Tailwind Talks
Claim This Podcastby Cole Baltz
Podcast Authority
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Podcast Overview
<p>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.</p><p><br></p>
Language
🇺🇲
Publishing Since
5/16/2025
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Recent Episodes
April 27, 2026
A Quick Recheck Before Closing Saves Thousands
Send us Fan Mail A real estate deal can look airtight on paper, then fall apart the moment you open the front door. That’s exactly what happens when we go back to Milwaukee to do a last walkthrough on a portfolio we’re about to close and the “light rehab” vacant houses hit us with humidity, odor, visible mold, soaked carpet, and wet subfloors. We unpack the real mechanics of how this happens: winter-to-spring thaw, properties that weren’t winterized, pipes that freeze and then burst, and wat...
April 26, 2026
How A Full-Time Pilot Closes $1.6M In Milwaukee Single-Family Rentals
Send us Fan Mail Twenty closings in a week sounds like chaos until you see the structure behind it. I’m Cole, a legacy airline pilot and military instructor pilot building a Milwaukee real estate portfolio on nights, weekends, and whatever layovers give me. This update breaks down a seven-day sprint that includes Blackhawk flights, my first Boeing 777 run from New York to Paris and back, and nearly $2 million in single-family rental purchases. I walk through two very different deals. First, ...
April 25, 2026
What A 100 Unit Rental Portfolio Really Earns
Send us Fan Mail A spreadsheet can tell you what a rental property should do. Operating a 100 unit portfolio tells you what it actually does when furnaces quit, water heaters fail, tenants pay with non-sufficient funds, and a basement backup lands on your lap.\n\nWe’re back after a busy stretch of airline and military flying, and I’m sharing a fully transparent March 2026 rental portfolio performance review from Milwaukee, Wisconsin. We walk through multiple LLCs from biggest to smallest and ...
46 total episodes available
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Frequently asked questions
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- What is Tailwind Talks?
<p>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.</p><p><br></p> - How often does this podcast release new episodes?
This podcast updates daily.
- Where can I listen to this podcast?
This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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