- The Essential Military-to-Civilian Transition Resource

What It Takes to Be Your Own Boss

by Ashley Feinstein Gerstle, Contributing Writer

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Article Sponsored by: CarMax

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Getting to call the shots, making your own schedule and having unlimited financial upside are just some of the things that attract people to starting a business or purchasing a franchise. It sounds flexible, powerful and extremely exciting, but what does it really take to start your own business? Are you cut out for it? What makes a small business or franchise successful? I had the opportunity to interview successful business owners on what it took to be their own boss, how they struggled and what they wish they knew before they started.

What inspired you to start your own business?

Business ideas can manifest in a variety of ways. You often hear of an ‘aha’ moment that kicks off an entrepreneurial journey. This was the case for Shannon Battle. She was a guidance counselor helping soldiers transition to civilian life while her husband was on active duty. She wanted to make her husband’s financial responsibility lighter and was inspired by the impact that his side business, ICAN Clothes Company (, had on those around them. She began exploring opportunities to help children, had a ‘divine encounter,’ and Family Services of America ( was born. Family Services of America provides a structured living environment and community-based programs for individuals with developmental disabilities, mental illness, social/behavioral dysfunction or substance abuse disorders.

Other businesses start with a personal need for a product or service. As a mother of two, this is how Grainne Kelly came up with the BubbleBum ( inflatable car booster seat. “My primary goal was to offer travelers a safe way to transport their kids,” she says. “I was frequently traveling between my native Ireland and England to visit a sick relative, and I always had to transport cumbersome fixed booster seats back and forth on the plane due to the lack of car booster seats available from car rental desks. I came up with the simple idea for an inflatable car booster seat and invented BubbleBum as an affordable, lightweight car booster seat that could travel easier than a child does. It weighs less than one pound and can deflate in minutes, making it easy to throw in a backpack when not in use.” Grainne created a product to solve her car seat travel woes and the BubbleBum is now sold worldwide, including in Walmart and Target stores.

What were the biggest challenges?

It takes a lot to go from an idea to a successful business. Small business and franchise owners experience significant challenges and setbacks along the way.

For Battle, the toughest aspect was financial. “The biggest challenges were wondering where the money would come from,” she says. “My husband partnered with me in my business and we used the resources around us. We didn’t have good credit and couldn’t qualify for loans. We never missed a meal thanks to my grandma. We worked during the week, and I hired someone to work the 12-8 shift and payed them from my work check. This lasted about three months.”

Kelly’s biggest challenge was around trust, intellectual property and expectations. “The biggest mistake I ever made was expecting that others would have the same degree of integrity as I do,” she says. “I visited a Chinese factory with my original design and did not ask them to sign the confidentiality agreement before sharing my design. While I was sitting in their office, the manager drove to Shanghai, three hours away, and applied for a utility patent. Now, I don’t talk to anyone about anything without first signing a confidentiality agreement. It has cost us tens of thousands of dollars, but I have learned so much about intellectual property along the way.” She advises, “Don’t expect anything from anyone and you won’t be disappointed.”

What do you wish you knew then that you know now?

Often, entrepreneurs wish they knew the things that would have prevented or lessened their biggest challenges. Battle would have liked to have been more prepared for the financial management side of her business. “I wished we knew more about financial management and how to use the company earnings to our advantage,” she says. “I also wish we knew how to estimate our risks and not make foolish business decisions based on pride and emotions.”

Kelly learned one of her most valuable business lessons from her father. “My father said, ‘It’s all up to you; don’t blame anyone else for you not making it.’ From a family of seven kids, we needed to be dying to have a day off from school and we were not allowed to get out of bed or do fun things if we were sick.” This taught her to work hard and be resilient. He would encourage her to figure things out rather than answering her questions directly. This made her resourceful and she started thinking for herself.

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