Steve Calascione
Hi, I'm Steven Calascione, a Franchise Advisor at Franchise Sidekick. Before Sidekick, I built and sold a successful property management business, worked in sales and marketing for over a decade, and ran multiple businesses, including construction and real estate development. As a franchise owner and consultant, I've been on both sides of the franchise world, giving me firsthand insight into what makes a franchise truly scalable and successful. I love helping entrepreneurs find the right business opportunity that aligns with their goals, and I bring a strategic, service-based approach to every conversation. When I’m not working, you’ll find me traveling, hiking, or chasing after my two toddlers.
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Q&A With
Steve Calascione
What do you love about franchising?
I love franchising because it’s the perfect balance between entrepreneurship and proven systems. It gives people the chance to step into business ownership with a clear roadmap for success—minimizing risk while still allowing them to grow, lead, and build something of their own. What excites me most is seeing people become entrepreneurs and take control of their future, creating a life on their terms. Helping others find the right franchise fit and watching them step into business ownership with confidence is what drives me every day.
What do you love about working with clients?
I love working with clients because every conversation is an opportunity to serve and make a real impact. Helping people navigate the path to business ownership—whether it’s their first venture or their next big move—is incredibly rewarding. I thrive on understanding their goals, uncovering the best opportunities, and providing the support they need to move forward with confidence. What drives me most is the ability to serve others by offering guidance, clarity, and a strategic approach to their journey. Seeing clients succeed and knowing I played a part in that success is what makes this work so fulfilling.
Tell us a little about yourself!
I am an entrepreneur, problem-solver, and adventure-seeker. I’ve built businesses, helped others launch theirs, and guided people through some of the biggest decisions of their lives. I love figuring out creative solutions, whether it’s in business or making an overpacked suitcase magically fit in a carry-on. When I’m not working with clients, I’m spending time with my wife, Giuliana, and our two kids, traveling, or getting outside as much as possible. I’ve explored nearly 30 countries, biked through Thailand, watched the sunrise in the Sahara, and whenever I’m near the ocean, you’ll find me scuba diving. At the heart of everything I do is a passion for service—helping others take the next step toward something bigger, whether it’s building a business, exploring new opportunities, or just having a meaningful conversation.
Favorite sidekick?
My favorite sidekick? Samwise Gamgee, hands down. The guy carried Frodo (literally and figuratively) when things got tough, stayed loyal no matter what, and had an unshakable belief in the mission. If there’s one thing I admire, it’s someone who shows up, does the work, and lifts others up along the way. Plus, he knew the value of a good meal—solid life priorities.
Learn how Sidekick advisors Reduce your risk when buying a franchise.
- Access to insider information that is exclusive to Franchise Sidekick clients
- A proven system thats help award over 5,000 franchise locations
- Vetted brands that have proven systems, strong economics and happy existing franchisees
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“A ship in harbor is safe, but that is not what ships are built for.”