Alright – so today we’ve got the honor of introducing you to Kyle Pemberton. We think you’ll enjoy our conversation, we’ve shared it below.
Kyle, thanks for joining us, excited to have you contributing your stories and insights. Risking taking is a huge part of most people’s story but too often society overlooks those risks and only focuses on where you are today. Can you talk to us about a risk you’ve taken – it could be a big risk or a small one – but walk us through the backstory.
I became a Barber back in 2017 and graduated from Boise Barber College with no real plans other than to learn the craft and making an income. Barbering was something I pursued after a long career in the culinary industry that started at a young age.
Growing up with a single Father, food was always on the table and a roof was a put over our head. But, times got tough in the 2008 economic collapse and it was time for me to step up and help out financially as well. This was what pushed me to become the best Chef I could be at the young age of 13. Working under many talented and passionate artists in the Kitchen showed me how much fun being good at what you do can be! There was only one problem… the Chef rarely gets the pat on the back that they deserve. And this is a very defeating feeling when you pour your entire self into anything.
Fast forward to 2015. I moved from Northern Michigan to Montana in hopes of starting an entirely new chapter and lifestyle. Loving the outdoors lifestyle and sheer beauty of the mountainous landscape, I was constantly in the woods. If I wasn’t working in the kitchen, I was outside pursuing complete solitude and peace in God’s Country.
I burnt out on Culinary around this same time as moving to Montana. This prompted me switching career paths and getting a position with a construction crew doing both commercial and residential building. I found out quickly that I did not enjoy the mindset or lifestyle involved in this job.
One day while getting a haircut from my Barber, I brought up the fact that I was frustrated with figuring out my future career and did not have the patience or want to pursue traditional college.
He jokingly said “Why don’t you look into Barber School?!”.
I replied with, “Is Barbering even a career? I thought Barbers were just old guys that didn’t want to retire and liked to talk!”.
I left my haircut perplexed and extremely curious to dig further into our brief banter about the possibility of me becoming a licensed Barber. Investigation ensued, I spent lots of days going into local shops and shaking hands. Meeting shop staff and picking their brains about why they got into the hair industry and what perks there were. The way I understood Barbering before attending school was that I could make a livable wage in a 40 hour work week and take off 2-3 days a week for personal time. This sounded exactly like what I was looking for. A slow down from the 90 hour kitchen and construction weeks I was already so used to. And a decent wage to support my future family.
After a few weeks of researching schools and the best cities to learn the craft, i settled on Boise Barber College in Boise, Idaho. Packed my stuff and made the move about 6 weeks after my conversation with “Max” the Barber about going to school. I had no connections in this town. No knowledge of how the city life worked or what i was truly getting myself into. I had a job at a restaurant to supplement my income while attending school 40-50 hours a week. I also took care of a Special Needs gentleman on some evenings.
Finances got tight about half way through the 7 month course. I had applied for financial aid but couldn’t get any help without both of my parents filling out the paperwork. My Mother was not a key part of my life during this time so i found it challenging to get the necessary paperwork done in order to get the financial assistance i needed to finish out school. I was at the point of pulling the plug and giving up completely. My best friend at the time bought me a plane ticket back to Michigan for the Thanksgiving Holiday break to help me decompress and bring me back around people i knew well. This was the turning point for my entire life and career.
After expressing the hard (but honest) truth, my friend “Jasmine” had encouraged me to continue to pursue my Barbering path. I was just too far into it to throw in the towel over a little bit of financial trouble. The only options… take a break and go back once i had the paperwork done and a little cash saved to survive. Or i could agree to letting Jasmine come support me through the rest of School in Boise as she requested.
“After all isn’t that what true friends are for?!”- Jasmine
Well i chose the latter of the options. I accepted help from Jasmine to finish out the final months of schooling. Not truly knowing what this may look like. But absolutely willing to do what it took to break the chain of financial stress.
“A raging waterfall of risk always dumps into a calm, flowing river of success if you don’t stop the flow of water.”- Me
Well, i got through the final months of school. Jasmine moved to Boise from Northern Michigan and worked multiple jobs to pay off my debt and put food on the table for the both of us. We ended up falling in love and creating a beautiful little family out of our relationship. Without the selflessness of my now Wife, Jasmine, i would truly not be where i am today. I am a successful Barber and Entrepreneur because of this gracious giving.
We now both own a brand dubbed “Man of the Woods” in the beautiful state of Montana with 2 locations. One being the first purpose built Mobile Barbershop in our state!
We have 2 perfect Sons that are beyond blessed with love and community support. Always rocking fresh haircuts too!
And beyond that, we have now been able to provide growth and life changing opportunities for individuals with potentially life altering pasts. Mentoring a few people dealing with similar life situations that both Jasmine and I have experienced. Giving them a sense of family, love and connection while empowering them through the challenges of growth!
Kyle, 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 was born in March of 1994 in Irving, TX. I have 2 half siblings (we have the same Mom and all different Dads). My Brother (Josh) is the oldest and my Sister (Kayla) the youngest. I am the middle child at 29 years young! My Parents divorced when i was 5 years old and my Dad and I moved to Michigan to be near family in times of need. My relationships with my siblings and Mother were on and off most of my childhood. I split time between Texas (Mom’s Side) and Michigan (Dad’s Side) from ages 6 to 14. At this time i felt as though sticking around Michigan was the best option for my future and have only been back to Texas a handful of times since then.
Without going into too much detail, my relationship with my Mother was not a close one after the divorce. Decisions were made that i was unable to control and from then on i concentrated more on myself than ever. Knowing if anyone was going to “break the chains” it would take an immense amount of self motivation and growth.
Entrepreneurship began…
My first brand was a free bicycle repair shop for the neighborhood kids that we peddled around with. They would cover the cost of supplies and i would provide the garage space and tools as well as any knowledge i had of the repair process. This venture was short lived as i knew very little about “Cash Flow” and “Overhead” being only 9 years old at the time.
Next on the list… a shot at the production/film industry in high school. I started a brand with my childhood best friend by the name of “Treestand Mafia”. Because anything with the word “Mafia” in it was obviously cool in 2008… This brand was an Outdoors based series of experiences in the woods while doing what we loved most… hunting. This brand lasted a few years just from merchandise sales and small time brand support from various companies that wanted the exposure to our social media following. It is still a dream to go bigger and way more professional in the future with a similar idea!
Now, onto my dreams and creations as and “Adult”.
After attending Barber school in 2016, i worked at a small Salon as the first Barber in the space. While working here i found it extremely challenging to build a clientele base in a very saturated market of extremely skilled Barbers and stylists. To set myself apart i started a weekly event that we called “Sensory Sundays”. This idea stemmed from a Special Needs client i had during my time at school. I saw the need for many others with sensory issues to keep their health and hygiene up through grooming. Thus creating a niche in the Special Needs community in Boise and becoming “The Chair Therapist”. Providing heavily discounted and sometimes free of charge haircutting services catered to their specific need in the shop environment. Dimming the lights, changing the music, locking the shop doors to not be bothered or distracted and following my clients around the shop cutting whenever and wherever they felt the most at ease. This sparked my next brand idea in 2018.
After moving back to Montana in 2017, it only made sense to bring “Sensory Sundays” with me to this new market. I helped out around the local homeless community and through our church for about a year. But was finding it really hard to tap into the time needed to truly pour my heart into giving back. I now had a Wife and brand new baby boy to provide for. My time was now being spent building a steady clientele in Bozeman becoming one of the busiest Barbers in the valley. Money became the goal. Passion was pushed to the side and financial growth was all i could think about. It truly tore me apart and burnt me out. By end of 2018 i was ready to give up on my barely started Barbering career. I had all the money i needed and more, but no time to give back or knowledge of how to give back in the right ways without burning both ends of the candle.
I made the decision to step away from the shop i was at. Sell everything we had and move our family onto a Converted School Bus to travel and give back. Taking my Barber tools with hopes of doing free haircuts for anyone in need. Lost and ready to find out where my passion truly lies in this life.
Commence brand 3 “The Art of Now”. My best shot at giving back through barbering and conversation. Traveling the United States by literally a tiny home on wheels with my Wife, 1 year old son and lab/retriever mix. Giving free haircuts to anyone in need in exchange for their story. Also providing “Hygiene Bags” with life’s necessities inside of them to give a little more comfort. We had partnered with the local Red Wing Boots store as well and were able to give away upwards of 50 pairs of footwear to Homeless, EMS, First Responders, Law Enforcement and Fire Fighters.
Unfortunately around the time of completion for our “501c3” Status, Covid hit. And we were shut down from traveling or cutting hair any longer. We successfully traveled through about half of the lower 48 and gave back hundreds of times. Making incredible connections along the way and forever changing our perspectives on the meaning of success. Lock down forced me to pivot once again and build my next brand… “Man of the Woods”.
Operating previously as “Chair Therapy Barber” in multiple locations but never officially launching a branded location weighed heavy on my heart. I had a vision for a well done and beautiful mountain town Barbershop from the very first year of haircutting in Montana. Big Sky was a close town to Bozeman and never had a purpose built traditional Barbershop to fill its ever growing need for mens grooming. The high end nature of resort towns is something i grew up in while living in Harbor Springs, MI. In fact Big Sky Resort is the “Sister” Resort to Boyne Highlands, which i happened to work at during my middle and high school years. So i knew how to build the brand, i had the vision, i just had to do the work and get the capital to achieve this.
In July of 2020 i had finished my business plan, signed a commercial lease in Big Sky and secured a loan for the all new and very first Barbershop in Big Sky… Man of the Woods! Our vision had truly come to life right before our eyes!
Big Sky has what we call “off seasons” when there is no real reason for the community to stick around. It is in between ski/snowmobile season and mountain bike/fishing season. These times get incredibly tough for a small business to operate. Our overhead is high and real estate continues to grow fast. Prices are on the constant rise and therefore we had to pivot from solely a brick and mortar location to also having a “Mobile Barbershop” on wheels.
This we call “Man of the Woods Mobile”. A 22’ trailer that my Father and I custom built at my home. With the help of many talented hands and creative minds we achieved something beautiful and one of a kind.
The mobile barbershop idea 100 percent stemmed from cutting hair on Sensory Sundays and for The Art of Now. I figured out a way to bring high quality haircutting experiences to the client. No matter who it is. Events, Weddings, Homeless shelters, movie sets, sports events… the list goes on! This brand went live most recently underneath of the Chair Therapy Hair Co. umbrella as the Sister shop to our Man of the Woods Big Sky location. We currently operate both locations with 4 Barbers total. The mobile location supplements the slower “off season” periods and gets us out of the shop to break up the monotony of daily routine! I plan to continue to grow this brand and see where it takes me from here!
Most recently i have been focusing heavily on self branding. Pursuing more of the educational and entrepreneurial side of business. Helping people learn from my mistakes and challenges along the way. Providing opportunities for those with potential to succeed alongside me and my family!
Any stories or insights that might help us understand how you’ve built such a strong reputation?
I think the thing that helps me build my reputation most within my market is the fact that i concentrate purely on connection and experience. When you care 100% about what you do and who you do it for, you will stand out from the crowd. Never ever pursue something part time unless you are doing it to supplement income to invest in something full time. Even when i was a new Barber and making $100 every 2 weeks, i worked full time in the shop. Learning how to separate myself from the noise and listen to my heart.
My connection is raw and often unfiltered. I charge for Barbering services because I have to. I’m not saying you should ever want to work for free. But it sure does lift the pressure when knowing even if you did it for free, you would still love it.
I constantly educate myself on new and advanced technique. I use resources such as a mentorship program and trade shows to connect on a professional level as well. Hair is an ever evolving industry and if you don’t keep up with it, it will not stop and wait for you. Trends change literally every day. So in order to keep up, i surround myself with great clients, mentors and friends that truly understand my passion for the art of Barbering.
How did you put together the initial capital you needed to start your business?
In order to fund my business i enlisted the help of a great friend of mine. As they say “We are in the people business” as Barbers. Our network can be very extensive and generally if you need it you can find it through your Barber.
My friend Brian works with numbers for a living but better yet, he is an excel master and had put together lots of job paperwork pertaining to financing water treatment facilities. A true wiz and also a client of mine that had become a friend in a very short time. We share a genuine love for business development.
Brian helped me put together a business plan outlining 10 years of projected profits and losses for the Man of the Woods brand. We spent countless hours after work and on the weekends perfecting this business plan. As i presented it to potential lenders, we would make the adjustments they suggested and re evaluate our numbers. Constantly making it more appealing and cutting out unnecessary expenses. I was willing to give up any amount i could to see this dream out.
After finally connecting with a local bank, we got the loan. It required us putting down literally everything we owned as collateral in case of a default on payment. But we are now on year 3 and have established an amazing relationship with our banker.
I believe building trust with your bank is key. Dress to impress, Walk in, ask for the commercial lending manager, and present your plan professionally and thoroughly. They want to help you get the loan if your plan makes sense. If not they will coach you on what needs to be adjusted in order for them to loan you the funds down the road. Don’t give up, just keep adjusting until the recipe works! 
Contact Info:
- Website: Motwbarber.com
- Instagram: @chairtherapy_barber @man.ofthewoods @man.ofthewoodsmobile
- Facebook: Man of the Woods Barbershop
Image Credits
Photo Credits @littlefishphotography @shanna_mae_photography @bozefoto