Tailwind Talks
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.
Episodes
46 episodes
A Quick Recheck Before Closing Saves Thousands
A real estate deal can look airtight on paper, then fall apart the moment you open the front door. That’s exactly what happens when we go back to Milwaukee to do a last walkthrough on a portfolio we’re about to close and the “light rehab” vacan...
How A Full-Time Pilot Closes $1.6M In Milwaukee Single-Family Rentals
Twenty closings in a week sounds like chaos until you see the structure behind it. I’m Cole, a legacy airline pilot and military instructor pilot building a Milwaukee real estate portfolio on nights, weekends, and whatever layovers give me. Thi...
What A 100 Unit Rental Portfolio Really Earns
A spreadsheet can tell you what a rental property should do. Operating a 100 unit portfolio tells you what it actually does when furnaces quit, water heaters fail, tenants pay with non-sufficient funds, and a basement backup lands on your lap.\...
The Six-House Deal That Pushed A Pilot To 100 Units
100 units sounds like a headline, but it’s really a paperwork moment, a spreadsheet moment, and a discipline moment. I’m sharing the deal that pushed my Milwaukee portfolio over the line: six single-family houses, all underwritten with a clear ...
How A Working Pilot Builds A Milwaukee Rental Portfolio
I just wrapped up Boeing 777 training and got signed off to fly the jet for real and the timing couldn’t be a better stress test for my real estate systems. When you’re gone for weeks, you don’t get to “run over and check” on a property. Someth...
A February Rental Portfolio Recap From 96 Milwaukee Units
$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 o...
777 Training And Real Estate Juggling
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 y...
Rental Rehab Walkthrough In Milwaukee
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 mon...
I Turned $103,000 Into $266,000 With 12 Rentals And Paid NO TAX (Full 1031 Exchange Breakdown)
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 ...
I Bought $700,000 of Real Estate With 2.5% DOWN (Here Are the Closing Statements)
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 $504...
How I Bought 10 Properties (14 Units) for $1.1M with Just $37K Down
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 th...
Paying Cash for Property? Why Dave Ramsey’s Advice Will Hold You Back
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...
Why I Just Bought 3 Duplexes — Even at 6.75% Rates | Real Estate Market Is Shifting
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 t...
How Your Landlord Gets Rich Off You (I’m One… and I Rent Too)
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, thi...
How I’m Buying over $1,000,000 in Rentals with No Cash Down
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 airl...
June Rental Portfolio Breakdown – The REAL Income & Expenses from 60 Units
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—...
This Deal Looks Good But Will Bankrupt You | Real Estate Rookie Mistakes
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 p...
I Funded This $60K Rental Property in Just 31 Minutes
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 r...
How I’m Managing $5.9M in Real Estate
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 pil...
Inside My 60-Unit Real Estate Portfolio: What I Actually Make Each Month
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...
Why the 1% Rule Will Make You Go Broke in Real Estate
The 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 Lost My Job as a Pilot — Here’s How I Survived (and What I’d Do Differently)
Imagine 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 explore...
Why I Rent While Owning Millions in Real Estate
Challenging 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 per...
How I Got Paid $125,000 to Buy a 4-Unit Rental With $0 Down
Ever 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...