Zen and the Art of Real Estate Investing with Jonathan Greene

Insuring Yourself and Your Real Estate Investments with Aaron Letzeiser


Starting a career as a landlord involves more than just acquiring properties. Safeguarding your assets is integral, along with understanding the intricacies of insurance.

In this episode of Zen and the Art of Real Estate Investing, Jonathan interviews Aaron Letzeiser, the co-founder of Obie. As a venture-backed insurance and risk management technology platform, Obie is dedicated to serving U.S. real estate investors. Aaron is also an active real estate investor and venture partner at Pioneer Fund.

Delving into Aaron’s start in real estate as an accidental landlord, Jonathan and Aaron explore why condos are an excellent initial investment. Their conversation extends to the distinctive features of Chicago’s real estate market, making it a favorable investment hub, and Aaron’s strategic expansion into the Carolinas for new assets.

Their conversation doesn’t stop at investments; it underscores property insurance’s role in investment decisions, reveals how technology is simplifying the insurance shopping process, and pinpoints the four common pitfalls investors encounter in insurance coverage. As the conversation concludes, Jonathan and Aaron shift their focus to mitigating tenant-related issues leading to insurance claims, the impact of previous claims on costs, and Aaron’s thoughts on securing budget-friendly insurance products.


Jonathan and Aaron go into deeper detail about:

  • Investors are moving away from popular areas like Florida, Texas, and southern Louisiana and toward places like the Carolinas because insurance costs are more predictable and have less propensity toward natural disaster events.

  • One surefire way to improve your insurance game is to find an agent specializing in the rental space.

  • The four biggest things to consider when purchasing insurance for rental properties include replacement costs, ordinance and law coverage, water backup, and loss of rent.


Insurance providers specializing in rental assets understand the importance of having the right coverages in place. Aaron Letzeiser’s insights as an experienced provider will help you better understand the questions you should be asking your insurance provider.

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