Samantha Callow: A Woman with Vision and Determination

To celebrate Women's History Month, we interviewed Samantha Callow of Calloway Storage. Read on to see how her vision and determination make anything possible.
In celebration of Women’s History Month, we set out to interview one of the female leaders within the storage industry. We chose Samantha Callow, whom I recently met at the Boxwell Summit for portable storage. A few minutes into our conversation, I learned that Samantha has three children of similar ages to my own. Naturally, that made me want to dig deeper into her life. What I found out is that she is also a lawyer, a professor, and an owner of a very lucrative storage business. Imagine that. With vision and determination, anything is possible. Besides her obvious strength of character and realness, what’s amazing about Samantha is her air of calm. Especially amidst her busy, full life. 
Samantha Callow of Calloway Storage
Samantha studied law at the University of Windsor and obtained her master’s degree in law at Osgoode Hall Law School, both in Ontario, Canada. While in her youth, Samantha spent a year traveling the world. She volunteered with a non-profit, international global organization, Up With People. Their vision is to build “an inclusive and sustainable world where people are equal in dignity and rights.” Currently, she is a law professor at Humber College and leads five classes per semester. She also co-authored a legal textbook used by colleges across Ontario. And, on top of all that, she owns and runs Calloway Storage.
When I asked her how she appears to do it all, she replied, “Working hard for yourself really matters.Samantha comes from a very entrepreneurial family that spans five different industries. It’s the “Callow-Way.” Her family owns and operates Budget Propane, a propane supplier in Ontario. They also own a national cake company called WOW! Factor Desserts, manufacturing desserts for the food service industry. The Callow family learned first-hand about the rewards and sacrifices of owning a family business from her parents. And Samantha used her determination to carry on the tradition.

Samantha recalls her father starting the business from a piece of paper and idea. Many of his deals were consummated by a simple handshake. Some offers were signed on a napkin.  

Samantha with her parents, Bob and Olga Callow
Relationships were key in business. Her mom supported her husband’s vision by taking on the bookkeeping function, even though that was out of her comfort zone. They all chipped in to make their business run smoothly, and as many business owners can attest, success comes with many failures along the way. Samantha explains, “You have to wear many hats when running a business, be nimble, and most of all, stay humble.”
How exactly did she get into storage, though? Samantha’s father taught her to think outside the box, to look forward with vision, and to keep dreaming.  In the words of her Dad, “When opportunity knocks softly, listen carefully, and have the courage to open the door.” Such was the case of the ‘storage’ concept. Few properties were readily available. But, all it took was one that stood out. And the idea blossomed from there! Samantha found one that would work for both storage and propane. So, in 2015, with vision and determination, Samantha took her father’s advice to purchase a self-storage facility.

The idea back then was for her to run the facility as an additional income opportunity. But Samantha doesn’t just “run things”. She runs with things. In her spare time, she learned the ropes from the inside out. She signed up for a self-storage operators certification course and met some great people in the industry. That’s how she found Boxwell. Samantha followed up with every reference, and she cold called other industry owners to figure out the best storage unit to use for her business. She instantly bonded with Rod Bolls (founder and CEO of Boxwell ). His passion and attention to detail reminded Samantha of her own. And that made it a done deal!

There were so many things to learn. For example, she needed to know how to process invoices and contracts, set up a new website, and communicate with customers. Samantha changed the facility’s name and had signage made. She worked through permits and hired contractors, cleaned out storage units, and ran storage auctions. Essentially, she learned the whole business. Samantha believes that you need to figure things out when it’s your own business and that, “It’s important to become masterful at each task.” 
Samatha building a storage unit
As a lawyer, Samantha knows the importance of doing her research. During her new storage venture, Samantha did just that. She tapped into her community, met with other storage facility owners, got ideas, resources, references, and overall industry knowledge. Over time, she was able to expand her existing facility with additional relocatable units. From there, she remembers asking, “How can we make our units available for people to rent off-site?” Basically, “what’s next?” And then the portable storage arm of her business was created. Working with towing companies and different delivery systems, she was able to transport portable containers directly to her customers. Again, seeing a need and figuring it out with a vision and determination.
Early on, Samantha and her siblings learned the power of a plan, or vision. As a child, she and her family would meet regularly and create their five-year plans. During COVID, her father initiated a meeting called “Project Vision.” This is where the family meets to discuss their business models from the 30,000 ft level. Here they can strategize what the next five years look like. What about the next ten? Leveraging each other’s business experiences to help grow and learn is powerful. Recently, Samantha helped create a best practice group with other portable storage businesses in the USA and Canada. Unfortunately, when COVID hit, they couldn’t meet up. In response, Samantha initiated and hosted a monthly Zoom meeting. This has led to an amazing network of operators whom they can each turn to with questions and concerns.   

Samantha and I discussed how complicated it can be to raise children. As any parent can attest, it takes a village, and being able to rely on others to help create a life balance has been key. Samantha is a passionate, active person with a long list of good books to read and places to travel. She is also a go-getter and an organizer. Along with a vision and determination, these are very crucial attributes while running a busy household, teaching students, and running a growing business! 

Some of the Callow crew
It’s important for Samantha to pass along this strong work ethic and strategies to her children. She involves all family members in the businesses as much as possible. This includes her children, grandchildren, nieces, nephews, and in-laws. She also says that it is “not uncommon to have at least five family members come out to help with a build.” They sometimes even turn it into a fun competition for the highest output! In Samantha’s words, “This is their legacy too, and they all realize the power of working together.”
The Callow family on a build
When asked about being a woman in the historically male-dominated storage industry, Samantha has a few pain points. She remembers feeling that others did not trust her to make decisions. “They would try to go around me or call my father and brother,” she says. Samantha needed people to take her seriously. So, she sought to find her “voice of expertise.” Sure, she knew how to figure things out, be resourceful, study, and walk the walk. But, for people to believe in her, she needed to be an expert in business – not just a mom, lawyer, and professor! Samantha soon realized that what she needed to do: 1.) Trust in her abilities. 2.) Make those tough executive decisions and run with it. 3.) Show up with a vision and determination 4.) Be ok with failure and not look back 5.) Surround herself with meaningful connections and network, network, network. 

Samantha attributes much of her success to her mentor, her father. He has always guided his children and grandchildren on the principles found in Tom Peters’ book, In Search of Excellence. To quote her father, “We don’t have to be the biggest, but we need to be the best at what we do. To serve with excellence.”  

I asked Samantha what advice she would give her 25-year-old self. Here’s what she had to say, “You don’t need to be an expert in everything. Have the courage to try it, do it with integrity, and don’t look back.” It’s that sort of positive energy and can-do attitude that brings Samantha where she is today. She leads by example, gives back to her community, and believes in being a part of the team (especially if it’s family). And she’s pushing to go further, always looking for what’s next. Samantha’s vision is to continue to expand, inspire, and lead — in all realms of her life.

Calloway Storage currently has three locations and offers self-storage and portable storage solutions. For more information about Calloway Storage,

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