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 • 13 episodes
Tailwind Talks
Latest 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