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Running on relationships .

There’s a nuance between networking and relationship building. While the former can feel superficial and, at times, self-serving, our podcast guest this week explains how the latter can impact your career and life, and how it has helped her grow as a professional and human.

Better to call it something like relationship-building because it needs to be a two-way street.

Raleigh Anne GrayFounder/ CEO of Must Love Sports


Katie Hankinson (00:02):

Hi, I’m Katie Hankinson.


Mickey Cloud (00:03):

… and I’m Mickey Cloud. And welcome to Building While Flying, a Sasha Group Podcast, where we interview business leaders about how they tackle challenges, stay resilient and navigate ever changing skies. Raleigh Anne welcome to Building Offline. Thanks so much for being our guest today.


Raleigh Anne Gray (00:26):

Just an honor. Thanks for having me Nikki.


Mickey Cloud (00:28):

Yeah. So Raleigh Gray is the founder and CEO of Must Love Sports. An organization founded in 2015 to empower and educate current and future industry professionals. She’s also the director of business development at DraftKings, where she’s currently working after Tom has been at Wasserman and the Players’ Tribune, Twitter, and ESPN. So we’re going to cover all those areas and more, but to start, could you just give the overview of Must Love Sports.


Raleigh Anne Gray (00:52):

Yeah, absolutely. So again, thanks for having me absolute honor, especially knowing who you’ve had on here before. So shocked you would think of me. But Must Love Sports it’s honestly more to a lot of things. It initially started as really just a group to bring industry females together because it was nice to be able to walk into a room. And I’ve had a conversation with just one person before that looked a lot like you, it more from there to really just bringing folks together to have conversations, regardless of gender about the changing areas of the industry, and really just having a forum where people could feel really comfortable. And then last summer during the pandemic folks like you and others were kind enough to lend their time to transition us from an LLC to a 501C3 and our organizational structure and help students who had lost their internships.


Raleigh Anne Gray (01:48):

It was a horrible time for a lot of people, it continues to be. The last summer was hugely detrimental to those students who had done a ton of work, gotten a great opportunity and then it evaporated because companies… and unfortunately, but rightfully so, couldn’t bring anyone into the office. So we were able to put together a 10 week internship program that was remote, that worked around people’s schedules so that they could actually do whatever they needed to do, be at work or otherwise… and learn from a lot of industry leaders. So we’ll run it back this year. We have a lot of learnings from the original cohort, but that’s where Must Love Sports was, is, and we’ll be going.


Mickey Cloud (02:27):

Yeah. Awesome. Well, I just want to touch on that genesis moment of knowing that Must Love Sports came from… trying to… It was focused on industry events to build and foster relationships, particularly for women in the sports industry. And I was curious if, was there a particular moment, you mentioned walking into a room and maybe seeing one person that is also a woman in the room, but it was it just the drum of that all the time, or was there a specific moment was like, “We got to do something about this.” Or was it more just like, “Hey, I’ve built out a career in sports and in this industry and I want to help make it easier for those coming up behind me.”


Raleigh Anne Gray (03:10):

It was all of that, but I will say there was one moment at the time I was working at Twitter, I was in sales. I had a pretty good quarter and I thought, “Wouldn’t it be nice to put some of this to work for people who have done a ton for me.” And that was initially this footprint of amazing females who had pulled me up coming out of business school, transitioning to a new area of industry where it was tech versus just strictly sports like I was when I was at ESPN.


Raleigh Anne Gray (03:38):

So honestly it came from that. And then it grew out of so many people enjoying that forum of just oftentimes we’re going to events or back when we could go to events. You would go into the event and there was always a purpose or an ask, and this just didn’t have that. It was to have a conversation to build relationships because you know as well as anyone it’s really easy to work with people who already have some sort of a common thread with, or at least understood, they’ve got two great kids and they live in Chattanooga, Tennessee, et cetera. Those types of just where people are doing jobs sort of thing. So that’s where it started, and then it morphed into that connectivity tissue that was so tied and important and building that with other folks in other areas.


Mickey Cloud (04:23):

Yeah. I think it’s interesting, because I think one of your super powers is relationship building and just the… I feel like there’s no one in the world that Raleigh isn’t two-step, at least two connections away from… but also you talk about it in terms of relationship building, not in terms of networking. And I guess I was curious if that was intentional when you set up the Must Love Sports brand and if so, maybe why or why not?


Raleigh Anne Gray (04:52):

It’s a good question. I think for some reason, networking has gotten this really negative connotation, particularly and I love LinkedIn by the way, but also in a LinkedIn culture where somebody will reach out and try and connect with you and you may not have met him. So it’s a little weird, it’s kind of, you get in the fright of like, “How do I know this person, am I supposed to?” And then it comes back around when somebody asks you, if you can make an introduction. You don’t remember where you met them, but that’s a whole nother conversation.


Raleigh Anne Gray (05:20):

For me and I talk a lot about this with students. It’s getting to know people. Again, elements of that person, whether it’s their birthday or their family, or why they’re doing what they’re doing. And then being able to not ask for anything from them until you really need it, right? Everyone’s going to need something in a traditional relationship or friendship over time. But I think it’s better to call that relationship building because it needs to be a two way street and conversational and growing with people over time and networking for some reason just feels a little more surface level than it is on the depth of everything.


Mickey Cloud (05:57):

And also it feels like it’s… you said it’s a two way street, but it is like when… I don’t know why, but in the context of networking, sometimes it feels like it’s just something that you’re trying to get for yourself as opposed to having it go both ways.


Raleigh Anne Gray (06:13):

Yeah, absolutely. And it needs to be something where if somebody feels comfortable enough to ask for a favor at some point, then the other person can reciprocate or they don’t ever have to, right? It’s just if you have that strong foundation, it’s going to be a lot more sensitive.


Mickey Cloud (06:29):

So what was it about… you mentioned the pivot from the LLC to the 501C3 and I assume… was that something that you had been thinking about pre-pandemic or was that something that pandemic hits, you’ve got Must Love Sports as kind of an events based business and then you saw the real need for students and the devastating loss of those internships and how could you provide value for them? So could you talk a little bit about the thinking that went into that pivot?


Raleigh Anne Gray (07:02):

Sure. I hadn’t actually thought about the events transitioning to the virtual event space, but the last event that we had from Must Love Sports was NBA ALL-STAR in Chicago in 2020, which arguably for a lot in the sports industry was the last time we were all together in one place just because that’s happened to be when that was. And that’s always in mid February, so very close to when the pandemic and Adam Silver shut down the world. But it honestly wasn’t so much of a cognitive transition, something that I just did based on planning it out. It was more so just seeing a need and then filling it. So during the time that the pandemic had started, I was hosting a lot of women’s in sports conversations because everyone was dealing with something.


Raleigh Anne Gray (07:52):

And that is true of everyone. Everyone’s going through something every day. But in particular, there were women in sports worried about how to handle working from home with a family or how to deal with the initial stress of all of the change that we just had. But then I had outreach from students because one of my favorite things to do is when friends are nice enough and I still think they’re crazy to include me in their classroom, but it’s my favorite thing is to go talk to students and empower them and hopefully help them.


Raleigh Anne Gray (08:21):

And several students that come to me and said, “I lost amazing internships, things that everyone would kill for to have.” And I just thought we got to put something together. And as I get older into what we’re doing, I really would prefer to just live a life where I’m actually helping people. It would be my goal just to do that every day. But somehow I’ve got to pay for my dog food and monthly BarkBox not for a sponsor, but love. So yeah, that’s where it came out of. And it really wasn’t something that was planned so much as just the way I like to focus on things.


Mickey Cloud (08:58):

Well, it was a sprint for sure. And so could you talk about… it was a need, this was spring time last year and internships were pulled from a lot of these students and the fact that you pulled off a 10 week internship equivalent program for the summer session last summer, could you talk about just the sprints that you had to do to pull that off?


Raleigh Anne Gray (09:31):

Yeah, sure. I got my first outreach from the students in, I would say that early April and we finally came out with how we were going to structure this. I say we by the way, because it takes… Must Love Sports doesn’t exist without people like you and your colleagues and everybody else who wanted to help and wanted to do something, but didn’t necessarily know how. So from a sprint perspective, it was honestly reaching out and getting educated from different stakeholders. So one, understanding the industry. Where different internships were. What needs they had to try and fill. Two, talking to educators who were scrambling because students were in such a tough position, not only for physical in-person school and how it had changed, but then also opportunities that would inevitably put students out of graduating because they didn’t actually get a course credit or something like that.


Raleigh Anne Gray (10:27):

And then three, just figuring out what people wanted to do managing their time, because everyone else was going through again, something too. So the sprint happened in that way and that it was a lot of quick learning from people. And then luckily enough, just based on already having propped up a website for things or all of that, it was pretty turnkey to actually get the word out. And then of course, the PR of Comms Engine really helped. We had an article and the LA Times, for example, which you and I being based more East Coast, our network being here was hugely valuable. Or I have a lot of friends who went to HBCU and we want to make sure that it’s hugely inclusive, not just of their community, but others. So that outreach and initial education PR point definitely helped along with the other three education sides.


Mickey Cloud (11:17):

And how many Must Love summer session participants did you have, students did you have?


Raleigh Anne Gray (11:24):

Yeah. So last year we had 350, and I would say there were about probably 190, 200 who came to every single thing. Again, we recorded stuff, made it accessible to students who had day jobs and things that they needed to maintain, but it was really cool, and what’s been fun since is to see the way that cohort has stepped together. And now as they’re graduating and moving into whatever you and I were lucky enough to go UVA together and meet each other and grow our careers alongside one another, some moving faster than others, total domination on that side, Mr. Cloud. But the cool thing would have been if we could have met all of the colleagues that we interact with at different capacities that back at UVA versus now in a different lane. So these students have the chance to get to know each other as juniors or rising seniors and in college, and that’s something that they’re taking as they graduate now.


Mickey Cloud (12:26):

That’s awesome. Well, I want to talk a little bit about balancing, launching Must Love Sports which for you was a bit of a side hustle, because you’ve always kept your corporate career as well. But it’s been a really prolific one, I think you’re underselling just the path you’ve created for yourself from ESPN to Twitter, to Players’ Tribune, Wasserman. You’ve seen the sports industry from a lot of different angles and so I was curious as to just about how do you balance having those? My day-to-day job wipes me out. I don’t have side hustles because I like to just unwind even today, but you find another gear where you’re then now doing… you’re building Must Love Sports as a brand and as now a 501C3. So how do you balance that?


Raleigh Anne Gray (13:24):

Yeah, it’s a great question. And I would say the biggest thing that I learned from one of my bosses and mentors at Twitter. You always have to be an expert in your craft, right? So you can’t have a side hustle and then let it impact your day to day job. There’s one you’re getting paid for it and the other you’re hugely passionate about. You’re hugely passionate about your two awesome kids and that’s what you do when you take your time off, right? That’s your side hustle and that’s a major hustle by the way, much bigger than anything I got going on. But I think when I think about what… be an expert in your craft, but then also making sure you have these passions, that’s how I balance it and it is… you’re right. I’m not going to be the person who says that it’s not a lot of work, but you just have to be really organized and making sure that if you’re leaning on other people for certain things, they know exactly what that is.


Raleigh Anne Gray (14:16):

I’ve got a great executive director this summer. He is an educator by trade. He was a camp counselor and ran a camp for forever. He understands that side and that’s why he balances me in that perspective. And that’s why I can grab some balance because I’ve reached out and gotten some help on that. So I think you just have to be really organized. You have to be focused on doing a side hustle that you’re passionate about. If you are not passionate about it, it will not succeed because you won’t want to put the time in it. So that’s how you balance it and you can’t let it get in the way of being an expert in your day to day if that’s the thing that’s actually putting the bill and something you are equally as excited about.


Mickey Cloud (14:55):

Yep. Well, I do want to talk about some of those companies specifically, whether it’s Twitter or ESPN or Players’ Tribune or Wasserman, DraftKings, where these are these all been either high profile or just high growth companies in the sports landscape. And so what are some of the learnings that you’ve taken from your day-to-day corporate world and how have those translated to when you put your entrepreneur hat, jersey on and go to build Must Love Sports?


Raleigh Anne Gray (15:25):

Yeah. I like the jersey part, we will we run with that. Played for the one on the front, right? Not the name on the back. Yeah. So for me, if you’re looking at a thread, which it’s tough to put one through any career, it’s definitely not linear. But ESPN, Twitter, Players’ Tribune, Wasserman, now Draftkings. They’ve always said somewhere I have at the intersection to media technology and sports, and sometimes one outweighs the other, right? I got to Twitter. I was now working in sports, but I had made my way into sports because that’s just what I’m used to and love. So if I think about the very degrees of corporate structure, right? ESPN, big company owned by Disney. Even at the time when I was working there. Twitter, it was fledgling in itself and came up and IPO when I was there. Players’ Tribune, small content driven, run by athletes, but run by also people that I worked with at ESPN.


Raleigh Anne Gray (16:26):

So I had a firm understanding of it, and then Wasserman bringing it all together, right? In the sense that I hadn’t worked at the epicenter of athletes. I hadn’t been a part of that and that’s what drives sports from commune an existing because they happened to be on the field pitch eyes, et cetera. So from a corporate perspective, those are all… and now DraftKings even five different lenses I get to see everything through. And I think it’s about identifying things you like about certain things and then things you don’t and recognizing whether you really don’t like them, because you’re holding a grudge or something, or if it’s really something that you can learn from. And the corporate structures of all of them, most of the leaders that I’m most admired were really candid, were driven with the culture and we’re helping to build that.


Raleigh Anne Gray (17:15):

But then also from that candor came what they were trying to work on. So now the corporate learnings that I take when I’m helping or building a team is like, do your best to be the one that’s super positive, but also grow in certain things. Let people know what you’re working on, my resting word I tell my team right now it’s awesome. Sometimes people will say some things that are not so awesome and I will respond, awesome. Great. No, no, that was a really bad thing they just said on a call and it absolutely derailed the entire project. So a lot of it is from the corporate structure, just identifying those people who you want to emulate, understanding how to make that a part of your day to day and then build from there. For me it’s always about people, not necessarily about structures or organizational elements, et cetera. It’s about learning from things in front of me.


Mickey Cloud (18:08):

Well, I think it makes a lot of sense as someone who experienced… when Mike and I from Vayner Sports led that session at Must Love Sports last summer, it was… I had done a lot of Zoom speaking by that point, at least more than I’d ever done before. But the students that were part of Must Love Sports, gave by far the most energy into a Zoom. And you’re just look at the comments and they’re really high quality questions, the follow up afterwards, I think you have certainly built that giving and positivity culture into… it’s translated from the things that you’ve liked in your corporate world over into Must Love Sports. And some that’s also just your personality, and I think it’s reflected even in how the students approached those sessions, so.


Raleigh Anne Gray (19:00):

Well, obviously that means a lot because Zoom has become a bit of a fatigue, no knock on the product but any type of video when you can’t be with the people you want to be with it’s tough. So that definitely means a lot, if you’re taking time, we wanted you to have fun. So come on back.


Mickey Cloud (19:20):

Well, I wanted to ask. The next couple of questions are going to be a little bit for me, but you had mentioned early on working with women specifically who had empowered you and added to your growth. And that was part of the inspiration behind even starting Must Love Sports. And I think you’re a sports junkie as well, and I know you’re friends with like Katie Nolan and some of these people that you… these emerging female voices in sports media. And I’d be curious to just hear your take on the progress that’s being made from having the Mina Kimes of the world and the Dana Jacobson’s and things like that, who were getting more prominent voices on platforms like ESPN and also have built really impressive personal brands through platforms like Twitter. And so just curious your take a little bit on just the emerging female sports broadcasting voices.


Raleigh Anne Gray (20:24):

Yeah. It’s something that’s so exciting even with developments today that are focused on just increasing the amount of female sports that are on television. I think that’s sad, there’s like 4% coverage and there’s obviously amazing women doing remarkable things, whether it’s in the NWSL or our women’s soccer team, not to harp on soccer that actually is participating in world cups and other things, not a total burndown there but you know what I mean? But I think what you want to see in anything, whether it’s gender related or any type of diversity element is you want to be able to see yourself in those people, right? So it’s really important to have those people on television and visible and then influence or setting or visible on other social media and digital capacities where a younger audience can look up.


Raleigh Anne Gray (21:17):

Bonnie Bernstein has become one of my really good friends, and I can’t believe that I get to say that I know her because I used to watch her on TV, and that’s why I want to go work at ESPN or CBS or wherever, because I just thought you were on television, by the way. This is why I’m genuine. I didn’t understand there’s a business behind all of that, but you have to be able to see people that you can emulate and going back to the type of corporate culture and the things that I learned there, the female side is so important to me. There’s also… and while it may be stereotypical, occasionally there’s some gender roles where people will push each other down, because they’re worried there’s not enough room. And that is absolutely what I want to counteract. There’s more than enough space. You just have to help others create it, right? And I think that folks like Katie or Mina or others are doing an amazing job in that. So it’s all about being able to see what you want to be and it’s usually important.


Mickey Cloud (22:17):

My next question was going to be around, I guess the… you mentioned the thread of the different career opportunities you’ve had and how those have… the lessons you brought over to Must Love Sports, but what’s the long-term vision for Must Love Sports? And you in general and the next steps around how you’re going to continue to build that out.


Raleigh Anne Gray (22:41):

Yeah. I’m glad you asked. You must’ve been reading my email to our executive director of this summer, Andrew [inaudible 00:22:49] but he and I are actually working on what does it look like next? Because I am hopeful that there will not be this need for students to have to have an alternative summer internship because they can be where they needed to be, right? And that’s something that I’m certainly hopeful comes to fruition. So in the absence of that, what are we providing to these students? I’ve talked a lot about the connectivity and the community. And honestly, last summer outside of the pandemic, we were going through a lot as a country. And it was nice to be able to have this safe space to come and talk about diversity and inclusion. It was nice to be able to talk about some of the students who were in a difficult position and maybe had to leave the country because they weren’t from here, but were on visas, et cetera.


Raleigh Anne Gray (23:40):

It was cool. And that’s a horrible lack of a better phrase, but it was amazing to have that space. So we’re trying to achieve from the next steps is to keep curating that community. Keep making sure that students have the ability to get to know each other, if they’re going to be in this industry sooner. And a lot of students last summer thought they wanted to be in sports, found a different side. Some people thought they wanted to be in marketing and then they talked to other people and they’ve figured out they want to go work at an agency like you guys and build brands, right? Instead of work inside the brand itself. So it’s all about that community experience, then obviously the connectivity within me and certain that people can explore and learn in a setting that’s comfortable.


Mickey Cloud (24:25):

Yeah. Awesome. Well, we can’t go through this podcast without talking about UVA Sports as well. And so I think I’m also just going to put it out into the universe that I think you’re going to be the best athletic director at UVA when that happens one day, which says a lot because Carla Williams is amazing.


Raleigh Anne Gray (24:48):

I was going to say, it’s tough to put me in that bucket and we already have the most phenomenal-


Mickey Cloud (24:48):

We do. We do but, there’s there’s room for everyone as you said. There’s room for everyone. So is that what this is all working towards? Is that what your career is building towards is you’re going to take over as athletic director UVA?


Raleigh Anne Gray (24:59):

Oh my gosh. That would be… that is the dream. I would love… honestly I just love to teach for the rest of my life because then I will actually hopefully have the chance of remaining technologically savvy with kids around me who know what’s going on, but what Carla does so well and what the best athletic directors anywhere do so well is engaging with the people that matter, which are the student athletes and those who are involved in the program itself, whether it’s periphery folks like you and I, who are obsessed, but I mean the coaches. If you’ve got a staff that loves you in such a difficult environment, and you’ve got students who couldn’t think of being anywhere else, because they like being around you, I’d say that’s a win. So she’s winning in my book.


Mickey Cloud (25:44):

Yes. She’s doing amazing things. I’m just putting it out into the universe.


Raleigh Anne Gray (25:47):

Thank you. I’m glad it’s out there, now it has to happen.


Nikki Cloud (25:49):

Now it has to happen. That’s the way these things work. All right. So the last question we love this Building While Flying analogy for us entrepreneurs because it speaks to the nimbleness, the flexibility, the foresight you need to operate in business but also because pilots are renowned for their inflight checklists, right? So when things go awry, they’ve got training that keeps them calm under pressure. So when you’ve got to make a tough decision for your business, for Must Love Sports, what’s your internal checklist or what’s your process that helps you get through?


Raleigh Anne Gray (26:22):

That’s a very good question. And I should know this since I’ve already listened to some of these, I should have been prepared. But honestly from a checklist perspective, and you talked a lot about the frenetic nature that can come around, the pilot side of things, right? Going through, have I done this? Have I done that? Et cetera before you freak out that you’re about to need to land the plane for whatever reason. And honestly you just have to step back, right? Because we have so many… I look around the room right now and just like how many devices I have in front of me and how much of that can actually take me out of thinking through the problem as opposed to just acting quickly.


Raleigh Anne Gray (27:02):

So the whole adage of counting to 10 honestly comes first on my checklist and counting to 10 in a productive way to say, “Okay, should I be reacting then this way? If so, why?” Getting your own opinion around it and then if you need to engage, if it’s not something proprietary, engage a couple of people who are your go-to right, say, “Am I thinking about this correctly?” And do you have that time? Do that. Lean on people, that goes back to the relationship building, because you’re not necessarily asking a favor per say, you’re letting that person know you’re vulnerable and you’d need a little guidance on something and you’re likely going to them because they have it. So honestly, the old adage of just counting to 10, stepping back and separating yourself, sometimes that can include for me like taking the dog on a walk and not bringing my phone if that’s an option. But those sorts of things of just disconnecting and then allowing yourself to build back up from the problem.


Raleigh Anne Gray (27:58):

That’s what my checklist usually is. And I know we’re not always afforded the amount of time to do that and you have to figure out a way to give it a half-life. But if it’s a major problem, you could take a moment and people will actually be a little bit, I think more willing to allow from that. It’s like when you answer a question here, if I don’t take a pause and I probably haven’t thought about it, right? So I’m sure I could come up with even better answer if I could go through my own checklist right now. But that’s how I think about crazy frenetic situations, which I know we all deal with every day.


Mickey Cloud (28:32):

Yeah. Awesome. Well, thanks so much Raleigh for chatting with me today and this has been awesome and we’ll talk soon.


Raleigh Anne Gray (28:42):

Absolutely. Thanks so much for the time.


Katie Hankinson (28:45):

Well, now that we’ve finished that thoroughly interesting interview, we’re getting ready to land, but before we do Nikki and I caught up on some of the themes and topics that stuck out to us.


Raleigh Anne Gray (28:55):

Yes, we’re liking this to the post game show, where we break down the key lessons we all can benefit from, including our students in Sasha Group. Here is The Sasha Sidebar.


Katie Hankinson (29:11):

Hey Mickey.


Mickey Cloud (29:12):



Katie Hankinson (29:13):

I just listened to your interview with Raleigh Anne and it was really awesome and super inspirational. What a cool woman.


Mickey Cloud (29:19):

Yeah. And I loved that she was a little bit of a different guest for us just because she’s… you heard she has a day job and her entrepreneurial pursuits are more of the side hustle, passion project for her. But I think it just goes to show there’s aspirational lessons across wherever you are and on maybe the scale of how deep in it you are.


Katie Hankinson (29:42):

Yeah, for sure. Can you talk a bit about how you… because you’re obviously connected to Raleigh Anne and retired to some of the summer internship work that she ran in the summer. Can you talk a bit about how you were part of Boston and how that played out?


Mickey Cloud (29:56):

Yeah. We met on the first day of college a long time ago now and we’re friends all throughout college, and then when we both graduated. We weren’t like super close thing in touch, but work actually brought us together a couple of times. She was… when we were working with the Miami Dolphins at Vayner, she was our rep at Twitter. And so I was like, “Oh, Raleigh Anne, how’s it going? I know you.” And then from there we just stayed in touch where I was following her move from Twitter to Players’ Tribune, to Wasserman.


Mickey Cloud (30:36):

And there were some opportunities where Wasserman is a similar agency to Vayner Sports. And so there were some connections there, and so we just stayed in touch through that over time. And when she came up with the idea for the summer internship program through Must Love Sports last summer, I immediately said, “Hey, let me know how we can help.” And she did it in a very way that only Raleigh can, is that she… whether you’ve met her for one podcast listening to her or you’ve known her like I have for many, many years. She can get you to do stuff and she can activate people. And so she said, Hey, listen, would you and Mike Nelligan from Vayner Sports do session on the…


Mickey Cloud (31:25):

Must Love Sports is all about introducing the entrance to professionals in the sports world and all the different ways you can work in the sports industry. So there were people from… some of our clients from NASCAR did sessions on what it’s like working at the league governing body. We came at it from the sports agency, but then also marketing agency that works with sports brands. So just trying to show the different ways that when someone says, “Oh, I want to work in sports.” What does that mean? And how that all the different ways that can happen and so probably I literally just went to all the people in her network that she’s amassed and had them talk about the different angles that they come into sport.


Katie Hankinson (32:06):

That’s brilliant. I also think what’s… and she alluded to this at the end of the conversation. There’s something so magical about the fact that there’s a serendipity to this terrible situation where a lot of people had lost their internships, we’re in… probably freaking out because there’s no way that they’d tee themselves up for a career. And only that awful situation at the pandemic could have created the conditions to then have this… what sounded like a really amazing group experience. So this collective pandemic experience birth this really awesome internship experience and all the relationships that those people built with their cohort of interns, it’s really different to how a typical set of interns would go have their summer experience.


Mickey Cloud (32:54):

Yeah. They had a 350 person group that had that collective like you said, the conditions that created a collective experience that at most, unless you’re working for a really big company. We’ve got two interns this summer that’s different than if you’re part of a collective of 350 people that are now part of your network and that you’ve interacted with and gone through the same program with.


Katie Hankinson (33:15):

Yeah, we’ve heard a lot I think from many guests about only this weird year would have set up the condition for certain things to happen, and now we need to figure out how to take some of those positives and recreate them or learn from them and apply them as we come out. Super cool. I also just thought some of Raleigh Anne just general life attitudes were amazing. The idea of… she talked a bit about, obviously Must Love Sports was very much started about helping women in the business raise their profile and support one another. And I love the idea where she talked about competition, that it isn’t a zero sum game and there is more than enough space, you just have to help others create it. I thought it was a really wise and powerful sentiment and really important for everyone to remember.


Mickey Cloud (34:09):

And especially just in an industry like sports, that’s so dominated by men. And she had to start off the top of her head, only 4% of sports that are broadcast on TV are women’s sports and that’s A, it’s a cry never heard that side before. But then B, the fact that in order to want to get into something, you have to see people that you want to emulate in that world.


Katie Hankinson (34:34):

Yeah. See what you want to be.


Mickey Cloud (34:36):

Right. And so that’s what she’s trying to create.


Katie Hankinson (34:41):

Yeah. That’s super important. And then I think the last one, aside from her, the fact that her resting state is awesome. Her resting word is awesome, which is awesome. I also liked the way she talked about teaching, which is clearly a true driver for her. A purpose for her it’s to teach, but the idea that teaching is something that you don’t just do to raise other people’s knowledge, but also to become savvy yourself. She gets to be more savvy about that because she works with kids. But the idea of teaching being a two way street, it was really interesting to me too.


Mickey Cloud (35:16):

Yeah. And it also dies into her point of view on relationships being a two-way street. And if you only come at it thinking of it as a one way thing, you’re never… it steers into the negative side of networking and things like that. But if you think of it more as a two-way street than relationship building, you’re going to get a lot of value out of it.


Katie Hankinson (35:37):

You essentially maximize the potential of that, connected. So what’s our question?


Mickey Cloud (35:44):

I think it’s something you just tapped into, right? Which is there a relationship that you had that was started as a work connection, but then you maximized it. You got more out of it because you went deeper with that person, that mentor, that boss, that colleague, that peer in an industry that is now impacted you in a much bigger way, because you have that two-way street.


Katie Hankinson (36:09):

The work full of connection have became a rewarding relationship.


Mickey Cloud (36:12):

Yeah. The work connection became a rewarding relationship. Here we go. Thanks for joining again and for Building While Flying with the Sasha Group today. I hope you learned as much as we did. We’ll meet you right back here next time for another flight. If you’d like to hear more about how business owners and brands are navigating these times, tune in to the next episode. And if you’re so kind, please rate and review us, plus we’d love feedback. So let us know what you think, what you’d like us to dig into next on Building Offline, across brands, businesses, marketing, and more.


Katie Hankinson (36:42):

Original music by Fulton Street Music Group.

Welcome to Building While Flying!

This weekly podcast is brought to you by Sasha Group. We’re the consultancy meets agency arm of the VaynerX family of companies. We help ambitious companies build strong brands that flex with the times through strategy, branding media and marketing.

In ever-changing times, businesses and brands have to shift and adapt. And across all sectors, there is an air of experimentation. Business owners are trying new things out in the wild;  building the plane while flying.

Our pilots, Katie Hankinson and Mickey Cloud, will be talking to a diverse range of business leaders and founders. They’ll explore how these guests tackle various challenges while staying resilient and committed to growth. Through these real-life examples of strategies put into practice, we hope to inspire you to experiment and develop your own strategies as we all navigate these uncertain times together.

Raleigh Anne Gray is the founder and CEO of Must Love Sports, an organization that empowers and educates current and future industry professionals.

She also is the Director of Business Development at DraftKings, following time spent at Wasserman, The Players’ Tribune, Twitter, and ESPN. Her career has been a continual intersection of media, technology, and sports. When the COVID-19 pandemic forced companies to cancel summer internships for college students and graduates, Raleigh Anne saw a need and opportunity to pivot. She changed Must Love Sports from an LLC to a 501c3 organization and launched a 10-week summer internship program for sports industry students impacted by the pandemic.


In her conversation with Mickey, Raleigh Anne breaks down how each step of her career—and the people she’s met along the way—influences her work with Must Love Sports. She talks about making side hustles successful and the positive changes she sees coming for women in the sports industry. Most importantly, Raleigh Anne breaks down the nuances between networking and relationship building, and how getting to know people can make a difference in your networking efforts.

Other in-flight topics:

  • Networking vs Relationship building
  • Being a woman in the sports industry
  • Pivoting your business based on need
  • Balancing a side hustle with a full-time career 
  • Applying learnings from your career to your side hustle/passion project
  • Emerging female sports broadcasting voices

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