Subscribe
Details
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).
The Entrepreneur Podcast is sponsored by Connie Clerici, QS ’08, and Closing the Gap Healthcare Group, Inc.
Transcript
SPEAKERS
Eric Janssen, HBA ’09, MBA ’20
Sukhinder Singh Cassidy, HBA ’92
Introduction:
You are listening to the Entrepreneur Podcast from the Western Morrissette Institute for Entrepreneurship Powered by Ivey.
In this series, Ivey entrepreneur and Ivey faculty member Eric Janssen will anchor the session.
Eric Janssen
Sukhinder Singh 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. Most while known for her most recent role as the President of StubHub of until 2020 but is also held a number of senior roles at companies like Amazon and Google perhaps you've heard of some of those On graduations she actually started her career in investment banking in New York before getting bit by the startup bug when she moved to Silicon Valley enjoyed 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 GM 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 as the founder of the board list an online marketplace to connect CEOs looking for board candidates with highly qualified women who are peer endorsed for board positions. In our conversation we focus mainly on preserve prioritization how you decide what to focus on as an entrepreneur or an executive what's the process for figuring that out in the differences in doing that at a startup versus a large company.
So can your shares are 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 Sukhinder as well as this introduction written and performed by students of my Hustle & Grit class. Enjoy.
(Music Playing) Sukhinder. That is her name. It’s a name we will remember for the rest of our days. It’s a name we will remember for the rest of our days.
Sukhinder
Wow, can I clap?
Eric
Yes, you can? Of course you can.
Sukhinder
Could you please tell me who recorded that?
Eric
Of course. Yeah.
Sukhinder
That is about that is truly the best welcome I have ever had, anywhere guys. I am like I'm saying it's so sweet. I freakin love it. Thank you.
Eric
Isn't it a special group?
Sukhinder
Well, let's put it this way, if you can write a song about me 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.
Eric
Yeah, they're great. This is. So this class, we can... 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 of time for us. Thank you.
Sukhinder
No worries, like I said you, to quote a dumb Movie Line “You had me at hello.”
Eric
Awesome, awesome. Well, this is.. to 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 thing. So I'd say that this is a very creative group, and probably the most entrepreneurial ambitious group amongst the HBA 2. So you're looking at the future of people who are going to do some pretty big things.
Sukhinder
I love it. That's awesome. Good to meet all of you.
Eric
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 backstory, 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.
Sukhinder
Yeah. Well, I happen to believe there is a big correlation. And I'll tell you why. So for you know, I grew up in St. Catharines, Ontario. My parents emigrated 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 sense, my mom just turned 90, but she practiced medicine until she was about 83 years old. That was 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. And so so they ran a medical practice. But I think the story I always tell people is 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 taxes, 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 when 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 Ledger's again. And so I kind of saw him write write a small business. But the thing I'd say to you is that he loves like, as much as you love being a doctor, he loves 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 were like to drive down the streets in Canada or the us right now you would see like, walk in clinics, right? I like health care, like operators right there, these conglomerates that lodge 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 center, because he imagined and then he bought a building, and he want to fill it 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 it off the street and get service anytime. And so literally, he bought a building, he thought he never filled it with many doctors, I think he filled it like with one or two. He created a brand like, like when we think about what happened in the medical medical professional, 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 a creative and an analytical exercise. So I watched all of that. And then my favorite other story about my dad, which tells you why 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 If 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 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. He had this gigantic magnifying glass and he would literally look at all of the stock price listings in the paper. And he even calls his broker every morning what this like jovial laugh, he's like, hey, Tom, let's buy XYZ because he loved trading stocks. And I like distinctly remember a long before I knew what tech was, it was probably like 1992, maybe 1990. My dad like called 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 AOL. And I remember the time being like, What the hell was AOL? And here's my dad, he was like, in his early 70s. And he's like taking swings at like buying stocks in the tech sector, because you could just see all the possibility. And then 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 his 70s, when I'm like, training him how to do Excel for his ledger. And I would find to all his drawers these different pages with passwords to different financial sites, like the Motley Fool, you know, the street.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 it was a 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'd become an entrepreneur. But you know, when you're going through it, you don't really think Yeah, right. And then you're seeing it all by osmosis. So to answer your question, I firmly believe that,
Eric
yeah, and so fast forward, then. So you went to went to Western graduated from Ivey, 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 Ivey, are trying to make the decision like, do I do the thing right away? Even if maybe I don't have the thing? Or do I go work somewhere else for so you didn't jump right into it? Even though you had the entrepreneurial upbringing?
Sukhinder
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 and group together and obviously some of entrepreneurship is people will find each other and say, let's grow, go through ideas, right? They would maybe if I had been grown up the same way you guys did, I would naturally think that. But when I was graduating, it was all about being a banker, or consultants. 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 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, and I got one and then about four or five years later, I mean, I was in my mid 20s, 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 a is you find a group of people, you brainstorm ideas, and you go now, how 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 wrong or 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 proximate with people who do and you brainstorm, or it happens to skill building and then going to do that, right. And either is okay, like, I look back at the training I had at big companies like Merrill, and sky. And I think that training was incredible, because it taught me financial literacy. And of course, half of running a 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 into 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 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 five to seven years before you know if your baby is going to be viable. You know, and so maybe you'll get lucky, it'll be 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 work 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 hire a whole crew view 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 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'd be training for entrepreneurship, I think the hurdle rate for an idea, isn't it, 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.
Eric
Careful what you wish for Sukhinder. You got a bunch of really engaged people here that might take you up, try to take you up on that offer. So...
Sukhinder
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 know, you can't do all of these things at once. But it occurs to me, certainly. So yeah.
Eric
So you say your early career in the after Merrill was in sort of made a name for yourself on the business development side. We I actually, I came back to Ivey to start a sales program. That's why I'm here. So but that doesn't launch until January. So a lot of people it's 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?
Sukhinder
Sure. So for those of you that, 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, or 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 biz dev is about, right? You're trying to do partnerships that open up markets, or you're trying to actually literally sell something.
Eric
So you started, 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?
Sukhinder
Yes, certainly biz dev and 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, you know, be Harley one day and run Shopify, you know, or start the next Shopify. You know, if you went into a sass company straight into sales, like literally, like, I'm going to figure out how to sell this software product to big companies. I mean, that's how a lot of that's the 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 then have them buy something on your site. But when you have a software company, you're typically selling to businesses, right? Either small or 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 guy, right door was john chambers. If you guys know Salesforce, it's run by a sales guy, 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 Dev 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, biz dev is, is also a path where people come out 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, bizdev must be more elevated than sales. 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 add 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 biz dev is a common path in I came out of investment banking. So my first job was Biz Dev, while I was an analyst at Sky and then I went into Biz Dev, and it is an entry path. So it's sales. And like I said, I think 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.
Eric
Yeah, that's funny. The hires that I've made out of Ivey have always when I offered the job of account executive, it's like, yeah, now I understand the job description. And I'm good with all of that. But can I have the title business development, and it definitely has to be their manager or director, even if you're not managing or directing anybody.
Sukhinder
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 you whatever you call them are not afraid, that of knowing that they have to bring in the money. Does that make sense? Like if you just want to do cool partnerships, instead of having to buzzle we measured? It's not a great track record for biz dev either.
Eric
Yeah. So you went from investment banking British Sky, Amazon, sort of into a startup and then to 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 structured sort of bounce back and forth. But then did a pretty like a long ish stint at Google, I think, almost six years. Can you like compare and contrast the differences between, like, say, startup and scale up? You know, like, the early days that British Sky or YODL? And versus how was it joining Amazon or Google that sort of had some of that structure already?
Sukhinder
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, if I go to a growth company, it's not entrepreneurial. I mean, I joined Google was 1100-1200 people, and I exited what it was 40,000 including contractors right now. It's like 100, and over 100,000 employees, maybe even close to 200,000. Right, I was an Amazon when it was 1000 people, and it's now I don't know, probably 2 million people, including the people in the warehouse. So but I mean, a head office. And so just to be clear, like they're all entrepreneurial journeys, But to answer your question, I'm, like, 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 1215 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, right? 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 founders, if you're the founder, everybody's gonna 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 is Sunday 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 volatile experience, it can be really fun, or really exhausting. And you want it 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 everyday like before, you know, you've created a product and you're like, how did that happen? Like, you look back into you, and you're like, wow, we did that, whether it fails or succeeds 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 looked at the people I was with the Amazon and Google 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 they 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 us, including my own, we recruited phenomenal talent, like I look back at the knee but yo really 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.
Eric
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 you As an entrepreneur, sort of learning how to set the right priorities is actually really hard. It's easy to say, right, have a 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, 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 at having done it at a bunch of different sized companies? How do you think about what to spend your time, resources, money on?
Sukhinder
Yeah, to 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 or service 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, de 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 okrs (Objectives and key results), I will say a couple of things that have been helpful to me. Number one, just on the OKR process, you know, I think a you know, how do you do it? First of all, you have to do it at least quarterly. If not, you know when 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 okrs is not generating perfect slides and lots of ideas. It's in picking, right. So I would just say when you do okrs. First of all, I think okrs are really essential even at a start up. Number two, when you do okrs, don't underestimate the value even if you've accompany five people even doing it because what forces is that discussion, because what what people will do is they'll throw everything out up like when you say do okrs, even at StubHub when I did them, people create decks, right, people have decks of okrs. And then the end of it, you're like what, like, 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 slim this down into like three or five things. So first of all, you have to constrain yourself to three 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 listen to everything. So then come into a room and literally say we've an hour like we'll 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 it 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 all 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 okrs, or 15, or 20, people just throw up a lot of stuff. The converse is you could 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've got like say like, Hey guys, these are 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 any two sided demand supply equation, it is likely that you need one side of it more than the other to jumpstart, right. So when you're saying, hey, how to 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 and not in a startup is they spend more and more time perfecting the supply. Oh, we have 10 people will really need before we can ever like see if people want it, we need 15 Oh, like we have this minimum viable product. But before we ever put it up on the internet, you know and start driving ads to it, we really need to spend another nine months perfecting it. So if there is an IT, I think a risk in setting your early okrs it's that people want to keep perfecting supply. You know why? Because it's very No, you're like well, the product should look like this and then look at but they spend all their time thinking 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 okrs and the okrs themselves top down and bottoms up constrain yourself to like throwing up a whiteboard 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 bad other valuable work, which is like a will people bite on what I'm putting together. So people want to endlessly cycle on the offering. And I'm like, Huh, get to the minimum viable offering. And instead a lot of time cycling, like their demand is a risk and prioritization, prioritizing, it's the people 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,
Eric
it's almost like you could solidify two of the buckets in the on the objective side for early stage companies, in my opinion, like, there's always going to be a building, like you need a product to sell, there's always going to be a selling, like building selling, there are other things, of course, but the building and selling I think are going to be the to two of the priorities all the time.
Sukhinder
Yeah, all the time. But I think they're always gonna be the 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, right, I'm sort of like, you kind of can be 50/50 for a while 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 what you're 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 put make it better and better like piece of hardware, I want to make it better, better game, like it's a kind of you just need to have enough to know people will want.
Eric
My wife calls it playing business, she always calls me on it, you know, like I could, I could Finnick forever on the landing pages and perfect. And I don't know, we need some more we need Actually, we 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, say StubHub as an example, was your role when assuming the I think you still did you said you did? Okay, ours, 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?
Sukhinder
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, right? Because you want everybody to feel included. The problem with going bottoms up is you end up with 100 page decks, which I often did when Okay, our processes...
Eric
I’m sure, they're beautiful, though, beautiful decks,
Sure, they're
Oh my god, and especially when you're the CEO, and everybody and we would do ours each quarter. So then, you know, you're bringing to I bought, I have what's called an extended leadership team, which was our managers and our directors and our VP, so if like, I want to see all the people who are holding major parts of the business, right, whether 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, right. And then what happens is, you honestly, you take your leadership team, and you lock yourself in the room, 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 bucketing, like these are rough priorities, right? Like the and then within that now construct your okrs. And that's probably a good, reasonable POV. And you know, you can do that from saying this is this yours, five strategies, and then you're like, Okay, guys, as you set up your okrs, they need to fit within these strategies, right to give people some guidance. And then the probably the most efficient is literally give people a very limited template. And you're literally like, and that's what we ended up with. In the end, I'm like, you have one page to do your okrs. That's it, and you want to end like, and we took the OKR process from like three days and hundreds of pages two days in hundreds of pages, because everybody wants to present their okrs I'm 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 it. And then you have an edit to do but it's much it's much simpler.
Eric
And then how do you so that's that's the setting of them? How did you What was your process to track it? Was it like weekly quarterly syncs? How did you make sure that you were staying on track and then adjust course?
Sukhinder
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. They're not going to move daily, right. Any new business is not moving daily. It's 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.
Eric
Yeah. Has that changed in whether it's your full time job like StubHub or whether it's you're not gonna call the side hustle? Because I know you put a lot of time into it. But the board list, you know, the board lists, I think, if I looked at the time, and you started that while you were at StubHub, correct.
Sukhinder
And while I was at join us, but it really I didn't hire CEO until I was at StubHub, because I didn't know what I wanted it to be.
Eric
Got it. So did you use did your process change at all, whether you were in it full time, like a Joyus or at StubHub or in it, you know, probably the equivalent of another full time job, but you know, it wasn't your sole, it wasn't your day to day?
Sukhinder
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 but the board list is more, it's my baby. So of course, you can even more than a board I'm on. Um, I think the benefit when you don't run it every day and somebody else does is you can be the 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 in or anything, 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 Edit of the Edit, which is like and being the push from top down, right? of like, luck is like, what should this stuff is going to matter. So we're just putting in okrs at the board list, and we it 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, okay, so we like yesterday, we did our first strategy session that we've ever done with all 10 as opposed to just me and the CEO. And we're like, Okay, guys, how do we set okrs for 2021 and okrs. For q4, we're set by her like her and I talked, she said, q4, okrs, for everybody. And then, and then for q1, we're like, let's bring everybody together have discussion. And then she'll set the okrs. Like, because it's appropriate, she's like, everybody got a chance to weigh in. We did it really succinctly. And now she's gonna set okrs. And everybody's aligned, because we did the conversation. So I'm sure her version of okrs will be much simpler. But it's still the same principle, which is, like, you know, give people a chance to enter voice in a very efficient period. The only thing I'll say about okrs is if you can't create a drawn out period, people will, like just expand the work to engulf it. And the results are no better than if you did it in an hour. This was like, you can take three weeks, you can take three hours, I bet you the results not going to be much better.
Eric
Yea. Timebox it.
Sukhinder
Yeah, Time box. You have to time box priority setting otherwise, people just obsess and pull more data. Yeah, perfect deck. Perfect deck, more bullet points, more detail around each. Okay. I'm like, doesn't really matter. Yeah, yeah. Typically,
Eric
I want to shift gears a little bit and get your perspective on something. We had a heated, I 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 we there was an article from Scott Galloway, who you know, give up your 20s and 30s, 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?
Sukhinder
Ah, let's see. 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 in how I work now, like a lot, right? Though, ironically, the bigger the company that you're running, the less read in new app, because you're beholden to time zones, and everybody else's schedule, and 1000s of people 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 way, because you can just get it right. Like you can just time bound how you want to spend your time and your day, to like, all of these, like, everything is put upon you by like a really large scale infrastructure
Eric
Quickly then Sukhinder. So you think if you look at your job at like president of StubHub versus CEO of your own startup, you had more flexibility and freedom as a CEO of a startup versus the president of stuff, for sure.
Sukhinder
I mean, if you'd like to be you know, because it StubHub and of course what COVID has changed everything, let's all agree on that. But at StubHub, I've got to see customers I'd 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 in Madrid can all be on If I'm the CEO, and I'm like, Hey, get an IV, and I actually miss you boys, 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 just won't happen. So maybe some of that infrastructure is related to international for sure. Because everything, everything I've run, it's big. It's been 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 have a start up is it's like, what's works for you when you're 20? People? You know, and, and a lot of that cycle time is spent on like management and communication, it just goes away. Yeah, so I just think there's a lot of freedom in in how you work even when you work as hard. So yeah, do I believe that you power in your 20s? And 30s? Sure. Do. I believe that I, my family would still say I power my 40s and 50s. And I'm like, ah, like, what the hell? Like, shouldn't you be, you know, toning it down. I brought like, I'd say my family complaints. I probably should tone it down now, too. But yeah, for sure. Because I think that really momentum creates compounding returns, if I asked you guys all like, Okay, do you want to start saving when you're 40? or 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 20s and 30s, the more career capital you're building, right? So I mean, at Google, I was a president, by the time I was 35, like, Well, actually, no, as well, I was a vice president, by the time, it was like great, one of the top 10 people in the company. So like, by the time I had my first child, I was 36. And I didn't delay it. By the way, it 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 walked to the office at 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 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, right. 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 of McKinsey, while everybody likes fed right pastor, so that she could, you know, have time with their kids, you know, what, like, that was a pretty good trade off, she's now like, you know, she got to the CEO suite of a major global financial future faster than any and the first of all women. And she took a completely alternate career path, including slowing down when, like, you know, 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, you know, when you hit the parts in your career, where maybe you really need the flexibility, you know, 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. I was able to say to Google, you're gonna pay for my daughter and my daddy, because I was really senior. If I had exited, you know, when I was manager what I have the same negotiating leverage when I needed it. I doubt it. Yeah. Yeah.
Eric
So then we we just finished an activity before you came in on on habits and try to establish some habits over the next few weeks to keep people that's a busy time for students, you know, exams coming into that right before the holidays. So like, what are some habits that are gonna keep you good as a person? So what what did you find kept you, your family? You're like, What? What systems? What habits? Did you set up to keep you whole human throughout the craziness?
Sukhinder
Yeah, um, 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'd be better. But once you've been on zoom all day, you feel tired in a different way, then right, interacting with people. So my days were longer at StubHub or SEO, but right now, like by five o'clock, I've had like, 10 zooms, 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 to 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 pay to take them to five practices. So when I switch off, I switch up I feel no guilt about like 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 binari 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, so. One can't get a hold of me. That's probably one of the biggest ones. Number two, I have no problem with like 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 the one of the very few things that like, I just like, I just don't think that anything. I binge watch, like I do all I have all the students all of you guys do, right? And I think you have to go to whatever that thing is that turns your mind off. So people are like, well turn off your device. And I'm like, Oh, actually, I'm so busy binge watching Friday Night Lights, I'm not gonna do that. But so I think for me, it's been about like, not over scheduling the rest of my life. So I'm kind of happy that not have it over scheduled, because so much of my life is number two, like, I indulge like, like, why not? But But I indulge in the things that switch my mind off. And then of course, I've lots of loves that. I'm sure many of you guys do. I love to ski in the summer, my family and I have like Tahoe, we'd love to wake surf like, of course, I've always said 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'd love to work. I love my kids. You know, 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. Like, I get my fill if I do those three things.
Introduction/Outro 41:25
So eliminating, eliminating the gray, I find people that are maybe more established are 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. Well checking their phone. Well, emailing on vacation, you know, they're either all in or not.
Sukhinder
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 dammit, I'm going to Italy. Like, I'm taking me alone, 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 got don't care about like, I'm the one who keeps my house clean. I could care less. Yeah, 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 somebody else has done their laundry or whatever I'm like, Okay, yeah, I don't want to do it like, yeah. So I think that the things I don't want to do, I'm like, yeah, it's okay. I'm not trying to be supermom, I think that would be very difficult. And I already I feel guilty for the things I don't do. So I don't need to feel guilty about I guess is the way I put it.
Eric
Yeah, good. I am an entrepreneur turned educator. I didn't expect to be here, but am at Ivey, 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?
Sukhinder
Um, well, look, I I have this thesis that people have a very mythical relationship between risk and reward. I will 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 a big reward, 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 the perfect idea, I shouldn't go leave aside the fact I think you should have an ambition, enough enduring ambition for your idea, right. And so I think people have 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 gonna 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 best you never do it.
Eric
Any advice to Sukhinder if she was graduating from HBA two things that you wish you would have learned known earlier back in the day?
Sukhinder
Overvalue the people Your you know, and because I think that you almost you can go into almost any situation and whether it fails or succeeds. If you're with tremendous people you'll have, you're likely to have a tremendous experience, and one that will pay back multiple ways. And I think the other cautions, like trying to go where you don't fit is also, you know, I felt like I spent so much time at Ivey 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 where I ended up of all the banks and right, because it 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 let you know, I think that I think that people factor has so much more to do with having a great experience than just what you're working on.
Eric
Great. And thanks for being open. Again. I think the team that introduced you wanted to say a few words before we let you go.
Students
Thank you Sukhinder for joining us today, I'm sure we as a class has learned a lot from your valuable advice and stories. So 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 aims to empower women and young women by funding various programs across Canada. So thank you again for your time.
Sukhinder
Well, thanks for doing that. And thanks for the amazing song. I can't wait for somebody send it to me so I can listen to it again.
Eric
I will absolutely send it to you. So Kendra, thank you so much for your time. I'm gonna play the song as you sign off, thank you so much.
Sukhinder
Thank you Take care,
(Music Plays)
Eric Morse
The Entrepreneur podcast is sponsored by Connie Clerici, QS ’08, and Closing the Gap Healthcare Group, Inc.
To ensure that you never miss an episode, subscribe to the show on your favorite podcast player or visit entrepreneurship (dot) uwo (dot) ca.
Thank you so much for listening. Until next time.