Zen and the Art of Real Estate Investing with Jonathan Greene

099: Insuring Yourself and Your Real Estate Investments with Aaron Letzeiser


Becoming a landlord involves more than just buying properties. You also have to protect your assets, which means knowing the ins and outs of insurance.

On this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Aaron Letzeiser, co-founder of Obie, a venture-backed insurance and risk management technology platform that primarily serves real estate investors in the U.S. Aaron is also an active real estate investor and a venture partner at Pioneer Fund.

Starting with Aaron’s entrance into real estate as an accidental landlord, Jonathan and Aaron cover why condos make a great first investment, the unique features of Chicago’s real estate market that make it a good place to invest, and why Aaron branched out to the Carolinas when he was looking for new assets. You’ll also hear why insurance should be a factor when you choose where to invest, how technology is making shopping for insurance products easier, and the four ways investors are falling short when it comes to insurance coverage. As Jonathan and Aaron wrap up, you’ll also hear two ways to mitigate tenant issues that can cause an insurance claim, how prior claims can impact your costs, and Aaron’s advice for finding an affordable insurance product.

Dig in deep and get the details on creating an insurance plan that works for your business with Aaron Letzeiser.

In this episode, you will hear:

  • Aaron Letzeiser’s start in real estate as an accidental landlord

  • Why condos make a great first investment

  • The Chicago real estate market and what makes it a good place to invest

  • His decision to branch out into the Carolinas and what makes it a better buy than Florida

  • The role of insurance in the decision to purchase an asset in a particular location

  • The questions you should be asking your insurance agent as an investor

  • Decreasing the mental load as a mindful investor

  • Aaron’s goal for Obie Insurance and how technology is making investing easier

  • What Obie does differently from other insurance companies that puts the real estate investor in the driver’s seat

  • The importance of understanding the replacement cost of your property and adjusting your policies accordingly

  • The four ways investors are falling short in terms of insurance coverage

  • Two ways you can mitigate issues that may crop up inside a unit

  • Natural disasters’ impact on the insurance market and adjusting your deductible according to what you can afford

  • Obie’s use of tech to give you an estimate of your insurance cost with plus or minus 5% accuracy

  • How prior claims can affect your costs

  • Aaron’s advice for finding affordable insurance

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If you enjoyed this episode, we’ve created a PDF that has all of the key information for you from the episode. Just go to the episode page at to download it.

Supporting Resources:

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