Entrepreneurs are all around you, from the corner grocery store to your hairstylist, the neighborhood Chick-Fil-A owner and even the kids’ lemonade stand in their driveway. Entrepreneurship isn’t just for those who build massive corporations or the latest rising tech giant on scene. It’s for everyday people who see a need or find a problem and believe they can do something about it. Becoming an entrepreneur isn’t just for people who have all the resources, but for anyone willing to put in the work, make a difference, and leave the world a little better than they found it.
L2Business is honored to share the stories of these everyday entrepreneurs, the ones in your community making an impact, dedicated to serving their customers well. They willingly share their wins, struggles, hopes, passion, and knowledge with you, the new, aspiring, and growing entrepreneurs, to remind you that you’re not alone in this wild journey of building something amazing. It is our collective, genuine hope you find comfort, wisdom, encouragement, and joy in these articles. We are pleased to welcome for this Entrepreneur Interview: Chris Gilmore.
Meet the Entrepreneur Interviewee
Chris is the quintessential, yet not stereotypical entrepreneur. Embodying the core of entrepreneurship, Chris is a multi-business owner with a diverse portfolio, sizing up and seizing opportunities that come his way. Although he said it wasn’t the intention to have multiple businesses operating at a time, he doesn’t think he could have it any other way.
“I’ve got the entrepreneurial type spirit. I just have to be my own boss.”
And be his own boss he did indeed. In 2016, Chris began his financial advising career at Northwestern Mutual following a conversation with his advisor and an “aha” moment. While in college, Chris witnessed firsthand what happens when the unexpected meets the unprepared. When a family member’s sudden illness led to financial insecurity, their struggle developed a desire deep within Chris to help other families break the secrecy of finances to better prepare for potential hardships.
While stationed in Afghanistan in 2019, Chris met a man who shared his affinity for a lesser-known sweet treat, Candy Raisins. What Chris didn’t know at the time was that connection would later lead to the acquisition of his favorite childhood candy company. As a proud new owner of Candy Raisins, Chris had important decisions to make including where the candy would be produced with the long-time factory closing and where he would store the products. The necessity for ample storage space opened the door for his third business venture: the building of a new warehouse facility.
With nearly 10 years’ experience, a diverse business portfolio, and intimate financial expertise, Chris has amassed a wealth of real-world knowledge. I got to sit down with him and get direct insights as we discussed how to seize business opportunities, optimize motivation in a variety of ways, and intentionally build an impactful inner circle.
Seizing Opportunities and Growth
When Chris was in college, he had no intention of working in finance; he was majoring in business after all and joined the sales team at PepsiCo. following graduation. During that time, a financial advisor kept calling Chris, much like Ferris trying to convince Cameron to join his spontaneous day off.
Deciding not to completely judge a book by its cover, Chris took a call that would change his trajectory. Realizing there was a way to help families like his, Chris researched financial service companies and kept coming back to one in particular. He saw an alignment between his mission and Northwestern Mutual’s ethics and values, making this the first stop in his entrepreneurial journey, building his business from scratch. Utilizing Northwestern Mutual’s name, resources, and reach, Chris has helped countless families secure a safer future, specifically finding joy in serving medical professionals as a nod to those who helped his family many years ago.
While entrepreneurial opportunities are typically cultivated, some happen to fall right in your lap. What started as a quirky connection over candy turned into a nostalgic opportunity for Chris to own the same candy brand that he enjoyed so much as a kid. One of the owners was looking to buy out, which gave Chris the perfect opportunity to buy in.
“I gave some ideas about trying new things and introducing the candy into different markets. He said, ‘I think you should just run the company.’ I know nothing about candy production, but the opportunity came, and I said, ‘Well this would be kind of fun.’”
Unlike his advising business, Candy Raisins was a well-established company with decades of success behind the name. With his ideas to update Candy Raisins and bring them into new markets, Chris’s primary focus was sustainable growth.
There were some logistics to be addressed following the acquisition, the largest, literally, was the need for storage space. Unfortunately, most rental spaces in his area were either too small or set up for office spaces, so Chris saw this as an opportunity to meet a need in his community.
A solution born out of necessity for his own business became an available solution for many others. Instead of building just enough storage space for Candy Raisins, Chris built additional space, not only filling a gap in his local community, but developing a supplemental source of passive income for himself.
Optimizing Motivation: Fear, Investment, and Passion
A key make-or-break factor for every entrepreneur is their ability to self-motivate. “The self-motivation as a business owner sometimes is difficult. You have to motivate yourself,” Chris explains. He said it’s important to know if you’re a stick or carrot person. Are you avoiding getting hit by the stick behind you, or are you chasing the carrot ahead of you? One of them is fear (hint: it’s the stick), and the other is determination.
If fear, or anxiety, become more of a de-motivator than a motivator, use the dragon analogy explained to Chris. If you imagine anxiety as a fire-breathing dragon ahead of you, it’s a massive object to get around or defeat. It can be daunting, overwhelming, or even feel impossible. If that fire-breathing dragon is instead behind you, the fire crawling up your back is motivation to keep moving forward.
With three businesses under his belt, I asked Chris if he’s ever gotten over the fear that comes with being an entrepreneur. He said, “You’re always going to have that fear,” but when you’re putting an income on the line that you need to buy groceries and pay bills with, it becomes “extremely motivating.”
Motivation also comes from the investments made into your business. “There’s always going to be some equity that’s not necessarily tied to financial capital that you have to put in,” said Chris. It can be sweat, time, work, labor, and intellectual equity, but what goes in comes out. “You’re not really going to acknowledge a successful business if you haven’t put in the equity.”
Knowing your “why” (Simon Sinek) and having a driving passion makes chasing the carrot possible in all times. Although Chris’s mission is to help anyone become financially stable, he said his wife noticed a significant difference in his demeanor with a specific client base.
Working with and for the people who bring him joy makes his work more than a job. “You know every time you help someone get that good feeling? I have that every day,” proclaimed Chris. When work aligns with personal passions, it not only becomes more enjoyable but also infuses every effort with purpose. Doing work that feels good in addition to does good not only enhances job satisfaction but also serves as a constant source of motivation.
Building Your Inner Circle
Through his ventures, Chris underscores fundamental entrepreneurial wisdom: the strength of your inner circle can be the difference between soaring heights and isolating valleys. It's not just about who you know; it's about who you journey with, and quality is better than quantity.
The key to building an impactful inner circle is knowing your own weaknesses, and inviting people who can fill them. “I don't have to be the smartest. I just have to know who that person is or where I go to get the resources,” explains Chris. He said the most important quality he looks for is knowledge expertise. When developing the contract to purchase Candy Raisins, it stipulated the previous owner had to stay on for a set time as a mentor, providing his industry expertise where Chris had none to which he credits the company’s current success.
In building his inner circle, Chris emphasizes the indispensable roles of legal counsel, a financial advisor, and a CPA. These professionals don’t just fill key knowledge gaps but also allow entrepreneurs to concentrate on their passion: building their business. It exemplifies the importance of strategic selection based on complementing skills and business needs.
Over time those needs may change, and the inner circle may fluctuate depending on where you are in the entrepreneurial journey. Some expertise is no longer needed, while new knowledge gaps arise and invite in new experts. When mentors you once looked up to become your competition, those roles must be changed out, too.
“If you have a mentor that is now someone you can start to compete with, it's time to get a new mentor. At that point, they’re an equal,” Chris clarified. He said a mentor should be someone you aim to be in 10 years, someone further ahead in your industry you can push yourself to be like.
Lastly, your inner circle should include non-businesspeople close to you, such as a spouse, family, or friends. While not everyone in your family or friend group needs to be part of the inner circle, having those who will genuinely celebrate your wins with you, lovingly nudge you forward when you’re down, and have the hard conversations when paths diverge from the best interest is equally as important.
Chris's Advice
To wrap up our interview, I asked Chris what advice he’d give to fellow entrepreneurs. Here are his five tips:
Have a schedule - It should take into account two things: the well-being of you and those around you. You can’t work your best if your basic needs aren’t met. Also, if you have others who rely on you, such as a family, remember that your time isn’t just your time; part of it needs to be shared with them to meet their needs as well.
Do something for yourself every day, something that makes you smile - It could be something directly for you or for someone else, like a note to your spouse, because you know it will make them feel good, and in turn, it makes you feel better, too.
Do something physical - Whether it’s working out, walking on a treadmill, or playing outside with the family, it’s important to get movement in each and every day.
Set aside time to think - Intentionally take time away from screens, people, work, and other distractions with just a pen and paper. The quietness allows your thoughts to develop naturally, creatively, and can lead to problem-solving solutions or new ideas.
Your word is extremely important - If you say you’re going to do something, do it. If something comes up, acknowledge it, and do your best to make it right. People remember what you do, but especially when you don’t follow through or when you go that extra mile.
To leave you with one last tidbit of encouragement, Chris highly suggests reading the inspirational book “The Strangest Secret” by Earl Nightingale where he shares “the key to success and the key to failure.” The key: we become what we think about.
“Part of that is just the belief you have in yourself,” said Chris referring to Nightingale’s work. “You have to believe in yourself; you have to succeed. No one else controls your future.”
Biography
Chris Gilmore
Aside from being a successful entrepreneur, Chris is a loving husband and father, Army veteran, and a dedicated advisor to all his clients. Chris also affirms he has no relation to Happy and is good at neither golf nor ice hockey.
For more information, visit christophergilmore.nm.com, connect through email at christopher.gilmore@nm.com, or call (262-366-7642).
About the Author:
Em is the co-founder of L2Business and Director of Communication. Her prior work as a reporter and editor sparked the idea to interview entrepreneurs and highlight their real-world entrepreneurial insights with new and aspiring business builders. When she's not busy with the business, you can find her yelling at the TV watching her alma mater Texas Tech or any hockey game she can find. Let's connect on Facebook!
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