The Entrepreneur Podcast
The Entrepreneur Podcast

Episode · 5 months ago

Playing at the highest level with Sukhinder Singh Cassidy

ABOUT THIS EPISODE

Fast Company called her one of the most creative people in business. Business Insider named her as one of the Silicon Valley’s top 100. And Ad Age says she’s one of the women to watch.

And why not? Sukhinder Singh Cassidy has had quite the career. Most recently, she was the President of StubHub, prior to which she co-founded a number of companies, and held senior roles at Amazon and Google. At Google, she was responsible for launching Google Maps and eventually leading Google's international operations in Asia Pacific and Latin America.

In another special episode of the Entrepreneur Podcast, Eric Janssen sits down with Sukhinder Singh Cassidy to discuss her incredible journey, and the importance of prioritization (and how that changes in startup and large company contexts).

Yeah, you're listening to the entrepreneurpodcast from the western Morrissette Institute for entrepreneurship poweredby I. V. In this series. Ivy entrepreneur and ivy faculty membereric Jansen will anchor the session. Suki Anderson Cassidy is known as oneof the most creative people in business by fast Company and has been named oneof Silicon Valley's 100 by business insider as well as the ad age women towatch. She is most well known for her most recent role as the President ofStubHub up until 2020 but has also held a number of senior roles at companieslike Amazon and Google. Perhaps you've heard of some of those on graduation.She actually started her career in investment banking in new york beforegetting bit by the startup bug. When she moved to Silicon Valley and joineda number of early in growth stage companies. She co founded a number ofcompanies in the financial services, in the content or commerce space but alsoheld long positions at google, where eventually she was the G. M. And avariety of roles and responsible for launching google maps and eventuallyleading google's international operations in asia, pacific and latinAmerica. She sits on a number of public and private company boards, includingurban outfitters and is the founder of the board list, an online marketplaceto connect Ceo is looking for board candidates with highly qualified womenwho appear endorsed for board positions. In our conversation, we focused mainlyon prioritization, how you decide what to focus on as an entrepreneur or anexecutive, what's the process for figuring that out and the differencesin doing that at a startup versus a large company. So Kinder shares heroutlook on entrepreneurial risk, offers advice for what path to choose out ofschool and gets into what it's really like to play at the highest level inSilicon Valley. Please enjoy this wide ranging conversation with Sue Kinder aswell as this introduction, written and performed by students of my hustle andgrit class enjoy. Remember, remember remember uh, wow, can I clap? You can, of courseyou can recorded that. Of course, of course, that is about that is truly thebest welcome I have ever had anywhere. Guys. I am like, I'm sorry, That's sosweet. I freaking love it. Thank you. Isn't it a special group? Well, unlessfor this way, if you can write a song about me and with my weird name and myweird background, I'm like even more impressed, but that was really, reallyspecial. So thank you. Yeah, it is an impressive group. Yeah, they're great.This is so, this class firstly, thank you so much for making the time. You'vegot a million things on the go and a busy family and we appreciate youmaking a little bit time for us. Thank you. No worries. Like I said, you toquote a dumb movie line you had me at Hello. This awesome, awesome, Well thisis, give you a bit of a background, but this class is called hustle and grit.So these are students. I think we focus a lot on the tactics ofentrepreneurship, but this class is a little bit more of the softer skills,so we work a lot on personal development, keeping yourself Sane andstable all the while, doing very hard things. So I'd say that this is a verycreative group and probably the most entrepreneurial ambitious group amongstthe HB two, so you're looking at the future of people who are going to dosome pretty big things. I love it. That's awesome. Good to meet all of you.Yeah, I wanted to start with a little bit about your backstory. So the teamthat introduced you did circulate a bio to the group. So they have a little bitof a back story but they didn't get into was sort of rewinding the tapeeven further back to your potentially entrepreneurial upbringing. I'm notsure if there's a correlation yet between parents that were entrepreneursand then the kids becoming...

...entrepreneurs. I understand that yourparents were entrepreneurs growing up. So tell us a little bit about that.Yeah, well, I happen to believe there is a big correlation and I'll tell youwhy. So, you know, I grew up in ST Catharines Ontario, my parentsimmigrated to Canada when I was two, so I grew up in Ontario and that's all Ican really remember. And my parents both ran and ran a medical practice togive you guys some since my mom just turned 90 but she practiced medicineuntil she was about 83 years old. That was my mom, my dad and my mom ran ajoint medical practice and he passed away unfortunately when he was 77 buthe worked up until the day he died virtually speaking. So they ran amedical practice. But I think the story I was telling people, my dad just lovedrunning a small business. So at like seven or eight years old when I say Iwas working for my dad and learning how to do his taxes. Like no joke. I wasentering like ledger entries like tax tax time at my family was like, youknow, way before excel or anything else. Like literally writing in a ledger. SoI probably knew how to do my dad's taxes price time. I was 11 or 12. Iwrote in my first, his first Excel spreadsheet when I was like 17 to belike, we're never writing hand ledgers again. And so I kind of saw him run asmall business. But the thing I'd say to you is that he loved like as much ashe loved being a doctor, he left running a small business. So he told meto work for myself, Obviously he wanted me to keep working for him. I thinklike how many of you know that if you would like to drive down the streets inCanada and the US right now you would see like walk in clinics, right? Likehealthcare, like operators right there, these conglomerates that launch all ofthese centers. I think when my dad, I think when I was like probably 13 or 14,my dad literally like branded his office. He called it the healthcareservice centre because he imagined and then he bought a building and he wantedfilled with a bunch of doctors and he was like probably 65 at the timebecause he thought that people should just be able to walk in off the streetand get service any time. And so literally he bought a building, hethought he never filled it with many doctors. I think he felt like with oneor two he created a brand. Like when we think about what happened in themedical medical profession, like my dad was on that a year, you know, yearsearlier and even though it never came to full fruition, like he was justalways creative and I know, I think you guys probably know that being anentrepreneur is both the creative and an analytical exercise. So I watchedall of that and then my favorite other story about my dad, which tells you howstrongly I believe that there is a correlation. I was probably, and again,you guys are super young. I'm old, right? But still young at heart. Ithink I was probably, you know, it was like I was before I went to MerrillLynch and I came home and my dad had really bad eyesight. So again, you guysdon't know this world, but you used to be that if you want to buy stock right,you call up your broker right? And you talk to your broker to buy stocks. Somy dad had terrible eyesight, you have this gigantic magnifying glass and hewould literally look at all of the stock price listings in the paper andhe would call his broker every morning like this, like jovial, laughing like,hey, tom let's by X Y C. Because he loved trading stocks. And I distinctlyremember a long before I knew what tech was. It was probably like 1990 to 19,maybe 1990. My dad like calls tom maybe maybe it's later because if I thinkabout maybe it's 93 94 maybe I'm at Western already. And he's like, hey tom,let's buy some A B O L. And I remember the time being like what the hell isAOL? And here's my dad, he was like in his early seventies and he's liketaking swings at like nine stocks in the tech sector because you could justsee all the possibility. And when he died many years later I was had tounfortunately go through his desk right at home. And again remember this guy'slike in the seventies when I'm like training them how to do itself for hisledger and I would find through all of his George's, these different pageswith passwords to different financial sites like the motley fool, you knowthe ST dot com, whatever, because he just kept setting up all thesepasswords, you just ingest as much information as he could from theinternet even though is of course like not really his generation, so so likethat is my enduring memory of how I...

...grew up and so obviously in hindsightI'm like of course I become an entrepreneur, but you know when you'regoing through it you don't really think right and then you're seeing it all byosmosis. So to answer your question, I firmly believe it. Yeah, so fastforward then. So you went to, went to Western, graduated from ivy but thendidn't jump into it right away. And I think a lot of students in this classbeing probably the more entrepreneurial people at ivy are trying to make thedecision. Like do I do this thing right away even, maybe I don't have the thingor do I go work somewhere else first? So you didn't jump right into it eventhough you have the entrepreneurial upbringing? Yeah. Well I think first ofall, I'm sure all of you have this issue right? Which is what happens ifyou don't know what the thing is, like what happens if you don't have an idea?So do you go find people in group together and obviously some ofentrepreneurship is people who find each other and say let's go through, gothrough ideas right by the way, maybe if I had been grown up the same way youguys did, I would naturally think that, but when I was graduating, ivy was allabout being a banker or consult and I'm sure there's at least half of yourclass that thinks that way. And for me, honestly, there was a period after Igrew up where I didn't actually automatically want to be anentrepreneur, I want to have a big career, I didn't even know what thatwas. So I just followed my friends into wanting an investment banking orconsulting job, right? And I got one and then about four or five years later,I mean I was in my mid twenties, I was like dreaming up ideas and I didn'tknow what to do, I didn't have a great idea. So I moved to the valley and Iultimately, you know connected with people who do so I think path is youfind a group of people, you brainstorm ideas and you go, now have B is you gostart skill building, right? And then you put yourself in proximity to peopleand I don't think there's any wronger right answer, I will tell you thatentrepreneurship happens when you're in proximity to people, even if you don'thave the idea, you get approximately people who do and your brain storm, orit happens to your skill building and then going to do that, right, andeither is OK, Like I look back at the training, I had a big companies likeMeryl and Sky and I think that training was incredible because it taught mefinancial literacy and of course half of running the company is knowing howto actually make it profitable and you know, and knowing how to sell and allthose things, but I didn't actually myself figure out how to be anentrepreneur until I picked up and moved to Silicon Valley, because I waslike, I don't have an idea, but if I put myself proximate to people who aredoing it, surely something will happen, and of course that's what happens right,you get in a startup. So I would say, like, if you're feeling this anxietythat, like, you have to choose right now, I think if you find a cohort ofpeople in a great idea, go now, if not go to a startup, go to a big company,like there's almost no bad path right out of school, if that makes sense,because what you do know is when you're an entrepreneur, you're going to learna ton, but it is seven years, kind of 5 to 7 years before, you know, if yourbaby is going to be viable, you know, and so maybe you'll get lucky and maybetwo or three, but that's really not often the case, so I do think that theprocess of entrepreneurship can unfold right away if you have a good idea, youcan keep working your day job and working at night, you can put yourselfin a startup and sometimes when you're in those environments, once you startlearning something, you get ideas and I can certainly say that later in mycareer, I have lots of ideas for companies to start. In fact, many timesI'm like, I should go higher, a whole crew of you and just like, Like gostart 10 companies at once, because I don't have the energy to start 10 atonce, but I certainly have the ideas for it, but early on, when I knewnothing, I really didn't have a good idea, you know, like just to sit inyour room by yourself and be like, what's my idea? What's my idea? Like?That's really hard. And so even though I be training for entrepreneurship, Ithink the hurdle rate for an idea isn't, you know, and how to foster ideas.Sometimes you need experience to have, and sometimes you just need a group ofpeople who are brainstorming and you know, putting a bunch of ideas upagainst a litmus test. So I don't think there's any wrong answer, careful whatyou wish for us to kenya, you got a bunch of really engaged people herethat might take you up, try to take you up on that offer. So I swear to God, Ido often think about starting a venture...

...studio, which is the model where youbasically say, okay, how do you run 10 ideas at once? The problem is, I'm alsothinking about what my own next day job is and you can't do all of these thingsat once, but it occurs to me certainly. Yeah, so, um, your early career in theafter Merrill was in sort of made a name for yourself on the businessdevelopment side. Um I came back to ivy to start a sales program. That's whyI'm here. That doesn't launch until january. So a lot of people, I'msurprised they don't know the words business development, customer success,account management, account executive, they don't even know what that is. Soyou made a name for yourself in doing business development for some early andgrowth stage companies. Can you unpack that? What does that mean? What did youdo? Sure. So, so it's effectively glorified sales, right? But let me besuper clear biz DEv is selling something that hasn't been structuredyet. It's basically going out and having conversations to figure out whatpeople want and making up as you go, a product that services their needs,right. Business development is also partnerships often where like maybe youdo know what the product is, but you're selling very strategically and it's notstraight up revenue, but business development either leads to a career insales where you're like, hey, I'm used to being on the hook for revenue. Butthe different defining factor is if the product isn't structured yet, you callit business development and then once it's like systematized, you call itsales and business development also can refer to other types of partnerships,partnerships for content licensing. You know, partnerships for a rev share,just being strategic about partnerships from marketing or distribution, whichper se are not quota filling jobs, but they are still designed to drivenonlinear economic value, right? Usually distribution or something else.So you're either driving customers or you're driving dollars, that'stypically what business is about, right? You're trying to do partnerships thatopen up markets or you're trying to actually literally sell something. Howdid you find yourself in that? Is that is that a common path from eitherbanking or consulting? Getting into an earlier growth stage company andjoining in a sales role? Is that a common path for people that this stepis certainly been steppin sales are both common and I would say two thingsto you. So in some ways sales is easier. So let's say one of you guys wanted togo, we hardly one day and running Shopify, you know, or start the nextShopify if you went into a SAS company straight into sales, like literallylike I'm going to figure out how to sell the software product to bigcompanies. That's a path to become a ceo of a technology company that sellsto other companies. Right? So often if you have technology companies that sellto consumers, it's about marketing, right? It's about literally can you geta customer off google at a good enough price and happen by something on yoursite. But when you have a software company, you're typically selling tobusinesses, right? Either smaller, big, often the heart of that company, ifit's not engineering its sales, it's straight up like, can you deliverrevenue? So if any of, you know the company Cisco, it's run by a sales, Godright. Or it was john chambers, if you guys know salesforce, it's run by asales, got marc Benioff knows how to sell better than anybody else. So it'svery possible that sales can also lead to the Ceo suite biz DMB is slightlydifferent in that it requires more creativity. Like you literally have tobe willing to figure out what it is to sell. and typically this DEV is um isalso a path where people kind of consulting or investment bankingbecause it's like a fuzzy or title and it has some sense of strategy, but Iwill tell you like I wouldn't necessarily, in your mind say, gosh,this dad must be more elevated themselves because if you know how tobring in the money, you are always in demand, if you know how to createpartnerships, but you can't really prove that they have value. It doesn'tmatter how strategic you are. Like does that make sense? So like, so I thinkthat when you guys think about it, this is a common path in, I came out ofinvestment banking, so my first job was busy to have, well I was an analyst atSky and then I went into this job and it is an entry path, so it's sales andlike I said, I think the difference is...

...really like feeling very uncomfortablewith like having to structure something versus already knowing what the thingis that you're selling. Yeah, that's funny. The hires that I've made out ofivy have always, when I offered the job of account executive, it's like, yeah,no, I understand the job description and I'm good with all of that, but canI have the title of business development and it definitely has to beeither manager or director, even if you're not managing or directinganybody. People love the business development title because it sounds somuch cooler and again, like don't get me wrong, I love business developmentand sales. I like them both. I think the most powerful business developmentpeople, whether whatever you call them are not afraid of knowing that theyhave to bring in the money. that sounds like if you just want to do coolpartnerships instead of have the fuzzily measured, it's not a greattrack record for biz deV either to be, so you went from investment banking,british sky, amazon sort of into a startup and then to google, so you sortof went like not smaller companies, but like structure, maybe a little bit lessstructure, maybe a little bit more structure and sort of bounced back andforth. But then did a pretty like a longish stint at google, I think almostsix years. Can you compare and contrast the differences between say, start upand scale up, you know, like the, the early days at british sky or your bellyand versus how was it joining amazon or google that sort of had some of thatstructure already. Yeah, sure. And I think again, the other thing for you,all to think about is they're all entrepreneurial. You know, when youthink about people think well off I go to a growth company, it's notentrepreneurial. I mean I joined google was 1112 100 people and I exited whenit was at 40,000 including contractors right now, it's like 100 over 100,000employees, maybe even close to 200,000, right? I was in amazon when it was 1000people when it's now, I don't know, probably two million people includingthe people in the warehouse. So, but I mean in your head office and so just beclear like they're all entrepreneurial journeys. But to answer your question,The biggest differences are when you're in a pure startup, as you guys know,there's a level of Camaraderie and just figuring it out with like 10, 12, 15people. That's very hard to be, you don't spend a lot of time educatingpeople on why something needs to happen, right? Like information travels veryfast. But the volatility of that experience is really high, like, youknow, I mean, people always talk about it, so people sort of think, well if Igo to a startup and have the best experience, maybe not because thevolatility all goes with the founder, so if you're not the founder, so ifyou're the founder, everybody is going to be responding to you and howvolatile you are, which makes for a really rocky experience. And if you'reworking for another founder, right? And somebody in their company, it's allabout how good or bad that founder is in the day to day running of thecompany because it's already a volatile experience. You don't know if you'regoing to fail right, it can be great or it can be awful. Like that is true,depending on the quality of the people you're around. So I think when you'rehaving a really vulnerable experience, it can be really fun or reallyexhausting and you want and it's fun if it's growing, but even if it's notgrowing, it's fun. If you're going through the process of innovation withpeople you really love, like you're figuring it out every day before youknow what you've created a product and you're like, how did that happen? Likeyou look back after you and you're like, wow, we did that. Whether it fails tosucceed, you feel this level of pride, but it's very volatile with the peopleyou work with. The benefit of a scale up is by the time you have productmarket fit and something is growing fast, here's what happens. It attractsa quality people so you look around and everybody is uniformly, like notuniformly, but they tend to be really super talented people. So like when Ilook at the people I was with the amazon and google with like those arepeople who are like holy smokes, like these are smart people and that'sbecause for a lot of the smartest people, the level of risk in a startupscares them. So they wait until it's probably as product market fit, so thenthey're going into the job is scaling but they don't have any of the highsand lows of like whether or not the...

...thing is going to work. So you miss outon that process of creation somewhat. But you enter in an environment whereyou can still grow and learn pretty fast and the quality of the people asit keeps attracting better and better people because once you have likemomentum, it's a lot easier to recruit like great talent. Now look, I've beenlucky enough that I would say every startup I've been at including my own,we recruited phenomenal talent. Like I look back at the people you totallyenjoy us and Polyvore even in the board list certainly, which is just startingand I'm really proud of it, but it's really quite hard to hire amazingtalent at a startup because you know, people like people have choices. Theydon't always want to take that level of risk. So today's class, we, the setupwas talking about how to set priorities. We talked a little bit about doing itin your business and in your life and then talked about habits. And I thinkin my experience as an entrepreneur sort of learning how to set the rightpriorities is actually really hard. It's easy to say right, have fewpriorities and have the, the object and the key results that lead up to the, tothe objectives. And I think the class is kind of like taking good notes, butlike okay, but like how does that really play out? So we talked about thewhat objectives, key results, sort of having, having priorities is important.We talked about why that's important in getting alignment across the wholecompany, but I'd love to dig into the how so how did you having done it at abunch of different sized companies? How do you think about what to spend yourtime, resources money on? Yeah. You know, it's a great question and nomatter what people say, it's really hard because if you just think about astartup at a minimum, you have two problems, supply of any product,reserves and demand. And no matter what you say, any product or service isultimately a marketplace, right? You're bringing something to market and youwant enough people to buy it. So at a startup you like, right To facto, youhave neither side. So even though people are like, well, you know,prioritized, you're like, well, you have neither side get both it up sothat you have like product market fit, right? So I think it's very easy to say,but it's hard to do. So let me just say that. And of course, the more you grow,the more options you have. So then it's hard to do again. I know you guys haveall looked at johN doors, okay, ours. I will say a couple of things that havebeen helpful to me number one, just on the, okay, our process. I think a, howdo you do it? First of all, you have to do it at least quarterly. If not, youknow, and you always presume that in a 10 person company people know how toprioritize. But as you guys can probably tell the most interestingexercise you can go through and okay, ours is not generating perfect slidesand lots of ideas. It's in picking right? So I would just say when you dookay RS. First of all, I think okay ours are really essential. Even at astartup number two, when you do okay, RS don't underestimate the value. Evenif you've accompanied five people even doing it. Because what forces is thatdiscussion? Because what people do is they'll throw everything out. Like whenyou say do okay Rs, even at StubHub when I did them, people create decks,right? People have decks of okay Rs. And at the end of it you're like, what?We just went through 100 items which of these are going to make the quarter andeverybody wants to list everything. So first of all, just the process oflisting everything is useful. But the most valuable process is what you callthe edit, like how you gonna slam this down into like three or five things. Sofirst of all, you have to constrain yourself 2, 3 or five things and numbertwo, I would just say constrain yourself and spending weeks on listingeverything. Because I think the most valuable thing you can do is ask peopleto like list there everything's and then come into a room and literally saywe've an hour, like we're gonna leave here with like the top three thingsthis quarter. And it's useful when you do it with five people. It's usefulwhen you do a 500. It's useful when you do with 5000. So I would just sayforcing the discipline of the end because what everybody does in settingpriorities is exactly what you mentioned. They do the beginning,everybody obsesses about listing everything that needs to get done. Youknow where the value is, All the value is in like Of all the shit we just putup on the board, literally what are the...

...three things that need to get done? Andit's amazing that whether, as I said, whether you're five people doing okayRS or 15 or 20 people just throw up a lot of stuff. The converse is you canjust say we'll just go top down and you know, to be honest, sometimes top downwhen you're starting like works like literally you're like, hey, you havethe founder that you got to like say like, hey guys use the three things weneed to get done and you say how, I mean, look at the end of the day, Iwould just say that in any two sided demand supply equation, it is likelythat you need one side of it more than the other to jump start, right? So whenyou're saying, hey, how do you pay to service people want from zero? It istypically true that you're going to have to spend some amount of time justconstructing the supply side, the value equation, the product, the prototype,you know, if you're aggregating something like all the supplyrelationships. But I think what people do too often in prioritizing in and ina startup is they spend more and more and more time perfecting the supply. Ohwe have 10 people will really before we can ever like see people want, we need15 oh we have this minimum viable product before we ever put it up on theinternet, you know? And start driving adds to it. We really need to spendanother nine months perfecting it. So if there is an A I think a risk insetting your early, okay ours, it's that people want to keep perfectingsupply, you know why? Because it's very known and you're like, well the productshould look like this and then look at but they spend all their time baking intheir head what the customer wants. So the only thing I would tell you is inprioritizing starting a company, you both a need to spend more time on theedit of people's okay rs and the okay ours themselves top down or bottom isup, constraining yourself to like throwing up a white board versionbecause it's the whiteboard version that people can actually remember andthen number two, just be careful that if you choose to prioritize the supplyside of any equation, all you're doing is delaying the really other valuablework, which is like, well people bite on what I'm putting together so peoplewant to endlessly cycle on the offering and I'm like get to the minimum bibleoffering and then spend a lot of time cycling like their demand. It there's arisk and priorities prioritizing. It's people to prioritize supply becauseit's more understood. The most scary thing is how to get demand for yourproduct, but it's the most value. It's almost like you could solidify two ofthe buckets in the, the objective side for early in growth stage companies inmy opinion, like there's always going to be a building like you need aproduct to sell, always going to be a selling building selling. There areother things of course, but the building and selling I think are goingto be the 22 of the priorities all the time, all the time. But I think they'realways giving priority and I would just say where to put the weight on them.People want to be, you'd be surprised how many people want to be 70% building30% selling. I'm sort of like, you kind of can be 50 50 for, you can be 70 30on building, but then you better flips to a minimum 50 50 maybe even arguably60 40 because otherwise you're just building in a vacuum and you're chewingup all your money and you don't even know people want selling. But you know,we all have perfectionist and we're all creative and so we all want to likejust make a better and better thing. Right? I want to make it better andbetter website. I want to make it better and better better better. Like,you know, piece of software. I want to make it better and better. Like pieceof hardware. I want to make it better, better game, but you just need to haveenough to know if people will one. My wife calls it playing business. Shealways calls me on it. You know, like I could, I could Finnic forever. On thelanding page isn't perfect. And I don't, we need some more, we need actuallyreally, really need to redo the logo and she'll say you're done playingbusiness now it's time to go. So she gives me the kick in the ass to go. Sois that, was that your role then as when you get into the more seniorleadership at technology companies, uh, stay StubHub as an example was yourrole when assuming I think you still did, you said you did okay are as yourrole was to then everybody sort of...

...rolls up their priorities to you. Andthen did you pick them or did you just say you need to pick, let's let'sdecide this in this room. What's interesting? I think that I think whenyou prioritize as you get more senior in the company gets bigger, first ofall, your first inclination is to go bottoms up because you want everybodyto feel included. The problem with going bottoms up is you end up with 100page tax, which I often did when okay our processes. I'm sure they'rebeautiful. They're beautiful. Dex. Oh my God. And especially when you're theCeo and everybody and we would do okay ours each quarter. So then, you know,you're bringing, I bought, I have what's called an extended leadershipteam which is our managers and our directors and RVP. So like I want tosee all the people who are holding major parts of the business, right?When it was Sports relationships or you know or see to see, you know consumerseller business. So I would say a couple of things, I'd say number one atfirst I did bottoms up to see everything and you quickly find thatthat's inefficient. And then what happens is you honestly, you take yourleadership team and you lock yourself in the room and you're like let's editlike literally right? And then you learn that if you really want people tofocus, you need to give them a high level bucket ng like these are roughpriorities, right? Like the and then within that now constructor, okay oursand that's probably a good reasonable P. O. V. And you know, you can do thatfrom saying this is this year's five strategies and then you're like okayguys, as you set up your okay ours, they need to fit within thesestrategies, right? You give people some guidance and then probably the mostefficient is literally you give people a very limited template and you'reliterally like, and that's how we ended up with in the end. I'm like you haveone page to dok ours, that's it. And you want to end like and we took theokay our process from like three days and hundreds of pages, two days andhundreds of pages because everybody wants to present their okay ours andlike everybody wants to present, everybody wants to be heard to like askinny template that we finished in two hours as 100 people. And then, and youknow, so you sort of impose a structure and then people have to fit within andthen you have an edit to do, but it's much, it's much simpler. So that's thesetting of them. What was your process to track it? Was it like weekly,quarterly sinks? How did you make sure that you were staying on track and thenadjust course? Yeah. You know, I mean, we would do it probably not a surprise.Again, number one, you have a KPI dashboard that people get daily orweekly or monthly, but typically the daily things that change in ourbusiness was like ticket sales, right? So like you have automated dailymetrics and then there's certain metrics that are only going to movelonger term, like bigger product ideas or initiatives are not going to movedaily, write any new business is not moving daily so tiny. So we would havea mid quarter check in where we looked at the numbers mid quarter and then endof quarter we would look at the numbers and the qualitative results. Has thatchanged in whether it's your full time job like StubHub or whether it's,you're not gonna call a side hustle because I know you put a lot of timeinto it, but the board list, you know, the board list, I think if I look atthe timing, you started that well you were at StubHub, correct while I was atjoyous, but it really, I didn't hire Ceo until I was at StubHub because Ididn't know what I wanted it to be. Did your process change at all? Whether youwere in it full time, like at joyous or at StubHub or in it probably equivalentanother full time job. But you know, it wasn't your soul, it wasn't your day today. Well I would say I'd say the benefit of having it be my side hustleor like I'm also a board member other places, but the board list is more,it's my baby. So of course I care even more than a board I'm on. I think thebenefit when you don't run it every day and somebody else does is you can be,you know, you can sort of force that pulling up and looking at what's reallyimportant because you know, the challenge when you're ceo or anyanything is that you see it all and you think it's all important and sometimesit takes stepping out of something and looking back to be like, what are thethings we need to get done? So I would say when it's a side hustle, I get themore fun job of being the editor of the edit, which is like being the push fromtop down, right, like look like which of this stuff is going to matter. Sowe're just putting in okay ours at the board list and he has a great ceo butwe it's not public yet, but we just raised our seed round of funding afterbecause I bootstrapped it to this point.

And so now, like we finally have likethe equivalent of 10 people at the company. So now I'm like, ok, so welike yesterday we did our first strategy session that we've ever donewith all 10 as opposed to just me in the Ceo. And we're like, okay guys, howdo we said, okay, here is for 2021 okay, I was for Q four were set by her herand I talked, she set Q. Four, okay ours for everybody. And then and thenfor Q one were like let's bring everybody together, have a discussionand then she'll set the okay ours because it's appropriate. She's likeeverybody got a chance to weigh in. We didn't really succinctly and now she'sgoing to set okay. Rs and everybody's aligned because we did the conversationso I'm sure the version of okay ours will be much simpler. But it's stillthe same principle which is like give people a chance to end a voice in avery efficient period. The only thing I'll say about okay are is is that youcan't create a drawn out period. People will just expand the work to engulf itand the results are no better than if you did it in an hour. You can takethree weeks, you can take three hours. I bet you the results not going to bemuch better. Time box it half the time box you have to time box prioritysetting. Otherwise people just obsess and pull more data. Perfect deck,Perfect deck. More bullet points, more detail around each. Okay. I'm like, itdoesn't really matter. Yeah, I want to shift gears a little bit andget your perspective on something. Um we had a heated say, heated debate, butwe had a good debate, good conversation around going like hell when you'reyoung to set yourself up and trying to establish or set up some semblance ofbalance. And I think we've had people on both. I've had perspectives fromboth. So we talked about Jason freed from 37 signals. You know, doesn't haveto be crazy at work. And we talked about, there was an article from scottGalloway who give up your twenties and thirties so that you establish someprofessional trajectory and that is that that allows you freedom later onin your career. Are you strongly in one camp or the other? Okay. I'll tell youwhat I believe and then I guess my family would say so we're pretty hardbut I do believe I've got a lot of freedom than how I work now. Like a lotright? So ironically the bigger the company that you're running, the lessfreedom you have because you're beholden to time zones and everybodyelse's schedule and thousands of people who depend on you. So ironically beingan entrepreneur, although it's much more mentally taxing, you have way morefreedom than you do as a large scale see away because you can just you knowlike you can just time bound how you want to spend your time and your notyet they to like all of these like everything that's put upon you by likea really large scale infrastructure just quickly there. So you, you thinkif you look at your job at president of StubHub versus Ceo of your own startup,you had more flexibility and freedom as the ceo of a startup versus thePresident of stubborn for sure. I mean if you like to be, you know, becauseit's StubHub and of course like Covid has changed everything, let's all agreeon that. But it's StubHub, I've got to see customers like and you know it alllike I have to go see our international offices, I have to pick time zones thatlike our china engineering team and me and Madrid can all be on. And if I'mthe Ceo and I'm like, hey and I, and I actually just see who believes you showup. Like you have to show up and feel connected to your employees so likewhat am I going to do? Just be like, hey, I opt out of these time zones,everybody like meet me on my time zone, that doesn't happen. So maybe some ofthat infrastructure is related to international for sure becauseeverything, everything I've run, it's Vegas and international, so that's abig part of it. But it's also just customers and like what works foreveryone. The benefit when you start up, is that what works for you and your 20people like, you know, and a lot of that cycle time that spent onmanagement and communication, it just goes away. Yeah. So I just thinkthere's a lot of freedom in how you work even though you work as hard. SoYeah. Do I believe that you power in your twenties and thirties? Sure. Do Ibelieve that my family would still say I power in my forties and fifties? Andthey're like uh like what the hell? Like shouldn't you be you know, toningit down? I probably like I'd say my...

...family complaints, I probably shouldtone it down now to Yeah, for sure, because I think that we're onlymomentum creates compounding returns. If I asked you guys all like, okay, doyou want to start saving when you're 40? You're saving when you're 20? Everybodyknows the answer. So if you want to put into the bank, like the more you cyclein your twenties and thirties, the more career capital your building, Right? SoI mean at google, I was the president by the time I was 35. Like, wellactually no, that was a vice president by the time it was like one of the top10 people in the company. So like by the time I had my first child, I was 36I didn't delay it, by the way, I wasn't like, hey, I'm not going to have a kidbecause I'm working. I was like, I just didn't get married until I was later,but you know, I wanted to the office of google and I was like, I'm pregnant,I'm running international and I really would love for you to pay for my daddy,for my daddy, for my nanny and my nanny and my daughter to travel around theworld with me and google said yes, because at that point I had enoughcareer capital that like the thought of losing me. So I had a lot ofnegotiating power in my later career. So I think that's what you get rightwhen you power in your 20s and 30s. But conversely, I mean look at the womanwho just became the first president or the first ceo of a major globalfinancial institution jane fraser at Citibank. She chose to be part time formany, many, many years as a partner at Mckinsey while everybody like spedright pastor so that she could have time with her kids. You know what likethat was a pretty good trade off. She's now, you know, she got to the ceo suiteof a major global financial system faster than any and the first of allwomen and she took a completely alternate career path, includingslowing down when she needed to for her kids the same thing with the ceo ofsara lee. So I just don't think you can say if you start off slow, you're notgoing to make it. That's not my point. But I think that when you put a lot inthe bank, when you have a lot of freedom personally, it does give youmore negotiating capital when you hit the parts in your career where maybeyou really need the flexibility to make a different choice. So let's put thisway, she was able to be a part time partner at mckinsey because she was apartner, You know, I was able to say to google, you're gonna pay for mydaughter and my nanny because I was really senior if I had exited, you know,when I was a manager, what I have the same negotiating leverage when I neededit. I doubt it. Yeah. So then we, we just finished an activity before youcame in on on habits and trying to establish some habits over the next fewweeks to keep people, it's a busy time for students, you know, exams cominginto the right before the holiday. So like what are some habits that aregoing to keep you good as a person? So what, what did you find kept you yourfamily, your like, what, what systems, what habits did you set up to keep youa whole human throughout the craziness? So first of all, I am fairly all ornothing as you can probably tell. So like people think I have a hard timezoning out, but I actually really don't because by the time I'm done my day andyou know, unfortunately, covid you think it be Better, but once you'vebeen on zoom multi, you feel tired in a different way than we've been rightinteracting with people. So my days were longer at StubHub or see you. Butright now by 5:00 I've had like 10 scenes and I'm done. But I would saywhen I'm done, I'm done. Like I, you know, if I go on vacation, I say people,I'm not checking email, I'm not checking email on the weekends. LikeI've resisted scheduling my kids because it's the two days of the weekwhere like we can all roll out of bed and I'm not like, I don't want to panicto take them to five practices. So when I switch off, I switch up, I feel noguilt about not checking my email for a day. Like I'm like, okay, you know what?I'm just not checking on saturday, anything can wait till sunday. So Ithink I'm very binary, like what I'm off, I'm off and when I'm on I'm on andI feel no guilt if like, you know, someone can't get a hold of me, that'sprobably one of the biggest ones. Number two, I have no problem withindulgences to just switch my mind off...

...and very few things switch my mind off.So like for me shopping, like, let me say that again, shopping, like I'mhappy to just shop because it's one of the very few things that like, I justdon't think about anything I've binge watched, like I do all, I have all thestudents, all of you guys do right, and I think you have to go to whatever thething is that turns your mind off. Some people are like, well, turn off yourdevice. I'm like, God, actually I'm so busy binge watching friday night lights,so I'm not going to do that. So I think for me it's been about like notoverscheduling the rest of my life, so I'm kind of happy to not have it overschedule because so much of my life is number two, like, like I indulge, likeI'm like, why not? But I indulge in the things that switch my mind off. Andthen of course I have lots of loves that. I'm sure many of you guys do. Ilove to ski. You know, some of my family and I have a house in like Tahoe,we love to wake. So like of course I have all the same things everybody elsedoes that are really fun to do and I try and do them, but I wouldn't saylike, I'm like, you know, I love to work. I love my kids. I love to switchmy brain off and I'm quite happy moving between those three things. Like maybeother people aren't happy with me. I'm like, I'm pretty happy I get my fill.If I do those three things, so eliminating eliminating the gray, Ifind people that are maybe more established or performing at a highlevel do a really good job of eliminating the gray. They're either init or they're not, they're not like half here while checking their phonewhile emailing on vacation. You know, they're either all in or not. Yeah.Well let's, yes, I think that's true. I think I'd put it slightly harsher onmyself. Like for sure there are times I'm always checking, you know, make nomistake. I'm just saying if I say to people, I'm off of email, I'm happy tobe off. Like if I go on vacation, I'm like, if I'm going to ITaly, I'm notthe person who's like, oh my God, let me check my email all the way to ITaly.I'm like, God damn it. I'm going to ITaly. Like I'm kicking, not checkingand I will not check, right? So, but obviously other times I'm checking, Iam much more like if this has no value for me, like I have no need to provethat, you know, I don't care about, like I'm the one who keeps my houseclean, I could care less. I mean if I can outsource it, I will and the onlything I really feel guilty about is my Children, right? If like, but I don'tfeel any guilt about like if some, you know, if somebody else has done therelaundry or whatever, I'm like, okay, yeah, I don't want to do it like, so Ithink for the things I don't want to do, I'm like, yeah, it's okay. I'm nottrying to be super mom. I think that would be very difficult and already Ifeel guilt for the things I don't do, so I don't even feel guilty about, Iguess is the way I put it. Yeah, good. I am an entrepreneur turned educator,didn't expect to be here, but I am at ivy and I'm wondering if you have any,is there anything we should be teaching entrepreneurs that maybe we're not orthings that we should be focusing on more that we're not today. How can webetter prepare these people to be effective either as entrepreneurs or tojoin early stage companies? Well look, I I have this thesis that people have avery mythical relationship between risk and reward. I'll say to people like youunderstand it's called the risk for a reason. So if you're going intoentrepreneurship of course you should aim and think before I get that, that'swhat motivates me. But if you think that the reward for risk is only thereward, I think that's a very flawed perception of risk. I think people movethrough the world thinking risk is binary thinking it's all or nothing ifit's all or nothing if I don't have a perfect idea, I shouldn't go leaveaside the fact. I think you should have ambition enough in doing ambition foryour idea, right? And so I think the people of this very mythical notion ofrisk and reward, including entrepreneurs and like I wouldn't saydon't have it because it's what gets you in. But I think that understandingthat you know, risk and reward will unfold over many cycles and it's goingto take more moves than you realize to get the ultimate reward. And sometimesyou won't even be able to correlate the...

...ultimate reward to the original riskyou took. And so I think it's fine to enter with this binary, Like I'm goingto take this because I want to be a billionaire, but pretty soon yourealize that you know, it's called risk for a reason. It doesn't always workout and it's still going to work out even if it doesn't always work out. Soyou want people to have enough kind of love and ambition to enter it. But Ithink you also want to be careful that you don't think it's this binary, largegigantic thing, which is all or nothing and thus you never do it. Any advice tosue kinder if she was graduating from HP two things that you wish you wouldhave learned known earlier back in the day overvalue the people and you know,and because I think that you almost you can go in almost any situation whetherit fails or succeeds. If you're with tremendous people, you're likely tohave a tremendous experience. And one that will pay back multiple ways. And Ithink the other caution is like trying to go where you don't fit is also, youknow, I felt like I spent so much time and I'd be wondering why all my friendswere getting the Goldman Sachs job or the Mckinsey offer and I couldn't, youknow, and I ultimately ended up at Merrill Lynch, but I'll tell you like,if I look at Merrill Lynch's culture, it was exactly right for me was superaggressive, it was right. It was like everything that I am, it's no surpriseto me now, but that's why I ended up of all the banks and right because it'ssort of where I fit in where it was easy. So sometimes I think we thinkthings have to be hard, but sometimes hard is not just about the task is hard,which we expect, but if it's hard with the people because of values or becausewho you are doesn't fit where they are trying to force fit, that is very hard.So just you know, I think that I think the people factor has so much more todo with having a great experience than just what you're working on. Great andthanks for being open to tender. I think um the team that introduced youwanted to say a few words before we let you go, thank you scandal for joiningus today. I'm sure we have the class has learned a lot from your valuableadvice and stories. So to thank you for your time and appreciate yourinspiration to future female entrepreneurs. We have donated $40 tothe Canadian women's foundation, your name and the family aims to empowerwomen and young women are funding various programs across Canada. Sothank you again for your time. Well, thanks for doing that and thanks forthe amazing song. I can't wait for somebody to send it to me so I canlisten to it again. I will absolutely send it to you sir. Kinder thank you somuch for your time. I'm gonna play the song as you sign off. Thank you so much.Thank you. Take care, take care. Bye. Uh huh. The entrepreneur podcast is sponsoredby Quantum shift 2000 and eight alum, Connie, clarity and closing the gapHealthcare group to ensure you never miss an episode. Subscribe to the showon your favorite podcast player or visit entrepreneurship dot u w o dot ca slash podcast. Thank you so much for listening. Until next time. Mhm.

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