Steve Calascione

Steve Calascione

Hi, I'm Steven Calascione. 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.
9.9
NPS Score

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2 yrs
Years in franchising
750+
Clients worked with
3
Businesses owned
“Steve was incredible. We fully felt like he had our backs and gave us very sound advice all throughout the process. He was very attentive and always made himself available when we needed him to bounce an idea or ask simple questions. When we decided we weren’t going forward, he could not have been more supportive even though we were walking away. A true gentleman in every sense of the word. I would highly recommend him to anyone looking into franchising.”

Ian M.

“It was a very good experience working with Steve. I can’t thank him enough for his help during the whole process of the franchise business I was trying to get into. He is a very kind person and very easy to work with. Steve supports through the whole process, and he doesn’t rush into the process. He gave us time and good suggestions on how to move forward. For example, while I was working with him, I had a situation where I needed more time to find financing options. He immediately suggested that I need to take more time to find options. I would definitely love to work with him again.”

Dinesh B.

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