Why Relationships Matter More Than Money (long term)

Tailwind Talks

Send us a text

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 Milwaukee properties by afternoon, showcasing the power of preparation and strong industry relationships.
Cole walks us through both deals with refreshing transparency. The first property, a two-bed duplex purchased for $112,000, generates nearly $1,900 in monthly rent with projected 30-40% cash-on-cash returns despite today's high interest rates. The second, a smaller single-family home acquired for $68,000 below the asking price, offers similar returns plus significant equity upside.
What makes this episode particularly valuable isn't just the impressive numbers—it's Cole's candid discussion about the importance of relationship building in real estate. By intentionally listing his own properties with agents who previously brought him deals (despite being licensed himself), Cole cultivated connections that now bring him off-market opportunities. This strategic investment in relationships has paid dividends far exceeding the commissions he forwent.
Cole doesn't sugarcoat the challenges either. From unexpected property damage to the complexities of using hard money financing, he addresses real concerns investors face. His philosophy of keeping commitments even when deals become less attractive than initially thought highlights why reliability matters more than short-term gains in building lasting wealth through real estate.
Drop a comment if you found value in these real-world deals and strategies! Cole plans to continue sharing actual investments rather than theoretical concepts, making this the perfect time to subscribe and follow his journey balancing aviation and real estate success.

פרקים

1. Introduction and Background (00:00:00)