Real estate can be unpredictable. Markets shift, unexpected repairs pop up, and deals that seem promising can turn into headaches. But for Matthew DeGuida, challenges are just opportunities in disguise. “You have to expect the unexpected in this business,” Matthew says. “It’s not about avoiding problems—it’s about knowing how to handle them when they come up.” At just 25 years old, Matthew has built a real estate portfolio worth millions by staying calm under pressure and finding creative solutions to tough situations. His story is proof that with the right mindset, even the biggest hurdles can lead to success.
Facing Challenges Head-On
Matthew’s first off-market deal was anything but smooth. The property was in bad shape, with everything from plumbing issues to structural concerns. On top of that, he had little experience dealing with such extensive repairs. “At first, it was overwhelming,” he admits. “I remember thinking, ‘Did I make a mistake?’ But instead of giving up, I broke it down into smaller steps and tackled each problem one at a time.” He worked closely with contractors, learning as much as he could along the way. By the time the project was complete, Matthew had turned a rundown property into a profitable rental—and gained valuable knowledge in the process.
The Power of Preparation
One of the ways Matthew handles challenges is by staying prepared. He approaches every deal with a detailed plan, accounting for potential risks and worst-case scenarios. “Real estate is all about being ready for the ‘what ifs,’” he explains. “What if the market shifts? What if a tenant can’t pay rent? What if a repair ends up costing twice as much? You have to think about all of that upfront.” For Matthew, preparation also means building a strong financial cushion. He keeps reserves to cover unexpected expenses, which allows him to stay flexible and avoid panic when something goes wrong.
Adapting to Market Changes
Matthew has seen firsthand how quickly the real estate market can change. Whether it’s rising interest rates, shifting demand, or new regulations, staying adaptable is key. “You can’t control the market,” he says. “But you can control how you respond to it.” One example is how Matthew shifted his focus to appreciating areas. By targeting neighborhoods with strong growth potential, he’s been able to weather market fluctuations and secure long-term value. “When you invest in areas with good schools, job opportunities, and future development plans, you’re setting yourself up for success,” he explains.
Turning Problems Into Lessons
Not every deal Matthew has made has gone according to plan. But instead of letting setbacks discourage him, he views them as opportunities to learn. “Every mistake I’ve made has taught me something valuable,” he says. “Whether it’s underestimating repair costs or misjudging a neighborhood, those experiences stick with you. They make you better.” One of his biggest lessons came from a property he nearly walked away from due to concerns about overleveraging. It was his first off-market deal, and the risks felt high. But after careful analysis, Matthew realized the property had untapped potential. He took the leap, and it ended up being one of his best investments.
The Role of Relationships
When challenges arise, having the right people in your corner can make all the difference. Matthew has built strong relationships with contractors, realtors, and other professionals who help him navigate the complexities of real estate. “You can’t do this alone,” he says. “Having a reliable team you trust is everything.” He also emphasizes the importance of good tenant relationships. By being fair and approachable, he’s built trust with his tenants, which has helped avoid conflicts and even opened doors to new opportunities. “One tenant recommended me to their neighbour who was selling a house,” he recalls. “That turned into another great deal for me.”
Advice for Aspiring Investors
Matthew’s ability to turn challenges into opportunities comes down to mindset. For anyone looking to get into real estate, he offers simple but powerful advice: stay calm and keep learning. “Don’t panic when things go wrong,” he says. “Take a step back, figure out your options, and move forward. The more you experience, the more confident you’ll get at handling whatever comes your way.” He also stresses the importance of taking action. “You’re never going to feel 100% ready,” he says. “But if you wait too long, you’ll miss your shot. Start small, learn as you go, and build from there.”
Looking Ahead
As Matthew continues to grow his portfolio, he remains focused on staying adaptable and learning from every challenge. His goal isn’t just to succeed for himself but to inspire others to see what’s possible in real estate. “This business isn’t easy,” he says. “But it’s worth it. If you’re willing to put in the work and learn from the tough times, you can turn any challenge into an opportunity.” For Matthew DeGuida, that’s what real estate is all about: resilience, creativity, and the determination to keep moving forward
