From Real Estate Agent to Investor | Corey Wayne Ogle on Smart Investing, Systems, and Building Freedom

A lot of people dream about financial freedom through real estate… but most never start.Why?Because they’re overwhelmed, afraid of making costly mistakes, or stuck believing they need millions to begin investing.The reality is… one bad property can destroy your momentum.Many first-time investors jump into deals too quickly, ignore warning signs, underestimate expenses, and end up underwater financially.And in expensive markets, it can feel impossible to even get startedIn this episode, Jeff Kikel sits down with Corey Wayne Ogle, a New York real estate advisor who is now making the transition from helping investors… to becoming one himself.After more than a decade in real estate, Corey shares:What he learned from watching successful investorsHow to analyze deals conservativelyWhy due diligence matters more than hypeThe importance of systems and processes in building freedomHow AI and social media are changing modern real estate businessIf you're serious about building your Freedom Day, this episode gives you a realistic look at how to start investing the smart way.👉 Subscribe and follow the Freedom Nation Podcast for more conversations on financial freedom, real estate, cash flow, and multiple income streams.Episode Takeaways:• Why Corey believes every investment must be analyzed conservatively• The importance of due diligence before buying investment property• Why working with a local buyer’s agent can save you from expensive mistakes• How Corey backed out of a deal after discovering hidden risks• The strategy behind investing in familiar markets first• Why systems and processes create freedom in business• How social media has become a major lead-generation tool in real estate• The differences between short-term, mid-term, and traditional rentals• Why real estate success takes years of consistency—not overnight luck• How AI is helping entrepreneurs plan and scale fasterAbout the Guest:Cory Wayne helps talented, heart-driven coaches turn inconsistent income into consistent $10K+ months—without sleazy tactics, gimmicks, or cookie-cutter strategies. Instead of telling coaches to “just post more,” they focus on what actually drives results: clear positioning, strong offers, and sales that feel aligned and ethical.They work with coaches who are stuck juggling a full-time job and a part-time coaching hustle that barely pays the bills, helping them identify the real problem—usually not their skills, but their strategy. Known for honest, constructive tough love, [Name] challenges coaches to stop hiding behind certifications and start building a business that supports the impact they want to make.Their philosophy is simple: sales is service, content needs a conversion path, and consistent action beats chasing every new marketing trend. Rather than chasing bigger audiences, they teach coaches how to attract the right clients and confidently make offers that transform lives—and businesses.Links:https://www.highline2hamptons.com/https://www.instagram.com/coreywayne/https://www.linkedin.com/in/coreywayne/Fast Five Questions:If you woke up and your business was gone, you have $500, a laptop, a place to live, and food, what would you do first? “I'm going to go to AI and I'm going to ask it the best ways to make a million bucks.”What is the biggest mistake that you have made in business? “My biggest business mistake… not starting a team of my own sooner.”What is a book that you would recommend? “One of my favorite books that I read is The 12 Week Year.”What is a tool that you use every day that you would recommend? “Instagram… it’s annoying, but it’s a necessary evil.”What is your definition of freedom? “Being able to wake up in the morning and not feel like I am in a panic… as long as I execute X, Y, and Z and do what I need to do, I’m going to be fine.”About Jeff: Jeff spent the early part of his career working for others. Jeff had started 5 businesses that failed before he had his first success. Since that time he has learned the principles of a successful business and has been able to build and grow multiple seven-figure businesses. Jeff lives in the Austin area and is actively working in his community and supporting the growth of small businesses. He is a board member of the Incubator.Edu program at Vista Ridge High School and is on the board of directors of the Leander Educational Excellence FoundationConnect with the Freedom Nation podcast at https://freedom-nation-podcast.captivate.fm/Connect with Jeff:Instagram: https://www.instagram.com/freedomnationpodcast/Twitter: https://twitter.com/JeffKikelLinkedIn: https://www.linkedin.com/in/jeffkikel/Thanks for listening!Thanks so much for listening to our podcast! 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