Sukhinder Singh Cassidy on Entrepreneurship (Podcast)

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. UH. 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 Sekenderson Cassidy. This is mesters in Business with Very Renaults on Bloomberg Radio. My special guest this week is Sekenderson Cassidy. She is a technology executive and serial entrepreneur. Previously she was president

of stub Hub. Her new book is Choose Possibility, Take risks, and Thrive even when you fail. Sekenderson Cassidy, Welcome to Bloomberg. Thank you so much for having me excited to be here. So let's talk about your career, which is really so interesting it it covers everything from UH finance and investing banking to technology. UM, let's begin at the beginning. You started at Merrill Lynch in the early nineties, a great time to start in investment banking. What motivated that decision

to go into finance? Um, well, a couple of things. Number One, I'd say the most more intelligent reason was because I wanted to 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, because like, well, if they're doing it, I should be doing to. So in some ways I call I call it a copycat goal.

I'm sure there are many ways I could have gotten financial literacy, but I was bound and determined to keep pay with my rather competitive colleagues to get a job on Wall Street. So you you head to New York, you started Merrill Lynch. Any formative experiences stay with you years later? What do you most remember from that era? Well, the first is, honestly, just to struggle to get the job,

believe it or not. And uh and I say that to people because often we look back on the careers of you know, others and think 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 number of banks. Meryl didn't even come to candidate or recruit, and they offered me one of those polite informational letters that said something like, if you're ever in New York City, would be happy to give

you fifteen a fifteen minute informational interview. And I remember saying to my father, I'm like, well, what is't that? They just rejected me and he said, well, why don't you take a train ticket and head down to New York. You never know? And um, and I was at the end of my rope. I've been searching for a job for over a year, I said, as I said, determined to at this job and not successful. And I took that train ride in fifteen minutes turned into a three

hour interview, and then they accelerated me to the final process. Uh, which, if you know, for investment banks, is 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, um and I got the job. So it was a pretty sweet, pretty sweet success after

a year and a half of trying. But it was very formative for me because it really informed and you know, I guess my view of how often you have to just keep choosing in order to get to the goal. You want keep keep banging away. So so, what what did you do for Meryl 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? Well, and I think this is probably the second former of

experience I had at meryll Um. So my role with the financial analyst, anybody who maybe has studied finance know that that's really a job where you create pitch books, books with facts and details about different industries. I was in the financial services industry group I was assigned to, and you really you know, create those books or what's called managing directors who go out and pitch you know, large companies on using their services M and A services, I,

p O services, what have you. And so the average analysts is spending you know, days and nights softened through the night, toiling to create these perfect pitch books. So I certainly had that experience, but I ended up working for a pretty eclectic young managing director called Henry Michaels. And Henry was you know, as detail orange as they could get, type smoking, you know, definitely capable of driving

others crazy. But he took a really deep and early interest in just teaching me about, believe it or not, the savings and loan industry. And I think he found me to be maybe uh rap students. And I freely admit after taking a year to get that job, I was just bound and determined to be successful um at it. So I was you know, very inquisitive, very curious, and as result, Henry kept staffing me and putting me, I

would say, on jobs with increasing responsibility. And so pretty early on I was going to meetings with CEO, so he would he would set up and let me attend. Of course I was carrying the pitch books, but that didn't really matter to me. The exposure did um and as a result I ended up working on an I

p O early the Long Islands, I think 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 something that early, and I got to go, you know, work on banking in the you know, in the European banking industry, and had just an amazing experience. So I gave Henry Michael's a lot of credit. Henry definitely skipped a bunch of players to teach me, and I, as I said, maybe my best contribution, as I was

a wrapped student. But the result was, you know, an experience where I got a lot of exposure so very quickly to kind of senior executives. Really really interesting. I have a specific recollection of the Long Island Savings Bank going I p O in the early I want to say, mid nineties, and eventually I was the analyst, and eventually it got acquired, and then that company got acquired and at 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 ben Well, I so ironically I made my way to the West Coast, not from the East Coast, but via London, because if you recall, Meryll sent me

to London. And when I was in London, I had spent maybe you know, two years with the bank, and the classic length of these programs is two years and then they expect you actually to move on, you know. So analyst programs are two years of 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. That I wanted to work for one company, and so I was able to secure a role with the cfo UM at a company called British Guy Broadcasting, one of the biggest satellite broadcasters in the world. Um, he recalled, this is part of news corps, kind of empire and uh. And luckily for me, I parlayed my job in finance to a job in finance inside of the company at at beast I B and then I was promoted to working UM for the CEO and the CEO UH there. So actually

it's probably more dramatic story. I was promoted. I was working first on the top floor for the you know, one of the two top bosses. And I've been there. I've been at beast IB for only a year. And I walked into my boss's office and I told him I quit. And he was shocked, and I said, I said, you know, I said, two things are true, David. Number one, I have this epic promotion. You know, I you know, I sit down the hallway from you. I get I get lunch every day. I'm on the you know, I'm

on the executive floor. I'm like, but you don't really use me. And it was true. My boss was very used to sort of operating like the load wolf is that UM as a sort of effectively president a 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, was at 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 you know, Ontario, Canada, where it gets pretty dark cold. You know, once you visit California, you sort of realized that it's possible to live in good weather all year long. Um. But the other but, the other truth was I wanted to be an entrepreneur. My father, you know, loved writting, Zoe love business. I had no idea how. I loved the Bay Area for the weather, and I sensed that it was you know,

that there were a lot of people starting companies. So I put my job. I um went skiing for three months in Whistler, um, and I moved to the I moved to California and bought a car, drove up the coast from l A to San Francisco. Luckily that that, you know, those friends of mine, their parents put me up at their very nice house and California until I found a job and I started over, how did you end up at? If you can't tell already? I was assarily impatient, uh, young woman, because you know I moved

to Farembound in that first six years of my career. I, as I said, I you know, I was looking for a job in the valley. I faund when and forlting the job I found, who was not nearly as positive and experience as I had hoped. Um as you as we just talked about, I actually had a really good experience at Meryll. I even had a good experience at Peach Guy b if you look at the fact that, you know, I got the ability, I was promoted and

I got to this. You know, I found a startup in Silicon Valley that was an interactive television which was you know, at least somewhat related to what I'd just done it, you know, a sky was in the TV industry. And then second day on the job, my boss told me I was scared the secretaries, and I was like, what what does that mean? What do you mean? What

do you mean? I'm like, I've just come from two industries that are highly male dominated, nobody ever told me I was scary and um, and thus began a rapid decline in our relationship. I felt like I wasn't getting

a lot of response ability. 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, Wow, if this is what it means to be in Silicon Valley, its supposed to be this meritocracy, you know, I'm supposed to be, you know, having the time of my life.

Maybe I'm not meant for this place. Luckily for me, UM, I started to think about getting another job, and a recruiter called and pitched this idea of you know, a company started by four Stanford PhDs in um I had this very cool technology. I took the interview. I didn't really understand fully the technology, but I loved them. They were smart, they were candorous UM, and so I switched,

and lucky, luckily for me, I made that switch. You know, um Jungly ended up building a whole engine for shopping for compared and prices across the Internet, and Amazon bought the company six months later, and that was really the start of my career in Silicon Valley just a great experience, but following a very poor one. Huh really, well, everything

can all be one in roses. Sometimes they're gonna miss tell us a little bit about what it was like working for Amazon and how closely did you work with Bezos back then, Well, believe it or not, that's then it was a pretty small company. There was about twelve hundred people. We were public, so everybody got exposure to Jeff, myself included. So what are some of those earlier those

early times like at Amazon. Well, first of all, as I said, everybody was you know, it was a small most company that you could fit most of Amazon in one or two buildings. That we made a couple of moves where you know, we were all in the same building. Number two. We all had to work in the warehouse, including you know, like the very top executives at Amazon, Jeff and Rick Dal's out. Like everybody had ships, had

shifts over Christmas, you had no day job. You literally all had shifts in the warehouse, which was a pretty amazing cultural you know cultural feat and by the way, that included like overnight ships. Um, you were picking and packing books, music, you know, books, uds, and videos. That's true, Um, Jeff had bought the company because he believed it or not in still for still had his vision of a day where Amazon should show you every product on the internet,

whether or not they had it in stock. So this early vision of marketplace. But Amazon at the time was just building out its own verticals, so what was it 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 had 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 um meat look into how sort of visionary he was even early on. Of course, you know, not nearly as sort of um daunting a presence as he might be now, just like, you know, very accessible, pretty goofy actually pretty quickly sense of humor. And I got to work with them specifically because I was one of the people selling merchants, you know, like people like Macy's and others on the idea of

putting their products on Amazon's website. So I got to pitch a few different retailers with Jeff, which was really neat. So I know this is going to be a very fanboy question, but I have to ask because there's a broader components about understanding or not the future. In the late nineties, in the early two thousand's, did you have any indication that Amazon would become the juggernaut that it become came or was thouse 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? 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. Oh, it's not just a movie studio. It owned the grocer. Oh it's not just the grocer, but it happens to own the largest infrastructure backbones for the way it's called

you know, Amazon Web services and other merchants. Like no way with that obvious, as I said, like literally, these were the days when we selling books, music and video and um launching new categories. And Jeff, as I said, like he was impressive, but he was also very accessible, funny, young, like he told me a few years older than I am. At best, and um, to know, I don't, I mean all the people that you think of now is it's

quite famous. Um, there was no indication, you know, as I said, now you might and I might say wow, buying a company in launch Amazon marketplace. Certainly they were early inklings that he used a vision to sell a lot of stuff and so he could say, hey, could I see this company becoming one of the larger retailers? Sure, but is defined by what Amazon is today? Um, yeah, no way to predict it quite quite fascinating that that's quite fascinating. So let's talk about your transition from Amazon,

uh to your next venture. You co founded a startup. Tell us a little bit about Yodley and what made you decide to say, well, this Amazon company is kind of fun, but let me see what I could build on my own. Well, remember we were chatting about that rather restless and impatient young woman. I don't think any of that solved when I was at Amazon. It was a great experience, by the way, And you know, remember I had never gone intending to be at Amazon. I

had gone to a startup right which got bought. And while Amazon was a great company, was up in Seattle, it was now public, and so there's me thinking, gosh, what am I going to get the chance to start my own company? And I know many people listening to this podcast will be like, really, you left Amazon to start your own company? Is that a really smart decision? Um? But in some ways, you know, Amazon to me still at the time still felt very big and um, and

I wanted to get there. So at Amazon and remember many of the founders of Jungle League, you know, have made a lot of wealth. Um, 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. Um, I've been at Amazon about

a year and I get into day. I get a call one weekend and sort of says, hey, you know, there's this professor from UCSC who's a computer science professor, and he's built this really cool technology that goes out 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 Junglie, but it has some analogies, and they're like, and they're looking for a business co founder. They have all these engineers that they need somebody to establish the business model, race the money. Um. And so I got one of those inbound calls and it was through that network of you know, angel investors who 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 suitably impressed. I was like, Wow, you just grabbed all my credit card balances and my bank balance and you know, my brokerage balance in one place and gave me this egrecated You nobody can do that. I'm just pretty revolutionary technology at the time. Um. And they offered me the opportunity of twenty nine years old to become what's called a co founder of the company and the first business executive. And I just jumped at

the chance. I love the technology, UM. I love the fact that I would be with There was five engineers at this company too, again very similar to Junglie. But now I was going to get a seat at the table as you know, as literally one of the executive team at such a young age and get to raise the money from venture capitalists, right a business plan. So uh so they were really very early stage. Yes, yes, yes,

I mean it was twelve engineers in a room. And as I said, and and I was just, you know, as effectively the first business leader to be hired at the company. And so I uh, I gave my notice at Amazon maybe a month later and moved right into Jungle Lee And we raised fifteen million dollars from venture capitalists within a month of that, and we were off

to the races. And you know, thus began kind of a six year journey to build you know what today many would consider the pioneer in really aggregating your financial information. I'm really proud of the fact that Yodally really did create a whole industry of companies that you know, we're able to access financial information using our services and our kind of technology backbone and build many of the financial

apps that you know people used today. Um so Yodally Yodally had a fifteen year run before it became public, and I was there for the verse five of those years. So let's work our way through this chronology a little bit. You end up at at Jungle which gets acquired by Amazon, and from to I'm at Amazon, and then when do you leave ninety? When do you leave amaz Oh? So you were only okay, Actually, so when their year, I mean it was year and you stayed. Um, did you

stay with Yodley until they were acquired by investment? No. I stayed with Yodley for five years. In that time, I had every job under the sun. I was predominantly responsible that we've talked about for uh for not just raising the money. We raised about a hundred million in the time I was there, in several rounds of financing, but I was I was responsible for sales and business development, selling our technology to all the banks and brokerage companies.

And so I stayed until two thousand and four. I helped us hire our CEO in two thousands, and he wasn't going anywhere, by the way. So I always say to people, I topped out at my own startups. Like literally, I'd had every job I've done, sales at Den Marketing, at don PR, I was our spokesperson, I raised money, and I in many ways, I was, you know, partnered very closely with the CEO and we had a great relationship. And in two thousand and four, I was like okay,

and now like what's my next horizon? Like I've been here five years and I've done all of these roles, but there was like, the company's not growing fast enough to give me an entirely career, you know what set of challenges. Um, And so that's I actually, for the first time, you know, I did what i'd call, you know, a more studied search, thinking I might start another company, um, but also thinking you know that I wanted to find the right idea. So I was pondering my next new

presuming I would start a company. When UM, I got the opportunity to start a new service at Google, which you know today we would call local and maps. And and let's talk a little bit about Google Maps. Uh. It's funny because it's so ubiquitous today we don't even think twice about, um, the miracle that is Google Maps. But back in the mid two thousand's, did anybody have any idea of what a massive technological breakthrough g maps? Where I remember playing with early versions of it and

just you know, had head exploding. What what was the thoughts like within Google about about Google Maps? Well, it's, um, it's a couple of things. So first of all. When I got to call Google originally called me you come to join them, and I actually said no, And I said, gosh, you guys are also quite big. Your twelve hundred people. Remember in my warped brain, you know Amazon is making twelve hundred people. So is Google. And I was like,

I'm going to start another company. I know. It's so funny and and um and Google called me back seven months later. They said, you said you wanted to start up opportunity. We have it. We have something Greenfield called maps and we said They said, Yahoo has a product called Yahoo Maps, a well has something called map Quest. Google has no products to help you search locally or find navigate locally, i e. Both find goods and services locally or businesses and navigate right because Google Local is

like search for business Google maps. Who search for a place is back today. They're very merged. Nobody thinks of them as different. Um and uh, and I studied. I studied the landscape. I went and interviewed Google, and within two weeks I said yes to the job because I was like, holy smokes. The yellow pages industry, which at the time was you know, those thick yellow books that everybody got to find places was a twenty three billion

dollar industry in annual advertising. And I was like, surely if Yahoo has some product in a well has a product, Google should have a product. And look at all the ad dollars available in this category and look at all the usage. That's pretty antiquated. Um So I said yes very quickly. Um and I have to point out that Yellow Books at billion dollars revenue. The obvious answer is

but not for long. But not for long. I mean, look, look digital really white staff business over you know, by the way, there were still Yellow Pages around the country and that around the globe, but nobody would think of that as a juggernaut industry. Um So, yeah, you know online really you know, really changed and transformed the face of local advertising fundamentally. But um, I would say, I knew it would be big. I mean that's what led me to move in that direction. I'd say, what was

unknown about Google service? And you appreciate this even by me. You know, I was paired with a product manager. I was the business person, meaning I had to go license to 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, Brett Taylor, um ironically now the president of Sales Force. He was my He was my product manager, and we had ten engineers and the you know, twelve of us built that product effectively. I

did the business deals. He you know, he guided the engineers. So on the one hand, the product could have been pretty straightforward like Yahoo A O L. 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, oh, the name of the road is like on the road, and visually it's just like a prettier experience, and it's you know, 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 Sergey and Larry. Early on, a guy named John Hanky showed Google, once we'd launched local and maps his cool technology that had satellite imagery called keyhole, and Larry and Sergay 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 person for seeing that that was really product vision and in that case led by the founders, I mean Brett, Brett liked the product too, but from what I recall, Larry and Sergay were really gung ho on buying the company and overlaying satellite technology on top of maps. And that's an example of sord 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 you know, it turns out very useful feature to have Google Earth on top of Google Maps, but like no commercial application, just super cool at least not then eventually yes, but not. But like when we laid over overlaid it, I was like, Okay, I guess if this is cool, I'm going to make if anybody, But what a what a great kind of product feature and

like kind of great vision. So um, those are some of the fun or experiences about building maps and you know, and then local as well. But 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 punch 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 to people who are much much younger than me, and they're like, huh, I didn't know I could do that with Google Maps. It's almost like, uh, you know, it's almost like a a a surprise feature when really it's a more part of of Google Maps. It's not an easter egg. Yeah. Absolutely, And to be honest, when we started the product, local

and maps were different things. You could type into the search box like you know, movie theater near me, and you would get literally a listing of results. Today, of course I'll show you the results on a Google Map as the preferred way for you to see those results. Like, yes, you can get a listing if you want, but every Google Search result has the 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. What's done? So what led you to leave Google to start joyous? Well, remember, I have one more big chapter at Google that's probably um that's ironically even bigger than my local and map chapter. Because I'm at Google. We've launched local maps. And what's happening is people are saying

to me. We'll saying to my boss, who is the cheap business officer of Google, Um, hey, we have all these other products that need us to license data, like we want to have um we want to have a library product. We want to have a scholar product, we want to have a shopping product. By the way, we wanted a video product. So I end up building a team that is all the licensing for all this other data types of data that we want to put online.

And so I'm running that team. You know, my team has gone from I've gone from being an individual contributed on running about thirty afford the business development executives and about in the span of a year. This is how fast Google was growing. And then my boss turns to me and said, Hey, Larry's or days 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, Um and build that business. So so, to be honest, I spent the next five years of my time of Google US there for six

years actually running our international business. I end up giving Local one, giving up Local one Maps and all those other teams, and I move over and run that business for five years and um, and that was the majority of my time at Google actually was which building our international business, which you know became renamed Asia Pacific in

Latin America. We entered China, we had at Brazil, we entered India, we entered I don't know eighteen different countries directly in a hundred nine indirectly, um until I ran that business until two thousand nine. And that was probably um my what I'm more known for its Google huh really really interesting. And then the startup it starts again and so oh nine, you head over to tell us about the genesis of joyous, Yes, so um, oh nine, I am, you know, three months pregnant with my third child.

I've had, you, got married, had a family. At Google. Um, I met 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. You know. It was obviou obviously Google. You know those two guys interest in leaving they don't even and it was Eric and Eric Schmidt as well. But it's also clear that any successor at Google would be from product or engineering. And so you know, and by the way, I mean pretty mighty company.

Sheryl Sandberg's might peer to an Armstrong who went on to read a well Nikesh Aurora who today runs power walls and 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 your point, I had to start a bitch again. I was thirty nine years old, and I thought, if I'm ever going to build another company, um, you know, this might be

my time. I'm you know, 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 ambitions and I went to a venture capital firm for nine months. I basically parked myself there. I had my third child. Um, I said to them, I want to study everything in

e commerce. Remember I started my careerit e commerce, write at Jungle and at Amazon, and it was like start to two thousand nine, and I believe that e commerce was going to go through another revolution in which people were shopping less for things they needed like you're you know, were things based on convenience and more based on want. So this is the era where fashion, you know, decre um experiences all start to rise as sort of marketplaces

on the Internet, and they're all just getting launched. By the way he looked, you know, back ten years, it was not obvious that Airbnb would be a big company. It was 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. So I study

sort of all the things in the landscape. And one company had been pursuing me very actively at something called Polyvore, which was sort of like an early version of pinterest um subsequently about by Yahoo several years later for three hundred million. And I actually, before I start my own company, I go to them first as a CEO who's replacing a founder. UM, so I go there for I go, I study 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, the founder and I but it heads. I wouldn't even say we, but it had heads overtly. He just wanted to run the company again. I came in as the 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 e commerce. This is what I mean when people

are like re entered e commerce. Whop. I was like, wow, he started your own next stup and I was like no, no, First I was the CEO of a startup where I battled with the founder and he wanted the company back and I gave up my like two thousand person multibillion dollar job at Google to stay all of the ten person startup. Like, let's not miss that part of the story, because it's a pretty you know, illustrative of the way. To your point, it all rolls, it's never all glorious.

We do talk. By the way, we're going to circle back to that because it's relevant with in the book of absolutely 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 a CEO and then the founder comes back, that exit was probably made a little less painful by whatever the the contract gave

you on the way at the door. Yeah, absolutely, by the way, I heavily negotiated said after constancy, you're right, I was very financially protected, but my ego, and we'll talk about that later, was just incredibly bruised. And I mean I was very humiliated, as you can imagine, have lost that battle. And we'll come back to that. But to your point, look, I start my next company, not wanting to because I just had this very brutal startup experience. Right.

And remember I'm still pretty relevant because I've been at Google, you know, I still have the sheet of Google and everythingson before at in Amazon. So I'm getting large company calls. In fact, I was at the final rounds of uh, the CEO job for you know, a travel brand you would well recognize. And at the same time, I had this idea for a video shopping startup because I had seen that at Google. You know, YouTube was starting and having a young women who were like hawking products. They

were called haulers in the day. They'd go shopping and show all their wares on their YouTube videos. YouTube wasn't shoppable, but I saw that trend without the Google. And then of course I've been a probably where the shopping startup in fashion and lifestyle, and all the brands wanted to work with us. They all wanted to somehow showcase their wears online and they want to do it with like great,

great content. So, um, while I'm interviewing to these larger company CEO roles, I have an idea to like effectively create a new version of TVC you know which again many people are doing video ship commerce today, think two thousand and ten, like eleven years ago, not that many people are thinking about this. Um. 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 know you called Joyous. UM. Yeah, that was my video shopping startup. And I ran it for six years and we sort of built literally studios, had brands, you know, give us products. We had curators who told the story. We we created a patented video player that had shot a shopping cart in the video player. UM. 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. UM. And that was an incredible experience. I mean again sort of like the risk of you know, trying to be an innovator. Uh, never something I would regret doing. UM. Obviously grinding hard, ultimately too early for the market, but nonetheless, like I sort of just embraced the idea of the e commerce was going to go through another revolution, and I sent all my time working on the video side of that equation.

When you say too early for the market. Joyous was still acquired by stack Commerce in why do you Why do you believe you were too early to that market? Well, first of all, we required for a very small sum. Like you know, nobody made anybody My venture capitalist didn't make any money. I didn't make any money. Um. But why I say we were too early? We raised you know, we raised close to fifty million dollars, which in today's world is not a lot of money. People raised that

in one round. We raised that in over six years. 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. Half the people in my office are their wardrobe is purchased via in Instagram, right. And then you have Facebook video where there's a lot of shopper blads like today's video. You know, there's really a video unit on Facebook that has a shopping card in it. You can watch video as an

ad and buy it. But when I am building this business, there is no Facebook video, there is no Instagram video, there's no snapshot, there's no a kick talk. So people aren't really used to watching video for anything other than content. Really like funny videos, short form videos on YouTube and really for quite a young audience. And like even Netflix is and it's you know, is building and growing, but it's as a long form video platform. Like we went to Netflix and 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 consumer is not used to like being on a site like you know, Instagram was just filters and products at the time and being honest 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, you know, what ends up happening is you're searching for cosumers who want that experience, and that can be very expective. We spent 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 um to keep you know, to keep growing the size of the customer base. And it was it was too expensive ultimately, So that's why we told we didn't sole self for some glorious reason. We sold because you know, a fifty million dollars in we were growing the revenues, but we could not find a path to profitability, so sold the technology and platform. 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 and automotive and go down the list of things you could buy that seems like that could have been a pretty natural fit. You can ask any startup and ask any startup ceo the past they go on to sell a company. I spent a year trying

to sell joy Is. That's the gritty nitty gritty truth. And think about my role of dex real pretty darn good right at the Amazon it is Google. I mean, I'm a known quantity by the way when you're this is one of the hard truths when you're running a money losing startup. You know, sometimes you can get people to bike, but often they think they can build it themselves. YouTube. You know, we had a conversation and they certainly thought they could build it themselves. I would say, up until today,

YouTube still doesn't have a shopping cart. Right, I was gonna you know that Calculus is always lessly frustrating, Right, that Calculus always seems to be, hey do we want to wait three years or drop eight hundred million dollars? And you know, leaprov the competition that seems to be the math that was done, and here it is. It's almost too And you still can't just purchase something on YouTube with a click the way you can on Instagram.

Yeah you cannot. Facebook is probably probably the best video shopping experience. Instagram has good shop ability, but it's adding shop ability because for a long time, Instagram, you know, was like kind of more pure. But it's adding it. Um But they all want it, right, Everybody talks about shop video, I mean everybody, and many people have enabled it.

So yeah, look, I would tell you I find it endlessly frustrating that I couldn't land the company at one of the places I think even today could use the technology. By the way, h I said QVC. If you were to look at the list of the people I talked to in the seventeen as time as 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 one in I literally could not get some of the best

platforms on the Internet to buy this pad technology. Now I alsomely sold it to another private company that's doing very well and was doing shoppable content and still is so you know, enjoyous as a brand still continues. It's just it's still painful to me because obviously I was early but right, and you know, that's one of the risks you have an entrepreneurship when you really do try

and innovate. Right, Maybe if I had started Joys five years later, it would have been an entirely different outcome. It probably would have been, but but hey, that's the way the internet roles. Huh. Quite quite fascinating. Let's jump right into a little background on Choose Possibility. You published a letter I don't know. Is that five years ago Tech Women Choose Possibility tell us about that? And is

that what led to uh into the new book? Well, Tech Women Choose Possibility was a letter and open up ed I wrote on a platform called v code, well non digital newsletter really at a time where everybody and myself included, which frustrated that the narrative on women in tech was incredibly negative. If you think about two thousands fifteen, you know many headline articles the Atlantic, the cover of many of 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 must startup entrepreneur and running joyous. And of course I have a multi faceted view of this. On the one hand, I think, hey, you know what, all things being equal, I was still food Choo, Silicon Valley. It is mostly maurocratic. It has been very good to me. I found my tribe right, I've been able to thrive.

Yet at the same time I remembered that early experience I had you recall where my boss told me I was too aggressive for the secretaries. And I now started a entrepreneur, and I hear firsthand stories from other amazing female entrepreneurs and how terrible their experience is fundraising and

you know, and and and just the biased experience. So I wrote the op ed by surveying a hundred women in tex from CEOs two entrepreneurs um asking for their opinions on being an entrepreneur and then their experience of

bias and discrimination. And in fact, what the you know, what the survey shows, which is why I write the letter, is what you'd expect, which is, you know, they you know, I think the majority had said we have directly experienced bias and discrimination, yet like eighties something percent still recommended entrepreneurship in tech and even for their daughters. They said if they didn't recommend us for their daughters, it wouldn't be because of bias, would be because their daughters maybe

don't want to entrepreneurship. And so you say, well, how can this duality exist? And the actuality is sort of what the letter says. It's basically says, hey, look, you know, by the way every day women get up and choose possibility. They choose to sort of make their next active tech and you can't be successful. So like, don't walk away from this industry, please, because so many women are being successful in increasing rate. But if you think it's all great,

it's not. And honestly, if I were in the tech industry, the call to action I was looking you know, to have happened is like, hey, you know, we think we can solve all the world's problems. We tell everybody else we can hear and silicide valley. Why are we not applying any technology solutions to the problem of gender and inclusion? Like really, like it's shocking to me that we'll talk about solving poverty and clean water and climate change, but there are no tech platforms to try and solve bias

and discrimination. And so that was what the letters that have positive that you can both have a positive experience personally yet still understand this is not what it should be and the rest of the tech industry need to take some responsibility for trying to equal equalize the playing field. So did it lead to the letter or did the book a little bit um The title is what I

mostly took from it. See, I think the notion that is a dual path, like there can be risk and reward and still danger or all those things can exist at the same time, and that's what we're always grappling with. What was the feedback to the letter when you published it. It's now at Foxy, but recode back then. What sort of response did you get? Overwhelmingly positive? Um, a lot more than I expected. To Keep in mind, you know,

we talked about risks we take in our career. Like many other people, I spent the majority of my career heads down building my own companies or building at larger companies. I really didn't try and use my voice actively on any like broad topic. So for me, it was a risk even write a letter. Right, I'm like, what will people think of me? Well, they think I like, you know, 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 in short of like for my gender. I wanted to see my capability. Um. 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 you know, 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. I mean, um, So I think it was maybe the first time I'd use my voice in any kind of way that offers maybe um a personal perspective, and found a little risky to do it. And I think I was validated and sort of trying to speak up by the response like that. And that was before places like Uber. Um, some of the engineers had had gone public about what a frat house that was inside you.

You predated that explosion that we saw elsewhere, right, Uber had its me to moment about a year later, and in fact, many companies did, and you started to see, you know, some of the very very bad behavior far beyond the microaggressions that many women talk about that um, you know, people of color and women experience, unfortunately to a far date greater degree than any of us think. So the letter predated it, but um, I think me too really expose some of the more flagrant and honestly

awful things people go through work. Sure, so let's talk a little bit about the book I don't. I don't want to overlook this. Um. I like the way you have this structured in three parts, going get Smarter, Get rewarded. Explain why you went with that structure. Sure, so, UM, obviously it's uh, it's probably obvious from this conversation that I've taken a decent amount of risk in my career. And I wrote the book because I think people have a very um, unrealistic sense of what risk and reward

looks like compared to how it really unfold. And so I structured the book in a way that really I didn't did not want it to be a memoir, but I structured in a way that goes from sort of basic lessons on risk taking, um, to sort of maybe more complex not ideas, but kind of uh, philosophies. And it really mirrors maybe the way I learned to take risk. You know, for me, it was really simple in the beginning.

And you know, we talked about those early moves. I made five or six moves in the span of seven years, right, so whether they worked out or not, I took a fair amount of risk, you know, and made a number of sequential choices. And then I think the middle is about being a smart risk taker. Nobody says, I don't say 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're asked 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 unfold over time? So organized it roughly in the order in which would happened in my lifetime, which is also the sort of order broadly speaking, which I learned these lessons, and some of the chapters really leap out with some real interesting questions that I wanted to bounce off of you, um, starting with why is the hero's journey the wrong metaphor for entrepreneurs? Well, you know, and not just to entrepreneurs, for people at

larger companies too. We have this idea, you know, when we look at the hero's journey, what we what we see and remember is just like one mighty choice the hero made that we could either lead to sort of

abject failure or glorious you know, glorious success. And by the way, we see that story just in you know, in um popular media, but even in the media that relates to, you know, the journeys of successful entrepreneurs, Like we're all watching what happens when Richard Branson, you know, goes to space, Like you know, it's just going to be ethically successful or something disastrous gonna happen, right, Like, there's all of the binary stories we see about people's

like big, singular choices, and I think and I call that the myth of a single choice in the book. The reality is that you know, most people who are taking risks, it's not one risk that led them to the reward. It is the 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, small, 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 you know, really rewards, you know, reward getting is about a system of unlocking multiple choices, and it's never just one choice. It's about be committing to the process, is continually choosing your way and your path. I like

that description. It's less cinematic but far more realistic. Another one that that jumped out that was kind of interesting and obviously, given how you've moved from New York to London to Silicon Valley, makes sense. Tell us why proximity beats planning, Well, it's interesting. I think one of the reasons people um see a risk is they like they

just don't like uncertainty. In fact, it's research that suggests that often people choose something not because they're convinced it's the best path, but because it simply reduced this uncertainty. So it certainty creates a lot of anxiety for people. So what's the anecdote 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 for the thing they don't know, and they plan from

afar right. So you can create this perfect plan of what you imagine the thing is that you want to go after, and you can add more and more detail 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 it's sort of a plan in your head with more and more detail that makes you feel you know less uncertain, but it's not getting you any closer to the 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 you know, environments or people that even roughly approximate the thing you think you want the thing you think you want, and two things happen. Number One, you learn a lot more by being proximate than planning from afar, Like did you say, hey, I want to be a chef and I'm currently a financial analyst. Like, let's say, well, how do you get yourself in circumstances

where you're in an array of chefts and restaurants? You know before you ever make a mighty lead 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 want is what you really want. Number Two, you get knowledge on how to achieve it because you're you know, you're approximate to people who've 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 know, you really get the opportunity to you know, to I would say apprentice under masters people are really good at it, and those people attract new

opportunity all the time. UM. 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. So let's talk a little bit about a less successful startup in your personal UM career polyvore, which is what preceded you joining UM. Joyous tell us about what went wrong there and the lessons that you learned. Sure well, first of all, I always say people, you can take smart risks, or try and

take smarter risks, but you don't never eliminate risk entirely. Right. You can do all the studying you want and set yourself up well and still fail. I mean that is why it's called risk after all, And certainly a poly woar I made a very studied choice. I entered the e commerce 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. Um. Yea. When I arrived at Polly War, I had a game plan that said, look, I'm taking over from a founder. You know, Silicon Valley is littered with founders CEO pairings that don't work, crumble. It's like a marriage, right, I mean, at best, your your odds of fifty percent out of marriage, and like I'd say they might be even slightly less out of founder CEO relationship because you have two people who have authority over

a company. Right. Um. On the one hand, you have, you know, a founder who has been used to running a company and obviously have control over it, including you know, financially through equity ownership, and then you have a CEO who's sort of theoretically bought into sort of be the adult.

So um So my point overall is that, uh, when you think about any start the founder CEO journey, you're like carrying somebody's with financial ownership of a company that's pretty large and moral authority with some of the theoretically has professional management skills, but also wants to set vision um. And that's what I entered to Polly bar and I think if I were to characterize in a nutshell, white

didn't work out. I think that, you know, at to the first three months, I was listening to what the founder had to say and didn't really wanna did not really want to disrupt the apple cart. I really want to listen and be a fossful partner. At month three to six, I started to sort of voice some of what I believe we should do with the company. And by the way, I said to the board, you know,

this is going to go one of two ways. Either, you know, my partner and I kind of share the same values and want this to work, or you know, there's a possibility that this person feels very threatened by you know, me voicing my own opinions. And I think the latter ended up happening. And at month six, you know, the founder basically said I want the company back. It's either to Kinder or me, and the board shows him and it was an INCREDI off we painful experience. And

so what did I learn from it? I think I learned one seminal lesson, which is, you can do all the studying you want, you know, 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 would 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 our passions.

Yet intrinsically, when we enter any new situation at work, we are, you know, inextricably 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 the boat with somebody 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 with 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 then I went that situation transpired, I went to my mentors and I said, oh, 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 you ever want to fight for a company? That's ten ten people big where quite frankly, what you're telling me about this story and

what's transpired. And by the way, I'm not going into the nity grade of how it transpired, which was thank 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? And I said, you're right, and so I actually like didn't fight for it. I was like, okay, you want to,

you can have it back. I'm out. You're right, this is not the right place for me, which was against every instinct I have. Is like somebody who wants to drive and control right just to give up. And they're like, yeah, you're right. And I look back on that situation and say, my mentors were right. 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 it feels challenging because it's an admission of failure, even though that's not what this was. Yeah, well, well, by the way I would say to people, it depends over what time frame you characterize that decision on a six month time frame or year time frame. That was a failed decision. And I call it a failure because I failed to have the impact. You know, It's different than Joyous, Right, we talked about why Joyce did or did not. We

just culmination as a video platform. But I can look back on those six years and see every innovation we achieved, see everything we've built, See the team we assembled and what they've gone on to do. See the fact that like we were the pioneer, and I can feel very proud because I know I had impact. It's probably where I had no impact. I was just six months. You know. 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. Um So I consider it a failure, but I also consider it a success. In the decision to join the commerce, you know, to leave Google and become a CEO. You know, I got to run my own company. I got to run stub Hub, like I mean, you know, I began a journey.

I got to become an e commerce investor, an e commerce board member like I have loved being in the Business e E Conference for the last ten years, and that would only have been possible because of my decision to join Pollymore however painful. So so anyway, I I think it was a personal failure, but I think in many ways, you know, the choices I made, some of them stuck, and those ones, you know, not all of them,

but several of them were successful. Hey, sometimes due diligence just doesn't identify every less cockroach that might that might come out. Absolutely absolutely true. You can't. You can't just research away all the inherent risk in the situation. You just make the best choice you can and then you need to have confidence in your ability to respond. So I have dozens more questions about the book, but 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. Sure, Well, what I always say to people is when we make a big choice, particually a big career choice, you know, most big choices unfold to sort of a meaningful reward and call it three to five years. It's hard to think about a work ambition that you couldggest that it is big enough to be exciting, yet so small that you could achieve it in six months. Right, it almost

doesn't happen. Um, So let's presume you make a big choice and you're like, hey, I want to ascend to this law. I want to be a CEO in the next three to five years, or I want to get 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, oh, yeah, now I need to execute my way to that reward. I didn't just choose that. Now

I need to execute my way to that reward. And so to the process of execution. Every day we're making littlar choices to find success. We need say like, okay, now we need to build the revenues of this you know, of this division. Oh my god, we need to restructure, Oh my god, we need to find in new ways to grow, and so on your way to your larger ambition. Every day you're making choices and producing outcomes you know

in this and you're just doing that picklically. So between you and that big reward is you know, a dozen, ten, a hundred 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 know you don't achieve that, you know that ultimate success, you don't get the promotion. But along the way, you built a great division, you doubled revenues, you launched new services. I

call all of those outcomes. You know, by the way you built a team that you know gave you a high satisfaction rating as a leader. All of those outcomes are still positive. There's still what I call your career capital. And in that process of just continuing to pursue results and impact, you've not only accumulated career capital, you've likely become more agile and more confident. So aren't those all things that are going to contribute to your 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 and 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 riginal reward. I can't tell you if you're going to get the original success

you imagine or something different. But I can tell you that 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, you know, will become the basis for your reputation, your confidence, your skills, and any future success you acquire. That is the reward for risk taking. And that's why I say they'll focus on success, focused on impact. Very interesting. Let's talk a little bit

starting with your role as president of stub Hub. What was that like? Did you have any surprising challenges you had to deal with in that role? I feel like that's the leading questions to tell you about just suseuch, but certainly I'm happy to share. So um I ran stub Hub from in that time. There's a lot of a lot of surprises, 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 lives. There's just really nothing like it. So and I'm also happy to be a big sports and entertainment fans, so that doesn't hurt UM. But when I think about the

things that were surprises, Number one, UM StubHub. If you know, the history was bought by eBay over ten years ago, and so was an EBA SIB sidiary, and UM I could have anticipated that eBay would continue to face, you know, shareholder pressure because it wasn't growing at the same rate as Amazon and its margins were declining. UM and in fact, that shareholder pressure came to task and an active Elliott.

Two activists joined the board Starboard and Elliott in yeah and no no in nineteen my goodness in January two and put pressure on the CEO, the then CEO to self stub hub as opposed to whole bit so Midway, I was only a year into my tenure when an activist joined the eBay board, and UH quickly became apparent that we were gonna end up selling the company and I was gonna be leading a sale process, which is not necessarily what I personally wanted, but UM, so that

I could have anticipated in the sense that they had had an activist once before, and certainly when I took the stub Hub job, it did occur to me that, um, that would be uh one potential risk that eBay itself, my parent company, would face pressure. UM. I expected more sort of earnings pressure, you know, pressure to deliver our numbers every quarter. Uh. There was an outside possibility of an activists, but that came to pass, and that led

to the sale of the company to StubHub. Sale. UM the honest the other unexpected event with Covid, and you know, ironically, stub hub sold for a record stub you know, four

billion dollars. We led a process that led to a successful transaction that closed on February, and I thought, as much as I was personally disappointed, you know, I recognized it as a very successful business outcome and I was going to go have to find a new job because very rarely there's the acquired company, you know, get to have its CEO run the combined company, and I certainly was not getting that job. Um. The original founder of StubHub bought back the company and he wanted to run

the combined company. H there's a thing with you and founders coming back to run companies. That's keep in mind. I've also been a founder three you know, three times, so um so I do understand that founder CEO dynamic And as I said, any 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 sure it's one part you go, one part of their baby. I get that, Yeah, you got it.

So and by the way, and in this case looks completely professional, like you have a founder who's been out of the company for twenty years and has nothing to do with me. A fifty years he had started a competitive ticketing company and now you want to come back. And by the way, he had been pushed 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 twenty five And so yeah, there's a lot involved in one 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, Dynamics. I just want to be clear, and let's put let's put some numbers on this, because really, so you oversee the spin out, the sale of stub Hub to a third party, and to put some numbers, eBay buy stub Hub for like three hundred million dollars in oh seven. It's barely a decade later, it's now late and you managed to sell stub Hub for over four billion dollars to via Go Go, which I think was smaller than StubHub at the time.

And ps, this is four months before the world is going to shut down thanks to COVID. That turned out to be a spectacularly time sale. Yes, I know, people give us a lot of credit in hindsight for that sale period. And I think and um and I and for eBay, just a tremendous outcome because to your point, we announced the sale in the fall of nineteen and the and the transaction closed like money in the bank for eBay on February. Wow. That's yeah, I know, people

say unbelievable timing. One thing to note is, you know everybody who was bidding to buy us in the strategic category was smarter than StubHub, because you know, we were the largest player in in in C two C ticketing right, Ticketmaster the other big player, and much bigger than us, but not the same category. So um So ironically, all of the people bidding to buy us were people that honestly I would have wanted to buy UM, but they were all smaller than us, but with big checks and

often you know, pe dollars behind them. So uh so look um successful as some for stub Hub. And then you know, I think I'm going to sail off into the sunset after you know, a reasonable but short transition period, and I do not expect to still be in the seat. You know, on March their teams, well, I think I think I'll be there, but it will be part of my transition um and on marched their team. The COVID hits the US sports and entertainment industry in a massive way.

At the beginning of the week, we are forecasting that, you know, we need to start to plan for closures, and I remember saying to our finance team, we're forecasting to be fifty percent down. Maybe we need to have down. No one should need to have a fifty percent case, you know, this is what's trying to think about. How no way. And by the end of the week, every sports league has suspended its season like literally something like

twenty thousand events canceled in like a week span. I mean when I say, you go from sort of you know, having a record sale to like an existential crisis that was us, you know, we were because we were no longer owned by eBay. We didn't have ebase balance sheet. We were owned by another private company who itself had to manage it because guess what, it's ben't ticketing to right,

So it's being affected internationally. We're being affected internationally and more importantly in the US, which is the majority of our business. And so we went from you know, record sale to cash crunch um. And it was on my watch, and so you can imagine I'm might feel responsibility for our business. I feel responsibility for employees. I feel responsibility that we do not go bankrupt um. And we rapidly

restructed the company over sixty days. I will say to people, if you want to know what that period, would like to look at my Twitter feed the amount of hatred I got from people. I mean, I understand that customers were very upset. We had to change policies on refunds. I didn't have the money on the floor. I didn't have you know, hundreds of millions of dollars to give

everybody their money back. The best I could do would give people credit, like I mean like literally, as like I'm trying to choose between the company not going under literally, which was yeah, how do you explain that to people? I did my best. I wrote a transparent note to our customers. I got tons of hate triad and it's fine. Like people were very frustrated. You remember the levels of everyone's frustration and people's money, so anyways, very intense. But

I'm very proud of the team. We we structured in a sixty day span and only once we finished the restructuring that I depart because I knew that Step Up could survive for an indefinite period until live events started to come back. And so you know, it turns out

that the definite period has been over a year. Obviously, um, I can't share any confidential numbers, but you know, the company, no, no, I'm proud of account of the fact that the company survived, right, And you know, 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 att here. The fact that you start stuck around, help them restructure and put them on better footing. Um, 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. Well, yeah, 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 your 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 Subhub team, like that is a team of people who share my values. And I was very proud to be leading a team that, you know, really made hard choices in a rapid period

into including choices that affected each of them. Think about that like people making choices about their own jobs, you know, to try and make sure Subhub survived and like, you know, as a leader, like a very painful period but also one of the most rewarding to be with that group of people. 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. Sure well, if you recall I wrote that open letter tech Women Choose Possibilities, and you said, how what was the reception? I said, it was very positive, and people kept saying to me, like, what are you going to do that? And of course I thought I was just writing a letter, right, I was like, well, did might just do it? I put out this opinion, and you know, 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 dcs of them starting to put more women on tech boards. You know, they would come to me and say, like the Kinder, what should we do about women in chests? And they have all these solutions for putting girls in stems into which i'd bespont and like, you can do that, but that will take generations. You realize that there meant

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 could really benefit from this experience. And ironically, you know, at that point were like oh oh, like yeah, you're you're, you're right, but they didn't do

anything about it. So when I started the Boardlist, a basically crowdsourced six names from thirty executives and entrepreneurs in the valley and I said, would you give me the names of women you think should serve on board? I'm gonna 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? We can't find any um, So we launched

a free service called the board List UM. It's not a nonprofit, but it is a mission driven kind of It was a mission driven startup. I started it at my side Hustle and twent and today the Boardlist is twenty thousand members, over ten thousand 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 board list. UM and so it's a marketplace for talent, um for diverse talent, and today it serves not just

women to people's color. And about a year ago we raised our first institutional rand, so I bootstrapped it for four years. I knew that you know, it was working, which it is quite well, UM, and it's needed more than ever. So the Boardlist is my my my own startup baby as the founder, but I'm not the full time CEO. I haven't what's the what's the track record of the board List in actually getting women and people of color placed on the boards of startups? Um, the

track record is quite good. Now I would characterize the track crack track track record two ways. Remember, we're not a search firm, We're a discussed platform, which means our core metric is like how many people come to the board List and search and then ultimately, you know, 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 two thousand women, two thousand companies from early stage to public have come to the board List searching for board members. UM. And as they said, the way I think about the board List is sometimes we are the accelerated of the journey. Sometimes you find the exact person you want on our platform. We are, you know, we consider our role to be a sore of talent um and to make sure that that board teak gets

successfully filled. So um. Yeah, and the companies run from Series A all the way to public public global companies. I think a few years ago when an activist put up to a United slate for the board, he used the boardlist entirely to put up an alternate slate through the board. Um, and we didn't even know if he just gave us credit. Afterwards he's like, oh, I used the boardlist for example. How how optimistic are you that technology is at least starting to head in the right

direction when it comes to both inclusion and diversity. Well, first of all, I think there are two or three different ways into 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 talent um. We're pretty unique and that we kind of you know, are focused on the boardroom. Um. But to sort of take away by some discriminations from the hiring practice. Hiring process,

by the way, there's a whole other set of companies. Yeah, I'm an investor in several that do things like, you know, help you confidentially report issues at the company in a productive way before it ends 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 bison discrimination to you know, anti harassment, to you know, proactive

consultation between companies and their employees to find solutions. So I'd say that is a positive to see that much technology kind of solution ng you know, 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 it, you need to see it. The number on absolute levels of women who are founding companies, you know, compared to any prior period in my lifetime,

is up into the right. People may say the 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 is for women and diverse people of color to start companies. And look at the number of female unicorns that exists, the female founded unicorns that exist today. I was lucky enough to fund one of the first, Katrina Lake at stitch Fix. You know, I was her early investor and she worked

with me at poly Bore. But since then, you have Whitney at Bubble, you have Rachel Carlson at Guild, you have um the founder of every Well, everywhere you look, there are women starting not just great companies, but very valuable companies. Audi at House houses the Unicorn several times over, I'm sure. And and so there's lots of examples of women who are building really valuable companies. So Canada, Canada just got funded at forty billion. It's got a Australians

emile founder. So I love seeing kind of these examples because I think it really, you know, a it inspires a whole generation of other diverse leaders to feel like they can do it. But more importantly, for all of those VC dollars that you know had, you know, I would just say unconscious fives going out and like under funding companies, they will be fomo about the companies they missed. Maybe they need to look at their own funding practices

and figure out why they missed. Some of these great deals, and often it comes back to you unconscious biased when these women and diverse leaders are early on looking for money. So so let's talk a little bit about um. 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 boys 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. Well, I think there are two types of pressure that BC firms are under. First is from the LPs. So the first thing that needs to change and is

changing is LPs. You know, the people who provide venture you know, money to venture capitalists, demanding to see staff on the rate at which they fund you know, people of color and women like how you know how equality driven as their own funding profile? LPs tablets all day after that, and number two, what does the profile look as the venture capital firm itself, like where their female partners?

You know, what's their own pipeline for development? Because we know that when you're diverse, you fund more diversely as well, right I E. Um, when you have more you know, women as partners, more women get funded. UM. So I think LP pressure is starting and it needs to continue. An LPs, I think need transparency on how your dollars are distributed and need to ask for that how in terms of pipeline versus deal bigger closed? And then number two pressure to keep these PC firms getting more diverse.

The second thing is it's what 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 like, that doesn't fit the normal pattern. You know, dollars slow

to where there's money. And so I think the other type of pressure is actually just performance pressure as you see you know, companies that don't come from your traditional backgrounds and founders either that perform. There's nothing like that kind of pressure, which is like, wow, what am I 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. 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 is keeping you entertained during the pandemic. Sure, well, I probably have three that are at the top of my list these days. First of all, Ted laugh Tho, I know about you, but my family's loves Ted Lasso. Such a feel good, funny, um funny show, so well done.

Season two not so good as season one, but I will just we're still tad laughs of die Hard Um On Amazon. A girlfriend of mine recommended mc mafia, which is actually a pretty um interesting for those of you who like uh, I would say finance or 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 um niche one and an interesting one. It's been a great series to watch. Succession. I'm waiting for

you know season two. I mean we all watched Succession and then I would say on the podcast side right now, actually, I am listening to do separate podcasts about um Elizabeth Holmes trial wants to drop out from ABC, and the other one is Out for Bad Blood from John Kerry, you who, as you know, is the original kind of journalist on this story. So I like listening to smart people that have just keep me abreast on on the trial, really interesting stuff. Tell us about some of your mentors

who helped shape your career. Well. First of all, my dad. I always talked about the fact that he was a doctor, but he was 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 trade trip down to New York that led to the job with Mary 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 eminent mentor for sure. And then I think the other group I had point to is, you know, I've been lucky to have a lot of kind of great people I worked for. They often are my best mentors because they know me well, and I know them well. Um, all the tribe a jungie. We talked about those four Indian entrepreneurs who started that company that I joined. I mean, my god. They became an angel investors in Yodeli, my next company. They introduced me

that opportunity. UM. One of them, Rom Scherry Ram was the first investor in Google. So when I made the decision to go to go to Google, and they called me because Rob pushed both of us us. He pushed them to call me and need to consider it. Um. And you know when the situation went awry at Polly War, the number one person I called was a guy named Bankey Harry and Ryan, one of those Juggli founders and the one I was closest to who 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 could have gave me the like, look me straight in the eye. Are these people you're tribe? Do they have your values? Advice? And tell me to get the hell out. So, UM, I really considered bank you probably the closest among that group, but all four have been very instrumental in my career. Let's talk a little bit about books. What are some of your favorites

and what are you reading right now. Well, one of my favorites, I'm like a very kind of speeky business person. Sometimes I don't like to read all business books, but there's something I really love. One of my favorites is McKenzie's Growth Beyond the hockey Stick. So, if you're a leader or CEO, who's always you ever grappling with how to get your company to grow faster? And obviously it's stub hub. I was trying to accelerate growth um and just paradigms for what works. It's like the new good

to Great. I always love Jim Collins Good to Great, but great. Growth Beyond the hockey Stick is McKinsey's analysis of that of what makes top performing companies over a thirty year period, and it's just got lots of kind of anecdotes I love. So that's the favorite business one that I always recommend. And then right now I'm reading Automic Habitts. You know, Automic Habits has long been on the best seller list, UM, and I wanted to know why. So I'm in the midst of reading it and so

far it lives up to its billing. Is just being refreshing simple, um surprisingly intuitive, Yet we don't do it enough. M quite quite interesting. What sort of advice would you give to a recent college grad who was interested in a career in either entrepreneurship, technology venture capital? What what would you tell someone like that? UM, I would say, Well, on the entrepreneurship and technology side, I would say, get proximate. You know I And today, luckily for us, getting proximate

doesn't mean you need to move to Silicon Valley. We

all live in a hybrid world. Old, But if you're contemplating to move into one of those areas and you don't know what it looks like like literally, maybe as simple as you know, doing a couple of informational interviews with people you find on linked In and maybe tapping your closing network and you know, figuring out who's doing something entrepreneurial and going to shadow them, and maybe like finding a side hustle, where's your new day you're at

a large company in the evening, you're moonlighting. These are always 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 could do to learn before you ever make a bigger move. UM venture capital is a much more

kind of traditional path. I would say, like, you can get there from technology um, but then they want to see that you've accomplished something inside of technology company, so that's possible. The other path is obviously a more traditional finance path through like you know business school and you

know classic financial training or consulting training. And our final question, what do you know about the world of g I could say finance, entrepreneurship, technology, venture capital today that you wish you knew thirty years or so ago when you were first getting started. What do I would know today that I wish I knew that 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 twenties 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. For other is as I said, it might be tapping into a side hustle or opening an st 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 really really, really int rereaking uh Sekenda. Thank you for being so generous with your time. We have been speaking with Kindersin 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 three hundred and eighty two of them. You can find those at iTunes, Spotify, wherever you feed your podcast fix. We love your comments, feedback and suggestions right to us at m IB podcast at Bloomberg dot net. You can sign up for my daily reading list at Rid Halts dot com.

Check out my weekly column at Bloomberg dot com. Slash opinion. Follow me on Twitter at rid Halts. I would be remiss if I did not thank the correct team that helps us put these conversations together each week. Mohammed is my audio engineer, Artika val Bron is my project manager. Michael Batnick is my head of research. Paris Wald is my producer. I'm barried, Halts. You've been listening to Master's in Business on Bloomberg RADI