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  • Writer's pictureBen Welch | Dan Mackin

101: Insurance Policies & Market Downturns with Ryan Letzeiser

Matt Aitchison - Real Estate Investor

Despite claiming that he left the intellectual role in the family to his brother, Ryan Letzeiser began his real estate journey in college. He went to Michigan State, got his bachelor's, and then shortly made his way over to Clemson University to pursue a master’s architecture. He took Real Estate Development as an elective and almost instantly realized he had gone down the wrong path.

His first summer while in Clemson, he decided to take an internship with a real estate private equity group in Florida as a way to casually dip his toes into the industry to feel out whether he was actually willing to jump ship and dive head first into real estate. Turns out, he loved it!

Some time (and some companies) after that, Ryan decided to do private investments on his own and started a tech company based on managing expenses and insurance for real estate investors. The motivation for this came from the experiences he had during his time working for those large billion dollar organizations in the commercial real estate space. He learned that the “little guys” were often at a disadvantage because they simply could not attract the business of more adequate carriers because they just didn’t make enough on their bottom line.

Up to date, Ryan is the acting CEO of Obie, managing risk for multi-family and commercial real estate investors alike. He looks to continue to grow his personal portfolio, and to continue providing better and better services for his clients looking to navigate their way around the real estate space.

Our takeaways from our conversation with Ryan:

1) As with insurance, you’d want a policy that covers you through and through in any case, but hope you’ll never actually have to make a claim with. And to be fair, that’s only really when you find out exactly what kind of carrier you’re working with. It can get ugly really quickly, Ryan says, and sometimes it is the brokers to blame. These such brokers push for policies in order to attract business that the carrier can’t necessarily handle and it is the investors who pay the price because their bottom line will be greatly affected once it is needed. You want to stay on top of your coverage as well because you don’t want surprises when the time comes to renew or change policies. You need time to choose the best coverage for your specific situation.

2) There are many niches in the real estate industry. If you find yourself in a position to be able to take a role within a large organization or company, it might be worth your while starting out. By working with a larger firm (that doesn’t even necessarily coincide with only investors either), you can learn a lot right away with the insulation of a large company, meaning they will guide you through the deals and issues and even absorb the costs. If you were a sole proprietor, you would have to navigate the waters all on your own with little guidance (if at all) and all the expenses would come right out of your pocket. At the end of the day, real estate investing doesn’t only consist of investors. There are many other people and services out there that investors need for their business. Just look at Ryan. Investors hire his company to manage their individual portfolios because their time (the investor) is better spent elsewhere.

3) The similarities between The Great Recession, The Retail Apocalypse, and today. While we don’t want to speculate on the future, nor do we want to feed into the fear about the economy, there are many similarities that are occurring today that were seen clear as day with hindsight from a decade ago. And truth be told, we probably really aren’t going to see any large effects of this quantitative easing or government stimulus until COVID-19 is all said and done. That will be when the larger shifts and corrections will begin. And the ironic thing is, Ryan said, folks had been predicting a recession (that never came) for years now. And once the economy had finally settled into a smooth cruise, this act of God struck us all and now look at us…

4) Hard times are when you find out what you’re made of. Ryan has now experienced two market downturns and he says that they only made him a better investor both times. And the same can be said for you. It’s easy to get deals and say you’re a great real estate investor when the market makes it so. But when it dries up and deals are far and few, that’s when you really get to roll up your sleeves and work on your craft. You will be tested and if you can handle yourself then, you will come out of the downturn stronger, smarter, and richer.

If Ryan could go back and talk to his 16 year old self, he’d tell him, “It will all work out.”

An unexpected benefit of real estate investing, Ryan said, was the ability to grow his network, and more importantly, learn from his network.

A piece of advice Ryan would tell his friends looking to get started in real estate would be to “Make sure that your [partnership] agreements are ironclad,” meaning they are written on paper and signed on the dotted line. Handshake agreements will not suit you well if push were to shove.

Ryan recommends using an HP 12C Financial Calculator to help you run the numbers on a deal on the fly.

Ryan recommends reading The Art of War by Sun Tzu to help you get insight on how negotiations work, as well as taking an MIT: Real Estate Economics course to help form your foundation on how real estate works in the real world.

If you’d like to get in touch with Ryan, visit: or contact him at

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