Lessons in Real Estate Investment

In this episode, we sit down with Jake Freeman, a powerhouse in distressed commercial real estate who’s quietly acquired over 150,000 square feet of industrial property in just 12 months—all while flipping half a dozen houses a month in Tulsa, Oklahoma. Jake shares how he transitioned from oil field work and horse training to building and selling two trash companies, eventually stumbling into real estate by way of roll-off dumpster rentals. He details his first industrial deal—a neglected metal recycling plant he bought for the price of a house—and walks us through the aggressive negotiation strategy that landed it. From cold calling for nearly a year, to leasing out properties while still under contract, Jake has developed a system so disciplined he claims he's never lost money. Along the way, we talk mindset, financial discipline, and why he lived in an $800 house while owning multiple properties and businesses. Whether you're looking to scale through systems or understand the real-life grind behind success stories, Jake's journey is a masterclass in leverage, patience, and calculated risk-taking.