We had the good fortune of connecting with Simona Greenfield and we’ve shared our conversation below.

Hi Simona, is there something that you feel is most responsible for your success?
The most important factor behind the success of my brand has been authenticity. From day one, I built this brand by staying true to my story, my values, and the women I represent. I share my journey openly the wins, the struggles, the glow-ups, and the setbacks and that honesty has created real trust with my audience. People connect with what’s real, and my brand stands as a reflection of that: raw, relatable, and rooted in purpose. It’s not just about products or content—it’s about building a community that feels seen, inspired, and empowered every step of the way.

Alright, so let’s move onto what keeps you busy professionally?
My “art” lives in my ability to turn real-life experiences into content that connects, empowers, and inspires. My brand is rooted in transparency I openly share my journey as a mom of four, my weight loss transformation, my plastic surgery experiences, and everything in between. What sets me apart is my willingness to talk about the things most people shy away from. I’m not here to present a perfect picture; I’m here to show the process, the pain, the healing, and the glow-up. I’ve built a space where women especially mothers can feel seen, heard, and supported.

Getting here wasn’t easy. There were moments of self-doubt, comparison, and even criticism. But I kept going because I knew there were women out there like me, searching for someone who would keep it real. The biggest lesson I’ve learned is that vulnerability is strength, and when you lead with your truth, the right people will find you.

What I want the world to know is this: my brand isn’t about selling a perfect image, it’s about showing what’s possible when you choose yourself. Whether it’s stepping into your confidence, healing your body, or just having the courage to be seen there’s power in your story, and I’m living proof of that.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
If my best friend came to visit me in Key West for a week, I’d make sure every day was filled with sunshine, laughter, and island magic. Here’s the perfect itinerary for the ultimate girls’ trip:

Day 1 – Welcome to Paradise
We’d start with tropical drinks and seafood at Latitudes on Sunset Key. After dinner, we’d stroll Duval Street, stop for a slice of Key lime pie at Kermit’s, and catch the iconic sunset celebration at Mallory Square with street performers and local artists.

Day 2 – Beach Day & Chill
We’d spend the day lounging at Fort Zachary Taylor Beach, Later, we’d grab Cuban food at El Siboney, then do a sunset sail with champagne and music to really set the vibe.

Day 3 – Explore Old Town
We’d rent bikes or a golf cart and explore Old Town, stopping at local boutiques and art galleries. Brunch at Blue Heaven We’d visit the Southernmost Point for photos and finish with dinner and mojitos at Havana Cabana.

Day 4 – Water Adventures
we’d book a day trip for snorkeling at the reef, kayaking through mangroves, or jet skiing around the island. After a sun-filled day, we’d do casual dinner and live music at Hogfish Bar & Grill on Stock Island for a more local vibe.

Day 5 – Spa + Sunset
We’d treat ourselves to a spa day at Ocean Wellness Spa or get massages at our hotel. Then we’d freshen up and head to Louie’s Backyard for fine dining by the water. Afterward, we’d visit a rooftop bar like The Saint Hotel’s for cocktails and girl talk under the stars.

Day 6 – History & Hidden Gems
We’d tour the Ernest Hemingway House, visit the Butterfly Conservatory, and maybe stop at the Key West Lighthouse for incredible views. Lunch at Café Marquesa, then we’d take cute pics around the colorful island homes and murals. At night, we’d do a fun drag show at 801 Bourbon Bar or karaoke for laughs and memories.

Day 7 – Wind Down & Reflect
On our last day, we’d do a slow morning with breakfast at Harpoon Harry’s and one last walk through the marina. Maybe we’d book a private paddleboard session or just relax at the pool before heading out. We’d toast one last time with Key lime martinis and soak in all the sunshine and memories made.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I want to dedicate my shoutout to the women in my life especially the moms who have been my biggest inspiration and support system. From my own mother’s strength and resilience to the countless women in my community who share their stories with me, their encouragement has fueled my drive. I also want to recognize the online sisterhood I’ve built through my platform so many of these women have walked similar paths, and their support, honesty, and vulnerability remind me daily why I do what I do. Lastly, I’d be remiss not to mention my kids being a mom of four has shaped my hustle, my perspective, and my passion for helping other women feel seen, confident, and empowered.

Instagram: Monalioness

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