
This Exec Got Her Start In Baggage Claim. Now She’s The VP Of The Largest Privately-Owned Airline

Sherrexcia "Rexy" Rolle is the 29-year-old woman taking Western Air to new heights, and it's all thanks to her badass business savvy.
For those of you who might not know, Western Air Limited is the largest black privately-owned airline in the Bahamas and Rexy runs it. Rexy, who is also a business attorney, currently serves as the Vice President of Operations and General Counsel for the thriving airline. Having accomplished VP status, as well as oversee the growth and expansion of the $90 million company all before 30, there's no wonder Rexy is going viral for her accomplishments!
In an industry dominated by men, Rexy is both entrepreneur goals and the definition of black excellence. The aviation czar is redefining what an executive looks like while encouraging other women to be themselves while breaking the mold in their respective field.
I was so motivated when I saw Rexy Rolle's story that I knew that I had to connect with her and learn more about how she has achieved a dream that some would think is impossible. I had the opportunity to speak to Rexy and she shared her story and phenomenal tips for women trying to making it in this entrepreneur game. Check out our Q and A with the top exec below.
Is it challenging being an executive in an industry where women are not as represented as men?
The lack of diversity in aviation is what makes me work harder and it gave me the adrenaline rush to compete on a higher level. Executive positions in the airline industry (e.g. pilots, mechanics, dispatchers) are overwhelmingly dominated by males, so for women searching for those high positions, they are often automatically looked down on as not being technologically informed.
You do have to be ten times more informed. You do have to be prepared for people to purposefully challenge you because they feel that you may not be aware of what you're doing. I always take my time to prepare in advance to know what we're going to be discussing because there is always someone around to try and challenge your qualifications. I'm okay with having to be three times as good as the next person because I'm not going to let anyone keep me from living my dream. I've wanted this since I was a little girl.
"I'm okay with having to be three times as good as the next person because I'm not going to let anyone keep me from living my dream."
When did you fall in love with entrepreneurship?
I was an inquisitive first grader and I remember going to school and the kids would always talk about what their mother did for a living. After hearing classmates boast about their parent's jobs at school, I went home and asked my mother what she did for a living. At the time, my mother, who gave birth to me at only 16 years old, said, "Well, I take care of you." In response, and this was me being a naive first grader, I said, "That's nothing!"
It was at that moment that I vowed to be a successful independent business woman. In hindsight, I owed my mother an apology for not understanding how difficult and honorable it is to be a full-time mom and wife. It was also a deeply personal wake up moment for my mother who took in my words and decided to push herself beyond her own limitations. Not too long after that conversation, my mother motivated herself to go back to school and receive a life-changing college education. She also encouraged me to dream beyond my wildest imagination, traditions, and gender.
There is an assumption that because your company is a family-based airline, that you may have just been given your position. What do you say to that?
That's not true. I started from the bottom and worked my way up. When I was a young girl, I worked as a baggage handler after school. Back then, the airline had its ups and downs. There were constant delays and management issues, but we learned from all of this and remained resilient. I went to school. I studied my field. I put in a lot of work. Believe me, there's nothing easy about my journey.
We all know entrepreneurship can be a little difficult. What is a tip you can offer budding female entrepreneurs?
My number one tip is you definitely have to have passion for what you do. You must love your work. You're going to hit so many roadblocks and encounter people who are 100% not going to believe in the vision you have. Or, just in the day to day business dealings, whether it's government agencies or other private businesses, you're constantly going to be challenged. So, if you do not have that passion for the specific niche that you're in, you will fade.
Number two, find allies. That doesn't necessarily mean somebody who is going to finance your dream, but finding someone who believes in it just as much as you do. Find a group of women who can support you and push you to be great. The circle you keep is a profound reflection of how successful you will be.
"If you do not have that passion for the specific niche that you're in, you will fade."
Do you think the diversity challenges in aviation are based on race, gender, or both?
Although it is definitely rare to see black women in the aviation industry, me living on the Islands, I believe the disconnect is more so based on gender. The aviation community is booming with so many underrated careers. I've noticed an increase of female dispatchers and ground support agents, but I have been pushing for administrative and executive positions as well. I also encourage people to forget any qualms about being underqualified for a technologically-driven field and pursue aviation just like any other industry that may interest you. There is always training, there is always educational support. If you want to get in aviation, please just do it!
What are some accomplishments that you are proud of?
I helped open the Bahamas' first private passenger terminal. I suggested adding even more routes and planes, and I'm now working towards obtaining my own pilot's license. Most importantly, for someone like me who started off as a baggage handler, it was crucial for me to take advantage of all opportunities that were presented to me.
I could have gone in two directions with watching this airline grow up as I grew up: either assuming it's there at my fingertips, or really taking a stance of wanting to improve upon what's already there. I wish for everyone to do the same in their lives. Take time to grow and learn every day. That's how you become great!
For more Rexy Rolle, keep up with her social media by following her on Instagram.
- Rexy Rolle | Airline Exec | Aviation, Business Attorney ›
- Rexy (@rexyisland) • Instagram photos and videos ›
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- 29-year-old woman running the largest black-owned airline in the ... ›
- Sherrexcia “Rexy” Rolle Runs The Largest Privately-Owned Airline ... ›
- Meet Rexy Rolle The Woman In Charge Of The Largest Black ... ›
- 29-year-old Bahamian airline owner continues family tradition ... ›
Abesi Manyando is a Journalist, Public Relations Specialist and Creative Writer obsessed with culture, art, and music. She intermixed her degree in business management and marketing with her love for writing to form the popular PR & Branding Development firm, Abesi PR eight years ago. She is now making art and writing her priority and is working on an upcoming children's book and creative projects that move her soul. You can follow Abesi on Instagram @abesipr and her blog, 7thandlotus.
'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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Lawd. Out Of All The Current Dating Trends, 'Floodlighting' Is One Of The Biggest Red Flags.
I remember when I went on my first official date with an ex of mine from back in the day.
Before I decided to do it, I knew that I was attracted to him and that we both had things like poetry, music, and pretty much all things Black culture in common (I also semi-vetted him beforehand because we had some friends in common) — beyond that, though, I didn’t know much. And so, after about 30 minutes into that date, he asked me a particular question, and at the time, I thought that it was beyond thoughtful: “Shellie, what do you look for in a man?”
As I quickly ran down my “Christmas list” of desires, as I came towards the end and then looked him in the eyes (because we were walking), he calmly and simply said, “I can be that.” Chile…CHILE. It took me close to a year of discovering so many cryptic things about him for me to realize that there is a really big difference between what someone “can be” vs. who they actually are — and that oversharing can set you up for dating a character more than a genuine individual. Lesson learned. Lesson freakin’ learned.
I can’t lie, though — when I recently read about a current dating trend known as “floodlighting,” from my own personal experience, that’s probably the closest that I’ve ever come to it. I think it’s because, since I’m so open with damn near everyone and also, since my past pattern has mostly consisted of taking friendships into something more (as opposed to dating people who I barely know), I’ve never really taken the classic floodlighting approach to try and connect with someone else.
I do have clients who have, though — and the trend is concerning enough that I definitely thought that it was worth writing about; mostly as a PSA to not floodlight and also to be cautious if you sense that someone is currently in the process of trying to floodlight you.
And just what do I mean when I say that? Read on, sis. Read on.
Floodlighting. According to Author Brené Brown.
Best-selling author, podcaster, and professor Brené Brown is a pretty popular person. Since quotes are my thing, that’s probably how I “connect” with her most because I like things that she has been credited for saying like “Maybe stories are just data with a soul,” “The dark does not destroy the light; it defines it” and “Shame corrodes the very part of us that believes we are capable of change.”
And since self-reflection is such a big part of her platform, it didn’t really surprise me when I found out that she is actually credited for coming up with the term “floodlighting.” It would seem that in her audiobook, The Power of Vulnerability: Teachings of Authenticity, Connections, and Courage, she stated this:
“Oversharing? Not vulnerability; I call it floodlighting. ... A lot of times we share too much information as a way to protect us from vulnerability, and here's why.
I'm scared to let you know that I just wrote this article and I'm under total fire for it and people are making fun of me and I'm feeling hurt — the same thing that I told someone in an intimate conversation. So what I do is I floodlight you with it — I don't know you very well or I'm in front of a big group, or it's a story that I haven't processed enough to be sharing with other people — and you immediately respond ‘hands up; push me away’ and I go, ‘See? No one cares about me. No one gives a s*** that I'm hurting. I knew it.'
It's how we protect ourselves from vulnerability. We just engage in a behavior that confirms our fear.”
If that was a bit challenging to follow, what Brené is basically saying is…well, you know how sometimes you will watch a post on social media by someone you don’t know, your first reaction is something like “Ugh. TMI.” and then you may actually say some form of that in their comment section? If others join in with your sentiment, the poster may follow up with a second video about that being why they don’t share their lives — it’s because people only take shots at them for doing so. Yeah, social media? Oh, there is PLENTY of floodlighting that goes on up in there, chile.
Okay, but what would be the strategy for floodlighting if it proves to be such a risky approach to connecting with other people? According to Brené, by sharing too much information about ourselves only to then receive some level of rejection for it — it’s kind of a “hurt you before you hurt me” kind of thing.
Meaning, “I’m not the best at cultivating intimacy and so, if I overshare and you pull back, I can make you be the ‘bad guy’ for rejecting me which makes all of this a test that you failed instead of my choosing to create an authentic connection and owning my part if things don’t end up working out.”
And yes, many people do this because, at the end of the day, they aren’t very comfortable with genuine intimacy. They also do it because they don’t really get that, when it comes to intimacy, another word should be the goal instead of vulnerability anyway.
I’ll explain.
It’s Important to Remember What Vulnerability Means
Ask pretty much any of my clients about what I think about the word “vulnerable” when it comes to marriage and they’ll tell you that I am not a fan. That’s because I lean into being pretty word-literal (as far as original definitions go) and I am aware that vulnerable means things like “capable of or susceptible to being attacked, damaged, or hurt,” “open to moral attack, criticism, temptation, etc.”
And y’all, for the life of me, I don’t know why anyone would choose to vow to spend their lives with an individual who they would need to be vulnerable with because, if your partner is susceptible to damaging you or they leave you open to attack or temptation — does that sound healthy to you? Yeah, me neither.
So, what word do I prefer then? Dependent. And what’s so wild to me is the fact that our culture is so used to the word “vulnerable” that many, even when it comes to their close connections, are far more uncomfortable with the word “dependent” — and boy, ain’t that a damn shame. Dependent is all that I want to be with my intimate dynamics because that’s all about “relying on someone or something else for aid, support, etc.” — and that is what you should do with your closest friends and definitely who you are in a romantic relationship with.
In fact, if the relationship is solid, it should be interdependent: “mutually dependent; depending on each other.” However, the thing to keep in mind with getting to the point where you can rely on someone is it takes time. While vulnerability, on some levels, can be rushed and semi-forced, dependency is an organic experience that occurs from life simply…happening.
Now keep all of this in mind as we explore how floodlighting reveals itself in a dating situation.
Floodlighting. When It Comes to Dating.
Once I processed floodlighting, as far as dating is concerned, it actually made me think of people who have sex very quickly in the beginning of a relationship. I’m pretty sure that at least 70 percent of us know of someone who has raved about a person who they’ve only gone out on a couple of dates with. However, because they’ve already had sex with them and it was really good, suddenly, they believe that they’ve met the one.
Y’all, it truly can’t be said enough that “an oxytocin high” does not true intimacy make — oh, but because it feels amazing, it can have you out here thinking that something lasting and real has transpired when really, there hasn’t been enough moments shared or experiences had to know that for sure. However, since the sex was rushed, it can cause you to want to speed up the relationship too. It can tempt you to be like, “I mean, if we’re great in bed, surely we will be amazing in other rooms of the house too.” Floodlighting is a lot like this.
If you meet someone and you like the potential of what it could be, you might be tempted to want to, like Brené said in her book: OVERSHARE. It could be oversharing as it relates to some personal traumas that you’ve experienced. It could be oversharing as it relates to intimate details about your past relationships. It could be oversharing as it relates to your mistakes and flaws. It could be oversharing as it relates to your sex life. It could be oversharing as it relates to all of the expectations and demands (along with why) that you have.
The reason for doing this? It could be that you’re hoping the person will take it all in without any pushback which will cause you to believe that you both are immediately on the same page or it could be that you are attempting to fast-track the relationship by believing that if you share all of who you are during date one or two (or even four), they will do the same and — ding — an instant relationship.
See, more than anything else, floodlighting is a test. It’s a bit manipulative. It’s potentially stressful. And, more times than not, it ends up backfiring. And then, if it backfires, because it was a test, you can blame them for not rising up to the occasion.
Please tell me that you get how toxic this all is. For one thing, no one wants to be tested like this. Secondly, it’s unfair to expect someone to be “all in” with a person who they are just getting to know. Third, you have layers to you — all of us do — and it can be overwhelming for someone to be expected to learn, retain, and even accept all of the layers at once. Yeah, one thing that I like about the term floodlighting is it has the word “flood” in it. Water? We’re made up of mostly water, so of course, it’s good for us. Being flooded by water, though? That could harm or even destroy us.
In many ways, trying to force intimacy onto another person…it manifests in a similar way. Of course, you should share what makes you…you. A bit at a time, though, while letting time do its thing. Too much too soon is…exactly that.
How to Cultivate Healthy Intimacy in the Beginning Stages of a Relationship
So, what are some things that you can do to avoid being a floodlighter?
See your intel as privileged information.
Everything about you is special and special things should be earned. That said, as you get to know someone, OVER TIME, you’ll be able to see if they can be trusted with your thoughts, feelings and ultimately your heart — and no, that can’t happen on the first couple of dates. Y’all, it really can’t be said enough that instant chemistry doesn’t mean that intimacy should be expected to happen overnight.
In other words, just because you see the potential for something awesome with another person, that doesn’t mean you shouldn’t wait to see if the individual’s words and actions, consistently so, can complement the elation that you feel. Share a little. See how they respond. At another time, share a little bit more. See how they react. Rinse and repeat. Patiently and intentionally so.
Stop trying to pull stuff out of people.
There are all kinds of ways to be manipulating and controlling — and deciding that someone should move at your pace in a relationship is a way to be both things. In other words, not everyone is emotionally unavailable or immature simply because they don’t want to share every childhood experience or their relationship stories with you by date three.
No doubt, a lot of people self-sabotage something that could’ve been good because they were rushing someone to move outside of their comfort zone — knowing damn well that they would’ve had a problem with that if the shoe was on the other foot. Chill…what someone wants to tell you, they will. If they don’t? All you can — and should — do is decide if you want to move forward or not. That doesn’t require force on your part to come to that conclusion.
Nervousness is one thing. Being fearful is something else.
If the reason why you’re floodlighting is because you’re scared that people will not accept you or that they will abandon you, it really is best to put dating aside for a season and get into some therapy. Because, while being nervous about a potentially new relationship is completely understandable, being afraid of organic intimacy and then doing things that can hinder or prevent it is something completely different.
Put the tests away.
Listen, if you recall the tests that you took back in school, I have no clue why you’d want to put others through tests now that you’re a big-time adult. Tests are stressful, pressuring and sometimes, no matter how smart you are, you’re not going to perform well on them because you’re simply not a good test-taker (some of y’all will catch that later). There’s no need to “test” someone to see if they can take all of who you are. Again, time will reveal that on its own.
___
Personally, I think that floodlighting is so common that folks don’t even realize that they’re doing it or how problematic it actually is. Hopefully, this helps to shed some light.
Vulnerability tests? Uh-uh.
Seeing if someone can be depended on to care for you as you are? Relax. Time. Will. Reveal.
Now go on your date(s) and have fun. Damn. #winkLet’s make things inbox official! Sign up for the xoNecole newsletter for love, wellness, career, and exclusive content delivered straight to your inbox.
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