We’re excited to introduce you to the always interesting and insightful Courtney Cole. We hope you’ll enjoy our conversation with Courtney below.

Courtney, appreciate you joining us today. Crazy stuff happening is almost as certain as death and taxes – it’s technically “unexpected” but something unexpected happening is to be expected and so can you share a crazy story with our readers

When we first started shipping Flying Dresses, every day was a learning curve, especially when it came to shipping procedures. One particular experience stands out vividly in my memory.

We received a special request from a client who was about to undergo chemotherapy for breast cancer. She wanted to wear one of our dresses for a photoshoot before her head shaving ceremony—a poignant moment she wanted to capture forever. It was a deeply touching request, and we were determined to make it happen.

However, a critical oversight occurred. We failed to double-check the zip code before shipping even though UPS suggested the change and the street address was the same, and the dress ended up in a town three hours away from our client’s location. The realization hit us like a ton of bricks, and panic ensued. Despite the stress and upset, we knew we had to act swiftly and decisively.

With UPS unable to assist in retrieving the package, we turned to Google Maps for a solution. The idea struck to reach out to local photographers in the area, hoping they might lend a hand. Cold-calling commenced, and on the first attempt, a compassionate soul answered—a woman amidst preparing dinner for her family.

In a moment of vulnerability, I explained the situation and the urgency of our client’s photoshoot. To our astonishment, she not only understood but offered her assistance wholeheartedly. As fate would have it, her husband was in the vicinity and retrieved the package from the doorstep where it had been mistakenly delivered.

Their act of kindness was overwhelming. After dinner, the husband embarked on a six-hour round trip to ensure our client received her dress in time for the photoshoot. The tears flowed freely as we witnessed the power of human compassion in action.

This experience taught invaluable lessons. From meticulous attention to detail to maintaining composure in times of crisis, it underscored the importance of resilience and problem-solving in entrepreneurship. Moreover, it reaffirmed our belief in the innate goodness of people and the strength of community support.

In the end, the photoshoot was a success, and our client’s gratitude knew no bounds. Beyond business, it was a profound reminder of the impact of genuine care and going above and beyond for those in need.

Courtney, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I’m Courtney, and am from the beautiful island of Maui, Hawaii. My journey into the world of entrepreneurship began during my college years in 2002 when I immersed myself in the bridal fashion industry. Despite graduating from college with a Business Degree, the traditional 9-5 grind didn’t resonate with me; I felt a calling for something more fulfilling.

At the age of 26, I took a leap of faith and opened a bridal boutique in San Diego, California. It was there that my passion for empowering women and celebrating their beauty blossomed. Over time, I expanded my boutique multiple times, creating a haven where women could find their perfect wedding ensemble. Eventually, my family’s decision to return to Maui led me to sell the boutique, but my dedication to serving brides remained steadfast.

Upon returning to Maui, I became Hawaii’s only Bridal Concierge and established Maui Wedding Dress Pressing, a service still thriving today. However, it was during the challenging times of the COVID-19 shutdowns that a serendipitous conversation with a disappointed bride sparked a new chapter in my journey.

As we lamented her canceled Flying Dress photoshoot in Greece, I was captivated by the concept and delved into researching it further. The idea resonated deeply with me, and I resolved to bring it to life for my bride. Despite the lockdown, we collaborated to create her dream shoot locally, and thus, Hi Flying Dress was born.

Hi Flying Dress is more than just a product; it’s a symbol of celebration and empowerment. We now ship globally, offering women of all ages the opportunity to elevate their special moments with our exquisite dresses. From engagements to anniversaries, our dresses capture the essence of joy and beauty, transcending borders and cultures.

What I’m most proud of is not just building a successful business, but creating a brand that empowers women to feel confident and beautiful during life’s most cherished moments. I want people to know that Hi Flying Dress isn’t just about the product; it’s about the experience and the journey of celebrating life’s milestones in style.

Can you talk to us about your experience with selling businesses?

Yes, I successfully sold my Bridal Boutique located in San Diego, California, which marked one of the most poignant milestones in my entrepreneurial journey. The process of building a business from the ground up can be all-encompassing, to the point where one’s identity intertwines with the business itself. While many entrepreneurs find solace and fulfillment in this symbiotic relationship, I realized that this fusion wasn’t entirely conducive to sustainable business practices.

Upon relocating to Maui in 2017, I initially entertained the notion of maintaining remote oversight of my business operations, periodically commuting to ensure its continuity. However, the challenges inherent in managing an absentee-owned enterprise soon became apparent. Despite the dedication of my exceptional staff and the solid foundation we had established, it became evident that such a setup was untenable for both the business and myself.

Thus, with a heavy heart, I made the decision to divest my ownership stake. The emotional weight of parting ways with a business I poured my heart and soul into lingers to this day. The mere sight of its former location evokes a profound sense of loss—a testament to the deeply personal connection I forged with my entrepreneurial endeavor.

In hindsight, while the decision to sell was agonizing, it was undeniably the right course of action. I’ve come to realize the importance of recognizing when to relinquish control, even when it means bidding farewell to something you hold dear. I offer the following advice to fellow entrepreneurs contemplating a similar transition: seize the opportunity to sell while your business is thriving, thereby maximizing its value. Delaying such a decision until the business falters risks diminishing returns and exacerbating the emotional toll of parting ways.

Moreover, I advocate for meticulous financial management and the implementation of robust operational processes. Clear documentation not only facilitates a seamless transition of ownership but also enhances the business’s appeal to prospective buyers, thereby maximizing its market value.

While the sale of my inaugural business venture was undeniably bittersweet, witnessing its continued success under new ownership brings a sense of validation. Knowing that many of my original employees continue to contribute to its prosperity serves as a source of immense pride and reaffirms the lasting impact of my entrepreneurial endeavors.

Has your business ever had a near-death moment? Would you mind sharing the story?

Navigating the treacherous landscape of entrepreneurship often feels akin to traversing a minefield, requiring sharp wit, agility, and unwavering resilience. One particularly daunting challenge we faced was managing payroll—an undertaking I am grateful to no longer contend with biweekly, though the burden of running the business solo presents its own set of trials.

As expenses at our Bridal Boutique surged, with monthly rental fees exceeding $17,000 and a team of 12 full-time employees to support—complete with health insurance and ancillary costs—the financial strain became palpable. There were moments when meeting rent obligations felt like threading a needle, and the specter of payroll loomed ominously, oftentimes squeezed out amidst the pressures of maintaining cash flow.

The anxiety of approaching payday with fingers crossed, hoping for a surge in sales to meet payroll demands, is an experience I am resolved never to revisit. In such dire straits, the only viable course of action is to either boost revenue or slash expenses. We opted for the latter, executing a strategic relocation of our Bridal Boutique to a more economical locale. While the new premises lacked the opulence of our former setting, the substantial reduction in rent—down to $6,000—provided much-needed relief and bolstered our financial stability.

During lean months, we resorted to drastic measures, liquidating inventory, renegotiating payment terms with suppliers, and forgoing personal compensation, all in a bid to weather the storm. It was a harrowing ordeal, yet imperative in regaining control over our ballooning expenses and charting a course toward solvency.

Ultimately, our concerted efforts to rein in costs proved instrumental in steadying the ship and preserving the viability of our business. This strategic pivot not only restored our financial equilibrium but also positioned us for a successful transition in selling the business.

In hindsight, the tumultuous journey served as a crucible of resilience, underscoring the imperative of adaptability and fiscal prudence in navigating the volatile terrain of entrepreneurship.

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