Shows
Tailwind TalksWhy Relationships Matter More Than Money (long term)Send us a textEver 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 relationships.Cole walks us through both deals with refreshing transparency. The first property, a two-bed duplex purchased for $112,000, generates nearly $1,900 in monthly rent with projected 30-40% cash-on-cash returns despite today's high interest rates. The second, a smaller si...2025-05-2208 minTailwind TalksI LOST 50K! (Worst Property 2024)Send us a textWhen 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 flow that would make any investor cringe.The culprit? A basement issue I drastically underestimated. What I thought would be a $10,000 fix ballooned into a $40,000 structural repair, effectively erasing any profit potential from this $90,000 wholesale purchase. The numbers tell the painful story: after ad...2025-05-2103 minTailwind TalksMy Best Rental Property of 2024 Made $13,926 (27% Return!)Send us a textTurning $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 generating substantial passive income.The numbers tell an impressive story: $47,311 in total rental income for the year, with $13,926.56 hitting my bank account after all expenses, taxes, insurance, and mortgage payments. What makes this even more remarkable is that this performance came despite an evic...2025-05-2103 minTailwind TalksThe Paradox of Playing It Safe: Why Inaction Is Riskier Than FailureSend us a textMortality 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 endless "what if" scenarios. We worry about failure, judgment, or disappointment until we've talked ourselves out of even trying. But there's something profoundly liberating about acknowledging our finite time: nobody survives this experience.This realization flips tra...2025-05-1903 minTailwind TalksStart Real Estate in 2025 with Just $5K (and what I wish I would have done) Tailwind Talks 002Send us a textBreaking 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 and delivers actionable strategies for getting started in today's challenging market. We explore the house hacking approach—purchasing a small multi-family property where you can live in one unit while renting the others—potentially living for free or even generating positive cash...2025-05-1927 minTailwind TalksYour Down Payment's Best Friend: Measuring Real Estate SuccessSend us a textEver 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 predictions to reveal what truly matters - how much money your property generates compared to what you put in. When you're considering tying up hundreds of thousands of dollars in a deal, this straightforward calculation tells you exactly what return you're...2025-05-1805 minTailwind TalksNapkin Math for Real Estate AnalysisSend us a textEver 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 part-time real estate investor, I've had to develop systems that maximize efficiency without sacrificing accuracy. I walk through a real single-family property that I viewed just this morning—from the initial asking price of $79,000 to our final negotiated price of...2025-05-1706 minTailwind TalksBuilding a $5.5 Million Portfolio While Working Full-Time as a Pilot (Tailwind Talks 001)Send us a textEver 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 teenager, using minimum wage earnings to fund his passion for flying. His first real estate purchase was a modest $100,000 HUD foreclosure bought with just $3,000 down. That single property became the foundation for his multi-million dollar portfolio. Unlike many real estate personalities advocating fo...2025-05-1712 min