The Entrepreneur Podcast
The Entrepreneur Podcast

Episode · 1 year 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 entrepreneur podcast from the western Morrissette Institute for entrepreneurship powered by I. V. In this series. Ivy entrepreneur and ivy faculty member eric Jansen will anchor the session. Suki Anderson Cassidy is known as one of the most creative people in business by fast Company and has been named one of Silicon Valley's 100 by business insider as well as the ad age women to watch. She is most well known for her most recent role as the President of StubHub up until 2020 but has also held a number of senior roles at companies like Amazon and Google. Perhaps you've heard of some of those on graduation. She actually started her career in investment banking in new york before getting bit by the startup bug. When she moved to Silicon Valley and joined a number of early in growth stage companies. She co founded a number of companies in the financial services, in the content or commerce space but also held long positions at google, where eventually she was the G. M. And a variety of roles and responsible for launching google maps and eventually leading google's international operations in asia, pacific and latin America. She sits on a number of public and private company boards, including urban outfitters and is the founder of the board list, an online marketplace to connect Ceo is looking for board candidates with highly qualified women who appear endorsed for board positions. In our conversation, we focused mainly on prioritization, how you decide what to focus on as an entrepreneur or an executive, what's the process for figuring that out and the differences in doing that at a startup versus a large company. So Kinder shares her outlook on entrepreneurial risk, offers advice for what path to choose out of school and gets into what it's really like to play at the highest level in Silicon Valley. Please enjoy this wide ranging conversation with Sue Kinder as well as this introduction, written and performed by students of my hustle and grit class enjoy. Remember, remember remember uh, wow, can I clap? You can, of course you can recorded that. Of course, of course, that is about that is truly the best welcome I have ever had anywhere. Guys. I am like, I'm sorry, That's so sweet. I freaking love it. Thank you. Isn't it a special group? Well, unless for this way, if you can write a song about me and with my weird name and my weird background, I'm like even more impressed, but that was really, really special. 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've got a million things on the go and a busy family and we appreciate you making a little bit time for us. Thank you. No worries. Like I said, you to quote a dumb movie line you had me at Hello. This awesome, awesome, Well this is, 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 of entrepreneurship, but this class is a little bit more of the softer skills, so we work a lot on personal development, keeping yourself Sane and stable all the while, doing very hard things. So I'd say that this is a very creative group and probably the most entrepreneurial ambitious group amongst the HB two, so you're looking at the future of people who are going to do some 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 team that introduced you did circulate a bio to the group. So they have a little bit of a back story but they didn't get into was sort of rewinding the tape even further back to your potentially entrepreneurial upbringing. I'm not sure if there's a correlation yet between parents that were entrepreneurs and then the kids becoming...

...entrepreneurs. I understand that your parents 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 you why. So, you know, I grew up in ST Catharines Ontario, my parents immigrated to Canada when I was two, so I grew up in Ontario and that's all I can really remember. And my parents both ran and ran a medical practice to give you guys some since my mom just turned 90 but she practiced medicine until she was about 83 years old. That was my mom, my dad and my mom ran a joint medical practice and he passed away unfortunately when he was 77 but he worked up until the day he died virtually speaking. So they ran a medical practice. But I think the story I was telling people, my dad just loved running a small business. So at like seven or eight years old when I say I was working for my dad and learning how to do his taxes. Like no joke. I was entering like ledger entries like tax tax time at my family was like, you know, way before excel or anything else. Like literally writing in a ledger. So I probably knew how to do my dad's taxes price time. I was 11 or 12. I wrote in my first, his first Excel spreadsheet when I was like 17 to be like, we're never writing hand ledgers again. And so I kind of saw him run a small business. But the thing I'd say to you is that he loved like as much as he loved being a doctor, he left running a small business. So he told me to work for myself, Obviously he wanted me to keep working for him. I think like how many of you know that if you would like to drive down the streets in Canada and the US right now you would see like walk in clinics, right? Like healthcare, like operators right there, these conglomerates that launch all of these 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 healthcare service centre because he imagined and then he bought a building and he wanted filled with a bunch of doctors and he was like probably 65 at the time because he thought that people should just be able to walk in off the street and get service any time. And so literally he bought a building, he thought he never filled it with many doctors. I think he felt like with one or two he created a brand. Like when we think about what happened in the medical medical profession, like my dad was on that a year, you know, years earlier and even though it never came to full fruition, like he was just always creative and I know, I think you guys probably know that being an entrepreneur is both the creative and an analytical exercise. So I watched all of that and then my favorite other story about my dad, which tells you how strongly 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. I think I was probably, you know, it was like I was before I went to Merrill Lynch and I came home and my dad had really bad eyesight. So again, you guys don'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. So my dad had terrible eyesight, you have this gigantic magnifying glass and he would literally look at all of the stock price listings in the paper and he 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 distinctly remember 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 think about 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 is AOL? And here's my dad, he was like in his early seventies and he's like taking swings at like nine stocks in the tech sector because you could just see all the possibility. And when he died many years later I was had to unfortunately go through his desk right at home. And again remember this guy's like in the seventies when I'm like training them how to do itself for his ledger and I would find through all of his George's, these different pages with passwords to different financial sites like the motley fool, you know the ST dot com, whatever, because he just kept setting up all these passwords, you just ingest as much information as he could from the internet even though is of course like not really his generation, so so like that is my enduring memory of how I...

...grew up and so obviously in hindsight I'm like of course I become an entrepreneur, but you know when you're going through it you don't really think right and then you're seeing it all by osmosis. So to answer your question, I firmly believe it. Yeah, so fast forward then. So you went to, went to Western, graduated from ivy but then didn't jump into it right away. And I think a lot of students in this class being probably the more entrepreneurial people at ivy are trying to make the decision. Like do I do this thing right away even, maybe I don't have the thing or do I go work somewhere else first? So you didn't jump right into it even though you have the entrepreneurial upbringing? Yeah. Well I think first of all, I'm sure all of you have this issue right? Which is what happens if you 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 of entrepreneurship is people who find each other and say let's go through, go through ideas right by the way, maybe if I had been grown up the same way you guys did, I would naturally think that, but when I was graduating, ivy was all about being a banker or consult and I'm sure there's at least half of your class that thinks that way. And for me, honestly, there was a period after I grew up where I didn't actually automatically want to be an entrepreneur, I want to have a big career, I didn't even know what that was. So I just followed my friends into wanting an investment banking or consulting 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't know what to do, I didn't have a great idea. So I moved to the valley and I ultimately, you know connected with people who do so I think path is you find a group of people, you brainstorm ideas and you go, now have B is you go start skill building, right? And then you put yourself in proximity to people and I don't think there's any wronger right answer, I will tell you that entrepreneurship happens when you're in proximity to people, even if you don't have the idea, you get approximately people who do and your brain storm, or it happens to your skill building and then going to do that, right, and either is OK, Like I look back at the training, I had a big companies like Meryl and Sky and I think that training was incredible because it taught me financial literacy and of course half of running the company is knowing how to actually make it profitable and you know, and knowing how to sell and all those things, but I didn't actually myself figure out how to be an entrepreneur until I picked up and moved to Silicon Valley, because I was like, I don't have an idea, but if I put myself proximate to people who are doing 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 anxiety that, like, you have to choose right now, I think if you find a cohort of people 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 learn a ton, but it is seven years, kind of 5 to 7 years before, you know, if your baby is going to be viable, you know, and so maybe you'll get lucky and maybe two or three, but that's really not often the case, so I do think that the process of entrepreneurship can unfold right away if you have a good idea, you can keep working your day job and working at night, you can put yourself in a startup and sometimes when you're in those environments, once you start learning something, you get ideas and I can certainly say that later in my career, I have lots of ideas for companies to start. In fact, many times I'm like, I should go higher, a whole crew of you and just like, Like go start 10 companies at once, because I don't have the energy to start 10 at once, but I certainly have the ideas for it, but early on, when I knew nothing, I really didn't have a good idea, you know, like just to sit in your 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, I think 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 of people who are brainstorming and you know, putting a bunch of ideas up against a litmus test. So I don't think there's any wrong answer, careful what you wish for us to kenya, you got a bunch of really engaged people here that might take you up, try to take you up on that offer. So I swear to God, I do often think about starting a venture...

...studio, which is the model where you basically say, okay, how do you run 10 ideas at once? The problem is, I'm also thinking about what my own next day job is and you can't do all of these things at once, but it occurs to me certainly. Yeah, so, um, your early career in the after Merrill was in sort of made a name for yourself on the business development side. Um I came back to ivy to start a sales program. That's why I'm here. That doesn't launch until january. So a lot of people, I'm surprised they don't know the words business development, customer success, account management, account executive, they don't even know what that is. So you made a name for yourself in doing business development for some early and growth stage companies. Can you unpack that? What does that mean? What did you do? Sure. So, so it's effectively glorified sales, right? But let me be super clear biz DEv is selling something that hasn't been structured yet. It's basically going out and having conversations to figure out what people want and making up as you go, a product that services their needs, right. Business development is also partnerships often where like maybe you do know what the product is, but you're selling very strategically and it's not straight up revenue, but business development either leads to a career in sales where you're like, hey, I'm used to being on the hook for revenue. But the different defining factor is if the product isn't structured yet, you call it business development and then once it's like systematized, you call it sales 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, which per se are not quota filling jobs, but they are still designed to drive nonlinear economic value, right? Usually distribution or something else. So you're either driving customers or you're driving dollars, that's typically what business is about, right? You're trying to do partnerships that open up markets or you're trying to actually literally sell something. How did you find yourself in that? Is that is that a common path from either banking or consulting? Getting into an earlier growth stage company and joining in a sales role? Is that a common path for people that this step is certainly been steppin sales are both common and I would say two things to you. So in some ways sales is easier. So let's say one of you guys wanted to go, we hardly one day and running Shopify, you know, or start the next Shopify if you went into a SAS company straight into sales, like literally like I'm going to figure out how to sell the software product to big companies. That's a path to become a ceo of a technology company that sells to other companies. Right? So often if you have technology companies that sell to consumers, it's about marketing, right? It's about literally can you get a customer off google at a good enough price and happen by something on your site. But when you have a software company, you're typically selling to businesses, right? Either smaller, big, often the heart of that company, if it's not engineering its sales, it's straight up like, can you deliver revenue? So if any of, you know the company Cisco, it's run by a sales, God right. Or it was john chambers, if you guys know salesforce, it's run by a sales, got marc Benioff knows how to sell better than anybody else. So it's very possible that sales can also lead to the Ceo suite biz DMB is slightly different in that it requires more creativity. Like you literally have to be willing to figure out what it is to sell. and typically this DEV is um is also a path where people kind of consulting or investment banking because it's like a fuzzy or title and it has some sense of strategy, but I will tell you like I wouldn't necessarily, in your mind say, gosh, this dad must be more elevated themselves because if you know how to bring in the money, you are always in demand, if you know how to create partnerships, but you can't really prove that they have value. It doesn't matter how strategic you are. Like does that make sense? So like, so I think that when you guys think about it, this is a common path in, I came out of investment banking, so my first job was busy to have, well I was an analyst at Sky and then I went into this job and it is an entry path, so it's sales and like I said, I think the difference is...

...really like feeling very uncomfortable with like having to structure something versus already knowing what the thing is that you're selling. Yeah, that's funny. The hires that I've made out of ivy 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 can I have the title of business development and it definitely has to be either manager or director, even if you're not managing or directing anybody. People love the business development title because it sounds so much cooler and again, like don't get me wrong, I love business development and sales. I like them both. I think the most powerful business development people, whether whatever you call them are not afraid of knowing that they have to bring in the money. that sounds like if you just want to do cool partnerships instead of have the fuzzily measured, it's not a great track 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 sort of went like not smaller companies, but like structure, maybe a little bit less structure, maybe a little bit more structure and sort of bounced back and forth. But then did a pretty like a longish stint at google, I think almost six years. Can you compare and contrast the differences between say, start up and scale up, you know, like the, the early days at british sky or your belly and versus how was it joining amazon or google that sort of had some of that structure already. Yeah, sure. And I think again, the other thing for you, all to think about is they're all entrepreneurial. You know, when you think about people think well off I go to a growth company, it's not entrepreneurial. I mean I joined google was 1112 100 people and I exited when it was at 40,000 including contractors right now, it's like 100 over 100,000 employees, maybe even close to 200,000, right? I was in amazon when it was 1000 people when it's now, I don't know, probably two million people including the people in the warehouse. So, but I mean in your head office and so just be clear 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, 15 people. That's very hard to be, you don't spend a lot of time educating people on why something needs to happen, right? Like information travels very fast. But the volatility of that experience is really high, like, you know, I mean, people always talk about it, so people sort of think, well if I go to a startup and have the best experience, maybe not because the volatility all goes with the founder, so if you're not the founder, so if you're the founder, everybody is going to be responding to you and how volatile you are, which makes for a really rocky experience. And if you're working for another founder, right? And somebody in their company, it's all about how good or bad that founder is in the day to day running of the company because it's already a volatile experience. You don't know if you're going 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're having a really vulnerable experience, it can be really fun or really exhausting and you want and it's fun if it's growing, but even if it's not growing, it's fun. If you're going through the process of innovation with people you really love, like you're figuring it out every day before you know what you've created a product and you're like, how did that happen? Like you look back after you and you're like, wow, we did that. Whether it fails to succeed, you feel this level of pride, but it's very volatile with the people you work with. The benefit of a scale up is by the time you have product market fit and something is growing fast, here's what happens. It attracts a quality people so you look around and everybody is uniformly, like not uniformly, but they tend to be really super talented people. So like when I look at the people I was with the amazon and google with like those are people who are like holy smokes, like these are smart people and that's because for a lot of the smartest people, the level of risk in a startup scares them. So they wait until it's probably as product market fit, so then they're going into the job is scaling but they don't have any of the highs and lows of like whether or not the...

...thing is going to work. So you miss out on that process of creation somewhat. But you enter in an environment where you can still grow and learn pretty fast and the quality of the people as it keeps attracting better and better people because once you have like momentum, it's a lot easier to recruit like great talent. Now look, I've been lucky 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 totally enjoy us and Polyvore even in the board list certainly, which is just starting and I'm really proud of it, but it's really quite hard to hire amazing talent at a startup because you know, people like people have choices. They don't always want to take that level of risk. So today's class, we, the setup was talking about how to set priorities. We talked a little bit about doing it in your business and in your life and then talked about habits. And I think in my experience as an entrepreneur sort of learning how to set the right priorities is actually really hard. It's easy to say right, have few priorities and have the, the object and the key results that lead up to the, to the objectives. And I think the class is kind of like taking good notes, but like okay, but like how does that really play out? So we talked about the what objectives, key results, sort of having, having priorities is important. We talked about why that's important in getting alignment across the whole company, but I'd love to dig into the how so how did you having done it at a bunch of different sized companies? How do you think about what to spend your time, resources money on? Yeah. You know, it's a great question and no matter what people say, it's really hard because if you just think about a startup at a minimum, you have two problems, supply of any product, reserves and demand. And no matter what you say, any product or service is ultimately a marketplace, right? You're bringing something to market and you want enough people to buy it. So at a startup you like, right To facto, you have neither side. So even though people are like, well, you know, prioritized, you're like, well, you have neither side get both it up so that 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 have all looked at johN doors, okay, ours. I will say a couple of things that have been helpful to me number one, just on the, okay, our process. I think a, how do you do it? First of all, you have to do it at least quarterly. If not, you know, and you always presume that in a 10 person company people know how to prioritize. But as you guys can probably tell the most interesting exercise you can go through and okay, ours is not generating perfect slides and lots of ideas. It's in picking right? So I would just say when you do okay RS. First of all, I think okay ours are really essential. Even at a startup number two, when you do okay, RS don't underestimate the value. Even if you've accompanied five people even doing it. Because what forces is that discussion? Because what people do is they'll throw everything out. Like when you 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 and everybody wants to list everything. So first of all, just the process of listing everything is useful. But the most valuable process is what you call the edit, like how you gonna slam this down into like three or five things. So first of all, you have to constrain yourself 2, 3 or five things and number two, I would just say constrain yourself and spending weeks on listing everything. Because I think the most valuable thing you can do is ask people to like list there everything's and then come into a room and literally say we've an hour, like we're gonna leave here with like the top three things this quarter. And it's useful when you do it with five people. It's useful when you do a 500. It's useful when you do with 5000. So I would just say forcing the discipline of the end because what everybody does in setting priorities is exactly what you mentioned. They do the beginning, everybody obsesses about listing everything that needs to get done. You know where the value is, All the value is in like Of all the shit we just put up on the board, literally what are the...

...three things that need to get done? And it's amazing that whether, as I said, whether you're five people doing okay RS or 15 or 20 people just throw up a lot of stuff. The converse is you can just say we'll just go top down and you know, to be honest, sometimes top down when you're starting like works like literally you're like, hey, you have the founder that you got to like say like, hey guys use the three things we need to get done and you say how, I mean, look at the end of the day, I would just say that in any two sided demand supply equation, it is likely that you need one side of it more than the other to jump start, right? So when you're saying, hey, how do you pay to service people want from zero? It is typically true that you're going to have to spend some amount of time just constructing the supply side, the value equation, the product, the prototype, you know, if you're aggregating something like all the supply relationships. But I think what people do too often in prioritizing in and in a startup is they spend more and more and more time perfecting the supply. Oh we have 10 people will really before we can ever like see people want, we need 15 oh we have this minimum viable product before we ever put it up on the internet, you know? And start driving adds to it. We really need to spend another nine months perfecting it. So if there is an A I think a risk in setting your early, okay ours, it's that people want to keep perfecting supply, you know why? Because it's very known and you're like, well the product should look like this and then look at but they spend all their time baking in their head what the customer wants. So the only thing I would tell you is in prioritizing starting a company, you both a need to spend more time on the edit of people's okay rs and the okay ours themselves top down or bottom is up, constraining yourself to like throwing up a white board version because it's the whiteboard version that people can actually remember and then number two, just be careful that if you choose to prioritize the supply side of any equation, all you're doing is delaying the really other valuable work, which is like, well people bite on what I'm putting together so people want to endlessly cycle on the offering and I'm like get to the minimum bible offering and then spend a lot of time cycling like their demand. It there's a risk and priorities prioritizing. It's people to prioritize supply because it's more understood. The most scary thing is how to get demand for your product, but it's the most value. It's almost like you could solidify two of the buckets in the, the objective side for early in growth stage companies in my opinion, like there's always going to be a building like you need a product to sell, always going to be a selling building selling. There are other things of course, but the building and selling I think are going to be the 22 of the priorities all the time, all the time. But I think they're always 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% building 30% selling. I'm sort of like, you kind of can be 50 50 for, you can be 70 30 on building, but then you better flips to a minimum 50 50 maybe even arguably 60 40 because otherwise you're just building in a vacuum and you're chewing up 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 like just make a better and better thing. Right? I want to make it better and better 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 piece of hardware. I want to make it better, better game, but you just need to have enough to know if people will one. My wife calls it playing business. She always calls me on it. You know, like I could, I could Finnic forever. On the landing page isn't perfect. And I don't, we need some more, we need actually really, really need to redo the logo and she'll say you're done playing business now it's time to go. So she gives me the kick in the ass to go. So is that, was that your role then as when you get into the more senior leadership at technology companies, uh, stay StubHub as an example was your role when assuming I think you still did, you said you did okay are as your role was to then everybody sort of...

...rolls up their priorities to you. And then did you pick them or did you just say you need to pick, let's let's decide this in this room. What's interesting? I think that I think when you prioritize as you get more senior in the company gets bigger, first of all, your first inclination is to go bottoms up because you want everybody to feel included. The problem with going bottoms up is you end up with 100 page tax, which I often did when okay our processes. I'm sure they're beautiful. They're beautiful. Dex. Oh my God. And especially when you're the Ceo 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 leadership team which is our managers and our directors and RVP. So like I want to see 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 consumer seller business. So I would say a couple of things, I'd say number one at first I did bottoms up to see everything and you quickly find that that's inefficient. And then what happens is you honestly, you take your leadership team and you lock yourself in the room and you're like let's edit like literally right? And then you learn that if you really want people to focus, you need to give them a high level bucket ng like these are rough priorities, right? Like the and then within that now constructor, okay ours and that's probably a good reasonable P. O. V. And you know, you can do that from saying this is this year's five strategies and then you're like okay guys, as you set up your okay ours, they need to fit within these strategies, right? You give people some guidance and then probably the most efficient is literally you give people a very limited template and you're literally like, and that's how we ended up with in the end. I'm like you have one page to dok ours, that's it. And you want to end like and we took the okay our process from like three days and hundreds of pages, two days and hundreds of pages because everybody wants to present their okay ours and like everybody wants to present, everybody wants to be heard to like a skinny template that we finished in two hours as 100 people. And then, and you know, so you sort of impose a structure and then people have to fit within and then you have an edit to do, but it's much, it's much simpler. So that's the setting 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 then adjust 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 or weekly or monthly, but typically the daily things that change in our business was like ticket sales, right? So like you have automated daily metrics and then there's certain metrics that are only going to move longer term, like bigger product ideas or initiatives are not going to move daily, write any new business is not moving daily so tiny. So we would have a mid quarter check in where we looked at the numbers mid quarter and then end of quarter we would look at the numbers and the qualitative results. Has that changed 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 time into it, but the board list, you know, the board list, I think if I look at the timing, you started that well you were at StubHub, correct while I was at joyous, but it really, I didn't hire Ceo until I was at StubHub because I didn't know what I wanted it to be. Did your process change at all? Whether you were in it full time, like at joyous or at StubHub or in it probably equivalent another full time job. But you know, it wasn't your soul, it wasn't your day to day. Well I would say I'd say the benefit of having it be my side hustle or 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 the benefit 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 really important because you know, the challenge when you're ceo or any anything is that you see it all and you think it's all important and sometimes it takes stepping out of something and looking back to be like, what are the things we need to get done? So I would say when it's a side hustle, I get the more fun job of being the editor of the edit, which is like being the push from top down, right, like look like which of this stuff is going to matter. So we're just putting in okay ours at the board list and he has a great ceo but we it's not public yet, but we just raised our seed round of funding after because I bootstrapped it to this point.

And so now, like we finally have like the equivalent of 10 people at the company. So now I'm like, ok, so we like yesterday we did our first strategy session that we've ever done with all 10 as opposed to just me in the Ceo. And we're like, okay guys, how do we said, okay, here is for 2021 okay, I was for Q four were set by her her and I talked, she set Q. Four, okay ours for everybody. And then and then for Q one were like let's bring everybody together, have a discussion and then she'll set the okay ours because it's appropriate. She's like everybody got a chance to weigh in. We didn't really succinctly and now she's going to set okay. Rs and everybody's aligned because we did the conversation so I'm sure the version of okay ours will be much simpler. But it's still the same principle which is like give people a chance to end a voice in a very efficient period. The only thing I'll say about okay are is is that you can't create a drawn out period. People will just expand the work to engulf it and the results are no better than if you did it in an hour. You can take three weeks, you can take three hours. I bet you the results not going to be much better. Time box it half the time box you have to time box priority setting. Otherwise people just obsess and pull more data. Perfect deck, Perfect deck. More bullet points, more detail around each. Okay. I'm like, it doesn't really matter. Yeah, I want to shift gears a little bit and get your perspective on something. Um we had a heated say, heated debate, but we had a good debate, good conversation around going like hell when you're young to set yourself up and trying to establish or set up some semblance of balance. And I think we've had people on both. I've had perspectives from both. So we talked about Jason freed from 37 signals. You know, doesn't have to be crazy at work. And we talked about, there was an article from scott Galloway who give up your twenties and thirties so that you establish some professional trajectory and that is that that allows you freedom later on in your career. Are you strongly in one camp or the other? Okay. I'll tell you what I believe and then I guess my family would say so we're pretty hard but I do believe I've got a lot of freedom than how I work now. Like a lot right? So ironically the bigger the company that you're running, the less freedom you have because you're beholden to time zones and everybody else's schedule and thousands of people who depend on you. So ironically being an entrepreneur, although it's much more mentally taxing, you have way more freedom than you do as a large scale see away because you can just you know like you can just time bound how you want to spend your time and your not yet they to like all of these like everything that's put upon you by like a really large scale infrastructure just quickly there. So you, you think if 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 the President of stubborn for sure. I mean if you like to be, you know, because it's StubHub and of course like Covid has changed everything, let's all agree on that. But it's StubHub, I've got to see customers like and you know it all like I have to go see our international offices, I have to pick time zones that like our china engineering team and me and Madrid can all be on. And if I'm the Ceo and I'm like, hey and I, and I actually just see who believes you show up. Like you have to show up and feel connected to your employees so like what 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 of that infrastructure is related to international for sure because everything, everything I've run, it's Vegas and international, so that's a big part of it. But it's also just customers and like what works for everyone. The benefit when you start up, is that what works for you and your 20 people like, you know, and a lot of that cycle time that spent on management and communication, it just goes away. Yeah. So I just think there's a lot of freedom in how you work even though you work as hard. So Yeah. Do I believe that you power in your twenties and thirties? Sure. Do I believe that my family would still say I power in my forties and fifties? And they're like uh like what the hell? Like shouldn't you be you know, toning it down? I probably like I'd say my...

...family complaints, I probably should tone it down now to Yeah, for sure, because I think that we're only momentum creates compounding returns. If I asked you guys all like, okay, do you want to start saving when you're 40? You're saving when you're 20? Everybody knows the answer. So if you want to put into the bank, like the more you cycle in your twenties and thirties, the more career capital your building, Right? So I mean at google, I was the president by the time I was 35. Like, well actually no, that was a vice president by the time it was like one of the top 10 people in the company. So like by the time I had my first child, I was 36 I didn't delay it, by the way, I wasn't like, hey, I'm not going to have a kid because 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 the world with me and google said yes, because at that point I had enough career capital that like the thought of losing me. So I had a lot of negotiating power in my later career. So I think that's what you get right when you power in your 20s and 30s. But conversely, I mean look at the woman who just became the first president or the first ceo of a major global financial institution jane fraser at Citibank. She chose to be part time for many, many, many years as a partner at Mckinsey while everybody like sped right pastor so that she could have time with her kids. You know what like that was a pretty good trade off. She's now, you know, she got to the ceo suite of a major global financial system faster than any and the first of all women and she took a completely alternate career path, including slowing down when she needed to for her kids the same thing with the ceo of sara lee. So I just don't think you can say if you start off slow, you're not going to make it. That's not my point. But I think that when you put a lot in the bank, when you have a lot of freedom personally, it does give you more negotiating capital when you hit the parts in your career where maybe you really need the flexibility to make a different choice. So let's put this way, she was able to be a part time partner at mckinsey because she was a partner, You know, I was able to say to google, you're gonna pay for my daughter 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 needed it. I doubt it. Yeah. So then we, we just finished an activity before you came in on on habits and trying to establish some habits over the next few weeks to keep people, it's a busy time for students, you know, exams coming into the right before the holiday. So like what are some habits that are going to keep you good as a person? So what, what did you find kept you your family, your like, what, what systems, what habits did you set up to keep you a whole human throughout the craziness? So first of all, I am fairly all or nothing as you can probably tell. So like people think I have a hard time zoning out, but I actually really don't because by the time I'm done my day and you know, unfortunately, covid you think it be Better, but once you've been on zoom multi, you feel tired in a different way than we've been right interacting with people. So my days were longer at StubHub or see you. But right now by 5:00 I've had like 10 scenes and I'm done. But I would say when 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. Like I've resisted scheduling my kids because it's the two days of the week where like we can all roll out of bed and I'm not like, I don't want to panic to take them to five practices. So when I switch off, I switch up, I feel no guilt 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 I think I'm very binary, like what I'm off, I'm off and when I'm on I'm on and I feel no guilt if like, you know, someone can't get a hold of me, that's probably one of the biggest ones. Number two, I have no problem with indulgences 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'm happy to just shop because it's one of the very few things that like, I just don't think about anything I've binge watched, like I do all, I have all the students, all of you guys do right, and I think you have to go to whatever the thing is that turns your mind off. Some people are like, well, turn off your device. 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 not overscheduling the rest of my life, so I'm kind of happy to not have it over schedule because so much of my life is number two, like, like I indulge, like I'm like, why not? But I indulge in the things that switch my mind off. And then of course I have lots of loves that. I'm sure many of you guys do. I love 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 else does that are really fun to do and I try and do them, but I wouldn't say like, I'm like, you know, I love to work. I love my kids. I love to switch my brain off and I'm quite happy moving between those three things. Like maybe other 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, I find people that are maybe more established or performing at a high level do a really good job of eliminating the gray. They're either in it or they're not, they're not like half here while checking their phone while 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 on myself. Like for sure there are times I'm always checking, you know, make no mistake. I'm just saying if I say to people, I'm off of email, I'm happy to be off. Like if I go on vacation, I'm like, if I'm going to ITaly, I'm not the 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 checking and I will not check, right? So, but obviously other times I'm checking, I am much more like if this has no value for me, like I have no need to prove that, you know, I don't care about, like I'm the one who keeps my house clean, I could care less. I mean if I can outsource it, I will and the only thing I really feel guilty about is my Children, right? If like, but I don't feel any guilt about like if some, you know, if somebody else has done there laundry or whatever, I'm like, okay, yeah, I don't want to do it like, so I think for the things I don't want to do, I'm like, yeah, it's okay. I'm not trying to be super mom. I think that would be very difficult and already I feel guilt for the things I don't do, so I don't even feel guilty about, I guess 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 or things that we should be focusing on more that we're not today. How can we better prepare these people to be effective either as entrepreneurs or to join early stage companies? Well look, I I have this thesis that people have a very mythical relationship between risk and reward. I'll say to people like you understand it's called the risk for a reason. So if you're going into entrepreneurship of course you should aim and think before I get that, that's what motivates me. But if you think that the reward for risk is only the reward, I think that's a very flawed perception of risk. I think people move through the world thinking risk is binary thinking it's all or nothing if it's all or nothing if I don't have a perfect idea, I shouldn't go leave aside the fact. I think you should have ambition enough in doing ambition for your idea, right? And so I think the people of this very mythical notion of risk and reward, including entrepreneurs and like I wouldn't say don't have it because it's what gets you in. But I think that understanding that you know, risk and reward will unfold over many cycles and it's going to take more moves than you realize to get the ultimate reward. And sometimes you won't even be able to correlate the...

...ultimate reward to the original risk you took. And so I think it's fine to enter with this binary, Like I'm going to take this because I want to be a billionaire, but pretty soon you realize that you know, it's called risk for a reason. It doesn't always work out and it's still going to work out even if it doesn't always work out. So you want people to have enough kind of love and ambition to enter it. But I think you also want to be careful that you don't think it's this binary, large gigantic thing, which is all or nothing and thus you never do it. Any advice to sue kinder if she was graduating from HP two things that you wish you would have 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 whether it fails or succeeds. If you're with tremendous people, you're likely to have a tremendous experience. And one that will pay back multiple ways. And I think the other caution is like trying to go where you don't fit is also, you know, I felt like I spent so much time and I'd be wondering why all my friends were getting the Goldman Sachs job or the Mckinsey offer and I couldn't, you know, 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 super aggressive, it was right. It was like everything that I am, it's no surprise to me now, but that's why I ended up of all the banks and right because it's sort of where I fit in where it was easy. So sometimes I think we think things 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 because who 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 to do with having a great experience than just what you're working on. Great and thanks for being open to tender. I think um the team that introduced you wanted to say a few words before we let you go, thank you scandal for joining us today. I'm sure we have the class has learned a lot from your valuable advice and stories. So to thank you for your time and appreciate your inspiration to future female entrepreneurs. We have donated $40 to the Canadian women's foundation, your name and the family aims to empower women and young women are funding various programs across Canada. So thank you again for your time. Well, thanks for doing that and thanks for the amazing song. I can't wait for somebody to send it to me so I can listen to it again. I will absolutely send it to you sir. Kinder thank you so much 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 sponsored by Quantum shift 2000 and eight alum, Connie, clarity and closing the gap Healthcare group to ensure you never miss an episode. Subscribe to the show on your favorite podcast player or visit entrepreneurship dot u w o dot c a slash podcast. Thank you so much for listening. Until next time. Mhm.

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