We were lucky to catch up with Caleb Wieske recently and have shared our conversation below.
Alright, Caleb thanks for taking the time to share your stories and insights with us today. We’d love to have you retell us the story behind how you came up with the idea for your business, I think our audience would really enjoy hearing the backstory.
I grew up in Canada as the youngest of 6 children. My father had nearly always been working for himself and when I was about 12 years old he took the risk of moving away from his previous business of carpentry, and starting a stone supply yard. Selling stone to landscapers and outdoor living experts to be used in all sorts of beautiful jobs around southern Ontario. While it was hard for the first few years as you can imagine, he pushed through together with my mom and they managed to grow that business to a substantial enterprise and employ over 15 people and do millions in revenue.
The reason I include this is twofold.
One because this provided tremendous inspiration to the whole family and was a great example of how in life and in business it’s rarely “who you know” or “just luck” that will make something work. But rather consistent effort, undying optimism, hard work and persistence.
The second reason is because at some point or another, every single one of my siblings,(me including) worked there. And we all got to learn so much about the high end outdoor living industry. From talking to clients, helping customers with design considerations, seeing completed jobs and the possibilities when it comes to this space, sourcing, purchasing and selling stone all over the country.
The idea of purchasing always interested me, and my oldest brother (Dustin Wieske) and I had always loved the idea of working for ourselves, so we left the family business (on good terms) to pursue our own ideas. My brother Dustin began working in real estate and I started a retail shop. Without spending too much time on this, fast forward 3 years later and my brother Dustin had bought, rented out, renovated and sold 3 properties in that time. And my start up retail shop had acquired over a 1000 customer accounts with a gross revenue north of 300k. Both of us had gained tremendous “on the job” experience and confidence from this period of time.
One day my oldest brother Dustin (8 year age difference) and I were going for a drive talking about life and business and we landing on the topic of the family business and the outdoor living industry. My brother recounted an interaction he had with a Canadian landscaper about how the outdoor industry in Southern Ontario is quite unique for 2 main reasons. It’s extremely large considering the size of the population (nearly every home has had high quality work done outdoors), and two the innovation and quality of the work is extraordinarily high.
We discussed how there may be an opportunity to take our knowledge and experience and move it into a market that might not have been exposed to the same innovations. The conversation lasted quite a while and ended with some action items for us both. We began doing research looking for where we believed the opportunity was the greatest as well as optimizing for our personal family lives.
Both of us loving America, and seeing an opportunity in the south, we landed on East Tennessee and the idea was born.
We chose Tennessee for many reasons but the chief ones were the following. The large separation from any Canadian influence (with regard to the outdoor living space) gave us a unique opportunity to showcase designs and use of outdoor space, as well as outdoor products that may have never been seen, giving us an edge. The more mild climate. This would allow us to offer outdoor spaces to our customers that could be used all year round! And the ability to service 6 States and millions of people within a rather short working distance.
We thought long and hard about what exactly the business would be trying to accomplish and formed a two pronged approach, Being that this business was to be a partnership, and that Dustin and I had garnered different experiences from running our previous businesses we wanted to Supply and Service East Tennessee and beyond. We wanted our company to be the one stop shop for all things related to outdoor living. On the supply side we wanted to have a retail store that would sell all the products our customers may need for outdoor living down to the most unique and esoteric ones so as to meet a need most other stores do not. And on the service side we wanted to showcase our knowledge and experience with designs that stood out. And a quality workmanship in our jobs, that would be built to last a lifetime.
(Supply examples: BBQs, Smokers, Pizza Ovens, outdoor fireplaces and heaters, Spices, rubs, Charcoal, Patio furniture etc.)
(Service examples: Board over board fence set in 6×6 posts, high end outdoor kitchens, unique outdoor structures)
(https://www.outdoorlivingsupply.com/)
We decided on the name “Outdoor Living Supply”. And formulated the following mission statement: “To Inspire, Supply and Service our customers to help them realize the beauty and utility in their outdoor spaces”
And after about 12 months of paperwork research and liquidating assets, me selling my business and my brother selling his real estate we accomplished our goal and started our business in the beautiful State of Tennessee.

Caleb, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Since this business is a partnership I will break this answer down for both partners (Dustin and Myself)
Dustin:
Dustin was the logistics manager for the family business, in charge of hundreds of deliveries of high quality stone all around southern Ontario. After leaving the Stone yard and going out on his own into real estate he specialized in high end house flipping. Spending more time on each house to achieve a beautiful fit and finish and yielding a the highest return on each property. In doing this for over 3 years he gained knowledge and experience in many different trades as well as the invaluable skills of communication and time and money management.
He is a tremendously positive and genuine individual and it’s quite literally contagious. It’s near impossible to be negative when working with him and this is a indispensable quality that helps him build phenomenal working relationships with people very quickly.
One of his most consistent sayings is “If it’s worth doing, it’s worth doing right” and he truly lives by this statement in all areas of his life. Never cutting a corner or taking the easy road when it comes to work, but also being an extremely present husband and father to his wife and 4 kids. This is what I would say, would constitute Dustin’s personal brand. Always going the extra mile for a customer with a smile on his face. Leaving every job having taken no shortcuts and operating with integrity and conviction that is not often seen. The quality of work he does is near unprecedented in today’s world of cheap and fast instant gratification.
Dustin’s specialty is Outdoor Kitchen design and installation. His ability to optimize an outdoor space and make the flow from an interior space to exterior one seamless, and then articulate that to the customer is incredible.
Caleb:
As assistant manager of the stone yard Caleb was responsible for the day to day operations of the yard like getting customers loaded in a timely fashion, ensuring the safety of the employees and forecasting stocking needs. This experience allowed him the opportunity to learn about purchasing and management. After leaving and starting on his own he founded and self funded a retail business. He worked 12 hour days alone for over a year trying to grow his customer base and his business. It paid off and he was able to hire multiple employees and focus less on the day to day of his business and more on purchasing and website development.
Caleb is an individual that is tough to outwork. He is consistently the first one to show up and the last to leave, but you’ll never hear him complain or even talk about that. He is quicker to listen than to talk and that has served him well as he is able to take, learn and follow advice from others and garner lessons from others experiences. And that has allowed him to avoid many mistakes new business owners may make. This is exemplified in that he started and self funded his retail store at the age of 20, with money he had been saving since he was a teenager! He sold it before his 24rd birthday for 210K! His ability to learn from others and then take calculated risks from that knowledge is a rare and exceptional talent.
Caleb’s love of purchasing is a tremendous asset to this business and to our customers as he is always searching for the newest and best products while ensuring everything else stays in stock for our customers. He is a kind, very positive and treats customers like gold.
Our businesses modus operandi exceptional customer service and unparalleled quality of work. We truly are not satisfied until our customers are.

How’d you meet your business partner?
While the story of how I met my brother may be a boring one……we grew up together, I chose this question to talk about how and why you should choose your business partner.
“If you want to go fast, go alone, if you want to go far, go together”. – Martha Goedert
When considering a business partnership the main thing to look for other than the total basics of “do we work well together” or “do we even get along so as to have a productive partnership” would be, do we have complementing abilities? It’s important to have this for a litany of reasons but perhaps chief among them is the ability to have one partner strong where the other is weak and vise versa. To have complementing abilities allows for ideas to flourish and for you to contend (civilly) with one another to plan and strategize for the business’ future. Two people who think differently and who can complement one another can produce a working bond that is far stronger then a sole proprietorship. ”
A cord of three strands is not quickly broken.”
How did you put together the initial capital you needed to start your business?
Caleb sold his business and Dustin sold his real estate.
While it’s easy to type, it was far more time consuming, stressful and difficult in real life. But when you have an dream, that you turn into an actionable plan you can make it happen. If you change your mindset to stop making excuses and realizing all your reasons not to do something that you really believe in are almost always just excuses, you will be astounded with what you are capable of.
Contact Info:
- Website: https://www.outdoorlivingsupply.com/
- Instagram: https://www.instagram.com/outdoorlivingsupplyusa/
- Facebook: https://www.facebook.com/outdoorlivingsupplyusa/
- Twitter: https://twitter.com/OutdoorLivingUS
- Youtube: https://www.youtube.com/channel/UCYrXaInsMGNGhkbOM7rX2uA
- Other: https://www.pinterest.com/outdoorlivingsupply/?invite_code=3d9ce3000d7746f38a092468c3a0df39&sender=1078330841937054314
Image Credits
We have the rights to the photos

