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. HACE 23 H

    A February Rental Portfolio Recap From 96 Milwaukee Units

    Send us Fan Mail $80,000 in gross rents can look like a flex, but it doesn’t tell you whether a rental portfolio is actually healthy. I’m Cole, a Milwaukee real estate investor juggling airline flying and military instruction, and I’m pulling back the curtain on my February recap with real spreadsheets, real expenses, and the kind of cash flow timing problems nobody posts on Instagram. We start with the vacancy shock that put me in a “robbing Peter to pay Paul” season and what it cost to stabilize big single-family and small multifamily rentals. I break down why gross rent is basically a headline number, then walk through what matters: turnover costs, trash-outs, snow removal, management fees, utilities, pest control, and the surprise repairs that eat a month alive. You’ll also hear how rent credits at closing can help your down payment while still leaving you temporarily behind when mortgage payments hit before property management distributions arrive. From there, I zoom out to strategy: when I choose to sell older Milwaukee buildings, how I think about raising rents without triggering a move-out wave, and why “passive income” is a myth even with a great property manager. I also map out my financing plan, including cash-out refinance opportunities and a hard money exit strategy, packaging duplexes and a single family for a credit union refi to escape 14% interest and lock in long-term debt. If you like transparent real estate investing content, subscribe, share this with a friend who thinks rentals are easy, and leave a review with the biggest expense you didn’t expect when you started.

    41 min
  2. HACE 1 DÍA

    777 Training And Real Estate Juggling

    Send us Fan Mail I’m in that uncomfortable stretch where everything matters at once: learning a new jet, keeping my airline job safe, staying current in the military, and still moving real estate deals forward. I just wrapped up Boeing 777 ground school after years on the 737, and I walk you through what training looks like now from touchscreen cockpit trainers to a systems test built from a massive question bank. We also talk about the bigger shift happening in aviation: iPads, electronic checklists, and a training culture that leans less on deep “walk me through the system” knowledge and more on executing under pressure when the scenario goes sideways. Then I switch over to the real estate investing update with real numbers. I closed a three-bed, one-and-a-half-bath single-family for $105,000 using hard money financing, including the upfront fee and the 14% interest-only structure. I explain why I’ll still pay that price for short-term capital, how the refinance plan works, and what “stabilizing” a rental really means before a local bank or credit union will want the loan. If you’re into BRRRR strategy, bridge loans, cash-out refinance decisions, and the tradeoffs between speed and cost, you’ll hear exactly how I’m thinking about it. We also get into scaling: multiple houses under contract, appraisal delays, portfolio momentum toward 100+ units, and why you can’t build at scale with a single lender. I share how to handle bank rejection without spiraling, when to internalize the feedback, and when to move on. I wrap with the most practical advice I keep repeating to new investors: keep your day job early, reinvest cash flow, and treat a great management company as the foundation that keeps the whole operation standing. If you got value from this, subscribe, share it with a friend who’s trying to buy their first rental, and leave a review with the question you want me to answer next.

    15 min
  3. HACE 2 DÍAS

    Rental Rehab Walkthrough In Milwaukee

    Send us Fan Mail A $105,000 Milwaukee house can look rough and still be a strong rental if you know what to inspect and what to ignore. We take you on a real walk-through of a 3 bed, 1.5 bath single family property that should rent around $1,700 to $1,800 a month, with a renovation plan that aims to stay under $10,000. The focus is practical real estate investing: make it clean, safe, durable, and rentable fast without turning a simple rehab into a months-long makeover.\n\nWe start outside where the expensive problems usually begin. I talk through why skylights and other roof penetrations belong on your risk list, what rotted trim under windows tells you, and how little missing exterior pieces can invite animals and water. Then we get serious about drainage: clogged gutters and poor grading can push water straight toward the foundation, leading to basement moisture and long term damage. If you want fewer surprises, you have to manage water first.\n\nInside, we go room by room with a landlord-friendly rehab mindset. Think refinishing or cleaning floors, fresh paint, replacing beat blinds, fixing outlets, and deciding when “good enough” saves you time. I explain why ripping out a kitchen backsplash or flooring can create scope creep, how to refresh bathrooms without a full gut, and why an upstairs half bath can be a hidden value add. Down in the basement, we talk flood history, why finished basements can be a trap in Milwaukee, how to think about braced walls, and which mechanicals might hit your budget.\n\nIf you’re planning your first flip, buying your first rental, or building a buy and hold portfolio, this walkthrough gives you a clear checklist for evaluating rehab costs and risk. Subscribe, share this with a friend who wants to invest, and leave a review with your biggest “deal breaker” on a house tour.

    18 min
  4. 30 ENE

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

    Send us Fan Mail 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
  5. 30 ENE

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

    Send us Fan Mail 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
  6. 30 ENE

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

    Send us Fan Mail 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
  7. 29 ENE

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

    Send us Fan Mail 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

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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.