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
13 episodes
I Hate Sales - But I Got My Real Estate License Anyway
Forget everything you thought you knew about real estate licenses - they're not just for salespeople. My journey getting licensed eight years ago wasn't driven by a desire to chase commissions or become the next real estate mogul. It was a stra...
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Season 1
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Episode 13
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8:39
Flying Jets By Day... Living In My Moms Basement By Night
The path to real estate wealth rarely looks like the glamorous stories we see online. Sometimes, it means making the uncomfortable choice to live with your parents well into adulthood or finding roommates to slash your biggest expense. That's e...
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Season 1
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Episode 12
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9:08
I Own $5M In Real Estate... But I Still Rent
Challenging conventional wisdom, I take you through my controversial but pragmatic approach to real estate. Despite owning millions in rental properties, I've made the strategic choice to rent my own home—and there's solid financial logic behin...
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Season 1
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Episode 11
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6:42
My Rental Property Burned Down - I Still Made $100K +
The unexpected call every property investor dreads finally came my way—a complete fire loss at one of my rental properties. Standing in the charred remains, the acrid smell of smoke overwhelming my senses, I faced the sobering reality that desp...
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Season 1
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Episode 10
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7:17
You Don't Need A $4,000 Course To Buy Rentals!!
Ready for some hard truth about real estate investing? You don't need to spend $4,000 on a guru's course to learn how to buy rental properties. This episode cuts through the hype and exposes the predatory practices of high-priced real estate "e...
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Season 1
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Episode 9
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6:09
Why Relationships Matter More Than Money (long term)
Ever wonder if you can build a real estate portfolio while working a demanding full-time job? Cole proves it's not just possible—it's happening right now. Fresh off his morning flight as an airline pilot, Cole closed not one but two profitable ...
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Season 1
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Episode 8
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8:44
I LOST 50K! (Worst Property 2024)
When a seemingly solid brick duplex turned into a financial disaster, I learned an expensive lesson about the hidden costs lurking beneath investment properties. This candid breakdown reveals how my worst property of 2024 generated $17,803 in a...
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Season 1
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Episode 6
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3:14
My Best Rental Property of 2024 Made $13,926 (27% Return!)
Turning $50,000 into a 27% annual return might sound like an investment fantasy, but that's exactly what happened with my best-performing property of 2024. Join me, Cole – airline pilot, military instructor, and part-time real estate investor –...
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Season 1
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Episode 7
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3:24
The Paradox of Playing It Safe: Why Inaction Is Riskier Than Failure
Mortality is the great equalizer—and realizing this simple truth can transform how we approach life's challenges and opportunities. Have you ever found yourself paralyzed by fear when considering a new venture? Whether it's investi...
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Season 1
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Episode 5
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3:49
Start Real Estate in 2025 with Just $5K (and what I wish I would have done) Tailwind Talks 002
Breaking into real estate investing can feel impossible when you're starting with minimal capital. The barrier to entry seems insurmountable with rising property values, high interest rates, and fierce competition. But what if you could launch ...
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Season 1
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Episode 4
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27:13
Your Down Payment's Best Friend: Measuring Real Estate Success
Ever wondered what separates successful real estate investors from those constantly feeding money into their properties? The answer might be simpler than you think.Cash on cash return stands as the ultimate metric for measuring real est...
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Season 1
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Episode 3
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5:38
Napkin Math for Real Estate Analysis
Ever feel like you're drowning in spreadsheets and second-guessing your real estate investment decisions? What if analyzing a property could be as simple as glancing at your watch? Today, I'm pulling back the curtain on my actual p...
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Season 1
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Episode 2
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6:27
Building a $5.5 Million Portfolio While Working Full-Time as a Pilot (Tailwind Talks 001)
Ever wonder how to build substantial real estate wealth while keeping your day job? Meet Cole, a full-time airline pilot, part-time military helicopter pilot, and real estate investor who's built a $5.5 million portfolio spanning 63 units—all w...
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Season 1
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Episode 1
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12:04