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
28 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
Why I Rent While Owning Millions in Real Estate
Challenging conventional wisdom can be difficult, but sometimes the numbers tell a story that can't be ignored. As a successful real estate investor managing a multi-million-dollar portfolio, I've made the counterintuitive choice to rent my per...
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Season 1
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Episode 22
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8:10
How I Got Paid $125,000 to Buy a 4-Unit Rental With $0 Down
Ever wonder how ordinary people create extraordinary wealth through real estate? The answer might be simpler than you think.Imagine purchasing a multi-unit property, living there at a fraction of market rent, and walking away with a six...
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Season 1
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Episode 23
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6:29
Can You Really Buy Real Estate With No Money? The Truth About Hard Money
Diving deep into the world of high-leverage real estate investing, this candid exploration of hard money lending reveals both its immense potential and serious pitfalls. Drawing from personal experience—including costly mistakes—I break down ex...
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Season 1
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Episode 21
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15:46
Why I Haven’t Quit My Job (Even with 60 Rental Units)
Ever wondered why someone with 60 rental units would keep their day job? I'm breaking down exactly why I've chosen to maintain my career as a legacy airline pilot and military instructor while building my real estate portfolio.The found...
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Season 1
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Episode 20
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13:37
6 Things I Look For Before Buying Rental Property
Wondering how successful real estate investors evaluate potential rental properties? In this transparent, no-nonsense breakdown, Cole—a part-time real estate investor balancing a career as both a commercial airline pilot and military instructor...
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Season 1
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Episode 19
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13:28
The #1 Real Estate Investing Tip I Wish I Knew Earlier | Why Partnerships Are a Superpower
Ever wondered why some real estate investors seem to scale their portfolios so quickly while others struggle for years to add a second property? The secret might be simpler than you think—strategic partnerships.Drawing from my experienc...
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Season 1
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Episode 18
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14:41
Closed on a Duplex & Single-Family with Hard Money | My Path to 100 Units
Stepping closer to my goal of owning 100 rental units, today marks another milestone as I close on two new properties—bringing my portfolio to 60 units after some recent sales and acquisitions. These seemingly ordinary properties reveal extraor...
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Season 1
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Episode 17
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12:07
The Housing Market is Broken – And It's Still Going Up
Ever wonder why housing prices keep climbing despite 7% interest rates and affordability at a 40-year low? You're not alone. The housing market continues to confound conventional wisdom, with properties selling well above asking price even as m...
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Season 1
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Episode 16
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13:45
Why Quitting Too Early Will Kill Your Real Estate Dreams
The dream of quitting your 9-to-5 to pursue real estate full-time tempts many new investors. But is rushing to leave your job actually sabotaging your long-term success? Drawing from a decade of experience balancing property investing with care...
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Season 1
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Episode 15
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11:50
How Im Investing In Real Estate Right Now (Despite High Prices)
Ever feel like you've done everything right in your career but still can't afford the home you want? You're not alone. As a commercial airline pilot, military instructor, and real estate investor, even I'm feeling the squeeze of today's housing...
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Season 1
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Episode 14
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8:25
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