I Can't: Invest in Real Estate (From Afar)

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Event Category

Online Classes

Event Overview

This is a virtual event.


If you’ve ever thought that real estate investing (from afar) sounded interesting but out of reach, or if you’ve never considered investing in real estate because your own market seems too expensive, this is for you. You’ll see that you don’t need $1 million or an MBA to get started. Instead, we’ll work together to determine whether or not long distance real estate investing is a tool that will enable you to live a more fulfilling and secure life, and, if it does, we’ll create a roadmap to help you find your first investment.

An informal session where actual numbers will be shared. Even the ugly numbers, you ask? ESPECIALLY the ugly numbers! (This offering pairs nicely withI Can’t: Budget!)


  • How to determine if out of state investing is the right fit for your personal and financial goals

  • Things to consider and prepare before you begin investing long distance (hint: know WHY you’re embarking on this journey and get your financial house in order)

  • Common mistakes and pitfalls and how to avoid them

  • Personal stories about what went right, what went wrong, and goals for the next few years


Kory Dieter is a Chicago-based real estate investor who began her investing journey by purchasing a duplex in 2016. She lived upstairs and rented the downstairs to help offset the mortgage costs. Two years later, she got the itch to keep investing but found herself frustrated because she couldn’t find property in her own city that met her criteria. Luckily, she was introduced to the concept of long distance real estate investing and jumped right in. Since then, she and her husband have creatively grown their portfolio by taking a leap in investor-friendly markets outside of Illinois using a couple different strategies. Today, she offers housing in 4 states to 25 different families. In addition to serving as a real estate investor, Kory spends her time as a chief of staff for a large health insurance company, experimenting with new recipes in the kitchen, and running or biking Chicago’s lakefront path with her husband, Brandon.   Instagram

I Can't: Invest in Real Estate (From Afar) is part of Mac & Cheese Productions ' I Can't series, where adults state they're unable to do something, they try it/learn about it with a bunch of other adults who also "can't," and everyone proves themselves wrong and not only does the thing, but enjoys it and says, "That wasn't so bad. In fact, kinda fun. Good for me! What's next?!" Past I Can'ts have included yoga, improv, draw, have a dog, side hustle, and buy a home. To see other current offerings head here.

To Bring

  • A device with Zoom downloaded on it and the ability to connect to the internet

  • Note-taking materials

  • Food/drink for yourself if you’d like

Minimum age

All ages welcome

Cancellation Policy


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A TEDx speaker and one of Brazen Careerist' s Top Twenty Young Professionals to Watch, Saya has discovered how to turn her love of creating community, challenging herself and those around her, and enjoying life to its fullest into her “job.” Via her company Mac & Cheese Productions℠, she helps others (and herself) live a Life of Yes℠. Saya is from Evanston, went to Boston College, and resides in Chicago.

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