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What happens when your business fails, and you lose everything? Kelly Shiley, CEO of Mary Square, joins the show to share her raw and inspiring journey from launching her business in the kitchen with a baby by her side to losing her home after a business deal fell through. Learn how she bounced back from early failures, the importance of believing in yourself, and how to persist when everything seems to be falling apart. Kelly shares insights on finding traction, understanding market gaps, and why failure is often the first step to success.
The Power of Persistence: Navigating Failure and Finding Your Niche
From Struggles to Success: The Inspiring Journey of Kelly Shiley
In a recent episode of The Boutique Chat Podcast, host Ashley Alderson sat down with Kelly Shiley, the powerhouse entrepreneur behind Mary Square, to share her incredible journey from humble beginnings to leading a successful brand. This candid conversation was packed with inspiration, honesty, and invaluable lessons for anyone in business or considering starting their own venture.
From Kitchen Table to Tough Beginnings
Like many entrepreneurs, Kelly’s business started in her home. After being a stay-at-home mom for eight years, Kelly decided to create a product while juggling life with three young children. However, her entrepreneurial dream quickly hit a rough patch—six months into launching her business, Kelly lost her house due to some unfortunate inventory decisions and a business partnership that went awry.
Despite this massive setback, Kelly stayed committed. “I thought I had made the biggest mistake of my life,” she recalled. Instead of giving up, Kelly spent the next two years working to pay off the debt, ultimately realizing she loved the industry she had entered. Her journey taught her resilience and the importance of learning from mistakes early on.
Turning Challenges into Learning Experiences
Throughout Kelly’s 13-year entrepreneurial journey, challenges were a constant companion. She faced situations like losing significant key accounts, which left her scrambling to cover six-figure expenses. Yet, every challenge shaped her into the businesswoman she is today. Kelly shared that the feeling of “What am I going to do about it? How can I fix this?” became a consistent part of her life as an entrepreneur.
Kelly credits her resilience in part to her husband, who supported her unwaveringly during the toughest times. “If they can figure it out, I know I can figure this out,” Kelly said, demonstrating her determination to overcome obstacles and prove to herself that success was possible.
Learning the Hard Way: Key Takeaways for Aspiring Entrepreneurs
One of Kelly’s biggest pieces of advice for aspiring entrepreneurs? Don’t dive headfirst into business without validating your idea first. “You have to have proof of concept,” Kelly emphasized. She learned early on that it’s essential to get market feedback before producing large quantities of a product. She was quick to highlight that naivety, thinking if you build it, customers will come, can lead to costly mistakes.
Kelly urged entrepreneurs to let go of ego and take feedback seriously. She described how she hustled, selling her products out of her car, at schools, and on Facebook, until eventually, she had to donate what remained after two years. These were the necessary steps to learning and getting it right.
The Power of Finding a Niche
After years of trial and error, Kelly found her niche—faith-based and inspirational gifts. She realized that by focusing on this specific market, she could build something unique and differentiate her brand. While the market for inspirational gifts like Bible covers and mugs might not be as large as the apparel industry, Kelly recognized that owning her space was key to establishing a strong foundation for her business.
Four years into her journey, Kelly decided to rebrand from “Scripture Art” to “Mary Square.” The name change was a necessary pivot, as she realized potential customers were walking by her booth due to preconceived notions about the original name. By rebranding, Kelly was able to attract a broader audience while staying true to her values.
Embracing Change and Expanding Into Apparel
Not one to shy away from challenges, Kelly eventually transitioned into apparel. “I have a little ADD with product,” she joked. She saw apparel as a consumable product that would bring customers back season after season, unlike the more static nature of gifts. Apparel became a natural next step in her brand’s evolution.
Though the apparel industry presented a steep learning curve, Kelly dove in. From sizing to tech packs, she took on the challenge of producing high-quality apparel and has since made Mary Square known for its unique prints and attention to detail.
Originality and Quality: Cornerstones of Success
Kelly’s dedication to originality shines through in everything Mary Square creates. Every single print produced by the brand is original and hand-drawn by her in-house team. “I don’t like the idea of buying prints that might end up with another company’s name on it,” she explained. This commitment to offering something special and unique sets Mary Square apart from the fast fashion industry.
For Kelly, it’s about more than just selling products—it’s about creating a brand people can trust for quality, uniqueness, and heart. She continues to be passionate about offering products that consumers know were made with thoughtfulness and care.
Blending Over Balancing
Kelly, a mother of three and business owner, challenges the conventional wisdom of achieving balance between family and work. She explains, “If you think about balancing, you’re going to fall. It’s not sustainable. Instead, I believe in blending.” To her, this means being all things — a mom, a wife, and a business owner — simultaneously, without feeling like she has to switch between roles.
Whether she’s at a field trip or in a board meeting, Kelly remains fully present in all aspects of her life. She’s learned how to blend these roles by making small adjustments, like walking on a treadmill during a meeting or taking calls while waiting for her daughter. “There’s no sustainable balancing. And I couldn’t have made it 13 years trying to balance it all.”
The Importance of Prioritizing Family
While blending is key, Kelly is clear about her priorities. One of her most critical pieces of advice is to prioritize your family, especially your relationship with your partner. “I always put my husband first, even before my kids, because I knew if our marriage failed, it would impact my kids. That’s the best gift I could give them.”
At the same time, Kelly emphasizes that her kids come before her business. “The business could be gone tomorrow, but my relationship with my kids — that’s everything. I can rebuild a company, but I can’t recreate my family.”
Learning to Say No
For parents struggling to manage all their responsibilities, Kelly has advice: you have to learn to say no. This involves having a clear sense of your priorities and knowing which opportunities are worth pursuing and which aren’t. For Kelly, protecting her family time was non-negotiable.
“I never lost sight of my priorities,” she says. “You need to make money to eat, but at the end of the day, family is everything.”
The Best Business Advice: Stay Debt-Free
As someone who has built a thriving business, Kelly shares another key piece of advice she received: stay debt-free. “A woman once told me that running a debt-free company gave her the most freedom,” Kelly recalls. “We’re a debt-free company, and it’s been freeing. You don’t have to stress about overhead when you have a bad month.”
This advice contradicts the common notion of raising venture capital to grow a business. Kelly’s experience shows that financial freedom and longevity in business can often come from staying out of debt.
Building Strong Retailer Relationships
When it comes to wholesale and e-commerce, Kelly highlights one major factor that successful retailers share: they engage with their customers. “Whether it’s through social media, store events, or their website, they know their customers and interact with them.” Building a community around your brand is crucial to success.
The Biggest Lesson: Hiring the Right People
One of the hardest lessons Kelly has learned in business is the importance of hiring the right team. “Hire for culture. You need people who are humble, hungry, and smart,” she says, referring to lessons from Patrick Lincioni’s book The Ideal Team Player. Finding employees who embody these traits has been a game-changer in growing her business.
Final Thoughts: Living Your Fullest Potential
As Kelly reflects on her journey, she emphasizes the importance of living out your fullest potential, no matter what path you take. “It’s never been about succeeding or failing for me — it’s about living out my potential. Whether I’m running a $100 million company or making $50,000 a year, I want to live fully and walk my own path.”
Ultimately, Kelly encourages everyone to pursue their unique path with passion and purpose, without comparing themselves to others. “Leave it all on the court, and then go take a nap,” she adds with a laugh.
For parents, business owners, and anyone juggling multiple roles, Kelly’s approach to blending — rather than balancing — offers a refreshing perspective on how to thrive without losing sight of what matters most.
Blending Over Balancing
Kelly, a mother of three and business owner, challenges the conventional wisdom of achieving balance between family and work. She explains, “If you think about balancing, you’re going to fall. It’s not sustainable. Instead, I believe in blending.” To her, this means being all things — a mom, a wife, and a business owner — simultaneously, without feeling like she has to switch between roles.
Whether she’s at a field trip or in a board meeting, Kelly remains fully present in all aspects of her life. She’s learned how to blend these roles by making small adjustments, like walking on a treadmill during a meeting or taking calls while waiting for her daughter. “There’s no sustainable balancing. And I couldn’t have made it 13 years trying to balance it all.”
The Importance of Prioritizing Family
While blending is key, Kelly is clear about her priorities. One of her most critical pieces of advice is to prioritize your family, especially your relationship with your partner. “I always put my husband first, even before my kids, because I knew if our marriage failed, it would impact my kids. That’s the best gift I could give them.”
At the same time, Kelly emphasizes that her kids come before her business. “The business could be gone tomorrow, but my relationship with my kids — that’s everything. I can rebuild a company, but I can’t recreate my family.”
Learning to Say No
For parents struggling to manage all their responsibilities, Kelly has advice: you have to learn to say no. This involves having a clear sense of your priorities and knowing which opportunities are worth pursuing and which aren’t. For Kelly, protecting her family time was non-negotiable.
“I never lost sight of my priorities,” she says. “You need to make money to eat, but at the end of the day, family is everything.”
The Best Business Advice: Stay Debt-Free
As someone who has built a thriving business, Kelly shares another key piece of advice she received: stay debt-free. “A woman once told me that running a debt-free company gave her the most freedom,” Kelly recalls. “We’re a debt-free company, and it’s been freeing. You don’t have to stress about overhead when you have a bad month.”
This advice contradicts the common notion of raising venture capital to grow a business. Kelly’s experience shows that financial freedom and longevity in business can often come from staying out of debt.
Building Strong Retailer Relationships
When it comes to wholesale and e-commerce, Kelly highlights one major factor that successful retailers share: they engage with their customers. “Whether it’s through social media, store events, or their website, they know their customers and interact with them.” Building a community around your brand is crucial to success.
The Biggest Lesson: Hiring the Right People
One of the hardest lessons Kelly has learned in business is the importance of hiring the right team. “Hire for culture. You need people who are humble, hungry, and smart,” she says, referring to lessons from Patrick Lincioni’s book The Ideal Team Player. Finding employees who embody these traits has been a game-changer in growing her business.
Final Thoughts: Living Your Fullest Potential
As Kelly reflects on her journey, she emphasizes the importance of living out your fullest potential, no matter what path you take. “It’s never been about succeeding or failing for me — it’s about living out my potential. Whether I’m running a $100 million company or making $50,000 a year, I want to live fully and walk my own path.”
Ultimately, Kelly encourages everyone to pursue their unique path with passion and purpose, without comparing themselves to others. “Leave it all on the court, and then go take a nap,” she adds with a laugh.
For parents, business owners, and anyone juggling multiple roles, Kelly’s approach to blending — rather than balancing — offers a refreshing perspective on how to thrive without losing sight of what matters most.
Blending Over Balancing
Kelly, a mother of three and business owner, challenges the conventional wisdom of achieving balance between family and work. She explains, “If you think about balancing, you’re going to fall. It’s not sustainable. Instead, I believe in blending.” To her, this means being all things — a mom, a wife, and a business owner — simultaneously, without feeling like she has to switch between roles.
Whether she’s at a field trip or in a board meeting, Kelly remains fully present in all aspects of her life. She’s learned how to blend these roles by making small adjustments, like walking on a treadmill during a meeting or taking calls while waiting for her daughter. “There’s no sustainable balancing. And I couldn’t have made it 13 years trying to balance it all.”
The Importance of Prioritizing Family
While blending is key, Kelly is clear about her priorities. One of her most critical pieces of advice is to prioritize your family, especially your relationship with your partner. “I always put my husband first, even before my kids, because I knew if our marriage failed, it would impact my kids. That’s the best gift I could give them.”
At the same time, Kelly emphasizes that her kids come before her business. “The business could be gone tomorrow, but my relationship with my kids — that’s everything. I can rebuild a company, but I can’t recreate my family.”
Learning to Say No
For parents struggling to manage all their responsibilities, Kelly has advice: you have to learn to say no. This involves having a clear sense of your priorities and knowing which opportunities are worth pursuing and which aren’t. For Kelly, protecting her family time was non-negotiable.
“I never lost sight of my priorities,” she says. “You need to make money to eat, but at the end of the day, family is everything.”
The Best Business Advice: Stay Debt-Free
As someone who has built a thriving business, Kelly shares another key piece of advice she received: stay debt-free. “A woman once told me that running a debt-free company gave her the most freedom,” Kelly recalls. “We’re a debt-free company, and it’s been freeing. You don’t have to stress about overhead when you have a bad month.”
This advice contradicts the common notion of raising venture capital to grow a business. Kelly’s experience shows that financial freedom and longevity in business can often come from staying out of debt.
Building Strong Retailer Relationships
When it comes to wholesale and e-commerce, Kelly highlights one major factor that successful retailers share: they engage with their customers. “Whether it’s through social media, store events, or their website, they know their customers and interact with them.” Building a community around your brand is crucial to success.
The Biggest Lesson: Hiring the Right People
One of the hardest lessons Kelly has learned in business is the importance of hiring the right team. “Hire for culture. You need people who are humble, hungry, and smart,” she says, referring to lessons from Patrick Lincioni’s book The Ideal Team Player. Finding employees who embody these traits has been a game-changer in growing her business.
Final Thoughts: Living Your Fullest Potential
As Kelly reflects on her journey, she emphasizes the importance of living out your fullest potential, no matter what path you take. “It’s never been about succeeding or failing for me — it’s about living out my potential. Whether I’m running a $100 million company or making $50,000 a year, I want to live fully and walk my own path.”
Ultimately, Kelly encourages everyone to pursue their unique path with passion and purpose, without comparing themselves to others. “Leave it all on the court, and then go take a nap,” she adds with a laugh.
For parents, business owners, and anyone juggling multiple roles, Kelly’s approach to blending — rather than balancing — offers a refreshing perspective on how to thrive without losing sight of what matters most.
Blending Over Balancing
Kelly, a mother of three and a busy business owner, challenges the conventional wisdom of achieving balance between family and work. She explains, “If you think about balancing, you’re going to fall. It’s not sustainable. Instead, I believe in blending.” To her, this means being all things — a mom, a wife, and a business owner — simultaneously, without feeling like she has to switch between roles.
Whether she’s at a field trip or in a board meeting, Kelly remains fully present in all aspects of her life. She’s learned how to blend these roles by making small adjustments, like walking on a treadmill during a meeting or taking calls while waiting for her daughter. “There’s no sustainable balancing. And I couldn’t have made it 13 years trying to balance it all.”
The Importance of Prioritizing Family
While blending is key, Kelly is clear about her priorities. One of her most critical pieces of advice is to prioritize your family, especially your relationship with your partner. “I always put my husband first, even before my kids, because I knew if our marriage failed, it would impact my kids. That’s the best gift I could give them.”
At the same time, Kelly emphasizes that her kids come before her business. “The business could be gone tomorrow, but my relationship with my kids — that’s everything. I can rebuild a company, but I can’t recreate my family.”
Learning to Say No
For parents struggling to manage all their responsibilities, Kelly has advice: you have to learn to say no. This involves having a clear sense of your priorities and knowing which opportunities are worth pursuing and which aren’t. For Kelly, protecting her family time was non-negotiable.
“I never lost sight of my priorities,” she says. “You need to make money to eat, but at the end of the day, family is everything.”
The Best Business Advice: Stay Debt-Free
As someone who has built a thriving business, Kelly shares another key piece of advice she received: stay debt-free. “A woman once told me that running a debt-free company gave her the most freedom,” Kelly recalls. “We’re a debt-free company, and it’s been freeing. You don’t have to stress about overhead when you have a bad month.”
This advice contradicts the common notion of raising venture capital to grow a business. Kelly’s experience shows that financial freedom and longevity in business can often come from staying out of debt.
Building Strong Retailer Relationships
When it comes to wholesale and e-commerce, Kelly highlights one major factor that successful retailers share: they engage with their customers. “Whether it’s through social media, store events, or their website, they know their customers and interact with them.” Building a community around your brand is crucial to success.
The Biggest Lesson: Hiring the Right People
One of the hardest lessons Kelly has learned in business is the importance of hiring the right team. “Hire for culture. You need people who are humble, hungry, and smart,” she says, referring to lessons from Patrick Lincioni’s book The Ideal Team Player. Finding employees who embody these traits has been a game-changer in growing her business.
Final Thoughts: Living Your Fullest Potential
As Kelly reflects on her journey, she emphasizes the importance of living out your fullest potential, no matter what path you take. “It’s never been about succeeding or failing for me — it’s about living out my potential. Whether I’m running a $100 million company or making $50,000 a year, I want to live fully and walk my own path.”
Ultimately, Kelly encourages everyone to pursue their unique path with passion and purpose, without comparing themselves to others. “Leave it all on the court, and then go take a nap,” she adds with a laugh.
For parents, business owners, and anyone juggling multiple roles, Kelly’s approach to blending — rather than balancing — offers a refreshing perspective on how to thrive without losing sight of what matters most.
In This Episode
- Kelly Shiley: Website | Instagram | Facebook | Wholesale
- The Ideal Team Player by Patrick M. Lencioni
- 2025 Boutique Boss Planner
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Must Have Resources
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- Boutique Summit 2024
- Small Business Marketing Handbook
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- Brand Owner Basics Masterclass
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