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.
Podcasting since 2025 • 33 episodes
Tailwind Talks
Latest Episodes
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...
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Season 1
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Episode 33
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15:05
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...
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Season 1
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Episode 32
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8:13
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...
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Season 1
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Episode 31
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17:08
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—...
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Season 1
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Episode 30
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18:42
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...
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Season 1
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Episode 29
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13:19