In a world where entrepreneurship is often seen as a linear path, Kyle Hamilton’s journey to success is anything but conventional. From aspiring brain surgeon to globe-trotting cook, Kyle’s story is a testament to the power of embracing life’s unexpected twists and turns. In this exclusive interview, Kyle shares his insights on navigating challenges, building relationships with clients, and adapting to the ever-changing landscape of the business world. Join us as we delve into the mind of a visionary entrepreneur who has carved his own unique path to success.
Interviewee Name: Kyle Hamilton
Company: birr agency
Intervirew Host: Jesse Samberg
The Interview
Let’s get started. First, we’d like to know more about how you started your business journey
Kyle Hamilton : I’ve taken a bit of a circuitous route into the roll of entrepreneur… When I left highschool, I had it mapped out that I would be a brain surgeon by the time I was 32. First year of university, my eyes were opened to all of the possiblities that truly exist in life. After my first year, I went to Europe. I was suppose to be gone 8 weeks, I ended up being gone for 8 months. My plan was to find a job as a waiter for 2 months, experience life as an 18 year old overseas, and come back to get on with school… I ended up getting offered a job as a cook (I had just learned to boil pasta before getting on the flight overseas so I could more than PB&J sandwiches). I told the restaurant owner that I didn’t know how to cook, and his response was, “Son, you’ve flown to the other side of the world, to find a job in a language that isn’t your mother tongue, in a culture you’ve only known for 2 weeks now. I think you’ve probably got the capacity for me to teach you everything I need you to know. And if I’m wrong, I’ll just fire you.”
That stuck with me. I stayed with the restaurant for 4 months, right through their busy summer season. To this day, my dad still jokes that I’m the only teenager he’s ever heard of who’s called home to tell their parents he was extending his stay in Europe, and oh, how do I go about wiring money back to you (instead of asking for money to be sent the otherway. Ha.)
I eventually got home, finished 2 degrees (but not without spending a semester studying in Sweden, and another year living in a van in New Zealand), and was on my way back to Europe to do a law degree, when I reached out to a former employer about a summer job. Again, what was suppose to be 8 weeks of work, has turned into 18 years living in the community of Fernie BC. I spent 5 years working at a backcountry cat ski operation, Island Lake Lodge (guests have included Justin Timberlake, and just last week, David Beckham). From that time working at the lodge in housekeeping, I ended up both starting my own photography studio that lead me to shooting campaigns for clients around the world, as well as managing 2 hotel properties at Fernie Alpine Resort. I eventually left the hospitality space to focus on photography, which eventually lead to me starting birr agency to help other businesses not only with content creation for their marketing, but also developing their marketing strategy and branding.
Reflecting on your business history, what stands out as the single greatest challenge you’ve successfully navigated, and how did you overcome it?
Kyle Hamilton : Whilst maybe not the “greatest challenge” anyone has ever faced, a very pivotal moment was making the decision to pursue photography, and start my entrepreneurial journey. Losing that regular pay cheque from being a hotel manager, especially with a wife an young daughter at home, was a leap of faith that I wasn’t sure I was ready to make.
But, with the help of my wife, who asked me,
“Okay, if you pursue photography, in 3 years we realize its not working out, can you go back to managing a hotel?”
“Well, I could definitely get back into the hospitality space, maybe not at a GM level, but it wouldn’t take me too long to get there.”
“And what about if you pursue hospitality for the next 3 years, but then decide its not the direction you want to go?”
“Well, it would be almost starting from scratch, as I’d need to reinvest in updated equipment, learn the latest trends and market needs, build up a client roster again, nothing that isn’t impossible, but, it will take me a good amount of time to accomplish.”
“Then, I think that answers the dilema. Go pursue the photography career.”
And from that point on, I haven’t looked back. I’ve often returned to this “crossroads” approach at looking at challenges, or two different opportunities, and applied similar critieria to my decision making matrix.
Businesses often face ongoing challenges. What does your business consistently grapple with, and how do you tackle these challenges head-on?
Kyle Hamilton : As an entrepreneur, I’ve been in involved in a number of businesses, from content creation agency work, to portrait and custom framing studio, to a tech startup developing VR/AR programs for workplace training with high-risk work environments. There are always challenges, as you say, which can either lead to success, or to failures. The thing I’ve learned over the course of my career is to embrace the failures, and not fear it.
With success, I find we rarely learn much from it. Something worked, so there is no need to review why, we can just move on. With failure, however, it provides us with tremendous opportunities for self-reflection, process review, assumptions review, and so on. With success, we may have simply been lucky, but we rarely analyse it to find out how or why we were successful. With failures, we tend to want to understand why it didn’t succeed like we thought it might. So, now, I don’t fear failure, but when it happens, I take the time to review everything to understand how I can improve for the next time, and not make the same mistakes twice.
Can you share with us the most unforgettable story involving a customer or client? What made it memorable, and what lessons did you draw from the experience?
Kyle Hamilton : I’ve got so many stories from my time as a photographer… some of them I can never share, some of them are not suitable for print, and some of them I’d rather forget. One story that stands out is from fairly early on in my photography career when I was focused on shooting weddings. I had met a bride to be at a wedding fair. We made plans to meet for coffee the next morning to meet with her and her fiance to discuss my services and their wedding plans. When we sat down to meet the next morning, the groom grumbled that he hated coffee. I made a bit of a smartass remark along the lines of, “I know its 5 o’clock somewhere, but didn’t think it would be appropriate to crack open beers before noon here…” The groom instantly started laughing, and agreed, its probably best we didn’t start drinking at 10am on a Sunday. We had a great chat, they were doing a destination wedding to Jamaica, and at the end of the meeting, the groom asked how I felt about drinking beer at 10am if I was poolside? I said that would be appropriate. They hired me on the spot. Fast forward 6 months, and I am at the airport for our flights to Jamaica. I am standing chatting with the bride and groom in the departure lounge, when a couple of their friends walk up. We are standing chatting for 10-15mins, when one of the friends turns and asks how I know the bride and groom? I said, I don’t, they’re paying me to be here. This got a quizzical look, and the groom laughed and explained that I was the photographer. Another person piped up with, “Really?! I tottaly thought you must have been a friend because you fit in so well with everyone!” The rest of the week was a blur with all of the activities, festivities and obviously the wedding. But from this one wedding, I think I ended up landing close to 6-figures worth of business, all as a result of being myself, being genuine, and recognizing that if I’m working with people I want to be around, I make much better imagery. I learned the value of being open to building a relationship with my clients, and not just seeing them as clients, but as future friends.
After this wedding, I made it fundamental part of my wedding business that before I would let a client send me a deposit or signed contract, we needed to sit down for a beer and get to know each other. I got some push back occaisionally, but explained, that I am quite literally some dude you just found online through a Google search, and on your wedding day, one of the biggest day’s of your life, I am going to be spending more time with you than your family and best friends. If we’re not comfortable with each other after meeting for a beer, then it doesn’t matter how good you think my art is, you’re not going to enjoy your wedding day, and I’m not going to create my best work if I can sense you don’t trust me.
Looking ahead, what are your current plans for your business when you retire?
Kyle Hamilton : While I would love to sell my business in the next 3-5 years, and for enough that I could retire, I feel like I’ve still got a good decade or so before I’m seriously considering that.
Navigating the small business landscape can be both challenging and rewarding. Can you share a bit about the specific hurdles you’ve encountered in areas like sales, marketing, and adapting to changing customer trends?
Kyle Hamilton : I feel like my time as a photographer has well prepared me for the changes, and required adaptations to the ever changing marketing landscape. When I first picked up a camera, was around the time that DSLR’s were starting to enter the consumer space. I had been looking at purchasing a new Canon film SLR, when a family friend who ran a photo studio made the suggestion to hold off a year, and see what happened with these new digital offerings. Since then, its been a seismic shift in that industry. Where as once a photographer could get hired to create some images, and then reliably license those images for years, a photographer is now a content creator that is expected to capture stills, motion, behind-the-scenes, and regularly post that content not just for their clients, but also to promote themselves to new clients. And the barriers to entry have disappeared. Anyone with a modern smartphone has a camera that is higher quality than the first digital camera I bought myself. This experience has opened my eyes to the fact that as a business leader, I need to always have my head on a swivel, and learn to recognize trends and directions before they start. Its also exposed me (no pun intended) to the need to look at every new technology, and think not just about its currnent intended functions, but, what else I might be able to do with it, that people aren’t talking about yet. A perfect example of this is the iPhone, and how what started as a means to communicate through voice, has really become a multimedia tool that many people use to capture their surroundings through photos and videos, and share it widely through social media. I’m looking at AI and thinking, yeah, its great right now to help write copy, write code, and play around with image generation, but, how else might I be able to apply this to both business and personal tasks?
Leaders Perception magazine would like to thank Kyle Hamilton and “birr agency” for the time dedicated to completing this interview and sharing their valuable insights with our readers!
Interested in connecting with the host of this interview series? Feel free to reach out to Jesse Samberg on LinkedIn: Jesse Samberg’s LinkedIn Profile