Heroic Investing
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HI 58 – Aligning Your Interests to Create Investment Staying Power


Episode: 58

Guest: Jason & Gary

iTunes: Stream Episode

Captain Gary Pinkerton joins Jason to share his story of how investing in income property gave him financial freedom and he describes how he used a life insurance policy to fund his investments. Later in the show, Jason and Gary answer listener questions about self-management, markets, and taxes received as part of the Apple Airpod contest.

Key Takeaways:

[02:59] A few things you probably didn’t know about submarines.

[06:09] Gary shares the most important lessons he has learned about income property investing.

[09:50] Leveraging prudent debt and getting credit for the appreciation is a 20% ROI.

[13:47] Gary wanted to go to work and make money on his own terms.

[17:51] Increase the efficiency of your properties by funding them in a different way.

[24:26] Looking at the benefits of using a life insurance policy to fund your investments.

[30:00] Self-managing income properties may give your tenants a better experience so they inhabit your property longer.

[33:23] Juan wants to know how to find the best property management company and how to set up his tax structure.




*The Airpod contest has ended