Meet Jordyn Shepherd

We’re excited to introduce you to the always interesting and insightful Jordyn Shepherd. We hope you’ll enjoy our conversation with Jordyn below.

Jordyn, so great to have you with us and thanks for taking the time to share your thoughts with the community. So, let’s jump into something that stops so many people from going after their dreams – haters, nay-sayers, etc. We’d love to hear about how you dealt with that and persisted on your path.

I persist because I know who I am — and I know why I’m here. There will always be people who try to define me by my past — who choose to throw my addiction in my face or put it on blast in hopes of turning others away from me. But the truth is, you can’t weaponize what I speak on openly, what I advocate against, and what I use to educate others so they don’t make the same mistakes I did. And I won’t lie — there are days when the weight of that is heavy. But I’ve done the hard work to move forward, and I remind myself daily that I am not my past.

Of course, it hasn’t been easy. Mistakes have been made — because I’m not perfect. But I’ve always tried to own that, to recognize when things have gone awry, and to keep learning and growing. More than anything, I’m grateful for the people who believe in me — who continue to lift me up and stand by my side, knowing who I truly am and what my mission is.

So even when the noise gets loud, I choose to keep moving forward — some days with grace, some days with grit, but always with love.

Thanks, so before we move on maybe you can share a bit more about yourself?

Professionally, my life is full — and I’m grateful for that. I’m co owner of Hamburger Mary’s Jax 2.0. After a year and a half, I was proud to bring back to Jacksonville a space where people can feel safe, secure, and celebrated. I built on the foundation laid by the previous owners of Hamburger Mary’s — expanding their hard work, adding my own spin, and placing a major focus on areas I felt could be improved. I would never claim credit for the reputation the original Mary’s earned; however, I am proud of the reputation that Hamburger Mary’s Jax 2.0 is beginning to set for itself. And in today’s political climate, a space like this matters more than ever. It was important to once again give our city a safe, joyful space to gather. Mary’s is more than a restaurant — it’s a stage, a celebration, and a home. And while it is proudly rooted in LGBTQ+ culture, it is a safe space for everyone — a place where all people, from all walks of life, can feel welcome, accepted, and celebrated. We host drag shows, brunches, community events, and nights where people can simply be themselves without fear or judgment. Seeing the smiles, the laughter, and the chosen family we create each night — that is what excites me most.

Next door, I’m launching Drag~On -a beauty and retail store that will offer cosmetics, lashes, wigs, and everything needed for drag, self-expression, or a great night out. But Drag~On is also designed to be a one-stop party shop. We’ll offer curated packages for birthday parties, bridal celebrations, bachelorette nights, “over the hill” parties, and more — complete with balloons, décor, and fun extras. The idea is that when guests arrive at Hamburger Mary’s, their table can already be glammed up and ready to wow — making their experience seamless and extra special.

In addition, we’ll offer makeover packages — for example, custom packages will include sending your person, a bride to be or birthday gal to see us, she can come next door for a pampering session as a treat to them and leave feeling fabulous meeting you right on time for the rest of the parties arrival. We’ve also had a large number of requests for drag makeovers — people who don’t normally do drag but have always wondered how they’d look fully glammed up. These sessions will be offered as well, and I’m excited to create those joyful, transformative moments for anyone who wants to experience it.

Beyond my businesses, I proudly serve on the Steering Committee for Equality Florida here in Jacksonville. I believe in fighting the fight so others don’t have to — especially in today’s political climate, when our LGBTQ+ community faces so many challenges. Whether through advocacy or providing safe spaces, my mission is to show up, speak out, and stand strong for those who can’t always do so themselves.

There is so much more to come — new shows, new events, and creative ways to expand what Mary’s and Drag~On can offer this city. But at the heart of it all, I’m here to build joy, resilience, and community. That’s what drives me every single day.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

Looking back, three qualities have had the biggest impact on my journey: resilience, empathy, and the willingness to keep learning.

Resilience, first and foremost. My past addiction and the challenges I’ve faced — both personally and professionally — taught me that life will knock you down sometimes. People will try to hold your past against you, and not everyone will cheer for your success. But you always have a choice: stay down, or get back up. I chose to get back up — sometimes with a full face of makeup, lashes hanging on for dear life — but I got up. For anyone early in their journey: please know, it’s okay to fall. What matters is having the courage to keep standing up and moving forward.

Empathy has also been a driving force. Whether I’m hosting a packed drag brunch at Mary’s, helping create safe spaces through Equality Florida, or preparing to open Drag~On next door — where we’ll soon offer everything from beauty products to drag makeovers — it all comes down to seeing and valuing people for who they are. I’ve walked through some dark chapters, which helps me approach others with more compassion — and a good sense of humor. Let’s be real: sometimes the best way to build a safe space is with your drink of choice, great music, and the ability to laugh at life’s absurdities together.

And finally — a willingness to learn. I’ve made mistakes. I’ve had to shift direction. I’m still learning every single day. Staying humble and teachable is what allows you to grow — and trust me, no one gets it all right the first time.For anyone starting out: don’t be afraid to ask questions, admit what you don’t know, and surround yourself with people who will challenge you to be better.

What is the number one obstacle or challenge you are currently facing and what are you doing to try to resolve or overcome this challenge?

The number one challenge I’m facing right now is navigating the weight of constant public scrutiny — especially as a trans woman, a business owner, and someone with a visible past. There will always be people who want to tear you down, spread misinformation, or judge you through an old lens. And when you’re working so hard to build something positive and create safe spaces, that noise can be exhausting.

But one of the biggest lessons I’ve learned is that not every word said about you — or every rumor spread — requires a response. You don’t have to fight every battle or constantly defend yourself. Sometimes the most powerful thing you can do is sit back, stay focused, and let the work speak for itself.

That’s what I’m doing. I lean on my support system —my best friend Brianna (co-owner) my boyfriend, my family, my team at Mary’s, my close friends and my community. I practice self-care, and I remind myself that perfection isn’t the goal — progress is. And every time I see a guest smile at Mary’s, or hear the excitement from people looking forward to Drag~On opening soon, or watch someone feel safe enough to be fully themselves at one of our events — that reminds me why I do this. The work speaks louder than the noise ever could, and that’s where I choose to put my energy.”

Contact Info:

• Website: https://www.hamburgermarys.com/jax
• Instagram: @jordynsinclair23
• Facebook: hamburgermarysjax
• Yelp: https://yelp.to/0ITf–azfH
• Other: @hamburgermarysjax2.0

Image Credits

The Drag Photographer