Tailwind Talks is a podcast for high-performing professionals who want to build serious real estate portfolios without leaving their careers. Hosted by an airline and military pilot turned investor, it dives into actionable strategies for scaling your real estate portfolio while balancing the demands of a full-time job.
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I Hate Sales - But I Got My Real Estate License Anyway
8:39
8:39
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8:39Send us a text Forget everything you thought you knew about real estate licenses - they're not just for salespeople. My journey getting licensed eight years ago wasn't driven by a desire to chase commissions or become the next real estate mogul. It was a strategic move to understand the rental property business from the inside out, granting me acce…
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You Don't Need A $4,000 Course To Buy Rentals!!
6:09
6:09
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6:09Send us a text Ready for some hard truth about real estate investing? You don't need to spend $4,000 on a guru's course to learn how to buy rental properties. This episode cuts through the hype and exposes the predatory practices of high-priced real estate "education" programs that target hopeful investors with limited resources. We break down a tr…
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My Rental Property Burned Down - I Still Made $100K +
7:17
7:17
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7:17Send us a text The unexpected call every property investor dreads finally came my way—a complete fire loss at one of my rental properties. Standing in the charred remains, the acrid smell of smoke overwhelming my senses, I faced the sobering reality that despite owning multiple properties, I had absolutely no experience navigating insurance claims.…
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I Own $5M In Real Estate... But I Still Rent
6:42
6:42
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6:42Send us a text Challenging conventional wisdom, I take you through my controversial but pragmatic approach to real estate. Despite owning millions in rental properties, I've made the strategic choice to rent my own home—and there's solid financial logic behind this decision. The current real estate market presents a perfect storm of challenges: sky…
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Flying Jets By Day... Living In My Moms Basement By Night
9:08
9:08
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9:08Send us a text The path to real estate wealth rarely looks like the glamorous stories we see online. Sometimes, it means making the uncomfortable choice to live with your parents well into adulthood or finding roommates to slash your biggest expense. That's exactly what I did – working as an airline pilot, flying military missions part-time, and gr…
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Why Relationships Matter More Than Money (long term)
8:44
8:44
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8:44Send us a text Ever wonder if you can build a real estate portfolio while working a demanding full-time job? Cole proves it's not just possible—it's happening right now. Fresh off his morning flight as an airline pilot, Cole closed not one but two profitable Milwaukee properties by afternoon, showcasing the power of preparation and strong industry …
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My Best Rental Property of 2024 Made $13,926 (27% Return!)
3:24
3:24
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3:24Send us a text Turning $50,000 into a 27% annual return might sound like an investment fantasy, but that's exactly what happened with my best-performing property of 2024. Join me, Cole – airline pilot, military instructor, and part-time real estate investor – as I pull back the curtain on a four-unit brick building that's defying expectations and g…
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Send us a text When a seemingly solid brick duplex turned into a financial disaster, I learned an expensive lesson about the hidden costs lurking beneath investment properties. This candid breakdown reveals how my worst property of 2024 generated $17,803 in annual income while racking up a staggering $50,425 in expenses – creating a negative cash f…
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Start Real Estate in 2025 with Just $5K (and what I wish I would have done) Tailwind Talks 002
27:13
27:13
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27:13Send us a text Breaking into real estate investing can feel impossible when you're starting with minimal capital. The barrier to entry seems insurmountable with rising property values, high interest rates, and fierce competition. But what if you could launch your real estate journey with just $5,000? This raw, practical guide cuts through the noise…
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The Paradox of Playing It Safe: Why Inaction Is Riskier Than Failure
3:49
3:49
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3:49Send us a text Mortality is the great equalizer—and realizing this simple truth can transform how we approach life's challenges and opportunities. Have you ever found yourself paralyzed by fear when considering a new venture? Whether it's investing in real estate, applying to flight school, or starting a YouTube channel, many of us get trapped in e…
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Your Down Payment's Best Friend: Measuring Real Estate Success
5:38
5:38
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5:38Send us a text Ever wondered what separates successful real estate investors from those constantly feeding money into their properties? The answer might be simpler than you think. Cash on cash return stands as the ultimate metric for measuring real estate investment success. It cuts through the noise of speculative appreciation and trendy market pr…
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Send us a text Ever feel like you're drowning in spreadsheets and second-guessing your real estate investment decisions? What if analyzing a property could be as simple as glancing at your watch? Today, I'm pulling back the curtain on my actual process for evaluating potential investment properties in under five minutes. As a full-time pilot and pa…
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Building a $5.5 Million Portfolio While Working Full-Time as a Pilot (Tailwind Talks 001)
12:04
12:04
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12:04Send us a text Ever wonder how to build substantial real estate wealth while keeping your day job? Meet Cole, a full-time airline pilot, part-time military helicopter pilot, and real estate investor who's built a $5.5 million portfolio spanning 63 units—all without quitting his aviation career. Cole's journey began humbly washing dishes as a teenag…
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