Cory B. George’s story is about learning how to take the right risks. He began his career in the automotive world as General Manager at Town & Country Ford in Evansville. Managing a busy dealership taught him leadership, negotiation, and the power of showing up every day.
In 2009, he shifted gears into real estate—a move that combined his love for numbers, strategy, and steady growth. Starting small, he built a portfolio that grew to over 100 rental properties and completed dozens of home flips. “You learn by doing,” he says. “You make mistakes, fix them, and keep going.”
Now, Cory is preparing to launch a real estate investment fund focused on private student housing throughout the Midwest. For him, it’s not just about business—it’s about creating stability in a market that serves young people and college towns.
Away from work, Cory’s interests in poker, blackjack, and baccarat reflect his approach to life: part strategy, part instinct. “At the table and in business, emotions can ruin good decisions,” he says.
He’s also a fan of luxury sports cars—machines built on precision, performance, and control.
Each stage of Cory’s journey shows the same pattern—patience, persistence, and calculated risk. He doesn’t chase every deal. He plays the long game.
What is your typical day, and how do you make it productive?
My day starts early—before sunrise. I check market updates, review property data, and go over emails while having coffee. Mornings are for decision-making; I try to do my most focused work before distractions hit. Afternoons are for meetings, property reviews, or phone calls with investors. I’ve learned productivity isn’t about doing more—it’s about doing what matters most first.
How do you bring ideas to life?
I start small. When I first began flipping homes, I tested one idea—a single renovation—before scaling. I take notes, run numbers, and ask, “What’s the worst that could happen?” If the downside is manageable and the upside is strong, I move forward.
What’s one trend that excites you?
Private student housing. It’s a steady sector that doesn’t swing wildly with the economy. Students keep enrolling, and colleges keep expanding. I’m focused on Midwest markets where demand outpaces quality supply.
What is one habit that helps you be productive?
I make a list of three non-negotiables each morning. If I finish those, the day is a win. Everything else is optional.
What advice would you give your younger self?
Don’t wait for perfect timing. The first deal, the first property, the first risk—start small, learn fast, and don’t fear failure.
Tell us something you believe almost nobody agrees with you on?
Most people think risk is dangerous. I think avoiding it is riskier. Calculated risks create progress.
What is the one thing you repeatedly do and recommend everyone else do?
Review your mistakes like a game replay. Whether it’s poker hands or a property deal, go back and see what worked and what didn’t.
When you feel overwhelmed or unfocused, what do you do?
I disconnect—no screens, no noise. I go for a drive or play a few quiet rounds of cards. That mental reset helps me think clearly.
What is one strategy that has helped you grow your business or advance in your career?
I learned to scale slowly. Managing 100 rental properties didn’t happen overnight. I grew one unit at a time, building systems before adding more.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early on, I overpaid for a flip because I got emotionally attached. The project lost money, but it taught me to let data—not excitement—drive decisions.
What is one business idea you’re willing to give away to our readers?
Mid-sized college towns are full of opportunity. Find one underdeveloped block near a campus and create housing that feels modern but affordable.
What is one piece of software that helps you be productive? How do you use it?
I use Notion to track projects and deals. It keeps notes, deadlines, and budgets in one place.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
The Millionaire Real Estate Investor by Gary Keller. It reminds me that success in real estate is built on small, consistent wins.
What’s a movie or series you recently enjoyed and why?
Drive to Survive. It’s about Formula 1, but it’s really about focus, risk, and precision—three things I relate to in business.
Key learnings
- Strategic risk-taking, when disciplined, builds resilience and success.
- Growth comes from patience and focusing on long-term fundamentals.
- Reviewing mistakes regularly leads to better decision-making.
- Emotional control is vital, both at the card table and in business.
- Consistent small wins are more powerful than chasing big breaks.