Kris Thorkelson is an accomplished entrepreneur and real estate investor based in Winnipeg, Manitoba. As the CEO and owner of Thorwin Properties, he has built a successful portfolio managing over 2,400 apartment units across the city. With a strong focus on providing high-quality housing and exceptional resident service, Kris has established Thorwin Properties as a trusted leader in the Winnipeg real estate market.
Kris’s entrepreneurial journey began after earning his BScPharm and BA from the University of Manitoba. He initially ventured into the pharmacy industry, co-owning multiple pharmacies, before shifting his focus to real estate in 2010. His strategic investments and commitment to long-term growth have been key to his success in real estate.
In addition to his business endeavors, Kris is dedicated to philanthropy. He has donated $500,000 to the University of Manitoba’s Pharmacy faculty and supports numerous local and global organizations. Outside of work, Kris enjoys golf, tennis, and travel, and values time spent with his family. His career reflects a blend of entrepreneurial drive, resilience, and a commitment to making a positive impact on his community.
What is your typical day, and how do you make it productive?
I like to get a head start before the rest of the world wakes up. I spend some quiet time reflecting, planning, and setting my priorities for the day. Once the workday begins, I focus on the most important tasks first, especially the ones that require deep concentration. I make sure to stay organized with a solid to-do list and manage my time well between meetings, property evaluations, and overseeing the operations at Thorwin Properties. I believe in leveraging my team, trusting them to handle their responsibilities, which allows me to focus on the bigger picture and long-term strategy. Being productive for me isn’t about being busy; it’s about focusing on what truly moves the business forward.
How do you bring ideas to life?
Bringing ideas to life starts with clarity and planning. When I have a new concept or idea, I first take time to thoroughly research and understand it. From there, I break it down into actionable steps and create a timeline. Surrounding myself with the right people, whether within my team or outside advisors, has been crucial in turning ideas into reality. I trust their expertise while ensuring the vision stays intact. Execution, consistency, and adaptability are key—sometimes ideas evolve along the way, but staying aligned with the end goal helps me stay focused.
What’s one trend that excites you?
The trend of sustainable and green building practices in real estate excites me. As more people are looking for environmentally conscious living, I see huge potential in incorporating energy-efficient features and sustainable materials in properties. Not only does this benefit the environment, but it also adds long-term value to the properties and helps with tenant satisfaction. I’m excited about how the real estate industry is embracing these changes, and I’m focused on being part of that shift within my portfolio.
What is one habit that helps you be productive?
One habit that helps me stay productive is the practice of prioritization. Every morning, I take a few minutes to outline my top three priorities for the day and focus on those before anything else. This keeps me from getting distracted by smaller, less important tasks. It’s easy to get caught up in the day-to-day, but staying laser-focused on what matters most has been key to maintaining productivity over time.
What advice would you give your younger self?
I would tell my younger self not to be afraid of making mistakes and not to rush. Early in my career, I was eager to build my business quickly, but I learned that success takes time and patience. Embrace the process, learn from setbacks, and always keep long-term goals in mind. Building a solid foundation is more important than jumping at every opportunity that comes your way. Stick to your vision and don’t be discouraged by obstacles.
Tell us something you believe almost nobody agrees with you on?
I believe that the pursuit of growth in business should always prioritize quality over quantity, even in a competitive market. Many business owners focus on rapid expansion, but I think it’s crucial to ensure that your current operations are running efficiently and up to a high standard before trying to grow too fast. In real estate, especially, providing exceptional service and maintaining a strong reputation is far more valuable in the long run than simply acquiring more properties.
What is the one thing you repeatedly do and recommend everyone else do?
I recommend everyone consistently reinvest in their business. Whether it’s improving the properties you own or investing in professional development, reinvestment is crucial for long-term success. I’ve always put profits back into growing and improving Thorwin Properties, whether through upgrading existing units, expanding my team, or researching new opportunities. It’s about keeping the momentum going and constantly positioning yourself for future growth.
When you feel overwhelmed or unfocused, what do you do?
When I feel overwhelmed or unfocused, I take a step back and go for a walk. Physical activity, like walking, helps clear my mind and gives me a chance to reset. I also try to simplify my to-do list and focus on just one thing at a time. Sometimes, the best way to deal with overwhelm is to give yourself space to breathe and avoid trying to multitask too much.
What is one strategy that has helped you grow your business or advance in your career?
One strategy that has been key to my success is building strong relationships with the people I work with—whether that’s tenants, contractors, or business partners. In real estate, your reputation is everything. Being transparent, building trust, and providing excellent customer service has helped me grow my business in a way that doesn’t just focus on profits, but on long-term, sustainable success.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
One major failure in my career was when I had to close my online pharmacy business due to regulatory changes in the U.S. It was a tough decision, but it forced me to adapt quickly and shift my focus to real estate. The key lesson I learned was resilience. Failure is a part of entrepreneurship, but how you recover from it is what defines you. I focused on what I could control, applied the lessons from my previous experiences, and pivoted into real estate, which led to new opportunities and growth.
What is one business idea you’re willing to give away to our readers?
One business idea I’d suggest is to focus on the rising demand for flexible and affordable housing solutions, especially in urban areas. The growing number of remote workers and changing lifestyles have created a need for short-term and flexible rental agreements. Investing in properties that cater to this niche, especially with quality amenities and streamlined booking systems, could be a lucrative opportunity for entrepreneurs.
What is one piece of software that helps you be productive? How do you use it?
I rely heavily on project management software like Click Up to keep my tasks organized. It helps me visualize my day-to-day priorities, track progress on long-term goals, and delegate tasks to my team efficiently. I use it to break down larger projects into smaller, more manageable steps and ensure that nothing slips through the cracks. It’s an essential tool for staying on top of everything.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
One book that has been incredibly valuable to me is Good to Great by Jim Collins. The concepts in that book about how companies transition from good to great have shaped many of the decisions I’ve made in growing my business. It helped me understand the importance of leadership, consistency, and building a strong culture within a company.
What’s a movie or series you recently enjoyed and why?
I recently enjoyed The Social Dilemma on Netflix. While it’s more focused on the impact of social media, I found it fascinating because it highlights how technology is changing human behavior and communication. As someone who is always looking for ways to stay ahead in business, it was a good reminder of how important it is to be aware of the forces shaping our world and how they affect business and society.
Key learnings
- Patience and Long-Term Vision are Key
- Surround Yourself with a Strong Team
- Reinvest in Your Business