Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan
Release Date: 05/01/2025
Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan
Straight Up Chicago Investor
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...
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Episode 370: How The Current 2025 Lending Market Differs From Previous Year
Straight Up Chicago Investor
What's Different in Today's Lending Environment and How do Chicago Investors Capitalize? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: Email the Show: Guest: Eric Workman of Link: Link: B ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson
Straight Up Chicago Investor
Erik Swanson, owner of Fernweh Property Group, explains how he’s developed a track record with investors that has allowed him to build a Tap Room business and an impressive real estate portfolio! Erik starts with very cool stories about his days in the music industry including working alongside some legendary bands! He dives into his first couple real estate deals including a FHA 203k loan and an intense story about a drive-by shooting at one of his properties! Erik discusses how he raised money to start an innovative, self-pour Tap Room business and emphasizes the importance of building a...
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Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event)
Straight Up Chicago Investor
Tom and Mark interview Joe Smazal of Interra Realty and Ann Reilly of Westward360 during NSBC’s Live Event! Conversations range from leasing trends to handling evictions and the state of the multifamily market in 2025. This show is full of valuable insights from two heavy hitters in the Chicago Multifamily Real Estate market! If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: Email the Show: Guest: Joe Smazal & Ann Reilly, Interra Realty & Westward360 Link: Link: Link: Link: ...
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Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg
Straight Up Chicago Investor
How do I incentivize and optimize renewals? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: Email the Show: Guest: Jeff Weinberg, Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey Ma
Straight Up Chicago Investor
Jeffrey Ma joins us to share his experience as a real investor, broker, and wholesaler including various creatively structured deals! Jeffrey starts by discussing his upbringing, start in real estate, and how he established a focus on wholesaling. He dives deep into “creative” deals including one deal where he was able to close on a property minutes before it would have been foreclosed on. Jeffrey explains how he’s gotten into bigger deals including a multifamily syndication and brokering a warehouse space that resulted in a six-figure commission! Throughout the show, Jeffrey is able to...
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Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon
Straight Up Chicago Investor
Wyatt Simon, owner of Full Circle Real Estate, discusses the successes and lessons learned in his journey to building a $20 million real estate portfolio! Wyatt starts by talking about how a successful BRRRR deal allowed him to gain momentum early on in his investing career. After a homerun deal, he shares lessons learned from a bad deal that involved getting caught doing construction without a permit and going significantly over budget! Wyatt explains the issues that arise from lack of liquidity even for high networth individuals. Throughout the episode, Wyatt drops powerful insights on...
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Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman
Straight Up Chicago Investor
How does credit effect DSCR loans? ============= If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content! Connect with Mark and Tom: Email the Show: Guest: Eric Workman, Link: Link: ----------------- Production House: Copyright of Straight Up Chicago Investor 2025.
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Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren
Straight Up Chicago Investor
John discusses his start in real estate over a decade ago and reflects on missed opportunities, lessons learned, and success stories! He shares practical advice on simply structuring partnerships and talks about Forte Properties’ plan for growth in the western suburbs. John dives into starting a property management company along with building and remaining loyal to a team to support his portfolio. Mr. Warren closes with motivating words on entrepreneurship and why you should take the leap of faith! If you enjoy today’s episode, please leave us a review and share with someone who may also...
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Episode 362: Free Money to Develop Affordable Housing? Learn How with Scott Henry
Straight Up Chicago Investor
Scott Henry, Founder of Celadon Partners, joins to discuss the ins and outs of Affordable Housing Development including tax credits, grants, and construction considerations. Scott starts by sharing his experience working at JPMorgan’s Low Income Housing Tax Credit investment group and his transition to developing affordable housing! He provides a case study of an adaptive reuse project and gets granular on how the acquisition opportunity was presented, how the capital was raised, and construction considerations. Scott shares notable due diligence stories and talks about what to look for in...
info_outlineMichael 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.
If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!
Connect with Mark and Tom: StraightUpChicagoInvestor.com
Email the Show: [email protected]
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.
37:47 Starting the REKAP Group!
42:53 What would Michael change in his RE journey so far?
46:14 What is your competitive advantage?
47:12 One piece of advice for new investors.
48:17 What do you do for fun?
49:24 Good book, podcast, or self development activity that you would recommend?
50:26 Local Network Recommendation?
50:43 How can the listeners learn more about you and provide value to you?
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Production House: Flint Stone Media
Copyright of Straight Up Chicago Investor 2025.