Using Positivity as a Superpower

How Airbnb rockstar Donny Wong turned entrepreneurial adversity into success

The Rockstar

It was a beautiful summer morning as I sat patiently at a popular breakfast café in downtown Calgary. As I took a sip of my coffee, I heard this voice “There he is.” In walks a stylish gentleman, rocking glasses, fitted joggers, and hairstyle. I was excited to finally meet this rockstar entrepreneur who constantly came up in conversation among the hustlers in the city.

It was the one and only Donny Wong. In passing, I’ve met him and heard many great things about him. However, I didn’t know what to expect entirely. I didn’t know much about him aside from the fact that many in the business community referred to him as a “hustler.” I’ve met many entrepreneurs in my life. However, specific energy resonates from someone who indeed oozes that go-getter vibe. They tend to light up the room with their smile, energy, and charismatic demeanor. Donny was one of those guys.

As a young man born and raised in a traditional Chinese household, focus and hard work was instilled in him. Like many Chinese people, Donny referred to his heritage as resilient. Chinese people are adaptable, he says. They can be placed anywhere in the world and will find a way to survive. 

“When a Chinese person first moves to a new city or country, the first thing they ask themselves is what business can I open up?” 

The entrepreneurial gene definitely was ingrained in him from the beginning, as this is precisely where his mindset was. Succeed at all costs.

In Chinese culture, success was often connected to being a doctor, lawyer, accountant or an internationally recognized profession. Rather than becoming a doctor, which many Chinese believe is the best path to riches, he went all in on entrepreneurship. Since leaving high school, he leveraged 100% of his time to build a life of happiness and freedom. Being a doctor wasn’t something that lit his fire. “Instead, I chased my own dreams. No jobs, no school, no sense of the odds, just a young soul drunk on wanderlust,” he says with a smile of confidence.


Opus Nightclub

At age 22, he bought his first nightclub, Opus Nightclub. Opus nightclub was Calgary’s first high-end super club which hosted the who’s who of Calgary’s social scene. In his words, he was “paid to party.” Five years later, the allure of popping bottles and partying till the wee hours of the morning took its toll. He wanted more. At 27, he decided to sell everything and move to Toronto to become a billionaire. With confidence and enthusiasm, he felt that if given the opportunity, he could accomplish this. Under the mentorship of 2 of Canada’s wealthiest people, he practiced, honed and mastered the art of sales. Going door to door selling water heaters was not only humbling as he was called a scam artist and told to get lost. Despite repeatedly getting doors slammed in his face, he laughed it off as it built up a thick skin. This experience tested his resolve and was precisely what was needed for him to build up grit. Donny knew that entrepreneurship wasn’t linear. He would constantly have to evolve so that when one door closed, he was prepared to walk through another door that opened.

Death and Adversity opened new doors of opportunity

After several bumps along the road, Donny made yet another pivot in his entrepreneurial journey. At 32 years old, he decided to become the CEO of his own Cannabis business, Booost CBD. In honor of a friend that passed away, he started this company as a way to share how Cannabis provided a few more months of life for his friend before he eventually succumbed to Cancer. His friend was one of the few people who truly believed in his ability to manifest his dreams, although manifesting his dreams wouldn’t come easy for him. He would have to decide yet again to be on the move. After grinding away in direct sales, Donny moved back to Calgary to take care of family responsibilities. After the death of his close friend, death would once again visit his loved ones. Within two weeks of arriving back in Calgary, he lost his sister. This devastated him. In such a short period, his close friend, sister and father passed away. It could have easily turned his typical upbeat self into a dark shadow of who he is. Finding himself homeless and destitute as he had to start all over, Donny never let his dream of financial freedom fade. He swallowed his pride and asked for help. His friend allowed him to stay at his condo for free while he sorted out his life. While surfing on a friend’s couch, he stumbled on the concept of Airbnb. Always the ever-adapting entrepreneur, Donny discovered the power of cash flow management and how rental arbitrage could be his way back to the top of the hill. “What if I could rent out where I live and generate income? I could sleep in my car or find another place to live while renting out my friend’s condo,” he says. That was it—a win-win situation. Make money using other people’s assets. Share in the revenue and trim enough profit to survive. Multiply this many times over and he could make a living off of this.

At 37 years old, he built one of the most successful Airbnb and Luxury Property Management businesses in Calgary. From coming back to Calgary with no money and a bag full of clothes to boasting a portfolio of over 80 properties, Donny is a symbol of resiliency and drive. He has pivoted several times as the pandemic forced him to explore not only short-term rentals but the consistency of long-term tenants. 


Donny’s Superpower

“I’ve been lucky enough to chase each mountain top for over 15 years, but it didn’t come without consequences. My personal finances being the #1 victim of collateral damage.”  Donny went from mortgaging his home to buy a nightclub to declaring bankruptcy to becoming one of the most well-respected people in the entrepreneurial community. When I asked him if he had one superpower, what would it be? His response was simple: ”being positive.” Regardless of what life throws at him, his ability to look to the positive side of any situation allows him to learn from his mistakes, adapt quickly and somehow find joy in the journey.

Since my first meeting with Donny over breakfast, I have had multiple conversations. Much of which leaves me enlightened and inspired. There is never an interaction where I don’t learn anything or walk away inspired. I recall him telling me, “Chop Wood. Carry Water.” This simple saying was a reminder to do the little things that many people don’t see. Do the things that are not glorious, like reaching out to people, adding more value than is expected and having impeccable follow through. As a proven entrepreneur, high ticket salesman, and man of importance, his goal is to help 1000 people win back their time by understanding the power of cash flow. Whether it’s his posts on social media, his youtube videos on airbnbs, his podcast “Ready, Set, SELL,” or his contributions to best-selling books, Donny believes that “Every choice you make makes you.”

Almost two years ago, I had that cup of coffee with him. To see him in action, the decisions he’s made, the success he has achieved, the adversity he has endured and the quality of man that he has become has been a pleasure. Good or bad, regardless of his choices, the person who walked along this hero’s journey remained humble, grounded and a man who has found his flow. Donny became the person he was always meant to be. An entrepreneur, a great human being and man filled with positive possibilities.

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