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Welcome to Target Market Insights. A podcast to help real estate investors navigate neighborhoods through the lens of local experts. In each episode, we speak to local specialists to learn about their market, useful tips, and the latest trends and developments. This show is designed to help you with the insights you need to win your target market.

Feb 27, 2019

After constantly working 12-hour shifts as a doctor, Charles Ayanleke realized that he was not truly rich. While he made great money, he was missing out on time and moments with friends and family. Fortunately, he invested in duplexes to earn passive income, which helped him to eventually retire as a physician. On this episode, he shares why it was important for him to leave the medical field for real estate and why he invests in the Jacksonville and Cleveland markets.  


Key Market Insights

  • Originally from Nigeria, lived in Ireland before moving to the U.S.
  • Has been in Florida for the last 8 years
  • Harsh winter of 2005 at Case Western in Cleveland, Ohio
  • 3 year residence in Cleveland and went to North Canton at Mercy Hospital
  • Got a job in Jacksonville and left snowy Midwest for sunny Florida
  • Bought 1-2 duplexes per year during early 2010s
  • Felt real estate was a better option than being a physician
  • You make money as a physician, but have to sacrifice family time
  • Worked 12 hour shifts; close friends started to die
  • Needed to figure out a way to buy back more of his time
  • If looking to create passive income you need to start educating yourself
  • So much free education available between podcasts, blogs and other resources
  • Sold primary for a loss in Cleveland during previous market cycle
  • Was working for Fannie and Freddie loans, but once he got 10 loans he needed to transition to large multifamily
  • Biggest difference between going from 2-4 units to larger properties (16 and 30 units), was hiring and managing third party vendors
  • It’s misleading to assume that long-distance investing will be hands-off
  • Realized Jacksonville market had peaked for small properties and wanted to get better cashflow
  • Looked at waiting out the Jacksonville market and decided to go to Cleveland as he had a competitive advantage in the market
  • Jacksonville Submarket – Class A - Southern Aspects, St. Johns School Districts, Riverside, Hillcrest, Murray Hill (the next Riverside)
  • Cleveland Submarket – Lakewood, Parma, Cleveland Heights, Mayfield Heights
  • Lower than $700 for rent will attract lower income residents


Bull’s Eye Tips:

Winning Your Market: Know your resources

Tracking Market Changes: Networking, Notifications

Daily Habit: Wake up early



Lifeonaire by Steve Cook


Rich Dad Poor Dad by Robert Kiyosaki


Miracle Morning by Hal Elrod 

Best Business Books:

Tax Free Wealth by Tom Wheelwright


Digital Resources




Tweet This:

“It doesn't matter how much income you earn, you will find people who make 100 times what you make”


Places to Grab a Bite:

Flying Iguana


Connect with Charles:


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