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

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Daniel Baker, owner of Teton Properties, explains how he’s built a portfolio with strategic house hacks and value-add renovations.

Daniel discusses his move from Memphis to Chicago to get started in real estate. He shares some hilarious stories on househack value-add projects and getting extremely gritty to get projects to the finish line. He then breaks down a deal that closed right at the onset of COVID in 2020. Throughout this episode, Daniel gives numerous examples of how getting scrappy and persevering can be a competitive advantage that pays huge dividends.

If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Daniel Baker, Teton Properties

Link: How to Win Friends and Influence People (Book Recommendation)

Link: Snowball (Book Recommendation)

Link: Jen Fritzshall (Attorney Referral)

Link: SUCI Ep 22 - Matt Fritzshall

Guest Questions

02:08 Housing Provider Tip - Consider making professional carpet cleaning a move-out requirement for tenants!

04:23 Intro to our guest, Daniel Baker!

07:35 Getting started in real estate with Marcus & Millichap.

18:46 Purchasing a Lincoln Square 4-Flat after a few house hacks!

26:48 Daniel’s top lessons learned after his first few projects!

29:41 Jumping into a deal with COVID looming.

39:33 Closing a deal while getting laid off!

44:40 What’s next for Daniel?

47:48 Daniel’s outlook on Chicago!

50:43 What is your competitive advantage?

51:11 One piece of advice for new investors.

51:30 What do you do for fun?

51:51 Good book, podcast, or self development activity that you would recommend?

52:22 Local Network Recommendation?

49:10 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.

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

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How Can I buy a new property before selling my existing property, while still not having my offer contingent on the existing sale?

If you enjoy today’s episode, please leave us a review and share with someone who may also find value in this content!

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: StraightUpChicagoInvestor@gmail.com

Guest: Perry Farella of First Community Mortgage

Link: Perry Farella - First Community Mortgage

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

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

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Real Estate Nate shares how he has accumulated 26-units with healthy cash flow all while having a demanding W2 job!

Nate shares lessons learned from his first few deals and compares small vs large multifamily buildings. He explains how he and his wife leverage their high-income W2 jobs to propel their real estate investments and hedge associated risks. Nate dives into his consulting business involving CRM system implementation. Nate closes with tips on financing 5+ unit buildings and emphasizes the importance of building a great team to set yourself up for REI success!

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: Nate Fernandez, Optimum Process Partners

Link: Nate's Instagram

Link: Nate's LinkedIn

Link: NBOA Chicago

Link: West Suburban Building Owners Association

Link: Extreme Ownership (Book Recommendation)

Link: SUCI Ep 196 - John Warren

Guest Questions

02:51 Housing Provider Tip - Power through difficult deals and keep the end goal in mind!

04:48 Intro to our guest, Nate Fernandez!

09:06 Lessons learned from Nate’s first deal!

16:17 Comparing 2-4 unit vs 5+ unit buildings.

20:16 Hedging risk with proper planning.

23:33 Setting up a property management system.

27:02 Nate’s system implementation consulting business and areas of focus.

30:43 Navigating pre-sale inspections.

35:57 Nate’s goals by 40!

38:05 Leveraging a W2 job to propel real estate investments!

40:55 How to finance 5+ unit buildings.

45:11 What is your competitive advantage?

45:53 One piece of advice for new investors.

46:19 What do you do for fun?

46:57 Good book, podcast, or self development activity that you would recommend?

47:50 Local Network Recommendation?

49:10 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.

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

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

Corey Oliver, CEO of Strength in Management, is back three years later to share additional insights on managing in C/D neighborhoods.

Corey starts by discussing recent compression of cap rates and investment financials in Chicago C/D class neighborhoods. He gets granular on the process for placing and managing CHA tenants. Corey breaks down how he sets investment return expectations for out of state investors looking to invest in lower income neighborhoods. Corey closes with exciting news about his upcoming development project which includes city grants and tax credits!

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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: Corey Oliver, Strength in Management

Link: NBOA Chicago (Network Referral)

Link: Corey's Original Episode 175

Guest Questions

02:38 Housing Provider Tip - Understand the risks of hydro-jetting old sewer lines!

04:07 Intro to our guest, Corey Oliver!

09:49 Cap rates and expense ratios in challenging neighborhoods!

15:16 Rent increase on subsidized housing tenants.

17:55 Managing CHA tenants.

32:00 Setting expectations on C/D class investments!

42:18 Corey’s upcoming development project!

61:21 What is your competitive advantage?

61:37 One piece of advice for new investors.

62:02 What do you do for fun?

62:43 Good book, podcast, or self development activity that you would recommend?

63:48 Local Network Recommendation?

64:08 How can the listeners learn more about you and provide value to you?

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

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

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

How can Chicago investors fund rehabs for 2-4 unit properties?

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: Perry Farella of First Community Mortgage

Link: Perry Farella - First Community Mortgage

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

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!

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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: 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?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.

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?

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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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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

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2025.