Straight Up Chicago Investor

Latest Episodes:

Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons Nov 13, 2025

Show notes

Luke Helliker is a buy and hold real estate investor that has leveraged networking, house hacking, and value-add strategies to build a successful portfolio.

Luke kicks things off by sharing how he acquired his first house hack and provides insights on the ADU process that he used to add a third legal unit. He lays out top considerations when converting a basement into a dwelling unit including the top dollar items. Luke talks about getting a 4-unit acquisition to the finish line, despite it involving violations and a difficult seller. Throughout this episode, Luke demonstrates how holding real estate for the long term has built him great wealth and how staying active in the market is the key to success!

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

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Guest: Luke Helliker

Link: Luke Helliker - DocuSign | LinkedIn

Link: EUBA

Link: SUCI Ep 345 - Joey Turano

Link: SUCI Ep 354 - Jake Fugman & Mike Scanlon

Link: SUCI Ep 389 - Sebastian Mysliwiec

Link: Rich Dad Poor Dad (Book Recommendation)

Guest Questions:

03:15 Housing Provider Tip - Ensure to perform periodic checks on properties to identify issues that tenants may not bring up!

05:03 Intro to our guest, Luke Helliker!

13:19 Luke's first deal: a 2-unit house hack!

20:18 How to leverage the ADU process.

27:20 Funding an ADU project.

41:09 Navigating investing with your significant other.

43:15 Acquiring a 4-unit building in a competitive market!

58:47 Lessons learned on the 4-unit acquisition.

65:30 Luke's next investment targets.

66:19 What is your competitive advantage?

67:15 One piece of advice for new investors.

67:59 What do you do for fun?

69:19 Good book, podcast, or self development activity that you would recommend?

70:01 Local Network Recommendation?

70:30 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 411: Shawn Good Creates Opportunity with Off Market Deals Nov 06, 2025

Show notes

Shawn Good is a seasoned attorney and real estate investor with vast experience acquiring and stabilizing off-market real estate.

Shawn kicks things off by discussing his first few deals which included a condo and an 8-unit building. He shares some funny stories on unfair partnerships he's been a part of and important points on due diligence when acquiring a property. Shawn explains how joining Collective Genius helped him take his law practice and direct to seller marketing to the next level. He closes with his 5-year plan and hilarious real estate horror stories!

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

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Guest: Shawn Good, Good Law Group

Link: SUCI Ep 292 - Dorian Bezanis

Link: The Collective Genius Podcast

Link: The Charisma Myth (Book Recommendation)

Guest Questions:

02:06 Housing Provider Tip - Ensure to have a lease on a departing residence when required for another loan!

04:03 Intro to our guest, Shawn Good!

08:25 Transitioning to an 8-unit building after a condo purchase.

13:38 House hacking and starting a law practice!

21:23 Simple partnership structures.

26:28 Generating off-market deal flow!

36:36 Shawn's 5 year plan.

46:44 Horror stories!

51:37 What is your competitive advantage?

52:18 One piece of advice for new investors.

53:27 What do you do for fun?

53:50 Good book, podcast, or self development activity that you would recommend?

55:00 Local Network Recommendation?

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

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Production House: Flint Stone Media

Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross Nov 04, 2025

Show notes

What the different ways I can adjust my offer to make it more attractive?

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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

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Link: SUCI - Resources

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Production House: Flint Stone Media

Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman Oct 30, 2025

Show notes

Eli Goodman of Illinois Real Estate Buyers gives the complete playbook on dealing directly with sellers to acquire off-market deals!

Eli starts with explaining the grind it took to get his wholesaling off the ground! He discusses the right way to communicate with distressed sellers to create win-win scenarios and also throws in a few horror stories. Eli shares the various processes for direct to seller marketing and how he's achieved success. He closes things to keep in mind when practicing wholesaling in Illinois to mitigate your risk!

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

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Guest: Eli Goodman, Illinois Real Estate Buyers

Link: Eli's Instagram

Link: Eli's Meet Up

Link: Never Split the Difference (Book Recommendation)

Link: Dan Clarton (Title Services Referral)

Guest Questions:

01:42 Housing Provider Tip - Leverage a HELOC on your primary residence for emergencies and to continue scaling!

03:37 Intro to our guest, Eli Goodman!

07:00 Getting a wholesaling business off the ground.

11:42 How to communicate directly with sellers!

17:18 Tactical tips on direct to seller marketing.

25:08 Building a list of cash buyers.

34:33 Outlook on Eli's wholesaling business.

37:07 Challenges of wholesaling in Illinois.

44:19 What is your competitive advantage?

44:45 One piece of advice for new investors.

45:00 What do you do for fun?

45:12 Good book, podcast, or self development activity that you would recommend?

45:29 Local Network Recommendation?

46:05 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 408: Chicago Suburb Land Development with Jim Paul Oct 23, 2025

Show notes

Jim Paul, Director of the ALPS Group, has over 2 decades of experience in land development and receivership.

Jim jumps right in by discussing an early 21-acre land development deal and the hurdles he dealt with there! He breaks down his Tuscan Hills and Canterbury Lakes projects - residential developments in Will County, IL. Jim explains how to get creative with land development design and how to finance these projects. Throughout the episode, Jim repeats the importance of due diligence to mitigate risks and protect yourself and your investors!

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

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Guest: Jim Paul, ALPS Group | Call Jim: (815) 469-3800 | Email Jim: jmp@TheALPSGroup.com

Link: Lee Iacocca Autobiography

Link: Building Industry Association Chicago

Guest Questions:

02:21 Housing Provider Tip - Considering replacing older appliances instead of spending on repairs!

03:25 Intro to our guest, Jim Paul!

05:40 Developing a 21-acre property with limited experience!

14:28 How to source land deals.

24:27 Getting creative with land development!

29:02 Financing land development.

34:03 Lessons learned from 20 years of experience.

35:45 The ins and outs of receivership.

52:22 Jim's plan for the next 5 years!

55:31 What is your competitive advantage?

57:25 One piece of advice for new investors.

58:41 What do you do for fun?

59:00 Good book, podcast, or self development activity that you would recommend?

60:50 Local Network Recommendation?

62:07 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 407: How to Take Advantage of the Different Zoning Labels in Chicago Oct 21, 2025

Show notes

What are the differences between R2, R3, R4, and R5 zoning?

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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

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

Link: SUCI - Resources

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Production House: Flint Stone Media

Episode 406: How to Quit Your W2 After 1 House Hack with Moises Correa Oct 16, 2025

Show notes

Moises Correa, Principal of Proximo Equity Group, leads a team that specializes in value-add multifamily real estate across the Midwest.

Moises provides the ins and outs of his first couple house hacks in Avondale and how he burned the boats and left his W2 job after the first one! He explains how he formed partnerships to purchase a large multifamily building in Louisville, KY and gets granular on the due diligence process. Moises shares great insights on capital raising and structuring partnerships to be able to take down these large acquisitions. He breaks down how he leveraged a broker relationship to acquire a deal in Fort Wayne, IN well below market value. This episode showcases how building a team and fostering relationships can truly pay dividends 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!

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

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: Moises Correa, Principal of Proximo Equity Group

Link: SUCI Ep 369 - Erik Swanson

Link: What It Takes (Book Recommendation)

Guest Questions:

02:50 Housing Provider Tip - Understand your leases entirely to avoid legal issues.

04:44 Intro to our guest, Moises Correa!

09:05 Early lessons learned in REI!

14:43 Moises' second acquisition.

22:03 Jumping into a larger deal in Louisville!

34:02 Capital raising and structuring partnerships!

45:45 Horror stories from Louisville deals.

49:46 Investing in Fort Wayne, IN!

57:48 What is your competitive advantage?

58:18 One piece of advice for new investors.

59:21 What do you do for fun?

59:54 Good book, podcast, or self development activity that you would recommend?

60:09 Local Network Recommendation?

60:28 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 405: $1 Billion in Real Estate Sales with Chicago Podcaster Joe Smazal Oct 09, 2025

Show notes

Joe Smazal, Senior Managing Partner of Interra Realty, has over a decade of experience selling mid-market apartment buildings and recently surpassed $1 Billion in transaction volume!

Joe kicks things off by sharing the genesis and overview of his "Real Estate Chicago Style Podcast"! He reflects on his career's progression and highlights that have led him to crossing the $1 billion mark in total transaction volume. Joe dives deep on the market trends for Chicago's North Side including prime neighborhoods like Lincoln Park and Lakeview. Joe closes with takeaways from some recent personal transactions and provides an optimistic outlook on the Chicago 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

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: Joe Smazal, Interra Realty

Link: Joe Smazal - Interra Realty LLC | LinkedIn

Link: Real Estate Chicago Style Podcast

Link: SUCI Ep 156 - Joe Smazal

Link: SUCI Ep 368 - Joe Smazal (NSBC Live Event)

Link: Mark Wilczak (Inspector Referral)

Link: Scott Weinstein (Field and Goldberg)

Guest Questions

02:38 Housing Provider Tip - Understand rules and regulations around security deposits!

05:00 Intro to our guest, Joe Smazal!

07:10 Joe's Real Estate Chicago Style Podcast!

15:25 Joe's path to $1 Billion of Commercial RE sales.

23:11 Chicago market trends in 2025.

31:27 Navigating the Predominance of the Block (606) Ordinance.

49:50 Joe's 5-year plan.

54:57 The outlook on Chicago!

58:29 What is your competitive advantage?

58:53 One piece of advice for new investors.

59:19 What do you do for fun?

59:51 Good book, podcast, or self development activity that you would recommend?

60:55 Local Network Recommendation?

62:09 How can the listeners learn more about you and provide value to you?

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Production House: Flint Stone Media

Episode 404: Lending Options For Non-Owner Occupied Investors With Chris Puleo Oct 07, 2025

Show notes

What are my lending options for a non-owner occupied investor?

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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: Chris Puleo of Puleo Group

Link: Episode 130: Chicago Mortgage Lending in this Inflationary Environment with Chris Puleo

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Production House: Flint Stone Media

Episode 403: Saving & Grinding Gets You "4" Properties Before 21 with Lantz Kurzawinski Oct 02, 2025

Show notes

Lantz Kurzawinski, Marketing Specialist for the Straight Up Chicago Investor Podcast, tells his story of grinding to succeed in real estate at an early age.

Lantz explains how he recognized his entrepreneurial spirit at an early age and decided to dive into real estate. He shares his experience as a leasing agent and how that led him to discover his enjoyment for getting his hands dirty. Lantz gets granular on partnering on a few BRRRR deals and the value he brought to the partnership despite not having much liquidity! He shares insights on closing a house hack deal with a hilarious story about living in a "work in progress" basement apartment! Lantz demonstrates how hard work and bringing value to others is very much the key to succeeding in REI like other areas of life!

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

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Guest: Lantz Kurzawinksi, GC Realty & Development

Link: SUCI Ep 253 - Jeff Nydegger

Link: The Obstacle Is the Way (Book Recommendation)

Link: Meditations (Book Recommendation)