Episodios

  • Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows

    Episode 414: Mark Ainley Breaks Down Chicago Suburb Rental License Must Knows
    Nov 20 2025

    SUCI Co-Host Mark Ainley is back in the hot seat to share insights on being an apartment operator in Chicagoland Villages and Suburbs!

    Mark jumps right in by giving a bit of history on why rental licenses were originally introduced. He gets granular on various village requirements for rentals including smoke detectors, GFCIs, and hot water heaters. Mark explains some hoops you can expect to jump through during Point of Sale inspections and how to expedite the process! He closes by breaking down tax transfer stamps and other transaction fees in the Suburbs so you can accurately factor this into your holding costs!

    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: Mark Ainley of GC Realty & Development

    Link: Mark's Instagram

    Link: The Science of Scaling (Book Recommendation)

    Link: It's How We Play The Game (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!

    03:16 Housing Provider Tip - Understand the updated CARES Act notice requirements!

    04:55 Intro to our guest, Mark Ainley!

    05:48 The history of village requirements for rentals.

    09:17 Considerations when investing in Schaumburg.

    17:27 Insights on permits and associated fees.

    21:38 Navigating point of sale inspections in different villages.

    31:46 What to know about tax transfer stamps!

    35:56 Overview on rental licenses, village inspections, STR licenses, and more!

    39:51 Book recommendations from Mark!

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    43 m
  • Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev

    Episode 413: Cost Seg Deadlines and Utilizing the Phased Approach with Cost Seg Kev
    Nov 18 2025

    When do I have to have my cost segregation done to ensure it is good for my 2025 taxes?

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

    Connect with Mark and Tom: StraightUpChicagoInvestor.com

    Guest: Cost Seg Kev from CSSI

    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: Episode 392: Cost Seg Kev Explains How Chicago Rehabbers Can Be Saving Tens Of Thousands Dollars

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    16 m
  • Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons

    Episode 412: Luke Helliker Leverages the ADU Process & Learns Many Lessons
    Nov 13 2025
    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! ============= 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: 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? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    1 h y 14 m
  • Episode 411: Shawn Good Creates Opportunity with Off Market Deals

    Episode 411: Shawn Good Creates Opportunity with Off Market Deals
    Nov 6 2025

    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

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

    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?

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    1 h
  • Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross

    Episode 410: How to Make Your Offer More Attractive to Sellers with Mark Ainley and Tom Shallcross
    Nov 4 2025

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

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

    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

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    19 m
  • Episode 409: How to Generate Direct to Seller Off-Market Deals with Eli Goodman

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

    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

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

    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?

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    48 m
  • Episode 408: Chicago Suburb Land Development with Jim Paul

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

    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

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

    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?

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    1 h y 5 m
  • Episode 407: How to Take Advantage of the Different Zoning Labels in Chicago

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

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

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

    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

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

    Production House: Flint Stone Media

    Copyright of Straight Up Chicago Investor 2025.
    Más Menos
    20 m