Tailwind Talks

Cole Baltz

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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    Why I Just Bought 3 Duplexes — Even at 6.75% Rates | Real Estate Market Is Shifting

    Send us a text Ever wondered when the real estate market would finally shift in favor of buyers? That moment has arrived, and I'm seizing the opportunities. Despite mortgage rates hovering around 6.75%, I've purchased more properties in recent months than I had in years. This past week alone, I closed on three duplexes (six units total) - including a remarkably clean $100,000 property generating $1,800 monthly in rental income. These "set it and forget it" buildings with new roofs, gutters, and minimal maintenance requirements represent my current acquisition strategy. But the rental property landscape faces significant challenges. Insurance costs have more than doubled on my older buildings, with premiums on properties from the late 1800s/early 1900s jumping from under $1,000 annually to nearly $5,600 combined. This dramatic increase has prompted me to strategically rotate out of aging properties into newer 1950s-60s constructions with lower maintenance burdens. Property taxes have skyrocketed, renovation expenses continue climbing, and lending costs remain substantially higher than historical averages. While rents have increased, they haven't kept pace with these mounting expenses. For aspiring investors, I offer this critical advice: be extraordinarily careful with your first few acquisitions, as they establish the foundation for your entire investment journey. Equally important - maintain your full-time employment while building your portfolio. Even with 87 units and approaching 100 by year-end, I'm nowhere near considering leaving my airline and military careers. Lenders strongly prefer employed investors because they demonstrate additional income capacity if properties underperform. The security of stable employment provides both financial protection and enhanced borrowing power. Many new investors mistakenly believe a small portfolio can immediately replace employment income, when successful financial independence through real estate typically requires years of consistent growth and management experience. What's your approach to building wealth through real estate while balancing other career commitments? I'd love to hear your thoughts and questions in the comments!

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    How Your Landlord Gets Rich Off You (I’m One… and I Rent Too)

    Send us a text Your monthly rent check is powering a sophisticated wealth-building engine for your landlord that goes far beyond simple cash flow. Speaking from the unique perspective of both a rental property owner and someone paying $2,000 monthly rent, this breakdown reveals the complete financial picture that most tenants never see. While cash flow (profit after expenses) is what most people think of when considering rental property income, it's merely the beginning. Each time you pay rent, you're helping your landlord build wealth through multiple channels simultaneously. Your payment reduces their mortgage principal, steadily increasing their equity stake. Meanwhile, inflation gradually increases the property's value while their debt remains fixed or decreases - creating a widening equity gap that represents significant wealth creation without additional effort. The tax advantages available to property owners further accelerate wealth accumulation. From maintenance deductions to depreciation benefits and the powerful 1031 exchange provision that allows tax-deferred property upgrades, the system provides landlords with remarkable financial leverage. Perhaps most compelling is the cash-out refinance strategy, where increased property values (driven by rising rents) allow owners to extract tax-free cash while tenants continue paying down the newly increased mortgage. Despite understanding these wealth mechanisms as an investor myself, I currently rent by choice. High property prices and interest rates make renting strategically sensible for my situation, providing flexibility while I wait for better opportunities. If you're renting, don't feel like you've "lost" at real estate - it's about making informed decisions that align with your current circumstances while understanding the complete financial picture.

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    How I’m Buying over $1,000,000 in Rentals with No Cash Down

    Send us a text How do you keep growing your real estate portfolio when interest rates make traditional cash-out refinancing impractical? The answer might lie in creative loan structuring and relationship banking. Cole, balancing careers as both an airline pilot and real estate investor, walks us through his innovative approach to expanding his portfolio toward his goal of 100 units. When faced with equity trapped in two triplex properties financed at 3.9%, he devised a strategy to avoid the prohibitive costs of refinancing at today's 6.75% rates while still accessing that capital for growth. The breakthrough came through combining his existing properties with a new 14-unit portfolio acquisition into one comprehensive jumbo loan. This consolidated approach allowed him to extract equity from existing properties while maintaining favorable financing terms. By negotiating the portfolio purchase from $1.4 million down to $1.1 million and structuring creative financing, he's positioned to add these properties with minimal additional capital investment. What makes this strategy particularly powerful is how it leverages banking relationships. Cole explains how maintaining connections with multiple lenders creates leverage in negotiations, allowing investors to secure more favorable terms. He also highlights an overlooked opportunity in today's market: while institutional investors chase larger multifamily properties, single-family homes and duplexes remain undervalued and present significant cash flow and appreciation potential. This episode isn't just about one deal – it's a masterclass in creative problem-solving, relationship building, and persistent deal-hunting. Whether you're just starting or looking to scale your existing portfolio, these principles of leveraging equity, maintaining banking relationships, and finding overlooked opportunities can transform your real estate investing journey. Listen now to discover how thinking differently might unlock your next level of growth.

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    June Rental Portfolio Breakdown – The REAL Income & Expenses from 60 Units

    Send us a text Ever wondered what real estate investing actually looks like behind the gloss of social media success stories? Drawing back the curtain on my 60-unit rental portfolio, I'm sharing every dollar that came in and went out during the month of June—something I wish someone had done for me when I was starting out. The numbers tell a story that might surprise you. While some properties performed brilliantly (one duplex netted $1,654 on $1,700 in rent), others barely broke even or required significant expense outlays. A single running toilet caused a staggering $1,000 water bill at one four-unit property. Multiple units required pest control for mice and bed bugs. Five separate eviction filings cost $349 each just to start the process. What becomes clear through this transparent breakdown is that scale matters tremendously in real estate investing. A single property that returned just $14.66 after expenses demonstrates why the "just buy one rental" advice falls woefully short—nobody's quitting their job on fourteen dollars a month. Yet when viewed as a portfolio, the performing properties balance out the underperformers, creating a more stable investment vehicle. As both a full-time airline pilot and military instructor pilot, I've structured my real estate investments to function without my daily involvement. This means paying management fees and contractor costs that DIY investors might avoid, but the tradeoff makes financial sense given my primary income sources. When you're working 23-hour shifts as I sometimes do, spending $101 to have someone replace an outlet is simply practical mathematics. The reality of rental property ownership involves constant decisions about rent optimization, maintenance priorities, and tenant issues. Should you raise rents on reliable tenants who are slightly below market rate? How do you handle the tenant who repeatedly clogs drains by pouring grease down the sink? These practical challenges rarely feature in investment seminars or YouTube success stories. Want more transparency like this? Let me know in the comments if these monthly breakdowns provide value, and I'll continue sharing the unvarnished truth about real estate investing—both the wins and the headaches. After all, making informed decisions requires seeing the complete picture, not just the highlight reel.

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    This Deal Looks Good But Will Bankrupt You | Real Estate Rookie Mistakes

    Send us a text Navigating the world of real estate investing can be treacherous for beginners, especially when sellers disguise money-losing properties as profitable opportunities. In this analytical breakdown, Cole—a part-time real estate investor, airline pilot, and military instructor—dissects a misleading 14-unit Milwaukee apartment listing that perfectly illustrates this danger. Cole takes you through his step-by-step evaluation of a $1.575 million property marketed with promises of substantial returns despite actually generating negative cash flow. With clarity and precision, he exposes how the seller manipulates numbers by inflating principal reduction claims and relying on speculative appreciation to mask the property's fundamental financial weakness. The property, requiring a hefty $315,000 down payment, would immediately lose approximately $600 monthly—a stark contrast to the 8.5% return advertised in the marketing materials. What makes this analysis especially valuable is Cole's exploration of risk factors that new investors frequently overlook. He demonstrates how interest rate increases during refinancing could dramatically worsen the already negative performance, potentially increasing losses to over $20,000 annually. He also highlights the significant opportunity cost of tying up capital in a non-performing asset, emphasizing that successful real estate investing must prioritize cash flow over speculative appreciation. Whether you're considering your first investment property or looking to sharpen your analytical skills, this detailed breakdown provides essential insights into separating marketing hype from financial reality. Take control of your investment decisions by learning how to run your own numbers, stress-test potential deals, and identify the red flags that could save you from costly mistakes.

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    I Funded This $60K Rental Property in Just 31 Minutes

    Send us a text Ever wonder how some investors seem to close deals overnight while others struggle for months? The secret isn't luck or connections—it's preparation and relationships. I recently transformed an ordinary text message into a fully-funded real estate deal in just 35 minutes. This wasn't through some complex strategy or inside connection, but rather by applying fundamental principles anyone can use: emotional discipline during negotiations, strong relationships with lenders, and a clear understanding of my investment numbers. The property—a $60,000 three-bedroom house in Milwaukee—demonstrates why staying grounded in your investment criteria is crucial. When competing offers pushed the price up, I increased my offer by only $1,000 rather than getting caught in an emotional bidding war. As I often remind myself: if your deal is good at $60K but bad at $61K, it probably wasn't a good deal to begin with. This disciplined approach has protected my portfolio numerous times. The most powerful moment came when funding was secured. Because I had built trust with my hard money lender through multiple successful deals, they pre-approved my loan within 31 minutes of my email—no lengthy applications or endless documentation required. This efficiency illustrates why relationship-building might be the most underrated skill in real estate investing. While the $600 monthly cashflow this property will generate isn't life-changing, the $60-70K in equity potential absolutely is. This perfectly captures why focusing on buying below market value creates wealth far faster than chasing cash flow alone. Rome wasn't built in a day, and neither is a sustainable real estate portfolio. What steps are you taking to build relationships with potential funding partners? Your next deal might be just one text message away.

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    How I’m Managing $5.9M in Real Estate

    Send us a text Unlocking the hidden power of real estate equity could be the key to exponential portfolio growth—yet so many investors leave millions in potential wealth sitting idle. As a part-time real estate investor juggling careers as both an airline pilot and military instructor, I've built a portfolio valued at nearly $5.9 million with approximately $2.3 million in equity, all starting from a single flip house. Equity represents the spread between what you owe and what your property is worth—and it's where true wealth accumulation happens in real estate. While monthly cash flow might seem attractive (my properties generate $55,000 in gross monthly rents), the long-term equity growth often proves far more powerful. Through this video, I open my actual portfolio spreadsheet to show exactly how equity positions build through various methods: buying below market value, forced appreciation through renovations, natural market appreciation, rising rents, and simple time in the market. My Milwaukee properties showcase how dramatically equity can build—some purchased just four years ago have already moved from 80% loan-to-value to under 40%, representing hundreds of thousands in gained equity per property. But this creates a fascinating dilemma: my portfolio now contains $2.3 million in "idle equity" that could theoretically fuel expansion to over $10 million in total portfolio value if leveraged properly. However, accessing this equity isn't as simple as many online real estate gurus suggest. Cash-out refinancing comes with significant limitations, particularly when it means replacing 4% interest rates with today's 6-7% rates. I share my current strategy for deploying this equity through portfolio purchases and value-add opportunities while maintaining the delicate balance between aggressive growth and financial stability. Whether you're just starting your real estate journey or looking to scale your existing portfolio, this transparent look at real numbers and actual properties will help you develop a more sophisticated approach to building wealth through property equity. Like and subscribe if you found this valuable, and comment with questions about your own real estate investing challenges!

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    Inside My 60-Unit Real Estate Portfolio: What I Actually Make Each Month

    Send us a text A rare glimpse behind the curtain of real estate investing reveals what actually works—and it's probably not what you've been told. Cole, a part-time real estate investor balancing a full-time airline career and military instructor role, shares the unvarnished truth about his 60-unit portfolio generating $55,000 monthly in gross income. Unlike the glossy success stories that promise quick riches, Cole demonstrates why focusing on smaller properties in Milwaukee has outperformed the conventional wisdom of chasing large apartment buildings. Three duplexes bringing in $6,000 monthly versus a four-unit at $4,000 with identical down payments? The math speaks for itself, especially when institutional investors are overpaying for larger complexes. The portfolio's financial reality deserves attention: roughly $17,800 in monthly loan payments, $6,400 for property taxes, $2,200 toward insurance, plus property management and capital expenses. While this leaves theoretical monthly profits of $8,000, Cole reveals why that number rarely materializes as planned. More importantly, he shares the discipline that's accelerated his wealth-building—reinvesting every dollar back into the business rather than extracting it for lifestyle expenses. Perhaps most valuable is Cole's insight into equity growth as the true wealth-builder in real estate. While cash flow keeps the operation running, the equity accumulation represents life-changing wealth. It's a refreshingly honest perspective in a field often characterized by exaggerated claims and overnight success stories. Want to build lasting wealth through real estate? Subscribe now for Cole's upcoming videos on equity management strategies and detailed property breakdowns that show exactly how his portfolio functions in the real world.

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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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    Cole Baltz
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    © 2025 Tailwind Talks
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    Tailwind Talks