Straight Up Chicago Investor

Andy Ahitow, Co-Founder of City Pads and 25-year real estate veteran, joins us to share his journey from building and selling a leasing business to becoming a successful multifamily developer!

Andy starts by explaining how he got into apartment leasing, built a leasing company, and his reasoning for eventually selling his original company. He breaks down his first development deal and gets into top lessons learned from various development projects! Andy provides tactical insights on apartment amenities and features with high ROI and others that may not be worth the added expense. He closes with his take on Chicago Zoning policy and modifications that can be made to promote development and bring much needed housing supply!

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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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: Andy Ahitow, Co-Founder of City Pads

Link: Andy's LinkedIn

Link: The Smerconish Podcast

Link: Acosta Ezgur (Zoning Attorney Referral)

Guest Questions:

01:38 Housing Provider Tip - Understand when toilet issues are considered emergency work orders!

02:51 Intro to our guest, Andy Ahitow!

08:52 Insights from growing and selling a leasing company.

11:20 Andy's first redevelopment deal!

17:18 Lessons learned from challenging deals.

26:48 Navigating partnership splits and starting new ventures.

34:44 High ROI apartment amenities and features!

42:47 Assessing supply and zoning across various neighborhoods

54:29 What's your competitive advantage?

54:47 One piece of advice for new investors.

55:17 What do you do for fun?

55:49 Good book, podcast, or self development activity that you would recommend?

56:20 Local Network Recommendation.

56:57 How can listeners learn more about you and provide value to you?

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

Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

What do investors need to know about the current Chicago market?

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

Guest: Jason Wagner, Greystone Realty, Real Life Investing with Jason Rachel Wagner

Link: SUCI Build Your Team

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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.

Oscar Medina of AMG Realty joins us to discuss his journey from wholesaling to a thriving fix-and-flip business at only 23 years old!

Oscar starts by explaining how transitioned into real estate after serving time in the military. He gives a super thorough explanation on subject-to deals including pros, cons, and top considerations when pursuing these kinds of deals! Oscar shares why he transitioned into flipping properties and breaks down how his most successful strategies for souring lucrative, off-market properties. Oscar closes with some financing tips and an ambitious outlook on his business!

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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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: Oscar Medina, AMG Realty

Link: SUCI Ep 387 - Alex Diaz

Link: Jimmy Vachachira (Attorney Referral)

Guest Questions:

02:24 Housing Provided Tip - Have an attorney contact to ensure you're staying compliant on your leases!

03:48 Intro to our guest, Oscar Medina!

09:53 Breaking down subject-to deals.

27:07 Navigating the due-on-sale class.

29:21 Oscar's translation to fix and flips!

38:17 Education in school vs jumping right into the work force.

40:12 Lessons learned from flipping real estate!

45:01 Options to finance deals.

51:44 What's your competitive advantage?

52:19 One piece of advice for new investors.

52:45 What do you do for fun?

53:04 Good book, podcast, or self development activity that you would recommend?

54:12 Local Network Recommendation.

54:55 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.

Bill Powers, who first joined us back in Episode 6, returns with his daughter Shannon Powers to share how their real estate business has evolved since 2021!

Bill and Shannon discuss how they've scaled their portfolio over the last several years, jumping into ground-up development in Florida, and lessons learned from investing in a declining market! They dive deep into short-term and mid-term rentals including identifying markets, underwriting deals, and best management practices. The duo explains how they've been able to have their STR/MTR business work in synergy with their traditional rentals. Bill and Shannon close with an outlook on their business and share Lake County areas with strong investment opportunities!

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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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

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

Guests: Bill and Shannon Powers, RTO Property

Link: Bill's LinkedIn

Link: Shannon's LinkedIn

Link: Secure Real Estate Management

Link: SUCI Ep 6 - Bill Powers

Link: The Diary of A CEO (Podcast Recommendation)

Link: Marcus Frye (Lender Referral)

Link: Jim Leech (Insurance Agent Referral)

Guest Questions:

02:07 Housing Provided Tip - Consider upgrading turf to cut lawn maintenance costs!

04:22 Intro to our guests, Bill and Shannon Powers!

07:26 Transitioning from SFH rentals to larger multifamily and ground-up development in Florida.

16:48 How to underwrite mid-term and short-term rental opportunities?

19:49 Getting granular on MTR/STR expenses!

30:41 Breaking down STR arbitrage and best practices.

39:19 What's next for Bill's business?

42:05 Villages and towns with strong upside!

45:02 What's your competitive advantage?

46:38 One piece of advice for new investors.

47:43 What do you do for fun?

48:19 Good book, podcast, or self development activity that you would recommend?

48:44 Local Network Recommendation.

49:31 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.

What simple steps I can take to find more deals in this market?

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

Guest: Mark Ainley of GC Realty and Co-host of Straight Up Chicago Investor Podcast

Link: SUCI Build Your Team

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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.

John Bradford, founder of PetScreening.com, joins us to discuss pros, cons, and mitigating risks associated with having pets in rental properties!

John jumps right in by sharing the top misconceptions that landlords have on pets and the opportunity costs of a no-pet policy! He gives a detailed breakdown on how to screen pets, spot fraudulent activity around pets and support animals, and how PetScreening streamlines this entire process. We get into some of the craziest pet data and pet screening stories that John has encountered! John closes by discussing where PetScreening and the rental housing industry is headed next.

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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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: John Bradford, PetScreening | Email John: [email protected]

Link: Atomic Habits (Book Recommendation)

Link: NARPM

Guest Questions:

02:23 Housing Provided Tip - Ensure your insurance is adequate to cover weather-related damages!

04:22 Intro to our guest, John Bradford!

10:53 Landlord misconceptions about pets.

21:11 Opportunity costs of a no-pet policy.

33:27 John's take on eliminating fraud around pets.

36:48 Surprising pet data!

43:31 Crazy pet screening stories!

46:22 The future of Pet Screening.

52:15 What's your competitive advantage?

52:34 One piece of advice for new investors.

53:08 What do you do for fun?

53:11 Good book, podcast, or self development activity that you would recommend?

53:32 Local Network Recommendation.

53:58 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.

Miguel Chacon, 25th Ward Aldermanic candidate and seasoned investor, joins us to discuss the past, present, and future of Pilsen and Chicago Housing Policy as a whole!

Miguel shares how Pilsen has grown over the last couple decades and the challenges that the neighborhood faces today! He breaks down limitations caused by Zoning and Ordinances and explains changes that tremendously help bring housing supply and affordability to Chicago. Miguel breaks down why he's running for Alderman of the 25th ward and shares his vision to bring better schools, housing, and opportunities to the ward. He closes with his competitive advantage, ways to develop vision, and tips for novice 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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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: Miguel Chacon, Compass

Link: Miguel Chacon's LinkedIn

Link: The Fran Spielman Show

Link: Chicago Cityscape

Guest Questions:

02:03 Housing Provided Tip - Remember to change utilities to your name when buying a new building!

04:27 Intro to our guest, Miguel Chacon!

06:35 The evolution of Pilsen.

17:18 Challenging ordinances for housing providers.

26:02 Zoning opportunities in Pilsen!

38:21 Why run for alderman?

44:07 Miguel's vision to improve the Pilsen community?

46:22 What's your competitive advantage?

47:07 One piece of advice for new investors.

47:52 What do you do for fun?

49:11 Good book, podcast, or self development activity that you would recommend?

50:06 Local Network Recommendation.

50:46 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.

What are the different financing products I can leverage as a Chicago investor?

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

Guest: Chris Puleo, Puleo Group

Link: SUCI Build Your Team

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

Connect with Mark and Tom: StraightUpChicagoInvestor.com

Email the Show: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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.

Mark Myers of Kiser Group joins us to share insights from over three decades of experience in senior housing investments and brokerage!

Mark starts with how he got involved with senior housing and the evolution of the asset class over the last 30 years! He shares the basics of senior housing underwriting and compares the operations and returns to multifamily investing. Mark gives a detailed breakdown on expenses, risks, and regulations to be considered when investing in this asset class. He closes the show with advice on getting off the ground as a new senior housing investor or broker and provides a very bullish market outlook!

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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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 Myers, Kiser Group

Link: Crime and Punishment (Book Recommendation)

Link: The SeniorCare Investor

Link: NIC Website

Link: ASHA Website

Guest Questions:

02:08 Housing Provided Tip - Remember to follow the law and change locks after tenant turnovers!

04:01 Intro to our guest, Mark Myers!

12:15 The evolution of senior housing!

17:38 The state of the senior housing market.

20:00 Underwriting basics for senior housing.

32:23 Comparing multifamily to senior housing investments.

38:07 Rules and regulations to be aware of.

45:11 Identifying hot markets and how to get in the game!

50:18 Getting off the ground as a senior housing broker.

55:35 Mark's outlook on the senior housing market!

57:37 What's your competitive advantage?

58:42 One piece of advice for new investors.

59:26 What do you do for fun?

61:19 Good book, podcast, or self development activity that you would recommend?

62:00 Local Network Recommendation.

63:13 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.

David Shifrin of Elite Properties Chicago returns to share how he has scaled his portfolio since his last SUCI podcast appearance in 2024!

David opens up by summarizing his portfolio and how he created cash flow in premier Chicago neighborhoods! He breaks down how a 1031 exchange works and gets granular with an example that led to the acquisition of a great multifamily asset in Avondale. David shares some lessons learned from a rough rehab project and talks about strategies to raise rents and property value without having to do significant renovation. He closes with his take on current investment opportunities in West Town and a bullish outlook on Chicago as a whole!

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: [email protected]

Properties for Sale on the North Side? We want to buy them. Email: [email protected]

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: David Shifrin, Elite Properties Chicago

Link: SUCI Ep 280 - David Shifrin

Link: David Shifrin's Bio

Link: NBOA Chicago

Link: Illini Inquirer Podcast

Guest Questions:

02:00 Housing Provided Tip - Consider a sump pump system to protect your properties during heavy rain falls!

03:12 Intro to our guest, David Shifrin!

05:40 Finding cash flow in class A neighborhoods.

08:00 Breaking down 1031 exchanges.

11:41 David's recent Avondale multifamily deal!

15:22 Pros and cons of paying down mortgages.

25:14 David's top lessons learned from rapidly building a portfolio.

29:24 Opportunities to be had in West Town.

40:06 David's outlook on Chicago!

44:20 What's your competitive advantage?

44:34 One piece of advice for new investors.

45:00 What do you do for fun?

45:42 Good book, podcast, or self development activity that you would recommend?

46:44 Local Network Recommendation?

47:27 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.