Full Transcript for 2: Sasky Stewart - Toronto Maple Leafs

do you have hockey in Australia? And you're like, yes, we've had it for like 105 years. But like all this trophy outside North, outside of North America is Australia, which It's hard to believe, but we're just not great at it. But when people find it, we like it. We're just not great at it. Christian Parsons: So certainly not a, uh, international powerhouse on the Sasky: No, we had like one player that played a couple of NHL games. That's it? That was really it.  Christian Parsons: So then you talked about  having an early passion for it, and then I'm assuming from there you made moves to intentionally get into the sport. Sasky: So growing up, I want it to be two things. I want it to be either a fashion designer. I wanted to be the statistician for the cricket broadcasts on Australian television. So I'd always loved sport, but I never had had a specific intention of working in sport because in Australia it's not necessarily a career path that you're on. Thinking about, particularly not when you're growing [00:04:00] up, where I grew up, it's very much, you know, you're thinking about what you're studying at university. They don't have a lot of the same sports management, sports marketing programs. There are a lot more traditional kind of things. So I got involved with hockey initially, just because I wanted to be involved. I was that kind of person. I wanted to help out as best as I could because I wanted to make it better. So I started as the team photographer and I was like 17, I think at the time we started with the Australian ice hockey league as a photographer. And by the end of like, I think that year and the next year I was like, okay, The photographer, the media person, the marketing, but like I basically ended up doing like almost everything over the next, like four years with this team. Um, and it was never really with the mindset of making it a career. It was just something that I really, really loved. Um, and so I was at law school at the time because I had convinced myself that I was going to go be a lawyer because I had some belief that legally blonde may have represented like some kind of correlation to the practice of law, which is incorrect. Um, [00:05:00] but yeah, I hadn't really intended to go into like, even my first, even my first internship in sport was never with the intention of getting a job and working in sport. All I had wanted to do was learn what I could, so I could bring it back to Australia to make our league better. It had never really kind of been a thought to me about working in sport until I think I got to the end of my degree and it became that time where I was like, okay, What am I going to do? And I applied to like 31 jobs. I applied to 30 law firms and one sports agency, and I got one interview and it was not at any of the law firms. And it was at that one sports agency. And I got the job out of that. And that's how I ended up. In sport, it was a whim that I kind of applied and fell into it because I had had all of that experience coming out as a graduate. Um, and then I kind of just fell in, in, in a lot of ways from one of those things to another, through how you do [00:06:00] through networks and things like that, except the Leafs, the Leafs I didn't fall into anything. I had to apply for that one and hustle. Christian Parsons: got it. Got it. But I mean, at the beginning, what it sounds like is like there's a real. What started as a, as a passion point, kind of became this thing that you were doing on the side, going through school. And then as serendipity would have it of the 31 jobs that you're applying to, the one that he gets back to you, and the one that you actually land is in sports. Sasky: yeah, the one I probably should do because I should never have been a lawyer. Not at all in any way. You've worked with me. I would have been terrible at this. Christian Parsons: , very cool. So  within that, one of the things that I, that I, that I know about you and your career is you were able to wrangle. A bunch of internships being remotely. And I, and I joke about this, but I mean, it is, that is a real skill and a real hustle. If you live in the city and yet you weren't,  you weren't living in Toronto. I don't believe at the time when you got in with the NHL. I believe that you also interned with through Washington, [00:07:00] correct me if I'm wrong. Sasky: Yeah, you're right. I wasn't in, I did these internships in North America. I came to do them, but the process of me getting them and convincing people and setting them up and all of that, um, I did from Australia because technically I'm not eligible for any internship program  these places have cause they're often contingent on school credit, which is how they get around the whole not paying people thing. So I didn't have that luxury and also probably didn't have quite the correct visas to do that either. So there was a little bit of like creativity on some of these things, but, um, yeah, I, I. Uh, the Washington capitals came about and it really kind of incredibly weirdly lucky way. Um, I had made these packages, website package, little thing, and I sent it to every team in the NHL because I wanted them to come and be an intern. For some reason, I sent it to the hockey operations department. I don't know. That's basically, I guess what I knew about. Um, and I mean, some of them actually invited me like, Hey, if you're in town, please come and say hi. And I got to do that. Meet a couple [00:08:00] of them who are now GM's. That was great. But I didn't get any kind of opportunity. Um, but at the time Ted Leonsis, who is the former chairman of AOL, uh, he owns the Caps as he still does. And he had an email that was public. That was like, you could email him with your opinions or your thoughts or your, like, this is what the team could do better. Or these, like, basically it was, it was a lot of like community based things. And I'm sure it was a lot of obscenity based things too. And I'm

sure his assistant. Like edited it out as well. But on a whim, I sent it through email to him. And about a week later, I got woken up at like five in the morning, by my phone going off with like a U S number. I was like, hi. And he's like, I'm hi, it's Ted Leonsis. And that was how I ended up. In Washington, he's like, okay, this is the person you emailed. Tell us what day you'll be here. And I literally showed up at the front desk and was like, Hey, I'm here for an [00:09:00] internship. At which point I found out that the department I was interning with may not be aware that I was coming. Um, Because Ted was just like, Hey, she is. , and that was, you know, I spent six or seven weeks there. , and it was also an amazing time to be in DC because it was the week after Obama had been inaugurated . So it was an incredible time to kind of be in the city. I was got to live at a youth hostel with a bunch like a house with a bunch of people from all over the world with such a great. Great experience. And I still managed to be in contact with Ted since today. You know, when we  lost to the caps, , in the playoffs a couple years back, I got a chance to see him. He's like, I'd like you to do well, but I was like, I understand completely, it's fine. I get it. You know, it's good. Um, but my, my second one, I went to, um, Uh, the, uh, silver tips who are Western hockey league team based out of Everett, which is just North of Seattle. , so people aren't familiar, the Western hockey league is one part of a three-part junior system where the majority of NHL players from kind of Canada and a lot of that come out of, , And I got that [00:10:00] because when I had been backpacking the previous time a friend had taken me to a game and introduced me to them being a person who let me follow him around for a day and showed me some stuff. And when the next year came around, I emailed him and was like, do you want me to come and work for you for free for two and a half months? And they're like, We've got seven staff members. So yes, yes we do. And I went and lived on my friend's floor for two and a half months. I mean, I was very lucky to be in the position where I could, I had like, I mean, I didn't really have a life, so I financially saved a lot of money by doing nothing, um, and was able to do that. But yeah, it kind of just was some really. Weird right place, right times. And also stubborn belief that you could do anything at that time. You grow out of that a little bit, but like at like 20 to 22, you're like , untouchable. Christian Parsons: Yeah, it sounds like a lot of  hustle, grind and belief, you're attributing it to luck and, and absolutely is lucky when Sasky: I think you make your own luck. Yeah. Yeah. You, you have to do the work so that when the luck [00:11:00] happens, you're in the right spot because, you know, it's that idea of someone asking for the right lottery numbers and God being like, you have to buy the ticket first. I can't make you win the lottery. If you haven't bought the ticket, you know, that's the kind of idea. And I subscribed to it. Like it's a two-part system. Christian Parsons: get in there, do the work and, and, and luck is luck. It's a huge part of that, especially in sports where there's so many people. Emailing Ted or, or offering to work for free. How do you stand out and how do you make a big Sasky: Being Australian. That was really, I can't say to someone, you, you need something to make you different go like I, there is being Australian was just who I was and obviously, but it was such a weird differentiating factor that it worked in my favor to get people's attention.  To get people's attention straight up. It was an incredibly useful tool that I like. parleyed very hard. Like my resume says, get a mate on it. And it is a very effective strategy. [00:12:00] Christian Parsons: Got it, got it. Got it. And so I want to  zoom in on something that you had said earlier where you're talking about you build, I think a portfolio or something that you were sending out to that for people who are trying to get in, you know, I think just unpacking that and trying to understand what you send and why you thought either it was successful or not. Sasky:  whatever I sent was something I made as a 19 year old with limited skills who wasn't like, I was never looking to get into design and art stuff.   I don't think there was something in that that really did. I think the thing that helped me with, you know, with Ted was, you know, as I said, luck, but it was really the, the narrative you're telling someone about why they should do this. You want to make it really easy for them to be like, Oh, I can just like, sure. I can like, like, yeah, that makes sense to talk to that person or that's a cool, neat thing, you know, and that's a hundred percent easier said than done. And once again, weighing heavily on, on being foreign [00:13:00] in that sense. Um, but I don't think anything was stupid unique with what I had done because I don't actually think that may have worked super well. I think if anything, it was whatever email I wrote that said, Hey, this is my story. This is what I want to do. Yada, yada, yada. And this is also. 11 years ago. I want to say this was now, like, I just had to do that. Math in my head was like, Oh yeah, it was at least 11 to 12 years ago that this was happening. Um, and so it is also a very different world then, like, I didn't have a Twitter account at this time. I got a Twitter account because when I joined the Caps, they were like, you need a Twitter account because you have to do things when Twitter, Australia hadn't discovered Twitter at this point, really? Like it was a while Christian Parsons: you couldn't LinkedIn stalk people, you know what I mean? Like Sasky: Man. LinkedIn is so useful for that nowadays. Christian Parsons: um,   it's really interesting because one of the things that I see and you've probably seen working, working in sports is just a

lot of people just [00:14:00] saying that like, Hey, I'm just, I just really love sports. And you're like, great. You look or sound or feel like the  25 other people that have emailed me this month that say that they love sports. You've you're not unique. You don't have a unique story. Whereas you being able to. Say , Hey, I'm, you know, an Australian woman who loves ice hockey, and I want to come over here and not only loves ice hockey knows ice hockey, and I want to come in and do X, Y, Z with you, then somebody walks away and then it's like, Hey, did you talk to Sasky? Yeah. The crew. You mean who's Sasky. Oh, the crazy Australian girl. Oh yeah, of course. Sasky: Yeah, I think that was definitely a big asset for me. And the other asset is in a lot of the things that I have. Applied for or been doing as is often the case in, in the sports industry. We're horribly over qualified for some about jobs. Like I have a law degree and a master's degree in marketing. Um, and I had just left a [00:15:00] high five figure salary in Australia, running the digital department for a company with like 65 stores and I'd come to Canada and I was like, sure. You can pay me this much an hour to, to do these things. Cause this is what I want to do. Um, and so that is part of what also helped me in that sense, being like this person is clearly insane and makes questionable life choices. Um, but I think it's that fact that for the most part, yeah. A lot of the people who are applying for sports jobs, who are, I guess in consideration who are probably the ability of being able to do it all have a basically very similar skillsets. You have similar degrees, you have similar, um, backgrounds, you have similar experiences for the most part. So if everyone kind of looks the same and it's a kind of a homogenous blog, it becomes about what thing can you do? Or what thing is on your resume that makes you seem a little bit. Different and you, you never known [00:16:00] what that person is going to find that, but, you know, I've read so many resumes with, for sports things, and it's very much the same thing. I studied this, I did this, I was the captain of this club. Captain of that club and, and that's all it tells me. It doesn't really, you know, I had this GPA. I couldn't even tell you what my uni, I mean, I could tell you what my university GPA was, but I don't tell people what my university GPA was. Cause it was not great, but like that doesn't like, I never looked at that either. Cause I was like, Whoa, you know, that's your ability to do an exam? Like I know how dodgy I was at university. Sometimes I like to think I'm competent at my job. But yeah, it is that, that finding. A differentiation factor, but also telling you what that could be is, is impossible practically, because you just don't know either. Christian Parsons: absolutely. And you don't know what that thing is going to be that connects with somebody else, right?  It can be super obvious, like where you grew up or where you're from or what you're [00:17:00] passionate about... Sasky: I definitely  had an intern who got the interview because she had been the captain of a women's rugby union program and had helped found it and helped build it. She didn't work in sport. She was coming from a social media marketing background kind of thing. But that caught my attention because a it's a sport left of  center and a women's sport is also a hard sell, you know, I know what it takes to get some of these clubs off the ground. And so that kind of gave me a really good indication of what this person was like and what they, what they were kind of how hard they were willing to work. And that kind of helped me get a better picture of them rather than just the artwork or the resume  Christian Parsons:  instead of just the experience, something that contextualizes the Sasky: Yes, that's it. Best way to put it. Yeah. Christian Parsons: Got it. Yeah. That makes a lot of sense. , anything else that somebody has done , in applying for a job when you were working at the Leafs or the CWHL or somewhere else where you were like, wow, okay. This stands out and I actually want to talk to this [00:18:00] person now. Sasky:  CWHL is a non-profit women's sporting league. We don't have extra people. They don't exist. You have interns. That's basically it. With the Leafs I didn't have staff or interns  like but I had bits and pieces. And what I found more impressive was I definitely had one girl who she wanted to work in sport. That was it. She had been my volunteer at the CWHL and an intern there, and she just never left. Her internship finished and she just didn't leave, which was great. Cause I could use that. But then when I moved to the Leafs and then she's like, Hey, is there any opportunity here? And so, no, I wasn't even working with me, but I helped her get into a specific area of something. And then she went from there to like, Getting herself involved with the Raptors and getting herself involved with TFC. And she, I like this girl hustled so hard and did such a great job of like networking through people that you always like, I want to help this person. Like they had such an infectious kind of, um, passion for what they [00:19:00] were doing. Um, But they will say at a very realistic understanding of the nature of what they were trying to get into and what sport does look like and what the realities of it can be. Um, so I think it was very nice to be like this person stood out because they still had that idealism that I remember from quite a while ago, but with the reality that I did not have at that age. Okay. Christian Parsons: Got it. Got it. So I think that makes a lot of sense, right? She. She was given an opportunity. She knocked it out of the park, did a good, good job was able to leverage it to the next opportunity and can just continue to do it and have people root for her and then bring a good energy. But also to your point, be a realistic as to what working

in sports is like, Sasky: Honestly, I think if you do internships and work for people and you work for good people, if you work for good people and you do good work, they will go to bat for you. For those jobs. There are numerous girls around hockey who have worked with me, or have been contractors [00:20:00] that have worked with me, who I have written references for, or gone to people and being like, you need to interview this person because. They do good work for you and you know what it was like when it was used. So you want to make sure someone does that. Cause you may have got some had, someone who did that, well, you may not have, but particularly as a woman, you're like, I want to see more women doing these jobs. So I'm going to proactively make sure I am helping get women into these jobs or getting them at least put forward. Um, and so I think that's a big thing, you know, that balance of that relationship, but whoever you've been working for and being able to use that effectively and. Welcome to the right people who are willing to help in that way is such an invaluable kind of asset .  Christian Parsons:  you make a really good point about working for the right people, right? How do you know that you're working for a good person in the interview?  Sasky: I've been so lucky for the most part with my career and had, had really good people who have obviously been great at their jobs. But I think the thing is it's not even how they [00:21:00] do their job, but they're good at what they do. Like, I mean, you like that makes your life easier, but the idea that you have people that will go to bat for you have a rational understanding of what you doing. Yeah. Uh, interested in you doing your job, but also in protecting you and particularly in the sports industry, it's so easy for people to just work themselves to death. And  the people who they report to you are just like, well, that gets the job done without thinking necessarily of what the, um, like the impact was like, I definitely. I remember calling one of my bosses,  I'm on my way out of an ER at like seven in the morning and being like, Hey, like I've just got to go home and get changed and this and that I'll bring the office. And they were like, what?  please do not come into the office. Like, I think one day someone told me that myself and my coworker, that we had to go to the aquarium and provide a report on the fishes. Cause he just wanted to make sure we had left the office at this point. [00:22:00] And I was like, okay. Christian Parsons:  To your point, the, the dark side of that hustle mentality that you said of like, just do everything and do anything that's possible is when can you turn it off? And what's the opportunity to  make sure that you're not going to burn out in six months , 18 months, two years, whatever that timeline is, you know, when the Red Bulls end what happens. Sasky: I was thinking about like things that you learned working in sport. And one of the big ones was when you had tweeted enough about Red Bull, that Red Bull starts sending you Red Bull. You may need to drink less Red Bull. And I can say this from experience because at one point I was like, Oh, they're just sending me all the new flavors to try and turns out three is the maximum Red Bulls I can handle in one day without like losing it. So I took my first job in sports at 21. So I spent three months with a sports agency, so Octagon Sports out of Sydney. And at the end of that kind of thing, I went to Melbourne to help essentially run a women's [00:23:00] professional football team and run all of the events for the entire state when it came to football. I think at one point I worked every day for eight weeks and the reason I stopped working everyday for eight weeks is because I totaled my car because I was so tired that when something in front of me stopped, I didn't react fast enough.   I didn't have a car then. And I had a cracked sternum, so it was really no use to anyone because an events coordinator, they can't pick up a box is not super useful. But I think that was one of the first times I really understood the idea that you can't just keep going and people who are allowing you to and requiring you to are missing the point or missing the picture.  Because it's very easy for people to be like, well, we just don't have any other option. You just have to do this.  I'd love to say that's when I learned the lesson, but it's not like, I, I think, I think in sport, it's almost like you have to burn yourself out [00:24:00] a couple of times .  At one point I was working the CWHL from nine to five, and then I would walk across town. I would work the NHL from six to two, um, a couple of days of the week and then on the weekend. So I was doing essentially 80 plus hour weeks, and I was just like, this is great. This is fine. And you burn out. You know, same with, you know, anything, anything that has, you're doing 60, 80 plus hours a week across, you know, a long period of time you're putting in, you know, extra, like three extra months work in eight months. It's just unfeasible. And I understand obviously that sports is driven on a lot of this completely. I been there, I get that, but there's a certain point where the balance of what it starts to do to you, you have to be super, super aware of. I think a lot of people I'm more aware of it now because this conversation about burnout, about mental health, about all of these things. Is not only more prevalent in society, but it's obviously more of a topic of discussion within sports teams.  it's  a conversation that is a lot different than when I [00:25:00] started working in sport, which would have been like 2010 or 11, something like that. It's a very different kind of, um, environment in that sense too. Christian Parsons: absolutely. And I like what you're saying about the conversation. Just be a lot more understanding or acceptable right now. And, and even if it is athlete led, right. If it

starts there, it's a lot easier if you're in a sports organization and one of the athletes speaks up about burnout or a mental health issue or something like that, that you actually referenced that because Sasky: Hey. Christian Parsons: Well, it's true because you know, there's such a deferential look of the sports side of any sports business. Hockey, basketball, football, any of that kind of stuff. They view the, the athletes and the team with such high regard that if something comes down from there now it's okay to talk about it within a, within a. Sasky: The majority of people are going to hear them, see the, like, hear those words, see these people and take so much from that. As far as like changing that narrative.  Athletes in sport is still one of the most powerful [00:26:00] things we have nowadays just to make any form of like social message in any way? No, because it is one of those few things that seems to in some way, cross nearly every single demographic, uh, boundary with some form in some way. Christian Parsons: Yeah. I mean, it's, it doesn't matter whether you are like a multi-million dollar real estate investor in Toronto, or in the outskirts of New Brunswick as a custodian in the local high school, you still, yeah, yeah, absolutely. Well, you know, but you still both suffer every playoffs when the Leafs don't make it. Sasky: A hundred percent. It's very funny. Um, often, and you and I have probably been party to people having this conversation at us about people's frustrations, that the people who are sitting in these seats, aren't real fans. They're not this, they're not that the idea becomes that there's obviously a real way to do this, and that's the only way to be a [00:27:00] fan. But the reality is those people. Uh, you know, often really are fans and they feel about the team the same way as you do, but they may show it differently or they may be in different circumstances.  Christian Parsons:  there's multi-generational sports fans, right. There are people who  become immigrants to a country, and that's the way that they learn the culture. There's people who aren't even interested in the sport, but then they appreciate an athlete or a design or a jersey or something, and they just want to be involved in the culture. There's a million different ways. There's no right way to be a sports fan. Sasky: My father and my brother hate sport . My mother sports mad .Will watch pretty much anything, not quite as much as what I will watch when it comes to pretty much anything but loves it. We'll watch every rugby league game all weekend, every weekend, all of the Olympics, all of that. So it is a very  generational thing, because I learnt a lot of this watching these things with her , and her mum was a massive sports fan. True. So it's come down generations through my family, just all down the female side. Christian Parsons: Yeah, absolutely. That's that's [00:28:00] awesome. And, and it's, and it's, and it's interesting and refreshing

to hear that . It's not just a dad and son going to a baseball park together, you know, that there's different ways for fandom to be passed along  and for the interest to be picked up.   You know, a little bit of a turn on this and direct it back to the career element. So you ended up managing social and digital for the Toronto Maple Leafs. That's big league. Talk me through the story of landing that role. Sasky: The job at the Leafs was essentially the only job in sport I have ever had that was an entirely cold application. I didn't know anyone on the inside. I was vaguely acquainted with the predecessor, but, um, not really enough to reach out. So I applied cold along with I'm told 400 other people.  They cut it down to an interview. We had to do a presentation.  Lucky enough they gave me a stuff about a past event and I had worked with it with an alternate sponsor. So I was well versed in it. And I had worked similar events with the NHL. So I [00:29:00] came in, at least with that. Like basis of it.  The Leafs was the only one that was a cold, cold thing. Uh, I think. I think in my career, almost the only one that's ever been like that.  Christian Parsons: Well, then you're one for one. Um, those are those that's. Yeah, that's a good, that's a good shot percentage. Even though it was a cold apply and didn't necessarily know anybody in there still, as you got into the process, you figured out, all right, I'm still going to leverage my network and my knowledge to prepare correctly, to get as much background so I can sound like, I actually know what I'm talking about when I'm talking about this event or this creative brief that you had to  deliver on. Sasky: I fully branded that thing. It was branded to the hilt. This needs to look like I gave you this deck from, within our office.  I was also lucky in the sense I'd been doing a lot of this same kind of work with the NHL and the CWHL and that thinking about how we're using digital to activate sponsorships, how we're creating experiences for people that can't be there, [00:30:00] all of those kinds of like, what are the different touch points that we can create to get to the largest amount of people. And I had had obviously experienced with that, which is good because that is essentially the job.   I think that's one of the things that actually really helped me is I think as far as experience comes in and I say this because I actually know several of the other people that were also in the same thing we didn't realize till afterwards, but I had come in with a very, a large amount of sports, specific hockey specific experience doing essentially this exact thing. So I was coming in for something where they could already see that I had done this and was capable of doing it. It's a lot harder to convince people to take the jump on someone. I came in, you know, for the most part, with my resume, a very safe bet. Until I started talking and then we, you know, we went a bit from that. Christian Parsons: Yeah. Talk talking as part of the interview process Sasky: Yes, it is. It is. Christian Parsons:  I totally understand that. Right. Like a lot of it was probably your previous experience [00:31:00] speaking for itself. Um, Sasky: Which is I think, any, any interview in any job application. Christian Parsons: Absolutely. And then the onboarding looking really easy. Right. You can really see you in the role. And Sasky: Yeah, I think they gave me the Twitter accounts on my second day there or my, the second game I was there.  It was like, you're in charge. And that was it. I was now in charge of all of the Leafs accounts.  Christian Parsons: So that's, that's a great segue. So what exactly does a digital manager for the Toronto maple Leafs do?  The day to day is not what, what I'm looking for. I'm just kind of trying to understand if you're trying to explain this. Yeah. From a broader sense, if you're explaining what this is to like a college kid or somebody who's trying to get into the industry, what do you say? Sasky: Can I say my job is to get abused on the internet for insane things, cause a hundred percent that is part of it. Um, do you feel like making the CBC today? Don't don't do this job?  I kind of explain my specific role as part project manager, part strategist, part copywriter. So you are project managing. Have you [00:32:00] got everything from the sponsorship teams? Have you got the videos? Has someone done? This is this here. Is everything going to be where it is so you can execute it. Okay. And then it's that strategy. How am I executing this? How am I structuring it? What am I trying to do? All of those kinds of strategic planning of how you're going to actually do this job.  And then the copywriting part is if you can't write, you can't do this job because you still have to write, you know, I think I would write easily a hundred social posts on a game day in some way or another so you have to be able to write.   It sounds illogical to say writing as an underrated skill, but I really think it is particularly when we've started to shift to such a short form.  The ability to understand how to create mood and feeling and tone. And all of those things in such short spaces is invaluable and is one of the best skills I think in that area you can kind of come with. And I was [00:33:00] lucky I have for a lot of my life always written, always read. So I had that sense.  I think in sport, in as a digital manager, I think there is jobs in sport where you may not need to know the sport inside now a hundred percent because your job is to understand the fans or this and that. And what makes them, what drives them and their association with the team. You don't need to know what. Whatever NFL things are. There's exactly how much I understand about, I was like, there's something with touchdown, like stuff. Yeah. So I'm like, you, you don't need to understand those things. You don't need to tell me the difference between like the red line and the

blue line and offside and this and that. But if you're doing this job, you need to be the person in your department almost that knows more than anyone else. You need to be as close as you can get to a walking encyclopedia.  You have to know history of the team. You have to know like even history of the language that you use when talking about the game. Cause there is such distinct language that goes with it. But yeah, project manager, strategist copywriter. [00:34:00] That's really it though. I did end up somehow with a TV show for a year. You know, digital, I think in some ways too, is whatever you make of it as well. It's like, this is what it is. And then here's this big scope for you to try and do something else. If you want to with it. Christian Parsons:  A lot of digital is very content based, right? So if you're comfortable creating content, whether it is you hosting a show or a podcast or writing  or taking pictures even right. All of that kind of stuff, just as long as you're comfortable with that, you're, you're able to experiment and see what works with your audience. Sasky:  I am very much a Jack of all trades. I have some things that I'm really good at, but I've worked as a photographer in some parts.  I can write, I don't like writing large amounts of things, but I can obviously write like, I'm excellent in social media size. You want me to write an article, baby? Not my favorite thing, but you know, I can do that. No, you've, I've done. Hosting and things like the more different facets that you can carry out, not necessarily an expert level, but it'll have like a level of [00:35:00] competency. You have to be able to understand how Photoshop works. It's also helpful if you understand how illustrator works, because I don't, and that has caused me problems sometimes. Can you edit small amounts of video because maybe your team doesn't have a video department and maybe you want to add that to your thing. So the more aspects of those kinds of skillsets that you can add in, um, the better. Christian Parsons:  Just riffing off of that for a little bit, one of the skills that you said was most valuable is really the skill of copywriting or writing. And you said that you read and you wrote a lot. Is that how you hone the skill? Was there deliberate practice involved? How did you make it such that you were, you got to the level that you needed to be for that job? Sasky:  I went to  law school is not the most fascinating place, but I wrote a lot of essays out of that. And through this, I was working with sports teams and doing their social and learning about those kind of things. And I was on Twitter. All the time.  It's expertise by just experience. Um, I do [00:36:00] think if you are coming into it and you don't necessarily feel comfortable in that sense, there was a lot of courses online that may offer you some like copywriting understanding that might give you some solid basis as a things . That can help you approach that because often it's a lot about thinking about a framework in that sense. I have a specific way that I think about the language I'm using . And for me, I focus a lot on what can I draw with emotions. What's going to elicit these specific reactions in a very kind of like. Broad am I watching the documentary, which the ending and the sweeping sunset kind of scenario thing, but like, that's my jam. Like you need overdramatic, I'm your girl . I think having some of that experience, even if you just did a Udemy course  being able to get something, to get your head around, that is always going to be helpful, but nothing will beat just writing things, just tweeting things, you know, sports things. Christian Parsons: No. Absolutely. Yeah. Sasky: My Twitter account is like you have [00:37:00] 45,000 tweets. I was like that doesn't surprise me. Christian Parsons: That's a lot of practice, right? That's, that's a lot of reps in, and, and I think you make a really good point of, of, you know, if you're taking a course, the purpose of the course is for a foundational knowledge, but really the learning comes from wrestling with words and comes from publishing and hitting send. Sasky: And seeing things go wrong and understanding that,  how you interpreted something was not how they interpret something and getting around those nuances. But that is not something that you can shortcut to but it's also not something that you need a journalism degree and to have worked at the school paper to get either there is a hundred percent, a middle ground.  Christian Parsons:  In terms of that, you know, from your, from your time managing digital within the Toronto Maple Leafs,  what would you say are some of your top memories either on the ice or in the office? Sasky: From just like an actual thing we got to do from a sheer cool and ridiculous factor, just one of those things and be like, oh man, we did Maid of the [00:38:00] Mist with the team. So  we did Niagara falls with the Toronto maple Leafs at training camp. And I have this photo of myself standing on the front of the boat with the niagara falls behind me in my Toronto maple Leafs poncho. And it was the most Canadian thing in existence.   It was, it was very much like here's the kind of culmination of everything that I had been working for. It was the start of my first full season with the team.  It was just so  absurd that that was happening. Um, Christian Parsons: Just hitting all the cliches, right? You're on the Canadian side of the Niagara falls. You're on, you're on the boat and you're with, uh, the Toronto Maple Leafs. Sasky: yeah. I was like, Oh yeah, this is and and Carlton the Bear. So you have Toronto Maple Leafs and a bear mascot, um, on a thing. What of my other funniest things was, we took the, we took the TTC actually uptown one day. Christian Parsons: So the TTC is the subway, Sasky: Sorry, TTC is the subway. Yes. So we took the subway uptown, um, and it was myself, someone else and Carlton the Bear, the mascot.

[00:39:00] And so we're just standing. On the subway with Carlton the Bear, who's just like chilling out, looking at people and stuff. I was like, this is also incredibly absurd. We got to travel for this. And we did that, but it's kind of more like the little, uh, bits of bit, or like getting to go to Fenway park. Cause we were in Boston between two games. Like those kind of things are often what I remember. Cause at a certain point from a sports sense, there is 82 plus games. And after a certain while a lot of them start to look the same.  I don't think I look at anything that I, I did particularly was like, this is a memory. Cause I loved all the things I did and was proud of them. But for me it was more kind of like the people in the moments. And that was really what I take out of any of the experiences for the most part that I've got to have on any of the sporting things. Christian Parsons: Yeah, it's really interesting that you're zoning in on, just the people in the relationships that are lasting as well as those kinds of  micro moments that are simply unique to you, right? Not, Hey, this [00:40:00] playoff game, not, Hey, this big hockey moment or anything like that, it's really, it's really interesting, right? Because it shows the personal side of the work Sasky: I did get to interview an astronaut and that was very cool. Christian Parsons: Commander Hatfield, Sasky: Yes. We interviewed Commander Hadfield for our show and it was, uh, we interviewed him and we interviewed will on it and they were just like very different and very surreal experiences as well. And I think those, yeah, you're right. Those are the things you remember. Oh, you remember? Your personal context to the event. Do you remember the playoff game? Because this happened in relation to that, I remember, uh, William Nylander scored with 1.9 seconds left in overtime. And I remember that because I was upstairs in the press box above me. Cause I was like, well, overtime, like this is going to go to shootout. And I remember it happening and literally screaming at someone and running back downstairs. I don't remember the goal really, but I remember that part of it, you know, and those kinds of like absurd, [00:41:00] Oh, what'd you do in game seven? I hid behind a curtain for large parts of it. know, like those kinds of things. Christian Parsons: Out of, out of anxious, excitement. She's saying Sasky: yeah. Yeah. I was like, I can't, I couldn't do anything. I was like, I have literally nothing I can do for my job right now. And I need to stand here and watch this, but I also want to hide at the same time. What are we going to do? Christian Parsons: Absolutely. Absolutely. So from, from some of those highlights, um, taking a little bit of a different tack, you know, why shouldn't somebody work in sports? What's the real deal? What are the, what are the things to know? So that somebody coming in can make an informed decision to, Hey, it's not just hanging out with Carlton, the bear on the subway platform. It's also this other stuff. Sasky:  I've never been as tired in my life as I was working in sport. And I think I was probably tired, not just this day or that day. I was tired for the entire time of all of the time that, , I worked there. In any of these places, [00:42:00] because particularly with social, it is, you're always on, it's always intense. There's always something. And there's always more, it's not a situation where you have, this is what I have to do, and this is my target. This is what I have to deliver. It's always, what more can you do? Because your fans always want more. There's never an end to what they may want from you and what you could deliver them. So it's so easy to like lose yourself in that.  I think working in sports , I think it's very, it's very easy for people to lose their own identity and their own self into being someone who works in sport, or I work in sport and this is what I do. And I think that can be really, really damaging in a sense . Who am I, what am I, what am I doing with my life?  I think it's very hard to say , why shouldn't you work in sports? Because you'd be like, because the hours are stupid, the pay is bad because you don't see your friends. You don't see your family. Your schedule is ridiculous. All of that, right. There's a million jobs where you could probably also say the same thing that aren't as cool as sport. It's [00:43:00] just that I think people's understanding of what working in sport looks like, or the reality of what working sport looks like. It's very much, one of those memes that's like, this is what my mum thinks I do. This is what I actually do.   And it's a lot more like, did you do three months overtime in eight months? Yes. How do you feel about that? You have to get friends that learn to check the schedule before they ask you to do something.  Christian Parsons: Especially when your schedule is posted online and they're like, wait, there's 82 games. You're like, yes. And then Sasky: No, my friends are hockey fans, so it was like, okay, girls, this is how it's going to work. Christian Parsons: Yeah, younger you is listening and actually doesn't give a shit about anything that you said, right? They're like, yep. I know that it's low pay long hours, no social life, all of this kind of stuff. And they're hyped to step into pro hockey. What do you tell them? What's an actionable thing that they can do to start. Sasky:  I think we touched on earlier is figuring out how to get experienced and figure out how to make yourself different. It's a really kind of shitty thing to say [00:44:00] because everyone should really get paid for their work and internships are by large part, unpaid. Right? And the lack of them being paid does a big disservice to our industry because they are a lot less diverse than they could be.  This is the reality of these things to too. You need to have those internships. That should be your first priority because no matter whether

you think you, you could do the job without it, it's always going to be easier for someone to hire the kid who's had an internship or two internships because they have, there's some comfort blanket there. So I think it's about finding the opportunities to get some form of experience to put on your resume, because it's like any job, you know, entry-level position two years experience needed, you know, it's that, that kind of idea. Um, but I think it's. It's also in part of that too, finding a way to be different. I can't kind of tell you what that is because it used to be social media or a blog or a podcast or this or that. And that doesn't necessarily always work now because a lot of these markets are saturated [00:45:00] with the same thing. So, you know, and it depends on what field you want to go into. Going into operations is different to going into communications is different, going into PR, which is different to all of, you know, each of them has their own facets. Um, But there's a lot of people come out of sports management and sports marketing programs at the moment with these like real blinkers about like, this is what I have to show and it's not anything they haven't thought about standing out and what they're doing and showing that they can also hustle and they've got this creativity and those kinds of things. Cause I think those are really invaluable assets when it comes to sitting is setting yourself apart in that sense. Christian Parsons: Yeah, absolutely. When you were saying about the sports management programs, I think at least from having a little bit of experience on the hiring side, I could give two shits if you have a sports management degree from this college or this college or this college, right? Like what you want to see is application in the real world. Sasky: Yeah. I don't know if. in my entire [00:46:00] career, anyone has ever asked me about my university experience. It's on my resume, but. It's the last thing on the last page of my resume . There are obviously are programs of people like this has prestige and this has that, but at the same time, people get caught up in that idea. So it may be helpful to you. And it may give you pathways in this, but you know, we, we we've dealt with a lot of kids who are, I did sports management here and you're like, okay, so did 60 other people in the same graduating class, you know, like I'm very much. I'm of the opinion that going to university and studying sports management or sports marketing specifically is potentially a bad idea. Because I think with both of these things and our industry, you are only going to benefit from having a broader understanding and then showing, you know, how to apply it to sports through internships or experience or other classes you've taken. Because when people come in [00:47:00] and they view it so narrowly, they are missing a lot of the other parts of the bigger picture. And at the same time, if sports doesn't work out for them, which is realistically, I think people need to consider based on how many kids are graduating with one of these degrees and how many jobs there actually are. Your degree is so specific that it can become very hard to parlay out to something. And I have numerous friends who have, you know, sports marketing degrees from like top, you know, like final four kind of like schools I'm using basketball because the only understanding I have, um, and. They can't really do anything with them. Cause they didn't get a job in sport and they're finding it practically impossible to parlay into other things. So they're ending up doing, not at all in any way, what they want to do or they're interested in because it just didn't like there wasn't enough of a, uh, of a net in that sense. Christian Parsons: Absolutely. And I think, you know, to anybody who is still, you know, who is in a sports marketing program or [00:48:00] sports management program, I think the opportunity is really to broaden your skillset outside of that with real-world experience. And that could mean get into sports and put your eggs in that basket, or that could mean go volunteer at an art gallery. Or go spend your summer internship doing sales or something like that, Sasky: I think having, uh, the broadest understanding, you can have the most amount of things when it comes to people is always going to be the best thing you can go about. Because our business is about people.  It is about people. And the more you can understand that from sales, from, you know, art, from communications from just all of those different elements, the better it is. Because the more you understand what drives them to do things, to follow things, to purchase things, do you support things the way that they do it, the way that they're differentiated, it's only going to be better for you showing your abilities into a sports team. Yes. Christian Parsons: Totally. And then even just stacking [00:49:00] those unusual things up against each other, help you go to our initial conversation, create that story, right? If somebody who's in a sports management program and works at an  art gallery or a museum on the weekend and understands culture and also has sales experience. Now, all of a sudden that person stacked together with sports management is so much of a stronger candidate than just, Hey, I took this program in this degree and then I entered over here. Sasky: Yep. I agree. Completely. Christian Parsons: Interesting. Okay. Um, so let's flip it a little bit. So what's the best advice that you've gotten or absorbed over your career? Sasky: I learned a lot from Jordan, who, who worked with our team about kind of that idea of how to go about my work. Because it was one of the largest places I'd been, there was a bigger ecosystem, all of those kinds of things, but it was the same kind of like our team had a really good kind of I guess attitude about knowing where to draw lines with other departments or other things and other this isn't

that, and, and learning to be able to [00:50:00] stand up for yourself and a lot of these things and being an end that you could, I think even if it's not an advice, I think being taught that that is a  possibility was, was a really good thing.    I learned that if someone tells you, you shouldn't be somewhere because you're a woman, unless it's the men's bathroom, that person is an asshole and you shouldn't listen to them.  I've had discussions with, yourself and other people through the beliefs with time that someone's always going to think for some reason or not that you're not good enough that you shouldn't be somewhere. And particularly being a woman who is Australian I've dealt with that my entire career, because I don't fit.  I've had people send me death threats via social media a bit because I shouldn't be doing my job. I stole it from a Canadian.    But I think I learned that you can spend your whole life trying to prove yourself to them to try and get their acceptance. Or you can accept that they're also assholes, whose judgments, who were just judging you and move on. And I highly recommend the second.  So I think that's probably one of [00:51:00] the best things I learned out of it, or that people helped teach me within sport. Particularly if you are more, a diverse person, you are a woman you're LGBT you a person of color any of those things, you're always going to stand out a little more and you're going to deal with that attitude and it sucks and it's hard and you shouldn't have to, but. There is two ways to deal with it. And, and that's eventually, eventually I came around to the second one  Christian Parsons: It sounds like there's actually  three lessons in there, right? The first one that you mentioned at the top of it, which I thought was very important was just the act of setting clear boundaries and reinforcing them. Right? Whether they're with coworkers, whether they're with work, whether they're with fans, whatever it is, it'd be like, this is the way that we engage. These are the rules of the game and continuing to reinforce them.  I think the second one was just understand there's a, there's a gap between other people's expectations and who you are. Right. If you're Australian 4' 11" and a woman and their [00:52:00] expectation is that you're a 6'1" one Caucasian gentlemen with a certain haircut and Sasky: And you're not wearing leopard prints. Christian Parsons: Yeah, absolutely. There, there's just, there's just a gap. And, and being aware of that before. As much as it sucks to acknowledge that and be it it's part of reality. And if you ignore it, it's not going to work. Sasky: I think there's a difference. And I, and I have this conversation with people frequently that these things shouldn't happen, but they are, and pretending that they shouldn't happen, don't happen easily going to help you when you experienced them anyway.  I get mad at it all the time. And this happened, you know, through my whole career, excluding working for women's sports teams. But, you know, it's, it's very much that you don't, this is the reality and you just have to kind of choose how you're going to deal with it. Uh, because that is the only option you have. Christian Parsons: And then I think the third thing that you said was that was very valuable, is  when you are confronted with those situations,  understanding when you [00:53:00] need to impact the situation and directly address it and, and understand when it's okay to just let go. Okay. A fan is yelling at me and I don't, it's an anonymous person on Twitter, like who gives a fuck? Sasky: Yeah, we, I had some, I definitely had some experiences that were "okay, these are people yelling at me. These are people who have photos of me and know where I live". What are the actionable differences between these two things? These, I know are a credible. You know, threats . And it's also understanding which battle is actually worth fight. Like what hill are you going to die upon? And is it worth it? Like, which really is that. And you know, for me, there's a lot of them that are obviously when you deal with people who are on social media, who are just crossing the line. That is something that you want to be like, Hey, we have to deal with this. We have to stop, you know, even such things as like how we ran our accounts, we didn't tolerate certain language. There was a carte blanche rule. That was it. You were out, it was done. You know, that was a battle. We [00:54:00] would fight because we were not interested in letting that happen. But you know, there's things on the other side where you're just like, yeah, well they're just being mean at each other. They're fine. Like they just calling each other like non offensive names. Go ahead, Christian Parsons: Yeah, exactly. Very creative. Not Sasky: Oh, yeah. Super creative. Definitely watch some python, but yeah, Christian Parsons: Um, all right, so we're going to wrap this up. Is there anything that I haven't asked you that you'd like to say to the audience? Sasky:  I love sport. So don't get me wrong. It's my favorite thing in the world. But I think what I've learned now, having come out on the other side is that I have learned in appreciation that the things I love might not need to be my life. Um, I loved hockey and I loved it dearly. And I say that in a past tense because I don't watch hockey anymore. I couldn't tell you the score of any game in the Stanley Cup Finals.  Didn't really watch a lot of it, because I had seen so much of it and [00:55:00] had encompassed so much of my life for so long that it just stopped being something I enjoyed. And so no matter how much I had loved it, it just didn't bring me pleasure anymore. So I watch a lot of car racing. I watch a lot of German football. But it's, it's not hockey anymore.  Uh, I think that working in sport. It's one of those things where you can't say to someone don't work in sport because you wouldn't never would because

we've all had amazing times. And there is nothing that you can say that would convince them otherwise. And they would never have convinced me otherwise.  Try and go into it with like the most open eyes you can. Cause there was a lot of highs. There's a lot of cool things, but in a lot of ways, there was a lot more of the lows and there was a lot more of the grind and there was a lot more of the things that could be damaging in a sense. And it's, it's that balance, , finding the right people along the way though helps because like you live and die by your coworkers. That's what gets you through. That's what helps you succeed? That's the things you remember, the people you shut the ship with the people that you hung out with, the people that were in the ridiculous situations with you. [00:56:00] Like all of that, like that's what you remember so, make sure that when you're going somewhere or if you're able to that, they seem like a good bunch, because that is going to be so important in a, in it's something this insane, um, So, yeah, I have, my final night was like, get people in what feels like the worst day of your life. who will buy you cheesecake and alcohol at 11:00 AM. They were excellent. Christian Parsons: That's amazing. Yeah, no, I think, I think, you know, choosing to work with good people, that's such excellent advice, you know, value yourself. And, and, and be aware of where you are from a mental health perspective, because as you get deeper and deeper understanding what those boundaries are, and, and you don't want to ever walk away, you know,  hating the thing that you used to love. Sasky:  Like hockey was my thing. I thought nothing could ever change that. I learnt that I was wrong. Um, and so I've now got a very different viewpoint on how I would go about those things going forward, you know, up if an opportunities have come up for me and I have gone, [00:57:00] you know what? I don't actually think I I'm ready. Maybe I might put myself back into that in the future, in a different position or a different level. But like now in this, I think I would, you know, I'm going to step aside and try something else for awhile. Um, And maybe come back if possible.  Christian Parsons: Yeah, I know. And just having a good reputation helps with that. Right. And having it a track record, and then going back to the diversity, you know, having a diversity of experience that you can apply to get back into it totally makes sense. Right. I think that our conversation I was having earlier was definitely about, you know, I think that.  Sometimes within sports, we just  focus on what's happening on the team to our left and the teams who are right in the same sport and realize that, you know what the competition for. Sasky: just sports teams. It's entertainment as a brand. The idea of people siloing. Um, I think, you know, they, they to say like, Oh, it's really hard to get into sports if you weren't in sports. I think that's in some ways less hard now than it used to be, because I think a [00:58:00] lot more people are looking to people with brand experiences. Advertising experience who can show a broader range of thinking a broader range of experience and who are now people that understand that this isn't a hockey team. It's an entertainment brand. The actual part, where they play hockey is irrelevant. You aren't going to make them win you aren't going to make them lose you work with what you've got, but what you've got. Is what you can do with it, you know, like what can you do with that brand .That is not a sports specific skillset and the experience at a high level in that isn't coming from inside sport.       Christian Parsons: A big, thank you to Sasky for joining us. A really honest and raw conversation about setting boundaries, tough lessons from working for an NHL club and how building a diverse set of experiences  really sets you up for success. It was awesome.  As you can see I'm new at this. So any feedback that you have that could help us make a better show is greatly appreciated.   Once again, I'm Christian Parsons. You can reach me @ThisIsParsons on Twitter and Instagram. You [00:59:00] can see our show notes and transcripts at mtcpod.com. That's M T C P O D.com.  I hope you're able to learn something valuable from every single episode of the show. If you found it helpful, I ask that you share it with friends. Now, get out there and get hired at sports.