Shows
2026-01-3121 minTailwind TalksI Turned $103,000 Into $266,000 With 12 Rentals And Paid NO TAX (Full 1031 Exchange Breakdown)Send us a textWant the real numbers behind selling five aging buildings and turning them into a cleaner, more scalable portfolio? We open the books on a 12-unit, ~$570k buy that we fully exited and rolled into roughly $1.4M of newer brick properties through a 1031 exchange. From timelines and lender prep to why standardized 1950s–1960s construction beats quirky 1900s basements, we get specific about what changed, what we learned, and what we’d do differently.We walk through the 2022 closing statement, including earnest money, origination fees, title costs, and how acting as our own...
2026-01-3116 minTailwind TalksI Bought $700,000 of Real Estate With 2.5% DOWN (Here Are the Closing Statements)Send us a textWant a real look at how “no money down” strategies actually work when the ink dries? Cole, a legacy airline pilot and part-time investor, opens the books on a six-month push to acquire five properties with hard money, then roll them into a $504K portfolio loan appraised in the mid-600s by income approach and likely near $700K by market value. We unpack every lever: high-cost points, 14 percent interest-only payments, seller credits, rent and deposit prorations, and why timing—not magic—made a $200K equity spread possible with modest cash out of pocket.
2026-01-3020 minTailwind TalksHow I Bought 10 Properties (14 Units) for $1.1M with Just $37K DownSend us a textA late-night email turned into 10 properties, 14 units, and a 21% bulk discount—proof that disciplined outreach and clean underwriting can still win on market. We pull back the curtain on how the deal came together: from the first message to the final wire, including the appraisal that valued the portfolio near $1.21M and the lender-friendly DSCR that made financing workable even at a 6.75% rate. It’s not a highlight reel; it’s the actual math, the trade-offs, and the parts that sting.We break down the rent roll assumptions, the 5% vacancy modeling, and th...
2026-01-3020 minTailwind TalksPaying Cash for Property? Why Dave Ramsey’s Advice Will Hold You BackSend us a textTired of being told you need to pay cash for your first rental? We put that myth on trial and lay out a clearer path for building a portfolio without waiting a decade. From the cockpit to closings, we share a working investor’s view on how time, inflation, and smart leverage actually move the needle.We start by breaking down the traditional cash-only narrative and why it fit the 70s and 80s better than today’s market. Wages have drifted from housing costs, and saving the full purchase price often mean...
2026-01-2916 minTailwind TalksWhy I Just Bought 3 Duplexes — Even at 6.75% Rates | Real Estate Market Is ShiftingSend us a textEver 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...
2025-08-0315 minTailwind TalksHow Your Landlord Gets Rich Off You (I’m One… and I Rent Too)Send us a textYour 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...
2025-08-0208 minTailwind TalksHow I’m Buying over $1,000,000 in Rentals with No Cash DownSend us a textHow 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...
2025-08-0117 minTailwind TalksJune Rental Portfolio Breakdown – The REAL Income & Expenses from 60 UnitsSend us a textEver 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 bi...
2025-08-0118 minTailwind TalksThis Deal Looks Good But Will Bankrupt You | Real Estate Rookie MistakesSend us a textNavigating 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 appr...
2025-07-3113 minTailwind TalksI Funded This $60K Rental Property in Just 31 MinutesSend us a textEver 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 criter...
2025-06-2811 minTailwind TalksHow I’m Managing $5.9M in Real EstateSend us a textUnlocking 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 migh...
2025-06-2717 minTailwind TalksInside My 60-Unit Real Estate Portfolio: What I Actually Make Each MonthSend us a textA 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? Th...
2025-06-2611 minTailwind TalksWhy the 1% Rule Will Make You Go Broke in Real EstateSend us a textThe real estate investing world is full of so-called "rules" that promise success, but few are as potentially destructive as the popular 1% rule. As someone who balances being a legacy airline pilot, military instructor, and property investor, I've seen firsthand how this oversimplified formula leads well-meaning investors straight to financial trouble.Today's property market with interest rates exceeding 7% makes this rule particularly dangerous. Let me walk you through the harsh reality: that $100,000 property generating $1,000 monthly might seem promising on paper, but once you factor in mortgage payments ($700+), property management (10%), property taxes ($300+...
2025-06-2406 minTailwind TalksI Lost My Job as a Pilot — Here’s How I Survived (and What I’d Do Differently)Send us a textImagine going from the cockpit of a commercial jet to facing unemployment overnight. That's exactly what happened when COVID-19 devastated the aviation industry and left me questioning everything I'd built. This raw, honest conversation explores the harsh reality of career vulnerability and the steps I took to rebuild financial security.The panic I felt during those first days of unemployment was real. Despite years of specialized training and experience as an airline pilot, I suddenly found myself competing with thousands of other displaced aviation professionals for vanishingly few opportunities. Had it...
2025-06-2208 minTailwind TalksWhy I Rent While Owning Millions in Real EstateSend us a textChallenging conventional wisdom can be difficult, but sometimes the numbers tell a story that can't be ignored. As a successful real estate investor managing a multi-million-dollar portfolio, I've made the counterintuitive choice to rent my personal residence rather than own it—and today, I'm sharing the eye-opening math behind this decision.After comparing my comfortable $1,900/month rental apartment to a similar condo for sale in Milwaukee, I discovered a staggering financial gap. The comparable condo, priced at $475,000, would cost approximately $4,800 monthly when factoring in today's 7.25% interest rates, $908 in monthly HOA fees, su...
2025-06-2108 minTailwind TalksCan You Really Buy Real Estate With No Money? The Truth About Hard MoneySend us a textDiving deep into the world of high-leverage real estate investing, this candid exploration of hard money lending reveals both its immense potential and serious pitfalls. Drawing from personal experience—including costly mistakes—I break down exactly how these loans work and when they make sense for investors at different stages.Hard money loans offer a unique advantage: lightning-fast closing capabilities that can help secure deeply discounted properties when sellers need to move quickly. With closings possible in days rather than months, investors can access deals others simply can't. However, this convenience come...
2025-06-2115 minTailwind TalksHow I Got Paid $125,000 to Buy a 4-Unit Rental With $0 DownSend us a textEver wonder how ordinary people create extraordinary wealth through real estate? The answer might be simpler than you think.Imagine purchasing a multi-unit property, living there at a fraction of market rent, and walking away with a six-figure profit – all without spending a dime from your savings. This isn't some get-rich-quick scheme; it's a legitimate strategy I used to generate $125,000 in profit while drastically reducing my living expenses.As both an airline pilot and part-time real estate investor, I discovered a powerful combination of tactics that allowed me to pu...
2025-06-2106 minTailwind TalksWhy I Haven’t Quit My Job (Even with 60 Rental Units)Send us a textEver wondered why someone with 60 rental units would keep their day job? I'm breaking down exactly why I've chosen to maintain my career as a legacy airline pilot and military instructor while building my real estate portfolio.The foundation of successful real estate investing isn't about quitting your job—it's about leveraging it. My steady income provides the financial safety net critical for those early investments. When I bought my first duplex, knowing I could cover the mortgage even if both tenants stopped paying created tremendous peace of mind. This stability al...
2025-06-1413 minTailwind Talks6 Things I Look For Before Buying Rental PropertySend us a textWondering how successful real estate investors evaluate potential rental properties? In this transparent, no-nonsense breakdown, Cole—a part-time real estate investor balancing a career as both a commercial airline pilot and military instructor pilot—reveals his six-point property evaluation system built from years of hands-on experience.Cash flow reigns supreme in Cole's investment approach. Forget complex appreciation models or speculative metrics—he focuses exclusively on cash-on-cash return, aiming for approximately 25% when possible. This straightforward calculation (annual pre-tax cash flow divided by total cash invested) immediately reveals how hard your money is workin...
2025-06-1313 minTailwind TalksThe #1 Real Estate Investing Tip I Wish I Knew Earlier | Why Partnerships Are a SuperpowerSend us a textEver wondered why some real estate investors seem to scale their portfolios so quickly while others struggle for years to add a second property? The secret might be simpler than you think—strategic partnerships.Drawing from my experience as a part-time real estate investor juggling careers as both a legacy airline pilot and military instructor pilot, I've discovered that my biggest regret wasn't a bad purchase or missed opportunity—it was waiting too long to bring on partners. While I hesitated until my second deal, I now recognize that partnerships are the...
2025-06-1214 minTailwind TalksClosed on a Duplex & Single-Family with Hard Money | My Path to 100 UnitsSend us a textStepping closer to my goal of owning 100 rental units, today marks another milestone as I close on two new properties—bringing my portfolio to 60 units after some recent sales and acquisitions. These seemingly ordinary properties reveal extraordinary lessons about creative real estate financing and spotting long-term value in today's market.When conventional banks wouldn't touch a duplex with non-paying tenants and verbal leases, hard money lending became my solution. Yes, at 14% interest and a 4% funding fee, it's painfully expensive. But sometimes the best opportunities require unconventional financing strategies. I walk you th...
2025-06-1112 minTailwind TalksThe Housing Market is Broken – And It's Still Going UpSend us a textEver wonder why housing prices keep climbing despite 7% interest rates and affordability at a 40-year low? You're not alone. The housing market continues to confound conventional wisdom, with properties selling well above asking price even as monthly mortgage payments have skyrocketed 90% since 2020.The mystery deepens when you consider that most people's wages haven't increased by even 5% during the same period. This fundamental disconnect between income and housing costs is reshaping the real estate landscape, particularly in previously affordable Midwestern markets like Milwaukee, where prices have jumped 7-20% year-over-year as buyers flee...
2025-06-0513 minTailwind TalksWhy Quitting Too Early Will Kill Your Real Estate DreamsSend us a textThe dream of quitting your 9-to-5 to pursue real estate full-time tempts many new investors. But is rushing to leave your job actually sabotaging your long-term success? Drawing from a decade of experience balancing property investing with careers as both an airline pilot and military instructor, this candid discussion reveals why your day job might be your most valuable asset when building a sustainable real estate portfolio.Banks and lenders scrutinize your employment status closely when you're starting out. Without established W-2 income, securing loans becomes significantly more challenging, especially for...
2025-06-0211 minTailwind TalksHow Im Investing In Real Estate Right Now (Despite High Prices)Send us a textEver feel like you've done everything right in your career but still can't afford the home you want? You're not alone. As a commercial airline pilot, military instructor, and real estate investor, even I'm feeling the squeeze of today's housing market—so much that I'm currently renting an apartment while owning multiple rental properties.My response? A contrarian investment strategy focused on properties many investors overlook. I'm targeting homes in Milwaukee's $100,000 range (plus or minus $20,000) that offer immediate cash flow while positioned for substantial appreciation. These aren't Instagram-worthy properties, but they mi...
2025-06-0208 min