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.

  1. JAN 30

    I Turned $103,000 Into $266,000 With 12 Rentals And Paid NO TAX (Full 1031 Exchange Breakdown)

    Send us a text Want 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 buyer’s agent helped reduce cash to close. Then we break down each property’s exit—what sold well, what didn’t, and why selling the package made more sense than picking off a single “winner” and trapping equity. You’ll hear where proceeds landed (~$266k after fees), how 1031 deadlines really feel in the middle of busy work and family schedules, and the practical steps that kept us inside the 45-day identification and 180-day closing windows. This is a case for operational simplicity. Brick, drywall, repeatable layouts, and cookie-cutter finishes let a management team run faster turns and predictable maintenance. We also dig into the choice to hire a listing agent on disposition—yes, it cost $30–40k, but it bought time, organization, and relationships that matter for future deal flow. Looking forward, we’re trading 12 older units for 20 standardized ones, aiming to push from 73 to 99 units by February, with a longer horizon of several hundred doors built on steady debt paydown and fewer surprises. If you’re mapping your own upgrade path, this walkthrough will help you plan funding, insurance, lender readiness, and timelines before the 1031 clock starts. Listen, grab the playbook, and tell us: good trade or bad trade? Subscribe, share with a friend who’s scaling, and drop a review so we know what to dig into next.

    16 min
  2. JAN 30

    I Bought $700,000 of Real Estate With 2.5% DOWN (Here Are the Closing Statements)

    Send us a text Want 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. We don’t just celebrate wins; we study the costs. You’ll hear how underwriting with a fast hard money lender ran into thousands per property, why a credit union later charged only $756 to originate the entire refinance, and how that delta can make or break a deal. We break down a wholesaled single-family with a steep assignment fee that still pencils thanks to strong rent and ARV, plus a duplex negotiated $30K under ask by self-representing and walking from a commission to win the price. Credits helped one standout close at just $995 out of pocket—paired with a reminder that credits aren’t free, they’re deferred obligations. If you want a grounded playbook for scaling with minimal cash, this conversation delivers the tactics and the warnings. We cover packaging properties for a portfolio loan, why lenders favor the income approach on rental bundles, how to manage balloon terms, and what to do when stabilization drives $50–60K expense months. The message is simple: speed costs money; knowledge and discipline pay it back. Listen, take notes, and decide where this strategy fits your market and your risk tolerance. If this breakdown helps you think bigger and smarter, subscribe, share it with an investor friend, and leave a review telling us which tactic you’ll try—or avoid—next.

    20 min
  3. JAN 30

    How I Bought 10 Properties (14 Units) for $1.1M with Just $37K Down

    Send us a text A 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 the expense stack that kept projections grounded. Then we contrast those careful numbers with reality: six units vacant at takeover, turn costs in the $2.5K–$3.5K range, and a plan to stabilize without losing the thread on cash flow. You’ll hear how bulk pricing created a spread versus selling individually, why a “sleepy” Milwaukee submarket fits a long-term strategy, and how small, targeted upgrades can shift value without overcapitalizing. We also talk leverage with clear eyes. A cash-out refinance from older assets provided most of the down payment, trimming fresh cash at close to about $35K. That choice isn’t for purists, but when debt is sized to durable income and backed by conservative underwriting, it can accelerate growth without gambling the portfolio. If you’re trying to source your next buy, we share the exact outreach approach used on MLS listings, the framing that earns responses, and the checklist for turning interest into a bankable deal. Hit play, get the numbers, and steal the playbook. If this breakdown helps, follow the show, leave a review, and tell a friend who’s hunting their next multifamily deal.

    20 min
  4. JAN 29

    Paying Cash for Property? Why Dave Ramsey’s Advice Will Hold You Back

    Send us a text Tired 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 means missing years of equity growth. We explain the true cost of the time lag, then show how fixed-rate debt lets you benefit from appreciation on the full property value while inflation quietly pays down your loan in cheaper dollars. The takeaway is simple: leverage is a tool, not a vice, and used well, it accelerates outcomes without gambling your future. You’ll hear candid stories of wins and mistakes: hard money used as a bridge, seller credits that erase fees, and the painful lessons that come from underestimating rehab timelines. We map a practical starter plan—target 20 percent down, build a relationship with a strong bank or credit union, and buy in steady, cash-flowing markets in the Midwest and Rust Belt. We also draw a bright line between good debt and predatory lenders, with tips to stress test deals for vacancy, capex, taxes, and insurance so your numbers hold up in real life. If you’re ready to trade waiting for doing, hit play. Subscribe, share this with a friend who’s stuck saving for “someday,” and drop a comment with your first market or your toughest lending question—we’ll pull ideas for future episodes straight from your notes.

    16 min
  5. 08/03/2025

    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!

    15 min
  6. 08/02/2025

    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.

    8 min
  7. 08/01/2025

    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.

    17 min

About

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.