The Work in Sports Podcast - Insider Advice for Sports Careers

The Work in Sports Podcast - Insider Advice for Sports Careers


Rashida Gayle, Founder Twenty Six Marketing Agency – Work In Sports podcast

November 18, 2020

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

Back in the early 2000s, which seems like yesterday, but in our fast-moving world was actually, like, 100 years ago,  I was the executive producer for a TV show featuring NFL MVP Shaun Alexander. 

Shaun is an incredible dude, and I loved working with him, but that’s not why I brought this up. I bring this up just to show how much things have changed in the last 15 years.

Back then, athletes had very few channels to share their personal stories, their point of view, their personality or perspective. Just a few of the top stars would have their own TV show, like Shaun, others may have weekly segments on sports radio, or maybe work with a local sports reporter for a newspaper feature.

Most everything from a personal branding perspective worked through the media.  

And then it all changed.

Social media played a huge role – players could now voice their own stories, share their own vision, create their own videos – and have a channel to distribute them. 

But even more than social media as a tool – there was also a shift in attitude, utilization of the leverage players have, of the demand THEY create. Many in the media call this the player entitlement era, where they now call the shots. The athletes make the demands and they have shifted the leverage of every negotiation.

I find that term kind of insulting, player entitlement. The word entitlement gives it a negative connotation, like how dare they express themselves or want for themselves, or demand for themselves. 

Entitlement to me has a connotation of being something that isn’t deserved, like a child acting like they should get the toy because they want it. It is their prerogative. 

In the instance of elite athletes, they are the product, they are the brand, they have every right in the world to express themselves, brand themselves, leverage themselves, for their betterment.

And they are doing exactly that. 

Sites like the Players Tribune give all players a voice to share the world through their eyes. More and more athletes are creating videos, negotiating deals, creating documentaries and building a huge personal brand – even college student-athletes will soon begin to profit off of their names, images, and likeness. 

Alas, the players don’t all go it alone. They often look for trusted advisors, creative visionaries who can enhance their portfolio and build their reach beyond what they imagined was possible.

One such visionary is today’s guest – Rashida Gayle, founder of Twenty Six marketing agency, a boutique full-service marketing agency servicing best in class talent [in sports and entertainment]. They maximize brand opportunities through smart marketing initiatives.

Rashida works with stars, like MLS MVP Josef Martinez, NFL Running back Devonta Freeman, N’Keal Harry of the New England Patriots, Justice Hill and Miles Boykin of the Baltimore Ravens, and many others.

Time to find out how she got where she is today, and where she sees the world of marketing heading — here’s Rashida Gayle. 

A quick caveat, when we first recorded this interview, Rashida was the Director of Talent Marketing at GSE Worldwide – she’s only recently starte...