For Matthew DeGuida, success in real estate isn’t just about finding the right properties or closing big deals. It’s about the people who make those deals possible—tenants, contractors, and even the community as a whole. At just 25, Matthew has built a thriving portfolio by focusing on relationships as much as numbers.
“Real estate is a people business,” Matthew says. “You can have the best properties in the world, but if you don’t know how to work with people, you’re going to struggle.”
This philosophy has guided every step of his journey, helping him create a business that’s as much about connections as it is about cash flow.
Starting With Tenants
Matthew believes that a good relationship with tenants is the foundation of any successful real estate investment. He makes it a priority to listen to their concerns, respond to issues quickly, and treat them with respect.
“Your tenants are the ones paying your bills,” he explains. “If you don’t take care of them, you’re going to have vacancies, late payments, and a lot of headaches.”
One way Matthew ensures tenant satisfaction is by keeping his properties in excellent condition. Regular maintenance, prompt repairs, and thoughtful upgrades make his rentals places people want to stay in long-term.
“It’s not just about the rent,” he says. “People want to feel comfortable and safe in their homes. When you provide that, they’re more likely to stick around.”
Matthew also works with tenants who may be struggling financially. Instead of jumping to eviction, he sets up payment plans and looks for ways to help.
“If someone’s trying their best, I’ll work with them,” he says. “Life happens, and a little understanding can go a long way.”
Building a Reliable Team
Matthew knows he can’t do it all on his own, which is why he’s put together a team of reliable contractors, realtors, and other professionals.
“Having the right people around you is everything,” he says. “They’re the ones who make sure the work gets done, the deals go smoothly, and the properties stay in great shape.”
Finding the right team wasn’t always easy. Early in his career, Matthew worked with a few contractors who overpromised and underdelivered. Those experiences taught him to vet people carefully and only work with those who share his values.
“Now I look for people who take pride in their work and care about the outcome,” he says. “It’s not just about getting the job done; it’s about doing it right.”
Connecting With the Community
Beyond his tenants and team, Matthew is deeply invested in the communities where he owns properties. He sees real estate as a way to strengthen neighborhoods and create lasting change.
“When you improve a property, you’re not just helping the tenant,” he explains. “You’re also helping the community. Better housing means better neighborhoods, and that benefits everyone.”
Matthew often collaborates with local organizations and officials to ensure his projects align with community goals. Whether it’s upgrading a property in a growing area or contributing to local events, he’s always looking for ways to give back.
The Ripple Effect of Relationships
Matthew’s focus on people has also opened doors to new opportunities. Word-of-mouth referrals have led to off-market deals, while positive relationships with local professionals have made challenging projects easier to manage.
“When you treat people well, they want to work with you,” he says. “That’s how you build trust, and trust is everything in this business.”
One example he shares is how a tenant’s recommendation led him to a neighbor who wanted to sell their home. That deal turned into one of his most profitable investments.
“You never know where your next opportunity will come from,” Matthew says. “That’s why it’s so important to build and maintain good relationships.”
Advice for New Investors
For those just starting in real estate, Matthew has one key piece of advice: focus on people first.
“A lot of new investors get caught up in the numbers, and that’s important,” he says. “But if you don’t know how to work with people, you’re going to hit a wall.”
He encourages new investors to take the time to learn about their tenants, their team, and their community.
“It’s not just about what you’re buying,” he says. “It’s about who you’re working with and how you’re making their lives better.”
Looking Ahead
As Matthew continues to grow his portfolio, his focus on people remains at the core of his business. He plans to expand into larger projects that can have an even greater impact on communities, while staying true to the principles that got him this far.
“Real estate is about more than just buildings,” he says. “It’s about the people who live in them, the people who work on them, and the communities they’re part of. When you keep that in mind, success follows.”
