Cory B. George has never been afraid of risk. Whether at the card table or in the boardroom, he sees decision-making as a mix of strategy, timing, and instinct. “Poker taught me patience,” he says. “You don’t win every hand, but you learn to stay calm, read the situation, and wait for the right move.”
That same mindset shaped his career. Today, George is preparing to launch a real estate investment fund focused on private student housing across the Midwest. But his journey into real estate started years before, with experiences that gave him both discipline and a willingness to think differently.
Early Career in the Automotive Industry
George first made his mark in the automotive sector. As General Manager at Town & Country Ford in Evansville, he learned the value of leadership and customer service. Running a dealership was more than moving cars. It was about people, process, and performance.
“I learned that every decision matters,” he recalls. “If you’re leading a team, you need to be clear, decisive, and consistent. The way you handle small problems sets the tone for how you’ll handle big ones.”
This management experience gave him skills he later carried into real estate. Negotiating with suppliers, motivating employees, and managing customer expectations all prepared him for the challenges of owning and investing in properties.
Building a Real Estate Portfolio
In 2009, George stepped into real estate. It was a turbulent time, with the financial crisis reshaping the housing market. He started by purchasing and managing rental properties. Over time, he scaled to more than 100 units under his control.
“I didn’t wait for perfect timing,” he says. “You learn by doing. I bought, I managed, I fixed problems, and I kept moving forward.”
He also completed numerous single-family flips, gaining hands-on knowledge of renovation, budgeting, and market cycles. This approach allowed him to balance short-term returns with long-term stability.
Through it all, he kept his process simple. “Real estate is about solving problems,” he explains. “If you can fix a roof, replace a tenant, or manage repairs without losing focus, you’re going to be successful.”
Launching a Real Estate Investment Fund
Now, George is preparing for the next chapter—launching a fund focused on private student housing in the Midwest. He sees this as both a business opportunity and a way to create stable value for investors.
“Student housing is resilient,” he says. “Universities continue to bring in students, and those students need a place to live. If you provide safe, affordable, and well-managed housing, demand will follow.”
His fund is designed to combine his years of property management experience with a structured investment approach. The goal is to scale beyond individual ownership into a model that can support long-term growth and predictable performance.
A Unique Blend of Work and Lifestyle
George’s story is also shaped by his interests outside of work. He has a passion for gambling—particularly poker, blackjack, and baccarat. For him, it’s not just about luck. It’s about decision-making under pressure.
“At the table, you need to manage your emotions,” he says. “You can’t chase every hand. That discipline carries over to business. I don’t chase every deal. I pick the right ones.”
He’s also drawn to luxury sports cars, appreciating both their engineering and their design. This passion reflects his belief in combining performance with precision.
These interests add dimension to his professional image, showing him as someone who values both calculated risk and personal enjoyment.
Lessons in Leadership
Looking back, George believes his success comes down to consistency and adaptability. He’s faced ups and downs, from market downturns to challenging tenants, but he approaches each with steady focus.
“Leadership isn’t about being perfect,” he says. “It’s about showing up every day, making decisions, and learning from what happens next.”
For those watching his next move, George’s story shows how risk, resilience, and focus can shape a career across industries. From running an auto dealership to managing a growing real estate portfolio, and now preparing to lead an investment fund, his path reflects both ambition and discipline.
And just like in poker, he’s willing to play the long game. “You don’t always win fast,” he says. “But if you stay focused and make smart decisions, you put yourself in a position to win big.”
Read more:
Cory B. George: From Cars to Real Estate Leadership
