Igor Mike Kajpust, president of Evolved Property Group, shares his REI journey which started at 17 years of age and spans across multiple states!

Igor breaks down his first few deals which includes an $800 land deal in Colorado and a distressed single family home in Indiana! He shares countless stories on auction properties, cold calling, and learning the process of wholesaling to create deal flow. Igor explains mistakes made on buying deals with quit claim deeds and due diligence. He gets granular on how he gained lead generation momentum through PPC, SEO, and various other real estate marketing strategies which propelled his business. Through the show, Igor shares entertaining stories that exemplify how taking massive action is the key to success in REI!

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

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

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

Guest: Igor Mike Kajpust, Evolved Property Group

Link: Igor's Instagram

Link: SUCI Ep 166 - J Scott

Link: ilFLS Website

Guest Questions:

01:35 Housing Provider Tip - Account for expenses related to lead plumbing lines when purchasing older buildings.

02:57 Intro to our guest, Igor Mike Kajpust!

04:52 Getting scrappy to find the first few deals.

19:00 Learning the process of wholesaling.

26:48 Transitioning to flipping properties.

35:01 Improving business processes and efficiency.

37:03 Building a rental portfolio in Chicago.

40:21 Distressed property horror stories!

47:45 Jumping into private lending in Chicago.

51:37 How to navigate the auction process.

57:57 What is your competitive advantage?

58:25 One piece of advice for new investors.

59:24 What do you do for fun?

59:57 Good book, podcast, or self development activity that you would recommend?

60:35 Local Network Recommendation?

61:00 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 2026.

What do real estate investors need to know about the Big Beautiful Bill?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Aaron Zimmerman, Brick House CPAs

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Team | Straight Up Chicago Investor Podcast

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

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Alderman Bennett Lawson discusses historical developments in his 44th Ward and how that success can be applied across the City of Chicago!

Alderman Lawson jumps right in by explaining the successful development in Wrigleyville including partnering with the Ricketts family! He breaks down successful developments including Advocate Masonic Hospital in Lakeview and across the 44th Ward. Alderman Lawson gives practical advice for developers to help increase the chance of having aldermanic support on potential projects! He dives deep on the ADU Pilot Program, its city wide expansion, and how it can best be leveraged to bring much needed housing supply to the city. This show is full of golden insights on Zoning and Development that you won't want to miss!

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

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

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

Guest: Alderman Bennett Lawson, City of Chicago 44th Ward

Link: Alderman Lawson's Instagram

Link: Chicago ADU Program

Link: Chicago's Great Fire (Book Recommendation)

Link: Tom Moore (Zoning Attorney)

Guest Questions:

01:55 Housing Provider Tip - Leverage rent payment services to allow tenants to build their credit history!

03:38 Intro to our guest, Alderman Lawson!

10:55 The development history of Wrigleyville!

18:20 Previous developments in the 44th Ward.

23:30 Advice for developers seeking support from aldermen.

27:18 The background of the Chicago ADU Program!

31:41 Lessons learned from the ADU Pilot Program.

44:08 Potential solutions for the housing supply issue.

48:50 What is your competitive advantage?

49:11 One piece of advice for new investors.

49:35 What do you do for fun?

49:48 Good book, podcast, or self development activity that you would recommend?

50:48 Local Network Recommendation?

51:15 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 2026.

Mike Scanlon of the Axon Group returns to share his personal real estate journey with several insights on how he has reached his success!

Mike starts by discussing his background prior to real estate and then jumps into his first property acquisition which was a rent-by-the-room condo house hack! He shares how he got gritty and creative to finance and acquire a pair of distressed properties in University Park. Mike breaks down how he identified value and got a down payment to purchase a prime 3-unit house hack in Lakeview! He explains how he grinded to build his real estate brokerage business and used commissions to fund his portfolio. Mike closes the show with how his investment strategy has shifted and with Chicago neighborhoods that he's extra bullish on!

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

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

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

Guest: Mike Scanlon, The Axon Group

Link: Mike's Instagram

Link: The Axon Group Instagram

Link: SUCI Ep 427 - 2026 Predictions with the Axon Group

Link: SUCI Ep 398 - Paul de Luca

Link: Never Split the Difference (Book Recommendation)

Guest Questions:

01:50 Housing Provider Tip - Consider offering tenants a valuable unit improvement when enforcing large rent increases.

03:23 Intro to our guest, Mike Scanlon!

10:17 Mike's start in real estate.

17:25 How Mike acquired his second deal.

23:45 Buying a prime 3-unit in Lakeview!

32:49 Building a pipeline of leads as a real estate broker.

37:16 A creative 8-unit deal in Melrose Park!

43:27 Mike's shift in investment strategy.

49:01 Up and coming Chicago neighborhoods!

50:25 What is your competitive advantage?

52:15 One piece of advice for new investors.

54:01 What do you do for fun?

55:23 Good book, podcast, or self development activity that you would recommend?

56:38 Local Network Recommendation?

57:33 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 2026.

What are the main differences in the 8.0 CAR contract vs the previous 7.0?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Chance Badertscher, Chance The Lawyer

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Team | Straight Up Chicago Investor Podcast

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

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Dan Nelson is a real estate agent and investor with over 2 decades of experience flipping properties and buying rentals!

Dan jumps right in by explaining his start in real estate and how success in poker helped fund his real estate business! He breaks down his first few flip projects including lessons learned and great tips on vetting contractors. Dan talks through the challenges of getting off the ground as a new real estate agent and provides advice for rookie agents. He gets granular on investment performance expectations across various Chicago neighborhoods including areas he is extra bullish on. Throughout the episode, Dan hammers home the importance of taking a 10,000-foot view letting time be your biggest asset when it comes to succeeding in real estate investing!

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

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

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

Guest: Dan Nelson, Dan Loves Houses

Link: Dan's Instagram

Link: Dan's Compass Page

Link: The War of Art (Book Recommendation)

Guest Questions:

02:03 Housing Provider Tip - Protect yourself against rental listing scams.

04:20 Intro to our guest, Dan Nelson!

13:02 How to find and vet contractors.

14:24 Dan's geographic area of focus!

18:01 Getting off the ground as a new real estate agent.

20:23 Chicago neighborhood expectations for investors!

30:25 Providing value as a real estate agent.

34:25 Common mistakes investors make when analyzing buildings.

41:33 Dan's outlook on Chicago!

44:23 What is your competitive advantage?

45:33 One piece of advice for new investors.

46:14 What do you do for fun?

46:25 Good book, podcast, or self development activity that you would recommend?

46:50 Local Network Recommendation?

47:14 How can the listeners learn more about you and provide value to you?

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Brendan McElhaney, founder of Cash for Chicago Houses, is a real estate wholesaler and investor who specializes in sourcing off-market deals through direct-to-seller marketing!

Brendan explains how he started in real estate with a house hack and how that helped him leave his corporate job to pursue real estate full time! He talks about renovation mistakes and leasing insights that he learned on his first few deals. Brendan dives deep on getting a wholesaling business off the ground, establishing a team, and lessons learned from wholesales gone wrong. He shares how he is leveraging social media to provide value to others and grow his business and also provides an outlook on Chicago. Throughout the show, Brendan demonstrates that hard work and grit have been the keys to his 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

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

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

Guest: Brendan McElhaney, Cash for Chicago Houses

Link: Brendan's Instagram

Link: Nick Jakubco (Attorney Referral)

Link: SUCI Build Your Team

Guest Questions:

03:19 Housing Provider Tip - Understand the limits on collectible security deposits.

05:09 Intro to our guest, Brendan McElhaney!

10:37 Leasing mistakes and lessons learned.

16:58 Getting a wholesaling business off the ground!

25:11 Wholesale deals gone wrong.

32:14 Building a reputation as a new wholesaler!

40:59 Establishing a wholesaling team and process.

43:34 Leveraging social media.

48:00 Brendan's outlook on his business and Chicago!

51:05 What is your competitive advantage?

52:24 One piece of advice for new investors.

53:08 What do you do for fun?

54:08 Good book, podcast, or self development activity that you would recommend?

54:42 Local Network Recommendation?

54:56 How can the listeners learn more about you and provide value to you?

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

How do I best prepare for an upcoming appraisal?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Tom & Mark, Straight Up Chicago Investor

Email the Show: StraightUpChicagoInvestor@gmail.com

Link: Build Your Team | Straight Up Chicago Investor Podcast

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

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.