Meet Challo Schott | Owner & Creative Director

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

Hi Challo, we’d love to hear about how you approach risk and risk-taking.
Risk has played a role in almost every meaningful thing I’ve done in my life and career. I don’t think I’ve ever really chosen the safe route. Most of the projects I’ve been involved in started as ideas that probably didn’t make sense to a lot of people on paper. Old buildings, overlooked neighborhoods, concepts that were intentionally different from what was trending at the time. I’ve always been more interested in creating something with identity than copying what already works somewhere else.

I think people romanticize risk a little too much though. Real risk is exhausting. It affects your relationships, your sleep, your finances, your confidence. There are long stretches where you question yourself constantly. But at the same time, I’ve learned that if you want to create something original, discomfort is kind of part of the deal. The moments I’m most proud of in my career usually came right after periods where things felt uncertain or borderline impossible.

I’ve also learned that risk becomes easier when you genuinely love building things. I don’t really think of myself as someone chasing money as much as someone obsessed with creating spaces, stories, and experiences that feel real and emotional to people. Bars, music venues, concepts, branding – all of it is creative to me. The business side matters, obviously, but the reason I keep doing it is because I still love the feeling of turning an idea into something people connect with.

A lot of my career has been built on instinct. Sometimes that works beautifully and sometimes it punches you in the face. But I’d rather fail doing something original than spend my life repeating safe ideas that don’t mean anything to me.

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
I’ve spent the last couple decades involved in hospitality, branding, design, and concept development across South Florida in places like Downtown Fort Lauderdale, Delray Beach, Miami Beach, Brickell, Wynwood, Pompano, and now Boca Raton. Moving through all of those cities exposed me to completely different cultures, nightlife scenes, and creative communities, which heavily shaped the way I approach business and hospitality.

Long before social media turned everything into a formula, a lot of us were building concepts more from instinct than analytics. Early on I operated a creative company out of FAT Village during a period when that area was still very raw and artist-driven. Being surrounded by photographers, painters, musicians, designers, and independent business owners had a huge impact on me creatively. There was a mentality of creating things because they felt real and exciting, not because they fit into a proven template.

Over the years I became involved in developing and helping shape a variety of hospitality concepts throughout South Florida. What has always interested me most is creating places with strong identity and emotional connection rather than simply opening another bar or restaurant. Music, atmosphere, branding, storytelling, lighting, art direction, and the overall feeling people walk away with matter just as much to me as the operational side.
Right now my main focus is Tall Boy in Boca Raton, which has become one of the most personal projects I’ve worked on. It’s a historic location with decades of history behind it, and instead of trying to erase that history, we embraced it and built around it. I think people are craving places that feel human again; places with personality, imperfections, stories, and authenticity.

It definitely hasn’t been easy. Hospitality can be exhausting financially, emotionally, and mentally. I’ve dealt with failed ideas, setbacks, brutal workloads, and plenty of moments where continuing didn’t seem logical. But I’ve learned that resilience and adaptability matter more than almost anything else. Original ideas usually take longer to be understood, but I still believe originality is what gives places lasting impact.

Any places to eat or things to do that you can share with our readers? If they have a friend visiting town, what are some spots they could take them to?
One of the things I love most about South Florida is that it really has everything if you know where to look. Every city has its own personality and rhythm. You can go from natural areas and quiet coastal towns to incredible nightlife, art, music, food, and complete chaos within the same day.

If I was showing someone around, Miami would definitely be part of it because I still think it’s one of the most interesting cities in the country creatively. There’s every kind of food, music, art, architecture, and culture imaginable layered into one place. I’m a huge fan of spots like Lagniappe because it feels unforced and timeless, and Sunny’s Steakhouse because it manages to feel both elevated and relaxed at the same time. Pizza Tropical is another favorite for a late-night slice after bouncing around the city.

Closer to home, I appreciate smaller neighborhood spots with personality. Second Rodeo in Boynton has a really good atmosphere and feels intimate in a way a lot of places don’t anymore. Lost Weekend has always been one of those easy spots where you can end up playing pool, talking for hours, and meeting random people. The Grove in Delray has a great energy too. It’s one of those places that feels distinctly South Florida without trying too hard.

And of course, at some point I’d have to bring them to Tall Boy in Boca Raton. A big part of why I built it was to create the kind of place I personally always wanted to spend time in. Good music, strong atmosphere, interesting people, no unnecessary pretension, and enough personality that every night feels a little different.
Music is always part of the experience for me, so somewhere like ZeyZey is high on the list because I love spaces that blend live performances, culture, food, and nightlife together naturally.

I also think people overlook how much natural beauty exists here beyond the nightlife side of Florida. Areas around Jupiter and parts of Miami still have amazing natural landscapes, water, trails, and old Florida energy that can completely reset your perspective after spending time in the city.

What I’ve always appreciated most about South Florida is the contrast. You can have a quiet afternoon near the water and end up in the middle of an unforgettable night a few hours later. There aren’t many places that offer that kind of range.

Who else deserves some credit and recognition?
A huge amount of credit goes to the artists, musicians, bartenders, cooks, designers, photographers, and creative people I’ve met throughout my life and career. A lot of the spaces I’ve built only became what they were because of the people inside them. I think hospitality is at its best when it gives people a sense of belonging or ownership, especially people looking for something more genuine than polished or corporate environments.

I also owe a lot to the early creative communities in places like FAT Village and Wynwood before they became what they are today. About ten or fifteen years ago there was this energy of people just building things because they believed in them, not because they were chasing trends or investment money. Being around that mentality shaped a huge part of how I approach business and creativity.

And honestly, I have a lot of respect for anyone willing to keep creating or building something original right now. It’s easy to become repetitive or play it safe. The people still making art, music, businesses, and spaces with real personality deserve more recognition than they usually receive.

Website: https://weneverrest.com

Instagram: /challoschott

Linkedin: /challoschott

Other: https://tallboyboca.com