An Entrepreneur’s Origin Story: Unveiling the Journey

Isaiah O’Connor

a 4 minute read


In this post, I delve into the challenge of answering questions like "What am I passionate about?" and "What can I become passionate about?" This introspective journey isn't a simple task; it demands a deep dive into one's inner self and thoughtful reflection on how we've evolved. Join me as I reflect on my past, unveiling what has led me to this point in my life. This narrative, my "Origin Story," focuses on the pivotal moments that shaped me into the entrepreneur I am today. I hope that as I share my journey, you may find some insights for yourself.

The Importance of an "Origin Story"

Why term it an "Origin Story" and not an introduction or a getting-to-know? A compelling origin story doesn't just reveal the "who"; it provides the essential "why." Consider one of my favorites, Spider-Man. At a glance, he's a person with superhuman abilities fighting crime for the greater good. However, delving into his origin story adds depth. Initially, he was a selfish kid seeking personal glory. It's only after facing tragedy that he understands the responsibility that comes with his power, encapsulated in the famous line:

“With great power comes great responsibility.”
— Stan Lee


This mirrors my journey. As I reflected on my past, I discovered not only an inherent entrepreneurial inclination within me but also the influence of two entrepreneurs in my upbringing. My mom ran a daycare at our house, and my dad operated his janitorial service for a period. Working with my dad, I now realize the value of that time spent with him. He instilled in me the work ethic required to persevere through long days, imparting an understanding of the intricacies of running a business. His determination to get the job done, rain or shine, even when unwell, left an indelible mark on me.

Surrounded by Entrepreneurial Influences

As I grew up, I found myself surrounded by entrepreneurial influences. My mom managing a daycare and my dad running a janitorial service unknowingly laid the foundation for my future endeavors. Working alongside my dad taught me the work ethic and determination essential for running a business.

During my childhood, I tested the entrepreneurial waters by selling golf balls and sodas. In college, the idea of starting a web design company crossed my mind. Although these early ventures were short-lived, the entrepreneurial spark within me refused to fade.

A Turning Point: "Youth With A Mission"

A significant turning point occurred when I pursued my dream of joining "Youth With A Mission." This chapter not only introduced me to my Norwegian wife but also ignited my passion for balloon twisting and teaching. These experiences laid the groundwork for my entrepreneurial spirit.

After my time with the missionary organization, reality hit as I faced the challenges of finding stable employment. Moving from California to Norway brought its own set of difficulties, including a year of unemployment and settling for a part-time minimum-wage job.

The Shift Towards Entrepreneurship

The tipping point came when I grew tired of the constant struggle and sought a vocation that resonated with my true self. Inspired by Dan Miller's "48 Days to the Work You Love," I entertained the idea of starting my own business. Motivated by the book, I reflected on my past and discovered a potential avenue: balloon twisting. Despite initial reservations from my wife, I believed I could turn it into a business, especially after receiving positive responses for charity events.

Challenges and Growth

However, the transition from employee to business owner wasn't as seamless as anticipated. The initial year brought in less income than a traditional full-time job. Despite setbacks, a stroke of luck and determination led to landing a major event company as a client. Recognizing the marketability of balloon décor in Norway, I took a course, rebranded my business, and shifted focus from twisting to décor. A mentor in the balloon industry played a pivotal role, suggesting changes that propelled my growth.

The journey of rebranding brought immense growth to my business, but, as with many, the landscape changed drastically with the onset of the COVID-19 pandemic. Despite facing a significant downturn, I managed to navigate the challenges and maintain a modest profit.

Launching The Bootstrap Blog & Podcast

While I was developing my business in the first five years, my friend and fellow entrepreneur Jason St. Clair and I kept in touch. Even though we were oceans apart, he witnessed the successful development of my business. In 2018, Jason contacted me with a crazy business idea after noticing my success. He asked if I wanted to join him in creating a business development website. He also inquired if I would mind writing a blog for it. So, on January 14, 2019, I posted my very first blog post. A few months later, we decided it would be fun to start a podcast as well, and this is how The Bootstrap Podcast and Blog were born.

Engaging in this endeavor truly helped me become a better businessman, as I had to conduct extensive research into different aspects of business to produce quality content. This, in turn, aided in the growth of my balloon business and enhanced my ability to assist others with theirs.

Facing External Challenges

In the aftermath of COVID-19, despite witnessing some recovery in 2022, the broader event and balloon industry experienced another significant blow in 2023. The Ukraine war disrupted helium supplies, a critical resource, creating an unexpected hurdle. This helium shortage, combined with Norway's overall economic downturn during this period, resulted in a perfect storm. Balloon artists, including myself, grappled with the harsh realities of diminished demand and heightened costs.

Embracing Change

With all these challenges and the need to provide for my family, I have decided that after a solid 10-year run, it's time to shift my business into the "extra income" category. This shift is accompanied by a greater focus on content creation. Adapting to the changing dynamics, I am leveraging my experiences to explore new avenues and ensure a sustainable future for my entrepreneurial endeavors. Stay tuned for more updates on this evolving chapter of my entrepreneurial journey.

Your Friendly Neighborhood Entrepreneur,

Isaiah O’Connor


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Until next time, I have been,
Your Friendly Neighborhood Entrepreneur,
Isaiah O’Connor

Isaiah O'Connor