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 • 28 episodes
Tailwind Talks
Latest Episodes
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...
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Season 1
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Episode 28
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11:11
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...
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Season 1
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Episode 27
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17:38
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...
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Season 1
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Episode 26
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11:54
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, ...
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Season 1
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Episode 25
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6:34
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...
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Season 1
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Episode 24
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8:55