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  • Writer's pictureJohn Casmon

Elevate Into Multifamily Apartments with Tyler Chesser, Episode 190

How do you get started in multifamily apartments? While Tyler Chesser was doing international marketing, he decided to transition into multifamily as a broker. Tyler received his CCIM certification, demonstrating his expertise in multifamily. After doing numerous deals, he decided he was on the wrong end of the table during transactions and decided to become an investor. His first deal as an investor was a passive investment, before being active in his home state of Kentucky. Tyler is the Co-Founder of CF Capital and hosts the Elevate podcast. In this episode, Tyler shares how he transitioned from marketing into multifamily as a broker, and then as an investor. Tyler also shares key stats on Louisville, Kentucky, how new investors can get taken seriously by brokers, and lessons from his Elevate podcast.

Key Insight

  • Transitioning from international marketing, to real estate investing as a broker

  • Detailed tips on how to quit your corporate job and move into real estate investing full time

  • Tyler’s approach to investing and why: Passive investor in Georgia, Active investor in Kentucky

  • Pivoting into multifamily syndication investing

  • A deep dive into the Louisville, Kentucky market for multifamily investing

  • How being a broker has helped Tyler become a better investor

  • What investors can do to be taken more seriously by brokers: Credibility is everything!

  • Tyler’s investing strategy for multifamily

  • The differences between being a broker and an investor

  • Building up an active portfolio while passive investing in other deals

  • What Tyler has learned in passive investing

  • Elevate: The value you gain from starting and producing a podcast

Don’t live a life that you tolerate.

  • Living in equanimity: What is it and why it’s important for a balanced life

  • Ask yourself this question in any situation for clarity: What lesson am I supposed to learn from this?

Bullseye Tips:

Apparent Failure:

First deal was a total failure but learned many lessons from it.

Digital/Mobile Resource:


Most Recommended Book:

Think and Grow Rich (reads it every year)

Daily Habit:

Reading (1 hour every morning)

Wish I Knew When I Was Starting Out:

No one cares about my ego

Current Curiosity:

The economy and where it’s headed.

Best Place to Grab a Bite in Louisville, KY

Porcini or Jack Fry’s

Connect with Tyler


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