Straight Up Chicago Investor

Latest Episodes:

Episode 372: Having Limited Capital and Scaling In Chicago Big Time with Kevin Schnell May 08, 2025

Show notes

Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com

Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement

Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com

=============

Kevin Schnell of Concord Capital has amassed a portfolio of over 400 rental units and has vast experience repositioning multi-family and mixed-use real estate investments!

Kevin hits the ground running with how he grinded early in his real estate career to learn his markets and efficiently prospect to generate deal flow. He discussed the valuable knowledge he gained while working with MO2 Properties, a Chicago-based rental property owner and operator. Kevin describes the journey of leaving MO2 Properties to start his own investment company. He closes the show with advice on adaptive reuse projects and motivating words on why Chicago is the place to be for REI!

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: Kevin Schnell, Concord Capital

Link: Kevin's LinkedIn Link: Getting to Yes (Book Recommendation)

Link: Liz Butler (Zoning Attorney Referral)

Guest Questions

03:05 Housing Provider Tip - Understand tenant chargebacks to protect yourself from tenant damages!

04:39 Intro to our guest, Kevin Schnell!

07:14 How to learn a market and prospecting.

15:57 Kevin's transition to MO2 Properties!

23:18 Strategies for cold calling sellers.

32:47 Leaving MO2 to start an investment business!

36:42 Kevin's current focus.

41:44 Considerations on adaptive reuse projects!

44:35 Why Kevin is doubling down on Chicago!

48:55 What is your competitive advantage?

49:18 One piece of advice for new investors.

50:12 What do you do for fun?

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

51:43 Local Network Recommendation?

52:05 How can the listeners learn more about you and provide value to you?

-----------------

Production House: Flint Stone Media

Episode 371: How To Break into Chicago Real Estate Investing in Your 20s with Michael Kaplan May 01, 2025

Show 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.

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: 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?

-----------------

Production House: Flint Stone Media

Episode 370: How The Current 2025 Lending Market Differs From Previous Year Apr 29, 2025

Show notes

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: 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

-----------------

Production House: Flint Stone Media

Episode 369: This Is How You Get Freedom of Time As a Chicago Investor with Erik Swanson Apr 24, 2025

Show notes

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!

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: 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?

-----------------

Production House: Flint Stone Media

Episode 368: Current Chicago Apartment Sales & Leasing Trends with Joe Smazal & Ann Reilly (NSBC Live Event) Apr 17, 2025

Show notes

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!

-----------------

Production House: Flint Stone Media

Episode 367: How to Get Out In Front of Renewals With Jeff Weinberg Apr 15, 2025

Show notes

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: 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

-----------------

Production House: Flint Stone Media

Episode 366: Networking Leader from Creative Financing to Six-Figure Commission Checks with Jeffrey Ma Apr 10, 2025

Show notes

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!

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: 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?

-----------------

Production House: Flint Stone Media

Episode 365: Building a $20 Million Portfolio Using BRRRR with Wyatt Simon Apr 03, 2025

Show notes

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!

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: 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?

-----------------

Production House: Flint Stone Media

Episode 364: Small Credit Items That Lead to Large Financial Impacts with Eric Workman Apr 01, 2025

Show notes

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: 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

-----------------

Production House: Flint Stone Media

Episode 363: 168 Western Suburb units In Less Than 10 Years with John Warren Mar 27, 2025

Show notes

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 find value in this content!

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: John Warren, Forte Properties

Link: Forte Properties (@fortepropertieschicago) • Instagram photos and videos

Link: Extreme Ownership (Book Recommendation)

Link: Luke Erlandson (Agency Lender Referral)

Guest Questions

02:53 Intro to our guest, John Warren!

03:18 Lessons learned from growing a 168-unit portfolio!

06:50 How to simply structure a partnership?

12:00 John's geographical focus and plans for growth.