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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 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 single-family home acquired for $68,000 below the asking price, offers similar returns plus significant equity upside.

What makes this episode particularly valuable isn't just the impressive numbers—it's Cole's candid discussion about the importance of relationship building in real estate. By intentionally listing his own properties with agents who previously brought him deals (despite being licensed himself), Cole cultivated connections that now bring him off-market opportunities. This strategic investment in relationships has paid dividends far exceeding the commissions he forwent.

Cole doesn't sugarcoat the challenges either. From unexpected property damage to the complexities of using hard money financing, he addresses real concerns investors face. His philosophy of keeping commitments even when deals become less attractive than initially thought highlights why reliability matters more than short-term gains in building lasting wealth through real estate.

Drop a comment if you found value in these real-world deals and strategies! Cole plans to continue sharing actual investments rather than theoretical concepts, making this the perfect time to subscribe and follow his journey balancing aviation and real estate success.

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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 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 adding taxes ($2,744), insurance ($968), and mortgage payments ($8,186), this property became an expensive education in thorough due diligence.

This experience highlights the critical importance of comprehensive inspections and maintaining substantial cash reserves. Had this been my first or second investment property, it could have derailed my entire real estate journey. Instead, it serves as a powerful reminder that even experienced investors can misjudge repair costs, and that portfolio diversification provides essential protection against single-property disasters. For new investors especially, taking your time with property assessments isn't just good advice – it's financial self-preservation. The $40,000 that disappeared into this basement could have funded additional profitable properties, a sobering reality check about opportunity costs in real estate investing.

What's your experience with unexpected property expenses? Have you encountered similar renovation surprises? Leave a comment with your stories or questions about real estate investing – I'm creating customized content based on viewer interests and would love to address your specific concerns in future videos.

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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 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 eviction and while using a property management company to handle day-to-day operations. This is real estate investing that truly works alongside a demanding career – not competing with it.

I walk through every financial detail, from my initial $50,000 investment on this $265,000 property to its current valuation around $350,000. Looking ahead, I also address the looming challenge of an adjustable-rate mortgage reset that will test this property's resilience. Whether you're just starting your investment journey or looking to expand your portfolio, this detailed breakdown offers valuable insights into multi-family investing that works for busy professionals. The path from my first single-family flip to this cash-flowing brick building shows that successful real estate investing is accessible even without millions in capital or quitting your day job. Ready to see how strategic property selection can transform your financial future? This episode is your blueprint.

Subscribe for my next video where I'll reveal my worst-performing property of 2024 – a stark contrast that highlights the critical lessons every investor needs to learn.

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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 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 traditional risk assessment on its head. The greatest danger isn't in taking action and potentially failing—it's in taking no action at all. When we truly internalize that our time is limited, the temporary discomfort of trying something new pales in comparison to the permanent regret of wondering what might have been. As a military flight instructor, I've seen countless people express interest in pursuing their dreams but remain frozen by fear, unable to take those first crucial steps.

What would you do differently if you embraced the perspective that the risk of inaction outweighs the risk of failure? How might your approach to your goals change? I hope this message reaches someone who needs it and provides the gentle push to move toward whatever matters to you. After all, we're all headed to the same destination—the only meaningful difference is what we choose to do along the journey. Take that first step. The clock is ticking for all of us, so you might as well make your limited time count.

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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 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 flow while building equity. With FHA loans requiring just 3% down for first-time buyers, this path remains accessible even with limited funds.

Beyond just buying property, we dive into the overlooked power of relationships in real estate. Finding the right broker (preferably an investor themselves), connecting with property managers who understand local markets, and building rapport with community lenders creates an ecosystem of knowledge that prevents costly mistakes. The $1,500 investment in a real estate license could be your most profitable move, providing insider access while allowing you to earn commissions on your own purchases.

For those truly cash-strapped, strategic partnerships offer another avenue. By finding partners who complement your strengths—whether they bring capital, handyman skills, or management expertise—you can accelerate your progress while sharing both risk and reward. The key lies in clear communication and aligned expectations from day one.

The most successful investors understand that real estate wealth isn't built overnight but through compound growth over time. By focusing on properties that offer multiple benefits—reduced living expenses, equity building potential, and management experience—you create a solid foundation for expansion. And by living in properties for the required occupancy period (typically two years), you can sell without capital gains tax, further accelerating your wealth-building journey.

Ready to transform your financial future with real estate, even with minimal starting capital? The path forward isn't about having all the answers—it's about taking that crucial first step while remaining committed to learning and growth along the way.

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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 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 getting on your investment.

While many investors get seduced by appreciation potential or recent rent growth trends, these factors don't guarantee future performance. The podcast host targets 15-25% cash on cash returns, with 20% providing enough buffer to withstand unexpected expenses without requiring additional capital contributions. In today's challenging market, finding properties yielding 25% has become increasingly rare, making 15% a more realistic target for most investors.

Property taxes represent a particularly insidious expense that often increases dramatically after purchase. Many investors calculate returns using current tax assessments without considering potential 20-40% increases that can devastate cash flow projections. Unlike rent increases, which face market limitations, property tax hikes are virtually guaranteed in most markets.

Ready to transform your real estate investment approach? Start evaluating properties based on actual cash performance rather than speculative future gains. Your investment dollars - and your financial future - will thank you. Share your thoughts on cash on cash return targets in the comments below!

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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 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 $74,000, and everything in between.

You'll discover exactly what I look for when walking through a property (hint: focus on the big-ticket items like roofs, mechanicals, kitchens, and bathrooms) and how I quickly estimate renovation costs without overthinking. I break down this property's projected monthly cash flow of $446, showing how a $30,000 investment (including down payment and renovations) can generate a healthy 17% cash-on-cash return.

This no-fluff approach strips away the complexity that keeps many would-be investors paralyzed. Whether you're evaluating your first deal or your fiftieth, you'll appreciate this back-to-basics method that relies on what I call "napkin math"—straightforward calculations that cut through analysis paralysis and get to the heart of what makes a deal work or not.

Got questions about my approach or want to share how you evaluate properties? Drop a comment below—I personally respond to all feedback, whether it's about the real estate content or suggestions for improving these videos. Your input helps make this channel better for everyone looking to build wealth through property investment.

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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 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 for immediate large-scale investments, Cole shares a refreshingly practical approach focused on gradual growth and strategic positioning.

One of his key insights is the critical importance of your first few deals. While experienced investors can weather unexpected expenses, newcomers need particular caution to avoid burnout. Cole also reveals practical hacks like obtaining a real estate license to earn commissions on purchases and save when selling. For busy professionals juggling careers with real estate aspirations, his time-efficient approach to property analysis—completing evaluations in under 20 minutes by focusing only on fundamental value drivers—provides a realistic framework for success.

What makes Cole's perspective valuable is his commitment to authenticity over hype. He's building a community for real operators rather than selling courses or promoting get-rich-quick schemes. Whether you're contemplating your first property purchase or looking to scale while maintaining your career, his journey demonstrates how disciplined investing and patient positioning can transform modest beginnings into significant wealth. Ready to see how your first $100,000 property might change everything? Join Cole as he documents his continuing real estate journey.