Straight Up Chicago Investor

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!

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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

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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?

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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?

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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

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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!

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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

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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?

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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

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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?

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

What do investors need to know regarding the proposed legislation for both the Road To Housing and Move Act?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Chris Puleo, Puleo Group

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

Email the Show: [email protected]

Link: Build Your Team | Straight Up Chicago Investor Podcast

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

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Arthur Barkan of Barkan Realty joins us to share how he rapidly scaled his multifamily portfolio to 80 units!

Arthur breaks down the ins and outs of investing in North Chicago, current market deal flow, and evaluating troubling tenants and potential evictions! He also shares strategies for scaling faster, tools to improve property management operations, and lessons learned from working with villages in the northern suburbs. Arthur gets granular on financing properties, capital recycling through refinances, and evaluating cash flow vs long-term net worth. He closes with his five-year vision to continue rapidly scaling his portfolio!

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

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Guest: Arthur Barkan, Barkan Realty | Call Arthur: 224-433-4553

Link: Arthur's Instagram

Link: Real Life Investing Podcast with Arthur Barkan

Guest Questions:

02:43 Housing Provider Tip - Understand cost segregation implications if planning to sell a property in the near term.

03:28 Intro to our guest, Arthur Barkan!

08:40 The ins and outs of North Chicago.

17:26 Assessing a potential eviction scenario.

26:17 Deal flow in today's market.

33:12 Strategies to scale faster!

36:53 Tools to streamline property management.

44:40 Dealing with the Village of North Chicago.

51:39 5 Year Outlook on Arthur's business!

57:37 What's your competitive advantage?

57:53 One piece of advice for new investors.

58:01 What do you do for fun?

58:22 Good book, podcast, or self development activity that you would recommend?

59:15 Local Network Recommendation?

59:23 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.

Jake Rome, co-founder of Backflip, joins us to share the wild journey from institutional real estate private equity to building a vertically integrated lending platform for fix-and-flip investors! Jake breaks down the return-on-equity math that makes single-family flips so powerful, then digs into the leverage and risk decisions that separate successful investors from those who blow up their portfolios. He explains why Backflip decided to service and securitize its own loans, what red flags show up in underwriting (wholesaler markups, seller concessions), and how Chicago's Cook County foreclosure timeline uniquely impacts local lending. Jake also shares his outlook on where the fix-and-flip capital markets are headed, plus how he's using AI to run his own real estate portfolio.

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

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Guest: Jake Rome, Backflip

Connect with Backflip: LinkedIn | Instagram | Careers

Link: Ready to fund your next deal? Apply with Backflip here.

Guest Questions:

02:07 – Housing Provider Tip: What to do when a tenant stops paying rent

04:04 – Intro to our guest, Jake Rome of Backflip!

06:07 – From institutional real estate private equity to startups

13:44 – How the idea for Backflip was born

19:25 – Breaking down return on equity on a fix and flip

23:27 – Understanding leverage, risk, and how much is too much

28:09 – Building Backflip: raising capital and servicing their own loans

34:13 – Underwriting red flags: wholesaler markups & seller concessions

39:17 – Where Backflip lends, and the Cook County foreclosure timeline

44:36 – Red flags for first-time construction loan borrowers

46:39 – What lenders actually look for: credit score, experience, liquidity

51:10 – Building community: closing dinners and "Burgers and Flips"

53:19 – The future of fix-and-flip lending and securitization

56:08 – Competitive advantage & advice for new investors

57:53 – How listeners can learn more about Jake and Backflip

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

How can Property Sentinel help me as a Chicago building owner?

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Connect with Mark and Tom: StraightUpChicagoInvestor.com

Guest: Jim McMahon, Property Sentinel

Email the Show: [email protected]

Link: Build Your Team | Straight Up Chicago Investor Podcast

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.

We're taking Straight Up Chicago Investor on the road for a special live episode from the NBOA Summer Soiree!

We catch up with some of Chicago's most active real estate professionals to get their takes on what's happening across the market right now. Jeff Weinberg breaks down a 65-unit 1031 deal, Nate Fernandez shares his latest western suburban acquisition, and Mike Glasser and Brie Schmidt discuss the future of NBOA and how housing providers can make their voices heard.

We also talk South Side building operations with Corey Oliver, property management efficiencies with CIC's Erica Myles, small multifamily investing with Noah Birk, rehabs and development with Gabe Horstick, and today's lending environment with Eric Workman.

Tune in for a fast-paced episode packed with boots-on-the-ground insights from investors and housing professionals across Chicagoland!

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

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Guest: NBOA Summer Soiree by NBOA Chicago

Guest Questions:

04:02 Jeff Weinberg breaks down a 65-Unit 1031 deal!

14:26 Nate Fernandez discusses his latest portfolio acquisition in the western suburbs.

18:15 The outlook of the NBOA with Mike Glassner!

22:47 How to make your voice heard as a housing provider with Brie Schmidt.

29:16 Keys to successful building operations on the south side with Corey Oliver.

35:13 Improving property management efficiencies with CIC's Erica Miles.

40:14 Small multifamily investing with Noah Birk!

46:55 The 101 of rehabs and development with Gabe Horstick.

54:58 Eric Workman shares where and how deals are getting funded.

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Production House: Flint Stone Media

Copyright of Straight Up Chicago Investor 2026.

Pablo Gonzalez of Vendoroo joins us to discuss how AI is changing the way real estate investors and property managers operate and scale their businesses!

Pablor shares insights on raising capital and building communities before diving into how AI can be implemented in real estate operations. He breaks down how Vendoroo uses AI to coordinate maintenance, understand tenant sentiment, and help property managers operate more efficiently. Pablo also discusses when it makes sense for landlords to implement these tools and shares his outlook on the future of property management as AI continues to evolve!

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

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Guest: Pablo Gonzalez, Vendoroo

Link: Pablo's LinkedIn

Link: Vendoroo Property Maintenance Call Test

Link: Play Bigger (Book Recommendation)

Link: JWB Real Estate Capital

Guest Questions:

02:22 Housing Provider Tip - Leverage AI and other tools to improve maintenance requests response time!

03:24 Intro to our guest, Pablo Gonzalez!

14:54 Strategies to raise capital.

26:45 How to build and leverage a community to grow your business.

36:20 Implementing AI to scale a business.

41:22 The value of Vendoroo!

45:40 Understanding tenant and client sentiment.

49:25 At what unit count does it make sense to implement Vendoroo?

53:32 The future of the property management industry.

60:40 What is your competitive advantage?

61:17 One piece of advice for new investors.

62:47 What do you do for fun?

63:20 Good book, podcast, or self development activity that you would recommend?

63:44 Local Network Recommendation?

65:25 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.