Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan

May 1, 2025

54:20

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Episode notes

Michael Kaplan is a real estate broker and investor who has grinded to become a top broker at 24 years of age!

Michael starts by explaining how he realized that college was not for him and pivoted to an entrepreneurial route in real estate! He explains the mindset required to start real estate investing and how he was able to acquire a 4-unit property in McHenry. Michael gets granular on how providing top tier service in leasing allowed him to get referral business which led to the creation of his team, the REKAP Group. Throughout the show, Micheal emphasizes the importance of a strong work ethic and transparency to gain the trust of potential clients and propel your business' growth.

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Michael Kaplan, The REKAP Group

Link: Michael's Instagram (@M.J.Kaplan)

Link: The REKAP Group's Instagram (@RekapGroup)

Guest Questions

03:31 Housing Provider Tip - Keep space heaters handy to be prepared for No Heat situations in winter!

05:00 Intro to our guest, Michael Kaplan!

12:13 Grinding as a newly licensed broker.

25:05 The mindset to start investing in real estate!

31:37 Micheal's first investment in McHenry.