fast enough to give me an entirely new career.


CASSIDY: With set of challenges. And so that, I actually, for the first time, did what I call a more studied search, thinking I might start another company but also thinking that I wanted to find the right idea so I was pondering my next move, presuming I would start a company when I got the opportunity to start a new service at Google which, today we would call Local and Maps.

RITHOLTZ: And let’s talk a little bit about Google Maps. It’s funny because it’s so ubiquitous today, we don’t even think twice about the miracle that is Google Maps. But back in the mid-2000s, did anybody have any idea of what a massive technological breakthrough G maps were? I remember playing with early versions of it and just head exploding, What was the thoughts like within Google about Google Maps?

CASSIDY: Well, it’s — it’s a couple things. So, first of all, when I got the call, Google originally called me to come join them and I actually said no. And I said, gosh, you guys are also quite big. You’re 1,200 people. Remember in my work frame, Amazon is big at 1,2000 people, so is Google. And I says I’m going to start another company.

RITHOLTZ: Hard pass.

CASSIDY: I know. So funny. And Google called me back seven months later. They said — you said you wanted a startup opportunity. We have it. We have something greenfield called Maps and we said -they said, Yahoo! has a product called Yahoo! Maps, AOL has what they call MapQuest, Google has no product to help you search locally or find — navigate locally. Either you find goods or services locally or business — and navigate, right? Because Google Local is like search for business, Google Maps is search for a place. In fact, today, they’re very merged. Nobody thinks of them as different.


CASSIDY: And I studied the landscape, I went into interview with Google and within two weeks, I said yes to the job because I was like, holy smokes, the yellow page industry, we have the time with those thick yellow books that everybody got to find places was a $23 billion industry in annual advertising. And I was like surely, if Yahoo! has a product and AOL has a product, Google should have a product and look at all the ad dollars available in those category and look at all the usage, it’s pretty antiquated.


CASSIDY: So, I said yes very quickly. And I do …

RITHOLTZ: I have to point out that yellow books are $23 billion in revenue, the obvious answer is but not for long.

CASSIDY: But not for long. I mean, look, digital really wiped that business over. By the way, there still yellow pages around the country and …


CASSIDY: … around the globe but nobody would think of that as a juggernaut industry. So, yes, online really changed and transformed the face of local advertising fundamentally. But I would say I knew it would be big. I mean, that’s what lead me to go in that direction. I say what was unknown about Google service and you appreciate this, even by me, is I was paired with a product manager, I was the business person, meaning I had to go license the data for like, roads and businesses to put underneath inside of that service, right? All that data was not online.

I had one product manager, Bret Taylor. Ironically, now the president of Salesforce. He was my — he’s my product manager and we had 10 engineers and the 12 of us build that product (ph) effectively. I did the business DLT, he guided the engineers. So, on one hand, the product could have been pretty straightforward like Yahoo!, AOL. But Google made two innovations that I think people will remember to this day.

Number one, believe it or not, just putting the name of the road inside of the road, not on top of the road was one innovation. You’re like, the name of the road is like on the road. And visually, it’s just like a prettier experience and it’s — it’s like the map is less crowded that way. But the second innovation, and this I give a lot of credit to Sergei and Larry, early on, a guy named John Hanke showed Google, once we’ve launched local and maps, this cool technology that had satellite imagery called Keyhole and Larry and Sergei were like, we need to buy that. We’re going to overlay that on Maps.

And that was the innovation, right? Overlaying satellite technology on top of maps, like hey, you can’t give me any credit as a business p person for seeing that, that was really product vision. And in that case, led by the founders. I mean, Bret like the product too but from what I recall, Larry and Sergei was really gung-ho on buying the compo and overlaying satellite technology on top of Maps. And that’s an example of sort of one of the things I admired about Google. They didn’t really care about how it would make money, it was just a very cool and differentiated in — it turns out, very useful feature to have Google Earth on top of Google Maps. But with no commercial application, just super cool, at least not then.

RITHOLTZ: Well, eventually, right? Eventually.

CASSIDY: Yes. But not — but like when we laid over — overlaid it, I was like, ok, I guess that this cool. I’m not going to (inaudible) to anybody but what a — what a great kind of product feature and like kind of great vision. So, those are some of the finer experiences about building Maps and then Local as well.

RITHOLTZ: You mentioned the integration of Local with Google Maps. I have a suspicion that a lot of people don’t realize how tightly integrated it actually is. What — I was in pre-pandemic, I was in Paris, and we were looking for a specific restaurant and you just punched restaurant in and Google Maps knows where you are and it just shows you on the Maps, it populates all the restaurants of that type in that area. And it’s absolutely seamless and I’ve showed that the people who are much, much younger than me and they’re like, I didn’t know I could do that with Google Maps. It’s almost like a surprise feature, when really, it’s a core part of Google Maps. It’s on an Easter egg.

CASSIDY: Yes. Absolutely. And to be honest, when we started the product local in maps with different things, you could type in to the Search Box, like movie theater near me and you would get literally a listing of results. Today, of course, they’ll show you the results on a Google Map as the preferred way for you to see those results.


CASSIDY: I guess you could get a listing if you want but every Google search result has a map embedded and like you, I actually often do all my local searching on Google Maps. I don’t even go to the main Google website. I can, but I just go to, like, Google Maps, and I type in, like restaurants near me, and I get all of them with the reviews and the results. And so, look, very, very, very fun product to have launched into the system (ph).

RITHOLTZ: So, what led you to leave Google to start Joyous?

CASSIDY: Well, remember, I have one more big chapter at Google that’s probably ironically even bigger than my Local and Maps chapter because I’m — I’m at Google. We’ve launched Local and Maps and what’s happening is people are saying to me, well saying to my boss, he was the cheap business officer at Google, um, hey we have all these products that need us to license data, like we want to have — we want to have a library product, we want to have a solar product, we want to have a shopping product. By the way, we want to have a video product.

So, I’ve ended up building a team that is all the licensing for all these other data, types of data that we want to put online. And so, I’m running that team, my team’s gone — I’ve gone from being individual contributor, I’m running about 30-40 business development executives in about — in a span of a year. This is how fast Google was growing.

And then my boss turns to me and said, hey, Larry and Sergei really have this ambition that we should grow our international business much faster, would you move over and run what we call Rest of World which is everything from China to Brazil, at the time we weren’t in China.


CASSIDY: And build that business. So, to be honest, I spent the next five years of my time at Google. I was there for six years, actually, running our international business. I ended up giving Local — giving up Local and Maps and all those other teams. And I moved over and run that business for five years and that was the majority of my time in Google, actually, which is building our international business which became renamed Asia Pacific and Latin America, we entered China, we entered Brazil, we entered India, we entered, I don’t know, 18 different countries directly and 109 indirectly.

And so I ran that business until 2009 and that was probably my — what I’m more known for at Google.

RITHOLTZ: Really interesting. And then the startup which starts …

CASSIDY: Again. Again.

RITHOLTZ: Right. And so, ’09, you head over to — tell us about the genesis of Joyus.

CASSIDY: Yes. So, ’09, I am three months pregnant with my third child. I’ve had, got married, have a family at Google. I’m at the pinnacle of my career. But it’s also clear that I am not going to be the CEO of Google. Like, it’s not happening, right? It was obvious that Google …

RITHOLTZ: Those two guys, they just have no interest in leaving.

CASSIDY: Those two guys, they don’t leave — and they were there and Eric Schmidt as well. But it’s also clear that any successor at Google would be from product or engineering.


CASSIDY: And so, by the way, I mean, pretty might company. Sheryl Sandberg is my peer, Tim Armstrong that went on to run AOL. Nikesh Arora, who today runs Palo Alto Networks. I mean, it was a pretty crazy, talented group. But all of us started peeling off in our own time. My colleagues, a lot of them went to larger companies, and I actually wanted, to you point, I had a startup itch again. I was 39 years old and I thought if I’m ever going to build another company, this might be my time. I’m older but I’m not so old that I wouldn’t — not start a company or go to something early and I — and I wanted to be a CEO.

And so, I combined those ambition and I went to a venture capital firm for nine months. I basically parked myself there. I had my third child. I said to them, I want to stud everything in ecommerce. Remember, I’ve started my career in ecommerce, right, at Junglee and at Amazon, and it was like circa 2009 and I believe that ecommerce was going to go through another revolution in which people were shopping less for things they needed, like, or things based on convenience and more based on wants.

So, this is the era where fashion, you know, décor, experiences, all start to rise as sort of marketplaces on the Internet and they’re all just getting launched, by the way. If you look, back 10 years, it was not obvious that Airbnb would be a big company.


CASSIDY: It’s not obvious that fashion would become one of the biggest categories, right? It’s just super early to think about anything other than price and convenience.

And so I studied sort of all the things in the landscape. And one company has been pursuing me very actively, something called Polyvore which was sort of like an early version of Pinterest. Subsequently got bought by Yahoo! several years later for 300 million. And actually, before I started my own company, I go to them first as a CEO who’s replacing a founder.

So, I go there for — I go — I studied the landscape. They tried to recruit me multiple times. I’ve been at a venture capital firm, I spent like really nine months looking for my next thing. And I took that job and within six months, I was out. I mean, I — the founder and I butted head. I wouldn’t even say we butted head overtly. He just wanted to run the company again. I came in as a CEO and within six months, he wanted the company back and that’s what he told the board.

So, I actually got, you know, I lost my first job outside of Google which was humiliating. So, that’s how I entered ecommerce. This is when I mean when people are like reentered ecommerce, people are always like, wow, you started your own next stop and I was like, no, no, first, I was a CEO of a startup where I battled with the founder and he wanted the company back and I gave up my, like, 2,000-person multibillion-dollar job at Google to stay out with a 10-person startup. Like, let’s not miss that part of the story because it’s a pretty, illustrated the way to your point, it all rolls (ph). It’s never all glorious.

RITHOLTZ: Wait until — by the way, we’re going to circle back to that because it’s relevant within the book of ..

CASSIDY: Absolutely.

RITHOLTZ: … what happens when you choose risks, what happens when they work out, kind of takes care of itself. But when it doesn’t work out, how do you respond to what is a disappointment or a failure, although I have to imagine if they hire you as CEO and then the founder comes back, that exit was probably made a little less painful by whatever the contract gave you on the way at the door.

CASSIDY: Yes. Absolutely. By the way, I heavily negotiated for that circumstance, but you’re right. I was very financially protected but my ego, and we’ll talk about that later, was just incredibly bruised. And yes, I was very humiliated, as you can imagine, to have lost that battle and we’ll come back to that.

But to your point, look, I started my next company not wanting to because I just had this very brutal startup experience, right?


CASSIDY: And remember, I’m still pretty relevant because I’ve been at Google, I still have the sheen of Google and everything …

RITHOLTZ: Amazon, before that. Sure.

CASSIDY: And Amazon. So, I’m getting large company calls. In fact, I was on the final round of CEO job for a travel brand you would well recognize.


CASSIDY: And at the same time, I had this idea for a video shopping startup because I had seen that at Google, YouTube was starting to have young women who were like hawking products. They were called haulers in the day. They’d go shopping and show all their wares on a YouTube videos. YouTube wasn’t shoppable but I saw that trend when I was at Google.

And then, of course, I’ve been at Polyvore, the shopping startup in fashion and lifestyle. And all the brands wanted to work with us. They all wanted to somehow showcase their wares online. And they want to do it with, like, with great content.

So, while I’m interviewing to these larger company CEO roles, I have an idea to like effectively create a new version of QVC which again, many people are doing video commerce today, but in 2010, like 11 years ago, not that many people are thinking about this.

And ultimately, I found that idea so compelling that despite myself, I turned down the safer CEO jobs and I took another startup risk and I started that company which you called Joyus. Yes, that was my video shopping startup and I ran it for six years and we sort of built literally studios, had brands give us products, we had curators who told the story, we created a patented video player that had shop — a shopping cart in the video player. We distributed that video player online multiple places at multiple different third-party websites to get people to shop and watch at the same time.

And that was an incredible experience. I mean, again, sort of like the risk of trying to be an innovator, never something I would regret doing. Obviously, grinding hard ultimately too early for the market. But nonetheless, like, I sort of just embraced the idea the ecommerce was going to go through another revolution and I spent all my time working on the video side of that equation.

RITHOLTZ: When you say too early for the market, Joyus was still acquired by StackCommerce in 2017. Why do you believe you were too early to that market?

CASSIDY: Well, first of all, we were acquired for a very small sum, like nobody made any money. My venture capitalist didn’t make any money, I didn’t make any money. But why I say we were too early, we raised — we raised close to $50 million which in today’s world is not a lot of money. People raise that in one round. We raised that in over six years.


CASSIDY: But when I say too early, if you think about it, today, we have Instagram video where people are used to the idea of looking at products in their feed. They’re also …

RITHOLTZ: Half the people in my office are — their wardrobe is purchased via Instagram.


RITHOLTZ: And then you have Facebook video where there’s a lot of shoppable ads. Like, today’s video, there’s really a video unit on Facebook that has a shopping cart in it. You can watch …


CASSIDY: … video as an ad and buy it. But when I am building business, there is no Facebook video. There is no Instagram video, there’s no Snapchat. There’s no TikTok. So, people aren’t really used to watching video for anything other than content, really, like sunny videos, short-form videos on YouTube, and really, for quite a young audience. And like, even Netflix is building and growing but it’s as a long-form video platform. But we went to Netflix, we said would you like to buy a shoppable show? Like we can give you shoppable shows. And like, nobody was interested. Nobody was interested in carrying shows that were about shopping.

So, we had neither interest from kind of any of the big platforms and all the platforms were really interested in content that was only monetized through advertising, right? So and the consumers not used to like being on a site like Instagram with just filters and products at the time. And being on a site where you could watch and shop products, so like when you have no consumer understanding of that and you put out a new innovation, you’re hoping they’ll adopt it, right?

But if they don’t — if it’s not something they recognize, what ends up happening is you’re searching for consumers who want that experience and that can be very expensive. You spend a lot more money on marketing and advertising in order to convert people into watchers and shoppers. And that was our — that was our case. We kept growing. We kept doubling every year but we really needed venture capital money to keep growing the size of the costumer base and it was too expensive, ultimately, so that’s why we sold.

We didn’t sell ourselves for some glorious reasons. We sold because at $50 million in, we were growing, the revenues, but we could not find a path to profitability.


CASSIDY: And so we sold the technology and platform.

RITHOLTZ: Let me ask an obvious in-hindsight question, you have a background at Google, YouTube is the fastest-growing video platform, wouldn’t your technology integrate with YouTube so that you can — and along the same way, the past decade, unboxing videos and all sorts of tech and fashion in automotive and go down the list of things you could buy, that seems like that could’ve been a pretty natural fit.

CASSIDY: You can ask any startup under — and ask any startup CEO, the path they go on to sell a company, I spent a year trying to sell Joyus. That’s the gritty, maybe, gritty truth. And think about my role at that. And my role of that …


CASSIDY: … pretty darn good, right?


CASSIDY: It has Amazon, it has Google, I mean, I’m a known quality. By the way, when you’re — this is one of the hard truths that when you’re running a money losing startup, sometimes you can get people to bite but often they think they can build it themselves. YouTube, we had a conversation and they certainly thought they could build this themselves. I would say up until today, YouTube still doesn’t have a shopping cart …

RITHOLTZ: Right. I was going to say …

CASSIDY: … (inaudible).

RITHOLTZ: That calculus is always …

CASSIDY: I know. So, it’s endlessly frustrating.

RITHOLTZ: Right. That calculus always seems to be, hey, do we want to wait three years or drop $800 million and leapfrog the competition? That seems to be the math that was done and here it is, it’s 2021, almost 2022 and you still can’t just purchase something on YouTube with a click the way you can on Instagram.

CASSIDY: Yes. You cannot. Well, Facebook is probably — I think is probably the best video shopping experience. Instagram has good shop ability but it’s adding shop ability because for a long time, Instagram was like kind of more peer that it’s adding it. But they all want it, right? Everybody talks about shop ability now. I mean, everybody and many people have been enabled it.

So, yes, look, I would tell you, I find it endlessly frustrating that I couldn’t land the company and ne of the places, I think, even today could use the technology. By the way, you’ve just said, QVC, if you were to look at the list of the people I talked to the ’17 as I was trying to sell my startup, I can only tell you, I found it fairly shocking, but this tells you also how early it was.

Like, today, video commerce is the hottest thing in 2021. IN 2017, I literally could not get some of the best platforms on the Internet to buy this kind of technology. Now, I ultimately sold it to another private company that’s doing very well and was doing shoppable content and still is. So, and Joyus, as a brand, still continues. It’s just — it’s still painful to me because, obviously, I was early but right.

And that’s one of the risks you have on entrepreneurship when you really do try and innovate, right? Maybe if I’ve started Joyus five years later, it would have been an entirely different outcome. It probably would have been. But, hey, that’s the way the Internet rolls.

RITHOLTZ: Quite fascinating. Let’s jump right in to a little background on Choose Possibility.” You published a letter. I don’t know was that five years ago? Tech Women Choose Possibility. Tell us about that and is that what led to — into the new book?

CASSIDY: Well, Tech Women Choose Possibility was a letter, an open op-ed I wrote on a platform called Recode, well, an individual newsletter. Really at a time where everybody, and myself included, was frustrated with the narrative on women in tech was incredibly negative. If you think about 2015, many had line articles, “The Atlantic” cover of men – “The New Yorker,” I think, all of these folks have articles about sort of where all the women in tech and how terrible it is and there’s also, like, a lot of great, you know, not so great stories about bias discrimination and so on.

And so, at the time I’m at startup entrepreneur, I’m running Joyus and of course, I have a multifaceted view of that. On the one hand, I think, hey, you know what? All things being equal, I would still choose Silicon Valley. It is mostly meritocratic, it has been very good to me, I found my tribe, right? I’ve been able to thrive.

Yet, at the same time, I remember that early experience I had, you recall, where my boss told me I was too aggressive for the secretaries.


CASSIDY: And I know startup entrepreneur and I hear firsthand stories from other amazing female entrepreneurs and how terrible their experience is, fundraising, and just a bias they experienced.

So, I wrote the op-ed by surveying a hundred women in text from CEOs to entrepreneurs, asking for their opinions on being an entrepreneur and then their experience of bias and discrimination. And in fact, with the — what the survey shows which is why I write the letters, what you’d expect which is they — I think the majority had said, we had directly experienced biased and discrimination. Yet, like 80-something percent, still recommended entrepreneurship in tech.

And even for their daughters, they said if they didn’t recommend it to their daughters, it wouldn’t be because of bias, it’d be because their daughters may be don’t want the entrepreneurship. And so, you say, well, how can this duality exist, that duality instead of what the letter says, it says basically, it says, hey, look, by the way, every day, women get up and choose possibility. They choose to make their next step in tech and you can successful.

So, like don’t walk away from this industry, please, because so many women are being successful in increasing rates. But if you think it’s all great, it’s not, and honestly, if I were in the technology industry, the call to action I was looking to have happened is like, hey, we think we can solve all the world’s problems, we tell everybody else we can here in Silicon Valley. I really not have find any technology solutions, the problem of gender and inclusion, like, really, like it’s shocking to me and we’ll talk about solving poverty and clean water and climate change but there are no tech platforms that try and solve bias and discrimination.

And so, that was what’s the letter sort of positive that you can both have and positive experience personally yet still understand this is not what it should be and the rest of the technology industry needs to take some responsibility for trying to equal — equalize the playing field. So, did it lead to the letter or the book? A little bit. The title is what I mostly took from it.

But I think the — the notion that it’s a dual path, like there could be risk and reward and still danger or harm …


CASSIDY: … all those things can exist at the same time. And that’s what we’re always grappling with.

RITHOLTZ: What was feedback to the letter when you published it at it’s now at Vox but Recode back then, what sort of response did you get?

CASSIDY: Overwhelmingly positive. A lot more than I expected. Keep in mind, we talked about risk we take in our career, like many other people, I spent the majority of my career, heads down, building my own companies or building larger companies. I really didn’t try and use my voice actively on any, like, broad topics. So, for me, it was a risk to even write the letter, right? I’m like what will people think of me? Will they think I, like, I’m putting myself out there for the first time as a female first and a leader second which is the exact opposite of how I ran my own career, right? I never wanted to be seen as sort of like for my gender, I want to be seen for my capabilities.

So, I think the letter was very well received and I think people just said, well, hey, thanks for acknowledging the reality but also being solution oriented. Like it was just a counter to the narrative that it’s also terrible and really, until all of our daughters become engineers, nothing can be solved.


CASSIDY: I mean, so I think it was the maybe the first time I use my voice in any kind of way that’s offered maybe a personal perspective and I found a little risk team to do it and I think I was validated and so they’re trying to speak up by the response like that.

RITHOLTZ: And that was before places like Uber, some of the engineers had gone public about what a frat house that was inside. You predated that explosion that we saw elsewhere, right?

CASSIDY: Uber had it’s Me Too moment about a year later. And in fact, many companies did and you started to see some of the very, very bad behavior, far beyond the microaggressions that many women talked about that people of color and women experienced, unfortunately, to far greater degree than any of us think. So, the letter predated it but I think Me Too really exposed some of the more flagrant and, honestly, awful things people do at work.

RITHOLTZ: Sure. So let’s talk a little bit about the book. I don’t want to overlook this. I like the way you have this structured in three parts. Get Going, Get Smarter, Get Rewarded. Explain why you went with that structure?

CASSIDY: Sure. So, obviously, it’s probably obvious from this conversation that I take in a decent amount of risk in my career and I wrote the book because I think people have a very unrealistic, sense of what risk and reward looks like compared to how it really unfolds. And so, I structured a book in a way that really — I didn’t — I did not want it to be a memoir but I structured it in a way that goes through sort of basic lessons on this takin to sort of maybe more complex, not ideas, but kind of philosophies and it really narrows, maybe the way I learned to take risk. For me, it was really simple in the beginning and we talked about those early moves, I made or six moves in a span of seven years, right?

So, whether they worked out or not, I took a fair amount of risk and made a number of sequential choices and then I think the middle of the doubt, being a smart risk taker, nobody says I don’t think certainly that this book is about just taking risk willy-nilly. It’s about how do you become a calculated risk taker, right? If what — we’ll ask you to lean forward and take more risk in your career, the question is you want to do it smartly.

And then the last, of course, really chapter really kind of talks to how, like, how many of these choices really unfolds overtime. So, organize it roughly in an order in which it happened in my lifetime which is also the sort of order, broadly speaking, which I learned these lessons.

RITHOLTZ: And some of the chapters really leap out with some real interesting questions that I wanted to bounce off of you, starting with why is the hero’s journey the wrong metaphor for entrepreneurs?

CASSIDY: Well, and not just for entrepreneurs, for people at larger companies too, we have this idea, when we look at the heroes journey, what we — what we see and remember, just like one mighty choice the hero made that would — could either lead to sort of abject failure or glorious — glorious success. And by the way, we see that story not just in popular media but even in the media that relates, the journeys successful entrepreneurs, like we’re all watching what happens when Richard Branson goes to space, like is this is going to be epically successful or something the disastrous is going to happen, right?

Like there’s all of these binary stories we see about people, like big singular choices and I think — and I call that the missing Myth of the Single Choice in the book. The reality is, that, most people who are taking risk, it’s not one risk that led them to the reward …


CASSIDY: It is a multitude of risks. And by the way, they’re not even all big. They may be small, small, small, big. Small, small, small, medium. Small, small, small. But — and they just keep pivoting in small ways until they realize the reward they imagined or a different one. So we have boiled the hero’s journey down to a single choice when, really, rewards — reward getting is about a system of unlocking multiple choices and it’s never just one choice. It’s about committing to the process of continually choosing your way. And your past.

RITHOLTZ: I like that description. It’s less cinematic but far more realistic. Another one that jumped out that was kind of interesting in, obviously, given how you’ve moved from New York to London to Silicon Valley makes sense, tell us why proximity beats planning?

CASSIDY: Well, it’s interesting. I think one of the reasons people see risk is they — like, they just don’t like uncertainty. In fact, there’s research that suggest that often people choose something, not because they invested the best path, but because it typically reduces uncertainty. So, uncertainty creates a lot of anxiety to people. So, what’s the antidote to that?

Well, for many people, it’s planning. Well, I’m going to do this but first I’m going to create a plan. So, they start planning to the thing they don’t know and they plan from afar, right? So, you can trace this perfect plan of what you imagine the thing is that you want to go after and you can add more and more details to that plan.

But the problem is, like you’re pretty far away from understanding what that new reality looks like. And so, while you’re creating a plan, it’s not like instead of planning your head with more and more detail, it makes you feel less uncertain but it’s not getting you any closer to action. So, often I say to people, like if you — if you know what you want or even if you don’t, get proximate to environment or people that even roughly approximately the thing you think you want, the thing you think you want.

And two things happen, number one, you learned a lot more by being proximate than planning from afar. Like, if you say, hey, I want to be a chef and I’m currently a financial analyst, like, what — say, well, how do you see yourself in circumstances where you’re in and around chefs in a restaurant before you ever make a mighty leap to go to culinary school because you can learn by being proximate whether or not that thing is even what you want, right? So, getting close helps you identify the thing you think you wanted what you really want.

Number two, you get knowledge on how to achieve it because you’re — you proximate with people who have already done what you want to do. And simply by studying them or being around them, you’re going to learn.

And the third thing is, well, if you really know what you already want, when you get proximate, you really get the opportunity to, I would say apprentice under masters. People are really good at it. And those people attract new opportunities all the time.

So, those are the reasons, I think, that proximity, getting close to what you want even before you know it exactly, has far more value than planning in the abstract.

RITHOLTZ: So let’s talk a little bit about a less successful startup in your personal career. Polyvore which is what preceded you joining Joyus. Tell us about what went wrong there and the lessons that you learned.

CASSIDY: Sure. Well, first of all, I will say, people, you can take smart risks or try to take smarter risks but you don’t never eliminate risk entirely, right? You can do all the studying you want and set yourself up — up well and still fail. I mean, that is why it’s called risk after all. And certainly, in Polyvore, I’ve made a very studied choice, I entered the ecommerce arena very knowingly, I wanted to be a CEO and the company, I mean, I’ve known the company for three years. So, I felt like I really had done my homework.

When I arrived at Polyvore, I had a game plan that said, look, I’m taking over from the founder, Silicon Valley is littered with founders, CEO, pairings that don’t work. They crumble.


CASSIDY: It’s like a marriage, right? I mean, at best, your odds are 50 percent on a marriage and, like, I’d say, they might be even slightly less on a found-CEO relationship because you have two people who have authority over a company, right?


CASSIDY: On the one hand, you have a founder who has been used to running a company and, obviously, have control over it including finance — financially through equity ownership and then you have a CEO who’s sort of theoretically bought in to sort of the adult. So my point overall, is that when you think about any startup founder, CEO journey, you’re like pairing somebody that’s financial ownership of the company that’s pretty large in moral authority with somebody who is theoretically has professional management skills but also wants this ambition.

And that’s what I entered in Polyvore. And I think if I were to characterize in a nutshell why it didn’t work out, I think that at so the first three months, I was listening to sort of what the founder had to say and didn’t really want to — did not really want to disrupt the apple cart. I really want to listen and be a thoughtful partner.

At months three to six, I started sort of voice some of what I believe we should do with the company. And by the way, I said to the board, this is going to go one of two ways, either my partner and I kind of share the same value then want this to work or there’s a possibility that this person feels very threatened by me voicing my opinion and I think the latter ended up happened and at months six, the founder, basically said I want the company back, it’s either Sukhinder or me and the board chose him.

And it was an incredibly painful experience. And so what did I learned from it? I think I learned one seminal lesson which is you can do all the studying you want, whenever you make a new choice, like the who that you’re partnering with, the who of the equation, is even more important than the what. I always say that to people like we make new choices based on the industry, based on the company, based on the company’s track record, based on passion, yet intrinsically, when we enter any new situation at work, we are inexplicably tied to whoever we’re working for or with most closely, right, and our experience working with them.

Do we share the same values? Do we have different strengths? Do we have complementary strengths? And I think I ended up in boat with something who at the end of the day, didn’t share my values, like, we really wanted to run the company not just — I wouldn’t even say it was different ideas of how we could get there, it was like we wanted to run the company differently, what we valued in leadership was different.

And so, when that — when that situation transpired, I went to my mentors and I said, my God, like the founder wants the company back, should I fight for it? And the very first thing my mentor said was, no. They said why would ever want to fight for a company that’s 10 people big where, quite frankly, what you’re telling me about the story and what’s transpired, and by the way, I’m not going to spend the nitty-gritty of how it transpired which was maybe not in keeping with my values, they’re like from all of the behaviors that have gone on, like, what makes you think that this would be a group of people that you want to tie yourself to going forward?


CASSIDY: And I said, you’re right. And so, I actually, like, didn’t fight for it. I was like, OK, he wants it, he can have it back. I’m out. You’re right. this is not the right place for me which is was against every instinct I have as like somebody who wants to drive and control, right? Just to give up and be like, yes. You’re right. And I looked back on that situation and say my mentors were right.

RITHOLTZ: One of the hardest things in business is knowing when to cut losses, when to, say, hey, whatever this decision that led us to this point was wrong and now let me just reverse engines and head out of here as fast as I can. But it feels challenging because it’s an admission of failure even though that’s not what this was.

CASSIDY: Yes. Well, by the way, I always say to people, it depends over what timeframe you characterize that decision. On a six-month timeframe or a year timeframe, that was a failed decision and I — I call it a failure because I failed to have impact. It’s different in Joyus, right? we talked about why Joyus did or did not reached its culmination as a video platform. But I can look back in those six years and see every innovation we achieve, see everything we built, see the team we assembled and what they’ve gone on the deal, see the fact that, like, we were the pioneer and I can feel very proud because I know had impact.

At Polyvore, I had no impact of those six months.


CASSIDY: It was painful and, like, and honestly, like a waste of my time and their time because nothing transpired that was positive, right? We just — I just exited.

So I consider it a failure. But I also consider it a success and the decision to join ecommerce to leave Google and become a CEO. I got to run my own company, I got to run StubHub. Like, I mean, I began a journey, I got to become an ecommerce investor and ecommerce board member. Like I have loved being in ecommerce for the last 10 years. And that would only had been possible because of my decision to join Polyvore, however painful.

So, anyway, I think it was a personal failure but I think, in many ways, the choices I made, some of them stuck and those ones, not all of them, but several of them were successful.

RITHOLTZ: Sometimes, due diligence just doesn’t identify every last cockroach that might — that might come out.

CASSIDY: Absolutely. Absolutely, true. You can’t — you can’t just research away all the inherent risks in the situation. You just make the best choice you can and then you need to have confidence and you’re building to respond.

RITHOLTZ: So I have dozes more questions about the book but I — I want to get to some other stuff. Let me ask one last question. I really like the title To Succeed, Forget Success. Tell us a little bit about that.

CASSIDY: Sure. Well, what I always say to people was when we make a big choice, particularly a big career choice, most big choices unfold to some of the meaningful reward and call it three to five years as far as to think about a work ambition that you could just — that it’s big enough to be exciting, yet so small that you can achieve it in six months, right? It almost doesn’t happen.

RITHOLTZ: So, let’s presume you make a big choice and you’re like, hey, I want to ascend to the level, I want to be a CEO in the next three to five years or I want to — at my current company or I want to be the head of this division, whatever it might be. At the end of the day, we make a big choice and we’re not done, right? Like once we’ve made a big choice, we’re like, yes, now I need to execute my way to that reward. But I didn’t just choose it, now I need execute my way to that reward.

And so, the process of execution, every day, we’re making littler choices to find success. We could say, like, OK, now we need to build the revenues of this — of this division. My God, we need to restructure, my God, we need to find new ways to grow. And so on your way to your larger ambition, every day, you’re making choices and producing outcasts, in this — and you’re just doing that cyclically.

So between you and that big reward is a dozen, 10, 100 more choices and every time you make a choice, you’re trying to produce a success, a learning, but some kind of outcome. So let’s say that, you don’t achieve that ultimate success, you don’t get the promotion, but along the way, you build a great division, you double the revenues, you launch new services, I call all of those outcomes, by the way, you built a team that gave you a high satisfaction rating (inaudible) 1:01:07.6, all of those outcomes are so positive. They’re still what I call your career capital.

And in that process of just continuing to pursue results and impact, you’ve not only accumulated your capital, you’ve likely become more agile and more confident. So, aren’t those all things that are going to contribute to our future success whether or not you’ve got the reward you want? They are. But we often only focus on the end goal. When really, I think what we should be focusing on is creating impact.

Every time we create impact, we create an indelible results or outcome that is the result of our own efforts in learning and agility. And that’s really like the reward for risk taking because I can’t tell you if you’re going to get the original reward. I can’t tell you if your going to get the original success you imagined or something different. But I can tell you this, if you pursue impact in every choice, that between you and that big reward, you’re going to create a lot of outcomes and those outcomes will become the basis for your reputation, your confidence, your skills, and any future success you apply. That is the reward for risk taking and that’s why I say they’ll focus on success, focus on impact.

RITHOLTZ: Very interesting. Let’s talk a little bit starting with your role as president of StubHub, what was that like? Did you have any surprising challenges you had to deal with in that role?

CASSIDY: I feel like that’s a weeding question.

RITHOLTZ: Just a touch.

CASSIDY: Well, I will tell you about — just a touch. But certainly, I’m happy to share. So, I ran StubHub from 2018 to 2020, in that time, there’s a lot of — a lot of surprise. Some, I could have anticipated and some I couldn’t. First of all, just a phenomenal and fun experience. If you’ve ever been in a business of live experiences and giving that gift to people of live, there’s just really nothing like it, so and I’m also happen to be a big sports and entertainment fan. So that doesn’t hurt.

But when I think about the things that were surprises, number one, StubHub, if you know the history was bought by eBay over 10 years ago and so it was an eBay subsidiary and I could have anticipated that eBay would continue to face shareholder pressure because it wasn’t growing at the same rate as Amazon and it’s margins were declining. And in fact, that shareholder pressure came to pass and activist Elliot, two activists joined the board, Starboard and Elliott in 2020, yes, in — no, no in ’19, my goodness. In January of 2019 and put pressure on the CEO, the then CEO, to sell StubHub as opposed to hold it.

So, midway, I was only year into my tenure when an activist joined eBay board and quickly became apparent that we were going to end up selling the company and I was going to be leading a sale process which is not necessarily what I personally wanted.


CASSIDY: But so that I could have anticipated in the sense that eBay had an activist once before and certainly when I took the StubHub job, it did occur to me that would be one potential risk that eBay itself, my parent company, would face pressure.

I expected more sort of earnings pressure, pressure that deliver our numbers every quarter, there was an outside possibility of an activist but that came to pass and that led to the sale of the company, the StubHub sale. The other unexpected was COVID and ironically, StubHub sold for a record sum, $4 billion. We led a profit — led with successful transaction that closed on February 13th, 2020. And I thought, as much as I was personally disappointed, I recognized it is a very successful business outcome and I was going to go have to find a new job, because very rarely, the acquired company gets to have a CEO run the combined company and I certainly was not getting matched. The original founder of StubHub bought back the company and he wanted to let me come run his company.

RITHOLTZ: There’s a thing with you and founders coming back to run companies. That’s …

CASSIDY: Well, keep in mind, I’ve also been a founder of three …

RITHOLTZ: Right. Right. Right.

CASSIDY: … so I do understand that founder-CEO dynamic and as I said, I mean, founders have an affinity for their companies that is really hard to — you can — I don’t know. It’s just hard to put any price tag or any …

RITHOLTZ: Sure. It’s one part ego, one part their baby. I get that.

CASSIDY: Yes. You got it. So and by the way, and in this case, look, completely professional. Like you have a founder who’s been out of the company for 20 years and has nothing to do with me — or 15 years.


CASSIDY: He had started the competitive ticketing company and now he want to come back, and by the way, he had his portion out of the company. So, if there was an ego involved here, it’s that the original founders pushed him out of the company in 20 — 2005. And so, yeah, there’s a lot involved in one that being able to come back and buy the company that you were once pushed out of. So, anyway I have nothing to do with that dynamic. I just want to be clear.

RITHOLTZ: And let’s put some numbers on this because, really, so you oversee the spin out, the sale of StubHub to a third party and to put some numbers, eBay buys StubHub for like $300 million in ’07. It’s barely a decade later, it’s now late 2019 and you managed to sell StubHub for over $4 billion to Viagogo which I think was smaller than StubHub at the time.

RITHOLTZ: My goodness, yes.

RITHOLTZ: And P.S., this is four months before the world is going to shut down, thanks to COVID. That turned out to be a spectacularly timed sale.

CASSIDY: Yes, I know. People give us a lot of credit in hindsight for that sale period and I think in — and I — and for eBay, it’s just a tremendous outcome because to your point, we announced the sale in the Fall of ’19 and the transaction closed like money in the bank for eBay on February 13th 2020.

RITHOLTZ: Wow. That’s unbelievable.

CASSIDY: Yes. I know. People say unbelievable timing. One thing to note is everybody who was bidding to buy us, in the strategic category was smaller than StubHub because we were the largest player in C2C ticketing, right? Ticketmaster is the other big player and …


CASSIDY: … aspect, not the same category.


CASSIDY: So ironically, all of the people bidding to buy us were people that, honestly, I would have wanted to buy. But they were all smaller than us but with big checks and often, PE dollars behind them. So, look, successful outcome for StubHub and then I think I’m going to sail off to sunset after a reasonable but short transition period and I do not expect to still be in the seat on March 13, well, I think I’ll be there but it will be part of my transition.


CASSIDY: And on March 13th, the COVID hits the U.S., sports and entertainment industry in a massive way. At the beginning of the week, we are forecasting that we need to to start to plan for closures and I remember saying to our finance team, we’re forecast to be 50 percent down. Maybe we need to have a 25 percent down. Maybe we should need to have a 50 percent case, you know? Just as we’re starting to think about how to …

RITHOLTZ: But not 100 percent case. Nobody was thinking of that.

CASSIDY: But not 100 percent case. No way. And by the end of the week, every sports league has suspended its season, like literally something like 2,000 events canceled in like a week span. I mean, when I say you go from sort of, having a record sales to like an existential crisis, that was us. We were — because we were no longer owned by eBay, we didn’t have eBay’s balance sheet, we were owned by another private company who itself (ph) to manage its cash, because guess what? It’s in ticketing too, right? So it’s being affected internationally, we’re being affected internationally and more important in the U.S. which is the majority of our business.

And so, we went from record sales to cash crunch and it was on my watch and so you can imagine I’m, like, fee responsibility for our business, I feel responsibility for our employees, I feel responsibility that we do not go bankrupt. And we rapidly restructured the company over 60 days, I would say to people if you want to know what that period was like, just look at my Twitter feed. The amount of hatred I got from people.

I mean, I understand it. Customers was very upset. We had to change policies on refund.

RITHOLTZ: On the fly. Yeah.

CASSIDY: Because I didn’t have the money — on the fly. I didn’t have hundreds of millions of dollars to give everybody their money back. The b est I could do would give people credit, like, literally, like I’m trying to choose between the company not going under …

RITHOLTZ: Right. In which case, you’ll get nothing. You’ll get …

CASSIDY: Yes, exactly. Literally which was, yes, how do you explain that to people, I did my best, I wrote a transparent note to our customers, I got tons of hatred, and it’s fine, like people were very frustrated. Do you remember the levels of everyone’s frustration, and people’s money. So, anyway, very intense but I’m very proud of the team. We restructured in a 60-day span and only once we finished the restructuring that I depart because I knew that StubHub could survive for an indefinite period until live events started to come back.

And so, it turns out that that indefinite period has been over a year. Obviously, I can’t share any confidential numbers but …

RITHOLTZ: Come one. Just …

CASSIDY: I’m proud of the fact that the company — no, no. I’m proud of the fact that the company survived, right? And …

RITHOLTZ: Yes. I mean, it looked dire for everybody. Anybody in the — in the live entertainment business, there was a genuine question mark, hey, if you’re going to close for six months or a year and have zero revenue, will you be able to survive? It was nice of — you could have easily said, hey, my job was to sell the company, I’m out of here. The fact that you start — you stuck around, help them restructure and put them on better footing, not everybody would have taken that choice. I think a few people would have said, hey, my job was to sell and it’s sold and we’re out of here.

CASSIDY: Well, I don’t know. Most leaders I know would know that that’s really not a choice, I mean, once you’re there, you’re there but I appreciate you saying it. Mostly, as I said, I’m super proud of the team because this is what I will say about risk, right? Risks come upon us that we never can anticipate versus ones that we can and in those moments, you see people’s agility and let me tell you, the StubHub team, like that is a team of people who shared my values and I was very proud to be leading a team that really made hard choices in a rapid period, including choices that affected each of them, think about that.


CASSIDY: Like people making choices about their own jobs, to try and make sure StubHub survived and like as a leader, like a very painful period but also one that’s rewarding to be with that group of people.

RITHOLTZ: So let’s talk about something else that reflects your values. Tell us a little bit about the board list, what it is and how it seems to be helping women advance their careers?

CASSIDY: Sure. Well, if you recall, I wrote that open letter Tech Women Choose Possibility and you said how was the reception, it’s very positive and people kept saying to me, like, what are you going do next? And of course, I thought I was just writing a letter, right? I was like, well, I didn’t just do it? I put out this opinion and …


CASSIDY: But it became clear to me that maybe there was something more to be done and I had been kicking around the idea, actually, with a number of VCs of them starting to put more women on tech boards. They would come to me and say, like, Sukhinder, what should we do about women in tech? And they’d have all these solutions of putting girls in STEM and to which I’d respond, I’m like, you can do that but that would take generations. You realized that they’ve been plenty of amazing women leaders in the Valley. I know them. I see them every day. Like, why don’t you just put them on your boards because you have all these early stage companies that should really benefit from this experience and ironically, at that point, they’re were like, like, yes, you’re right.

But they didn’t do anything about it. So when I started the board list, I basically crowd sourced, 600 names from 30 executives and entrepreneurs in the Valley and I said, would you give me the names of women you think should serve on board, so I’m going to put them on a website and then people can come and look for great women leaders for their boards and they can no longer say where are all the great women who can’t find any.

So we launched the free service called theBoardlist. It’s not a nonprofit but it is a mission-driven kind of — the mission driven startup. I started it as my side hustle in 2015. And today, the board list is 20,000 members, over 10,000 women and diverse leaders that you could go to the site today and look for for your board. You can also recommend people to the Boredlist. And so, it’s a marketplace for talent, for diverse talent.

And today, it serves not just women but people of color. And about a year ago, we raised our first institutional rounds, so I bootstrapped it for four years. Have I used it? It was working which it is, quite well. And it’s needed more than ever. So, theBoardlist is my own startup baby as a founder. But I’m not the full-time CEO. I haven’t …

RITHOLTZ: What’s the …

CASSIDY: … CEO in place.

RITHOLTZ: What’s the track record of theBoardList and actually getting women and people of color placed on the boards of startups?

CASSIDY: The track record is quite good. Now, I would characterize the track record two ways. Remember, we’re not a search group, we’re a discovery platform which means our core metric is like how many people come to theBoardList and search and then ultimately find a board member, whether it’s through us or whether we were just part of their journey.

And to date, we’ve helped over 2,000 women, 2,000 companies from early stage to public have come to theBoardList searching for board members. And as I said, the way I think about theBoardList is sometimes we’re the accelerator of the journey, sometimes, you find the exact person you want on our platform. We are — we consider our role to be a source of talent ant to make sure that board get successfully filled. So, yes. And the companies run from Series A all the way to public.


CASSIDY: Public global companies. I think a few years ago, when an activist put up a united slate for the board, he used theBoardList entirely to put up an ultimate slate for the board. And we didn’t even know. He just gave us credit afterwards. He’s like I used theBoardList. So, lots of …

RITHOLTZ: That’s great. How optimistic are you that technology is at least starting to head in the right direction when it comes to both inclusion and diversity?

CASSIDY: Well, first of all, I think there are two or three different ways to answer that question. Number one, there are lots of platforms now that try and solve bias and discrimination and everything from the hiring process to sourcing diverse talents. We’re pretty unique and that we kind of — are focused on the boardroom. But to sort of takeaway bias and discrimination from the hiring process — hiring process, by the way, there’s a whole other set of companies, I mean, investors and several that do things like help you confidentially report issues of the company, in a productive way before it ends — it ever ends up in the press and give companies the chance to arbitrate and to solve your problems, right? As an employee.

So, I think that we’re seeing all sorts of platforms that run from bias and discrimination to antiharassment to proactive consultation between companies and their employees to find solution. So, I’d say that is a positive to see that much technology kind of solutioning, try and tackle this problem in equality. That’s great.

Number two, and I think this is important, people often say, like if you want to be, if you need to see it, the number on absolute levels of women who are founding companies compared to any prior period in my lifetime is sort of up until the rise. People may see that percentages are still small and that’s true but women are getting more venture capital, there’s more pressure, obviously, not just put women on boards but to provide funding sources for women and diverse people of color to start companies and look at the number of female unicorns that exist — female-founded unicorns that exist today.

I was lucky enough to fund one of the first, Katrina Lake of Stitch Fix, I was her early investor, and she worked with me at Polyvore. But since then, Whitney at Bumble, you have Rachel Carlson at Guild, you have the founder of Everlywell. Everywhere you look, there are women starting not just great companies but very valuable companies, (inaudible) is a unicorn several times over, I’m sure. And so, there’s lots of examples of women who are building really valuable companies. Canva, Canva just got funded at 40 billion. It’s got an Australian female founder.

So, I love seeing kind of these examples because I think it really, A, it inspires a whole generation of other diverse leaders who feel like they can do it, but more importantly, for all of those VC dollars that had, I would just say, unconscious bias going out in like underfunded companies, there will be FOMO about the companies they missed. Maybe they need to look at their own funding practices and figure out like why they missed some of these great deals and often it comes back to unconscious biased when these women and diverse leaders are early on looking for money.

RITHOLTZ: So let’s talk a little bit about you mentioned venture capital, I work in finance where there’s clearly a diversity issue with both women and people of color, it’s very much been an old boy’s network for many, many decades. Lots of signs that it’s changing. Venture capital is actually worse than traditional Wall Street. Tell us about what has to happen for that to change and are you seeing signs that they too are moving in the right direction?

CASSIDY: Well, I think there are two types of pressure that these firms are under. First, it’s from their LPs. So the first thing that needs to change and is changing is LP. The people who provide venture, money, the venture capitalist, demanding to see stuff on the rate of which they fund, people of color, and women, like, i.e., how equality driven is their own funding profile. LPs have the ability to do that (ph).

And number two, what does the profile look as the venture capital serve itself? Like where there female partners? What’s their own pipeline for development because we know that when you’re diverse, you’d fund more diversely as well, right, i.e., when you have more women as partners, more women get funded.

So, I think LP pressure is starting and it needs to continue and LPs, I think need transparency on how your dollars are distributed and you need to ask for that in terms of pipeline versus the (inaudible) it closed. And then number two, pressure to keep these VC firms getting more diverse.

The second thing and it’s I — what I identified is like the inflicted pressure of performance as we start to see more kind of companies that don’t look like the average Valley company and I don’t just mean it’s a woman or person of color, it could be a company that started in Canada. It could be a company that started in Kansas, it could be a company that started in India. Like, that doesn’t fit the normal pattern. Dollars flow to where there’s money.

And so, I think the other type of pressure is actually just performance pressure. As you see companies that don’t come from a traditional backgrounds and founders either that perform, there’s nothing like that kind of pressure which is like, wow, what I’m missing out on that I need to be a part of. So, I think both kinds of pressure need to happen. Performance pressure as well as LP pressure.

RITHOLTZ: So, I know I only have you for a few minutes. Let’s jump to our favorite questions that we ask all of our guests starting with tell us what you’ve been streaming these days, give us your favorite Netflix or Amazon Prime or podcast, whatever’s keeping you entertained during the pandemic.

CASSIDY: Sure, well I probably — there’s three that are at the top of my list these days. First of all is “Ted Lasso.” I know — but my family loves …

RITHOLTZ: So good.

CASSIDY: … loving “Ted Lasso.” Such a feel-good, funny, funny show. So well done. Season 2, not so good as Season 1 but I will just say we’re still “Ted Lasso” diehards. On Amazon, a girlfriend of mine recommended “McMafia,” which is actually a pretty interesting — and for those of you who like, I would say, a finance — sort of financial services and the mob, it’s a fictional series on a British-Russian financier who gets involved with the wrong folks. That’s a really niche one and an interesting one. It’s been a great series to watch. “Succession,” I’m waiting for. Season 2, and we all watch “Succession.”

And then I would say on the podcast side, right now, actually, I am listening to few separate podcasts about Elizabeth Holmes trials, once “The Dropout” from ABC and the other one is “Bad Blood” from John Carreyrou, who as you know, is the original kind of journalist on this story. So, I like listening to smart people, just keeping abreast on the trial.

RITHOLTZ: Really interesting stuff. Tell us about some of your mentors who helped shaped your career?

CASSIDY: Well, first of all, my dad. I always talk about the fact that he was a doctor but he’s also an entrepreneur and he really loved working for himself and I think he made the idea of entrepreneurship so accessible for me. Remember, he’s also the guy who told me to take that train trip down to New York that led to the job with Merrill Lynch. Like, if there was ever a champion of possibilities, even small ones, all the time, it was my father. So, he is my pre-imminent mentor, for sure.

And then I think the other group I’d point to is I’ve been lucky to have a lot of kind of great people (inaudible), they often are my best mentors because they know me well and I know them well. All those tribe (ph) at Junglee. We talked about those four Indian entrepreneurs who started that company that I joined. I mean, my God, they became an angel investors in Yodlee, my next company. They introduced me that opportunity.

One of them, Ram Shiriram was the first investor in Google. So, when I made the decision to go to Google and they called me, it’s because Ram pushed both of us. He pushed them to call me and need to consider it.

And when situation went awry at Polyvore, the number one I person I called was the guy named Venky Harinarayan, one of those Junglee founders and the one I was closest to to continue to know me and invest in all the companies I founded and I just said, what do I do here? And he was the one who sort of gave me the, like, looked me straight in the eye, are these people your tribe? Do they have your values in life? And told me that get the hell out.

So, I really consider Venky probably the closest among that group. But all four had been very instrumental in my career.

RITHOLTZ: Let’s talk a little bit about books. What are some of your favorites and what are you reading right now?

CASSIDY: Well, one of my favorites, I’m like a very kind of geeky business person sometimes. I don’t like to read all business books, but there’s some I really love. One of my favorites is McKinse’s “Growth Beyond the Hockey Stick.” So if you’re a leader, a CEO, whose always — you’re ever grappling with how to get your company to grow faster, and obviously, at StubHub, I was trying to accelerate growth, and just paradigm to what works, it’s like the new Good To Great. I always loved Jim Collin’s Good to Great but great — “Growth Beyond the Hockey Stick” is McKinsey’s analysis of the — of what makes top-performing companies over a 30-year period. And it’s just got lots of kind of anecdotes I love.

So, that’s my favorite business one that I always recommend. And then right now, I’m reading “Atomic Habits.” “Atomic Habits” has long been on the bestseller list. And I wanted to know why so I’m in the midst of reading it and so far, it lives up to its billing as just being refreshing, simple, surprisingly intuitive, yet, we don’t do it enough.

RITHOLTZ: Quite interesting. What sort of advice would you give to a recent college grad who was interested in the career in either entrepreneurship, technology, venture capital, what would you tell someone like that?

CASSIDY: I would say, well, on the entrepreneurship and technology side, I would say get proximate. And today, luckily, for us, getting proximate doesn’t mean you can move to Silicon Valley, we all live in a hybrid world. But if you’re contemplating moving to one of those areas and you don’t know what it looks like, like, literally, maybe as simple as doing a couple informational interviews with people you find on LinkedIn. It may be tapping your closed-in network and figuring out who’s doing something entrepreneurial and going to Shadow DOM (ph). It may be like finding a side hustle where during your day you’re at a large company, in the evening, you’re moonlighting.

These are all ways to get proximate to what you know and I’d say that’s far more the case for entrepreneurship and technology because there are so many sort of gig economy hustles that you do to learn before you ever make a bigger move.

Venture capitalism, much more kind of traditional path, I would say, like, you can get there from technology, but then they want to see that you’ve accomplished something inside of technology companies, so that’s possible. The other path is, obviously, a more traditional finance path, through, like, business school and classic financial trading or consultant training.

RITHOLTZ: And our final question, what do you know about the world of, gee, I could say finance, entrepreneurship, technology, venture capital today that you wish you knew 30 years or so ago when you were first getting started?

CASSIDY: What would I know today that I wish I knew then? I always say to people, like I think what I wish I knew then is that it doesn’t need to be a mighty choice to enter these areas. You can enter in a small way. And like I said, I made — I made what I would consider now a relatively small move. Yes, I quit my job, but I was like in my mid-20s and I moved to Silicon Valley. Like, I would just say, this idea that you don’t have to have the big idea to get started, the big idea can come later, just get close and start with something small.

For me, that was a move to this area rather — just like I said, it might be tapping into a side hustle or opening an FT (ph) store, like you can learn everything you need to know about these areas in small acts, not waiting for one, big perfect idea to show up and galvanize you.

RITHOLTZ: Really, really intriguing. Sukhinder, thank you for being so generous with your time. We have been speaking with Sukhinder Singh Cassidy, author of the new book which I have right here, “”Choose Possibility”: Take Risks and Thrive (Even When You Fail).”

If you enjoy this conversation, be sure and check out all our previous interviews we’ve conducted over the past seven years. There are about 382 of them. You can find those at iTunes, Spotify, wherever you feed your podcast fix.

We love your comments, feedback, and suggestions. Write to us at MIB You can sign up for my daily reading list at Check out my weekly column at Follow me on Twitter @ritholtz.

I would be remiss if I did not thank the crack team that helps us put these conversations together each week. Mohammed is my audio engineer. Atika Valbrun is our project manager, Michael Batnick is my head of research. Paris Walt (ph) is my producer. I’m Barry Ritholtz, you’ve been listening to Masters in Business on Bloomberg Radio.




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