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 • 38 episodes
Tailwind Talks
Latest Episodes
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 ...
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Season 1
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Episode 37
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16:12
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...
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Season 1
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Episode 36
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20:17
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...
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Season 1
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Episode 35
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20:14
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...
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Season 1
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Episode 34
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16:21