Founder & CEO Of Haik Khachatryan AKA The Tipsy Cargo Boss - S6E20 (#210)
Boss Uncaged
Founder & CEO Of Haik Khachatryan AKA The Tipsy Cargo Boss - S6E20 (#210)
October 19, 2023
In Season 6, Episode 20 of the Boss Uncaged Podcast, S.A. Grant sits down with the Founder & CEO Of, Haik Khachatryan. Welcome back to the Boss Uncaged Podcast, where we explore the journeys of entrepreneurs who have overcome incredible odds to achieve success. In today's episode, we have a fascinating guest joining us: Haik Khachatryan, also known as The Tipsy Cargo Boss. From a young age, Haik displayed a questioning and inquisitive nature, but also faced some of the worst times of their life early on, leading to struggle and emotional pain. However, those experiences shaped Haik into the resilient and tenacious person they are today. Haik is the Founder & CEO of, a unique business that combines their passion for wine with their belief in repurposing containers. They've created a two-story container, with a wine bar on the bottom and a lounge and cigar bar on the top. But their entrepreneurial journey extends far beyond their wine business. They are also a podcaster, using their platform, Boss Uncaged, to share valuable insights and information about the ups and downs of entrepreneurship. In this episode, Haik shares their experiences of transforming pain into purpose and turning challenges into opportunities. We delve into their unconventional path to success, from being a high school dropout to becoming a multimillionaire. Haik also opens up about the role of art in their life and how it helps them find balance amidst the pressures of entrepreneurship. So, join us as we dive deep into Haik Khachatryan's incredible story, and discover the secrets of their success on this episode of Boss Uncaged. Let's uncage the boss!
I am a first generation Armenian-American, very proud to be born in Worcester, Massachusetts to amazing parents. I was always high energy and very misunderstood. I had a troubled upbringing and always felt like I never fit in, and my spirit was different. I went through a lot of turbulence and I had a disease that I don’t want to get to in depth, but I was not supposed to live past the age of 11, so I had come to grips with my death at a early age which caused me to reflect and have the self talk that no child should bare. Something amazing happened within me. My pain turned to purpose. You could say that my mind broke and what breaks you put together even better. So this has led me to be a self motivator, action taker, risk taker, and always living in the moment . I am a spiritual person that has a connection with the divine essence within us that spared my life, so I am always grateful and see the positive in everything. growing up I had a chip on my shoulder always getting into trouble not listening or paying attention in class fighting diagnosed ADHD. Thank God my parents didn’t put me on the medication, never took any medication in my life and I got expelled in 10th grade and was a high school dropout.
I am a self realization follower, serial entrepreneur, business owner, inventor, Yogi!

Title: From Adversity to Achievement: The Unconventional Journey of a Serial Entrepreneur

Welcome to the extraordinary tale of a life shaped by adversity, determination, and a relentless pursuit of success. From battling dyslexia and ADHD to facing brushes with the law, my journey has been far from conventional. Yet, against all odds, I embraced my unique vision and transformed my life into one of entrepreneurial triumph. Join me as I recount the inspiring chapters that led me from embarrassment to empowerment, creating eight successful businesses and achieving the status of a multi-millionaire.

Chapter 1: A Journey Through Challenges
From an early age, dyslexia and ADHD presented formidable challenges. I struggled to fit into the traditional education system, leading to the decision to drop out of high school. These hurdles seemed insurmountable, and for a time, I felt trapped by my circumstances.

Chapter 2: Brushing With the Law
The path I initially walked led me into run-ins with the law. My choices were reckless, and my actions often led to disappointment for my family. The weight of embarrassment weighed heavily on my shoulders, but deep within, a spark of determination flickered.

Chapter 3: Embracing Entrepreneurial Spirit
As I navigated through adversity, I discovered a flicker of entrepreneurial spirit within me. My unconventional mind saw opportunities where others saw obstacles. I channeled my energy into creating businesses, each one a reflection of my unique vision and tenacity.

Chapter 4: The Rise of a Serial Entrepreneur
With unwavering determination, I ventured into the world of entrepreneurship. Business by business, I defied expectations and achieved success in diverse industries. My dyslexia and ADHD, once perceived as setbacks, became assets in this realm of innovation and creativity.

Chapter 5: Visionary Thinking and Multi-Millionaire Status
With a heart set on turning dreams into reality, I honed my visionary thinking and embraced calculated risks. I fearlessly pursued new ventures, seizing every opportunity to bring my ideas to life. Through dedication, hard work, and an unwavering belief in myself, I surpassed financial milestones and achieved the coveted status of a multi-millionaire.

Chapter 6: Empowering Others and Paying It Forward
As success found me, I recognized the importance of empowering others to embrace their unique strengths and talents. My journey from adversity to achievement serves as a testament that challenges can be catalysts for greatness. I am committed to paying it forward, inspiring and supporting others to unleash their potential and pursue their dreams fearlessly.

My life's tapestry weaves a story of defying odds and embracing the power of perseverance. From dyslexic with ADHD and a high school dropout to becoming a serial entrepreneur and a multi-millionaire, my journey has been unconventional and awe-inspiring. My experiences have taught me that adversity can be a catalyst for greatness, and the key to success lies in our ability to believe in ourselves, turn challenges into opportunities, and never shy away from visionary thinking. As I continue on this remarkable path, I am committed to empowering others to rise above their circumstances and unleash their true potential, just as I have done on this extraordinary journey of triumph.

Chapter 7: The Transformation: From Pain to Purpose
The journey from adversity to achievement was not just about overcoming challenges; it was a transformation of my very being. As I embraced the power of resilience, I tapped into an innate visionary spirit that I never knew existed within me. Building brands and creating the world's first shipping container franchise were not merely milestones; they were manifestations of the transformation I underwent.

Chapter 8: Unveiling the Visionary Within
Looking back at my turbulent past, it is almost surreal to think that I, too, once struggled with doubt and uncertainty. However, my pain and tribulations became the catalysts that unlocked the visionary within me. Each setback fueled a desire to create something extraordinary, something that would not only redefine my life but impact the lives of others.

Chapter 9: The Birth of New Horizons
With a newfound sense of purpose, I embarked on ventures that defied convention and reimagined industries. The creation of the world's first shipping container franchise was a testament to my vision's power, turning an unorthodox idea into a global phenomenon. Each brand I built stood as a testament to my resilience and unyielding belief in the potential of my dreams.

Chapter 10: A Taste of Innovation
Beyond the world of commerce, I ventured into the realm of winemaking. My passion for innovation spilled into the creation of ten exclusive wines, each bearing the mark of my dedication to excellence. As a winemaker, I crafted flavors that carried the essence of my journey, turning the bitter moments of the past into a tapestry of rich, exquisite tastes.

Chapter 11: Purpose-Fueled Inspiration
The realization of my visionary potential served as a beacon of hope for those who faced struggles similar to mine. I discovered that my purpose extended beyond personal success; it was about inspiring others to find their inner strength and transform their pain into purpose.

From a troubled youth to a visionary entrepreneur, my life's journey has been nothing short of extraordinary. Overcoming dyslexia, ADHD, and various challenges, I turned my pain and tribulations into purposeful action. As I built brands, created the world's first shipping container franchise, and ventured into the world of winemaking, I discovered the transformative power of resilience and determination.
My story stands as a testament to the human spirit's potential for growth and achievement. From the depths of uncertainty, I emerged as a visionary, inspiring others to embrace their uniqueness and unlock their true potential. My past has shaped me, but it does not define me. Today, I stand proudly as a visionary entrepreneur, winemaker, and above all, an advocate for transforming pain into purpose.

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