Embracing the Ups and Downs
Every entrepreneur faces challenges—it’s part of the job description. What separates those who succeed from those who give up is the ability to adapt, learn, and push through when times get tough. As someone who’s spent over a decade growing Thorwin Properties into one of Winnipeg’s most respected real estate companies, I’ve encountered more than my share of obstacles. But each one has offered a lesson, and each one has shaped the leader I’ve become.
Overcoming business challenges isn’t about having all the answers—it’s about developing the mindset and resilience to keep moving forward. Here’s what I’ve learned through the years.
Starting Small, Dreaming Big
When I first entered the real estate market in 2010, it wasn’t with a massive investment or a ready-made empire. It was with a single property and a vision. Like many entrepreneurs, I started small and had to learn fast. Managing that first building required attention to detail, long hours, and plenty of trial and error.
I quickly realized that real estate was as much about people as it was about property. Listening to tenants, responding to their needs, and treating them with respect laid the groundwork for everything that came after. It taught me that if you focus on service and quality from day one, you can build a brand people trust.
Navigating Economic Uncertainty
One of the toughest challenges any business can face is an unstable economy. From interest rate hikes to unexpected market downturns, economic forces beyond our control can impact everything from cash flow to tenant retention.
When the COVID-19 pandemic hit, it tested our entire industry. Like many property owners, I had to think quickly and compassionately. We worked closely with residents who were struggling financially, set up flexible payment plans, and made sure no one felt abandoned. It wasn’t just about protecting our business—it was about protecting our community.
That period reinforced a powerful lesson: your values are your guide. In moments of uncertainty, leaning into compassion, flexibility, and communication makes all the difference.
Learning to Delegate and Trust
As Thorwin Properties grew, I faced a new kind of challenge—letting go. When you’ve built something from the ground up, it’s natural to want to stay involved in every detail. But sustainable growth depends on building a strong team and trusting them to carry out your vision.
Learning to delegate wasn’t easy, but it was necessary. I focused on hiring people who not only had the right experience, but who shared my passion for community-focused, ethical business. Once I had the right team in place, I could focus more on strategy, innovation, and long-term growth.
If I could offer one piece of advice to other entrepreneurs, it’s this: don’t try to do it all yourself. Surround yourself with people who are better than you in their areas, and trust them to lead.
Staying Grounded During Growth
Growth is exciting, but it can also be overwhelming. As we expanded our portfolio to over 2,400 units, I knew we had to stay true to our roots. That meant maintaining high standards for resident service, continuing to invest in property improvements, and always listening to feedback.
Scaling a business without sacrificing quality is a balancing act. It requires strong systems, clear communication, and a commitment to consistency. One of the strategies that’s worked well for us is conducting regular check-ins across our properties—ensuring that tenants feel heard and staff feel supported.
Even as we’ve grown, I still try to stay connected to the day-to-day operations. It keeps me grounded and reminds me of why I started this journey in the first place.
Innovating for the Future
Another key to overcoming business challenges is staying forward-thinking. Markets evolve, technology advances, and customer expectations change. To remain relevant, we need to keep innovating.
At Thorwin, we’ve embraced smart technology, eco-friendly upgrades, and modern design to meet the needs of today’s tenants. Sustainability is no longer a luxury—it’s a responsibility. Investing in greener buildings not only reduces our environmental impact but also improves tenant satisfaction and long-term value.
Innovation doesn’t always mean major changes. Sometimes, it’s small tweaks—a better way to communicate, a more efficient maintenance process, or a smarter way to track performance. The key is staying curious and open to new ideas.
Giving Back Along the Way
One of the most rewarding parts of my entrepreneurial journey has been giving back. Whether it’s supporting local organizations like Agape Table or contributing to global causes through Canadian Lutheran World Relief, philanthropy is deeply woven into my business philosophy.
Business challenges often remind us of our broader responsibilities—not just to profit, but to people. No matter how busy things get, I always try to make time for community involvement. It keeps our work meaningful and reminds us that success is about more than just numbers.
Final Thoughts
The road to success is never smooth. But every challenge is an opportunity—to grow, to learn, and to lead with greater purpose. Looking back, I’m grateful for the tough times because they’ve shaped my perspective and made me a better entrepreneur.
To anyone facing obstacles in their business: keep going. Focus on your values, take care of your people, and don’t be afraid to ask for help. Resilience isn’t about being perfect—it’s about being persistent.
— Kris Thorkelson