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.

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.

What's Different in Today's Lending Environment and How do Chicago Investors Capitalize?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Eric Workman of Renovo Financial

Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans

Link: Build Your Team | Straight Up Chicago Investor Podcast

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

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 track record to raise money. He shares keys to growth in real estate and explains how he runs his businesses all while traveling across the world on a regular basis!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Erik Swanson, Fernweh Property Group

Link: Erik Swanson's LinkedIn

Link: Eric Workman (Network Referral)

Guest Questions

04:24 Intro to our guest, Erik Swanson!

09:58 Transitioning from the music industry to real estate!

15:28 Drive-by shooting at Erik’s 5-unit building.

18:16 Lessons learned from rehab projects.

20:35 Starting a self pour tap room during COVID!

30:11 Erik’s keys to explosive growth in real estate.

37:36 Reputation building to raise money.

41:57 What’s next for Erik?!

49:12 What is your competitive advantage?

49:50 One piece of advice for new investors.

50:36 What do you do for fun?

50:50 Good book, podcast, or self development activity that you would recommend?

51:33 Local Network Recommendation?

52:23 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.

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: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Joe Smazal & Ann Reilly, Interra Realty & Westward360

Link: Joe Smazal's LinkedIn

Link: Ann Reilly's LinkedIn

Link: SUCI Ep 156 - Joe Smazal

Link: Northwest Side Building Coalition (NSBC) Website

Guest Questions

00:30 The State of Chicago’s NW Side Commercial Real Estate.

04:33 Leasing trends and strategies!

10:18 Dealing with evictions in today’s market.

17:17 Who is transacting in multifamily real estate in Chicago?

20:58 The evolution of the tenant pool and the market in Chicago.

24:53 Rapid fire Chicago real estate questions!

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

How do I incentivize and optimize renewals?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Jeff Weinberg, Drexel Properties

Link: Jeff Weinberg Shares Property Management Expertise on the Straight Up Chicago Investor Podcast

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

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 eloquently convey his approach to real estate and life which revolves around enjoying the process and being grateful for the present moment!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Jeffrey Ma, Keller Williams Preferred Realty

Link: Jeffrey's Instagram

Link: Chicago Real Estate Investors Meetup

Link: Eli Goodman's LinkedIn

Link: SUCI Ep 326 - RJ de Leon (Network Referral)

Link: Mind Management, Not Time Management (Book Recommendation)

Guest Questions

02:53 Housing Provider Tip - Keep a bag of ice melt at your properties in the event of unforeseen slippery conditions!

04:27 Intro to our guest, Jeffrey Ma!

12:10 Gaining momentum in real estate and getting into wholesaling!

19:11 Jeffrey’s journey to creative deals.

25:18 Case studies of “cool” deals!

29:44 Jeffrey’s most “unconventional” deal to date.

36:46 Getting into bigger deals including a 6-figure commission!

40:06 The Origin Story of Jeffrey’s and his partner Eli’s meetup.

43:02 What’s next for Jeffrey?!

48:35 What is your competitive advantage?

49:00 One piece of advice for new investors.

49:23 What do you do for fun?

49:58 Good book, podcast, or self development activity that you would recommend?

51:21 Local Network Recommendation?

51:42 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.

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 mentorship, staying disciplined, and starting with the end in mind!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Wyatt Simon, Full Circle Real Estate

Link: Wyatt's Instagram

Link: Wyatt's 7 Figure Mastermind

Link: Your First 100 Units (Wyatt's Book)

Link: 7 Habits of Highly Effective People (Book Recommendation)

Link: Jake and Geno (Network Referral)

Guest Questions

03:30 Housing Provider Tip - Understand appliance warranties and reconsider extending warranties!

05:09 Intro to our guest, Wyatt Simon!

11:16 Wyatt’s first BRRRR deal.

14:50 A third deal, gone bad!

19:47 How to start direct-to-seller marketing.

28:02 Ins and outs of “subject to” financing deals.

34:07 Navigating liquidity concerns.

37:56 Wyatt’s 5-year outlook!

41:12 What is your competitive advantage?

41:37 One piece of advice for new investors.

42:53 What do you do for fun?

43:10 Good book, podcast, or self development activity that you would recommend?

44:16 Local Network Recommendation?

44:52 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.

How does credit effect DSCR loans?

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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: StraightUpChicagoInvestor@gmail.com

Guest: Eric Workman, Renovo Financial

Link: Workman Lending Team - Renovo Financial - Real Estate Investment Loans

Link: Build Your Team | Straight Up Chicago Investor Podcast

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.