Raleigh Anne Gray: Must Love Sports CEO - Work In Sports Podcast

Hey everybody, I’m Brian Clapp, VP of Content and Engaged Learning for WorkInSports.com and this is the Work In Sports podcast.

Not a day can go by without there being some messaging that directly affects the young people of our world. 


When I was growing up in the 80s and 90s we felt the burden of nuclear war, I remember being fearful every time a plane flew overhead they were carrying a nuclear bomb set to destroy us…. Yes, I was slightly neurotic. 

But the theme of the decade was War Games. It felt like we were in constant threat of massive military action. 

Compared to the onslaught young people are facing today - that seems trite. 

Job prospects are down, industries are failing, people are dying en masse -- you don’t need me to recite the hateful mess that 2020 has become. 

I feel for all of you, and that is not patronizing, that is truly from the heart. I think of all of you daily who are doing so much right to prepare yourself for professional life and create the best version of yourself… and yet, the opportunity, in many ways, is being taken from you.   

I read someone yesterday pitching a concept, a marketing plan, with the main thrust being a push for people to 

“Find Something New” …

“Find Something New” 

Your career and life may be in shambles, your goals may be in disarray, your internships are canceled and your dreams look to be off track, you are collecting unemployment, you don’t have healthcare, you are afraid of a highly contagious virus killing people around you … but hey, just find something new. 

As if it was that easy. 

Personally I found this upsetting. 

Kind of like Marie Antoinette saying to the poor people of France without bread to eat…  “Let them eat cake” 

These words essentially claim the unemployed just aren’t creative enough - they need to just find something new! 

A mantra like this says - the burden is on you, just shift and do something else. You’re on your own kid, figure something out.

Now, I’m all for personal accountability, I think we all need to own our path, make our choices, adjust, learn new skills, adapt…. But these are really, really strange times. 

This is abnormal. 

Our current events are something none of us have any experience with, so in my worldview, the burden is on all of us to come together and help each other

Not just pass the buck, not just put the burden back on the individual and say “figure your own shit out”. The time is now to help...and that burden fits firmly on my generation. Those of us with employment, those of us who can help, those of us who can guide and assist and mentor. 

No one exhibits this spirit more than today’s guest Raleigh Anne Gray

Raliegh has a career in sports as impressive as they come -- ESPN, Twitter, The Players Tribune, Wasserman -- she has the iconic sports brand royal flush on her resume. 

But that is not where this story stops, it’s barely the beginning. 

A few years ago Raleigh launched her own LLC, Must Love Sports, and I’ll let her explain the details of that venture. BUT, when coronavirus hit, she immediately identified a problem facing the young college-age professionals and set out to fix it. 

Internships were being canceled everywhere. College students need experience, but also,  many need the specific internships credits to graduate! 

So now imagine you are a college student, who’s internship has been canceled, but you need to intern to graduate. Well, now, that’s a problem you didn’t see coming. 

Here comes Raleigh. 

Must Love Sports pivots their business model, puts together a summer session virtual internship program, and offers it FOR FREE. 

355 students sign up. Raleigh is changing lives. 

This is community action. This is a collective move to work together and force positive change, to help others, to work as a team in the game of life. 

I couldn’t be more excited to have Raleigh on this show -- here she is, my friend Raleigh Anne Gray


Questions for Must Love Sports CEO and Founder Raleigh Anne Gray


1: There are so many interesting parts of your career and journey I want to dive into - ESPN, Twitter, The Player Tribune, Wasserman – literally the biggest names in sports -  but let’s start with what is happening now in your world. 

In addition to your work at Wasserman, which is really exciting, you are also the CEO and founder of Must Love Sports, you launched this venture 3 years ago -- clearly you have too much time on your hands – but give us the high-level view of Must Love Sports, what was it designed to achieve?

2: We often talk in our business about being agile – making change fast and adjusting quickly to the world around us. When I was at CNN or Fox Sports, everything happened slowly, but at a smaller org, we can move quickly. 

You did just that when COVID hit, you identified a problem with internships and set out to fix it. Tell us about summer session with Must Love Sports – both the inspiration and the execution and process.

3: The program started in June - what have you learned now that you are into the thrust of it? and will this be a permanent part of Must Love Sports? will you continue down this virtual internship path?

4: We as employers across all industries demand some level of experience in our new hires, usually coming in the form of internships. But internships are naturally exclusive. 

Many people can’t afford to intern for free, especially over the summer when it is their best chance to earn needed money, and that creates a bigger gap between those who can afford experience vs. those who can’t. 

Is this system broken?  And if so, how do we fix it? 

5: Let’s pivot to you and your background – BA in History at UVA - then ESPN as a marketing coordinator. You hear history degree and you think Law School, professor, author – so why did you turn to sports?

6:  What did this first experience at such a large established organization like ESPN teach you about the sports industry?

7: After ESPN on to Twitter which in 2012 wasn’t the behemoth it is today, how different was it jumping to a company in i’s upward growth curve rather than already established like ESPN?

8: In your last year at Twitter you were the Director of Live Content, when I was in the broadcast media we were always battling for media rights since that is the real revenue generator.  Was that the battlefield for social media platforms too, acquiring and monetizing live content? 

9: At both ESPN and Twitter, and later at Players Tribune, you were on the content/marketing AND the partnership sales/ad sales side – how important was it for your career to understand revenue generation, and the marketing and content side?

10: Your work at Players Tribune giving a voice to athletes dovetails beautifully into your current work at Wasserman – at Wasserman you are the senior director of athlete exchange.  I’m so jealous of this… tell us what your current role entails.

10: I love the concept of athletes getting and using their voice AND controlling their brand. Growing up the only way I could hear from Michael Jordan or Larry Bird was to read their quotes in the paper or watch ESPN. 

How exciting is it that players are now able to speak directly to their target audience and build their own voice in an authentic manner?

11: Where does this concept of athletes as media channels go from here?

12: I know you are terribly busy so we’ll finish up with this – you have a unique perspective in that you are highly experienced in the sport industry, but also dealing directly with college age students trying to break in. You actively engage in both sides of the journey.

As you interact with these students as part of your virtual internship program, are you noticing any specific skills or traits that are underdeveloped for success in the real world, and that listeners in this audience should possibly focus on to help them find opportunity and success?

By Brian Clapp | July 15, 2020
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