We’re excited to introduce you to the always interesting and insightful SKYLER MASON. We hope you’ll enjoy our conversation with SKYLER below.
SKYLER, thanks for joining us, excited to have you contributing your stories and insights. How did you come up with the idea for your business?
How did SKYIN come to be? It’s a question that delves into more than just a timeline of events; it’s a journey into the very heart of human aspiration and the profound desire to connect. SKYIN wasn’t born out of a single moment, but rather a convergence of ideas, a singular vision by an individual who saw beyond the immediate horizon.
At its core, SKYIN emerged from a fundamental understanding: that in our increasingly complex world, the need for clarity, connection, and inspiration has never been greater. We observed a landscape where information often overwhelms, where genuine human interaction can feel diluted, and where the spark of innovation sometimes struggles to ignite amidst the noise.
From this understanding, a vision began to coalesce. It started with a poignant moment in my own life – my first journey to Africa as a young boy, a trip that opened my eyes and heart to a world of breathtaking beauty, vibrant cultures, and an undeniable sense of belonging. That initial spark ignited a lifelong passion, leading me back to Kenya repeatedly throughout my adolescent life. I immersed myself in the culture, spending countless hours learning from and living among the Maasai tribe, whose profound connection to the land and their rich traditions left an indelible mark on my soul.
This deep immersion presented a crossroads: continue within my family’s successful business, a path of comfort and familiarity, or forge an entirely new one, driven by the desire to share the wonders of Kenya with others. The choice became clear. SKYIN was born from that decision, a commitment to offering more than just a trip, but an authentic, transformative experience. It’s about inviting people to witness Kenya not as mere tourists, but through the eyes of someone who has lived its rhythms, felt its pulse, and understands its heart – a journey crafted from a local’s perspective, designed to inspire, connect, and leave a lasting impression, just as Kenya did for me.
Ultimately, SKYIN is a testament to the power of shared purpose. It’s a living entity, constantly evolving, shaped by the contributions of everyone who becomes a part of its journey. Its origin is not a closed chapter, but an ongoing narrative – a continuous unfolding of inspiration, connection, and the pursuit of a brighter future, for individuals and for the world at large.


SKYLER, 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?
My journey into the heart of Kenya, and eventually into founding SKYIN, is deeply personal. It’s a story rooted in an unwavering passion, integrity, and discipline—all stemming from the profound love I hold for the people I work with in Kenya, whom I consider my extended family.
My entry into this industry wasn’t a calculated business decision at first, but rather an organic evolution born from a deep-seated connection. I had been returning to Kenya repeatedly throughout my adolescent and adult life, immersing myself in the Maasai culture. Each departure felt like leaving home, and upon my return, friends couldn’t help but notice the palpable excitement and joy that radiated from me. It was my friend who, after witnessing this enthusiasm repeatedly, inspired me to consider transforming my personal passion into a company that could offer others the same immersive and authentic excursions I cherished. I saw the potential for a business that allowed others to experience Kenya not as tourists, but as participants in its vibrant life.
Building SKYIN, however, was far from easy. Despite having grown up within my family’s successful business, this was my venture, and navigating the intricate web of international, national, and local regulations and laws proved to be a daunting, all-consuming task. The discipline required to get up each day, knowing the immense challenges ahead, and to not rest until I had given my absolute best effort, was paramount. It’s a discipline I apply to every aspect of SKYIN, ensuring that every detail is meticulously handled.
At SKYIN, we specialize in providing immersive journeys across Kenya. Our flagship offerings include exclusive immersions into an actual Maasai village, allowing our clients to experience firsthand the rich traditions and daily life of this incredible community. Beyond these unique experiences, we pride ourselves on curating custom itineraries for clients who demand and expect nothing less than excellent service and quality. Watching a guest experience their first safari, witnessing their awe at the majesty of the wildlife, or seeing the pure joy of exploring the vibrant marine life within the Indian Ocean—these are the truly poignant moments that, as the founder of SKYIN, inspire me each and every day. These transformative experiences fuel our commitment to creating unforgettable journeys, reinforcing the profound impact Kenya has on all who visit. We understand that discerning travelers seek more than just a destination; they seek a transformative experience tailored to their desires.
What truly sets us apart, and what problems we solve for our clients, stems from our unwavering dedication. Our numerous five-star Google reviews are a testament to our commitment to both our direct clients and the travel agents who partner with us, ultimately benefiting their customers. We meticulously craft every journey to ensure it exceeds expectations, providing unparalleled access and authentic experiences that go beyond the typical tourist offerings.
What I am most proud of is the profound excitement and joy realized by those who embark on a SKYIN journey. These are not just trips; they are travels that touch the soul, offering a transformative experience that resonates long after returning home. For potential clients, followers, and fans, I want you to know that SKYIN is a brand built on love—love for Kenya, its people, and the incredible privilege of sharing its wonders. Our work is about more than just travel; it’s about fostering connection, inspiring personal growth, and creating memories that are truly life-changing. These journeys are designed to be so much more than just a trip; they are an invitation to discover a piece of yourself within the heart of Kenya.


How about pivoting – can you share the story of a time you’ve had to pivot?
When I first realized my passion for creating a business which provided authentic journeys across Kenya, I had strong ideas of what I thought that should look like. Immersive day-long experiences with indigenous tribes, vetted homestays, thoughtful and impactful safari excursions, all had to resonate with something more… they had to be honest and transformative. Establishing the foundation for these pillars of my company proved enriching yet intense, but I was resolved to offer travelers an opportunity to engage actually into and with the people of Kenya as I had growing up. In my mind, by providing this, it would dramatically aid colleagues, friends and communities in my African “homeland” with a sustainable livelihood and ensure long term growth opportunity.
One of my initial challenges was procuring a creative agency to help me with my brand; my identity in the professional world. As most entrepreneurs know (or learn quickly), one’s outward appearance can have a profound impact on the receptivity of your audience. I was raised in my father’s startup business which, through hard work and grit, was very successful. I knew the importance of resonating with my audience and falling short would be professional suicide.
I hired an agency and got to work. After months of effort (and capital), I was ready to launch. With a website and social media prepped, I was thrilled to begin. People were counting on me and I didn’t want to disappoint. Unfortunately, in the pursuit of ensuring an authentic journey for my future clients and transparent relationships with agents and travel partners, the branding and marketing effort fell flat. I was crushed.
On the advice of a colleague, I had a meeting with a creative director whose background in film and branding proved to alter the course for my business and how it was perceived. We spent days discussing the significance of connecting honestly with my audience and how to best achieve this. Unfortunately, the takeaway was that my current brand didn’t reflect who I was or what I wanted my company to be. The imagery and choice of logo was void of the vibrancy and passion of the company’s mission. I wanted the voice to reflect the energy for the journey ahead and without it, it was a travel company without heart, without its soul. I had “checked the boxes” of executing marketing deliverables, but hadn’t realized my efforts didn’t reveal the authenticity of the custom, immersive itineraries provided and the meaningful transfigurative excursions.
We began again in earnest and what has resulted has been nothing short of exhilarating and undeniably successful. The brand fully reflects who I am and the sincere expression of authentic and immersive journeys SKYIN offers. Connecting to and believing in the value of creating a business which doesn’t just say something is authentic, but actually providing an experience that is genuine, helped my audience share in what is important – honest moments. People crave to have this simple truth afforded them through excursions which create lifelong memories. By assuring my brand reflected that, every touchpoint continues to ring true.
I love what I do and by admitting the value of correcting mistakes taken, SKYIN flourishes. I encourage others to remain true to who you are and seek to authentically represent yourself and your business. We’ll make errors along the way no doubt, but we will be able to correct the course as well, by knowing who we are and what we stand for.


Any stories or insights that might help us understand how you’ve built such a strong reputation?
My reputation, I believe, is built on an unwavering commitment to personal investment—a commitment that transcends the typical client-provider relationship. For me, every guest, every travel agent, isn’t just a transaction; they are an extension of my own deep and abiding connection to Kenya. This business isn’t merely a venture; it’s the tangible outcome of a lifelong love affair with a country that captured my heart as a young boy and continues to inspire me every single day.
When someone chooses SKYIN, they are choosing to entrust us with their dreams of experiencing Africa. And because those dreams mirror my own profound experiences, I feel a personal responsibility to ensure that their journey is nothing short of transformative. I want each traveler to feel the wonder, the mystery, and the remarkable beauty of Kenya as I have. I want them to connect with its vibrant cultures, be awestruck by its majestic wildlife, and find solace in the pristine beauty of its Indian Ocean beaches. This unique trinity—wildlife, culture, and coast—is unparalleled anywhere else in the world, and it’s a privilege to share it.
This level of personal investment permeates every facet of SKYIN. It’s reflected in the relentless dedication of my team, both here in the United States and on the ground in Kenya. Their pursuit of perfection isn’t just a professional goal; it’s a shared passion. We painstakingly curate every itinerary, obsess over every detail, and anticipate every need, all driven by the desire to provide the ultimate luxury journey. We understand that we are not just selling trips; we are facilitating profound, soul-stirring experiences that create lasting memories and forge deep connections. It’s this genuine care, this deeply personal commitment, that I believe truly defines SKYIN and has allowed us to build the reputation we cherish.
Contact Info:
- Website: http://www.liveskyin.com
- Instagram: https://www.instagram.com/liveskyin/
- Facebook: https://www.facebook.com/liveskyin/
- Linkedin: https://www.linkedin.com/company/live-skyin
- Youtube: https://www.youtube.com/channel/UCfKCj1zahPmPxwJwMmn9CNA/featured
- Other: Email: mailto:[email protected]



