Straight Up Chicago Investor

Hosted by Straight Up Chicago Investor

BusinessInterviews guestsExplicit

Website RSS feed

Episodes

492

Latest episode

Oct 2026

Language

About the show

Are you a real estate investor in Chicago or someone looking to invest in the Chicagoland Market? If so, this podcast is for you! We break down the neighborhoods, different sides of the city, and surrounding suburbs so you can understand the uniqueness of investing in Chicago real estate. The hosts and guests are Chicago investors and Property Managers who are making it happen in and around the Windy City. We share information, winning strategies, obstacles, success stories, and most importantly, lessons learned. If you are looking for ground level information and want to learn what has worked and not worked in Chicago, you are in the right place.

Listen to episodes

60 recent

November 5, 2026Episode 4891 hr 9 min

Episode 489: Cook County Property Taxes: Where You Can Save with Molly Phelan

Molly Phelan, property tax appeal attorney at Siegel Jennings, joins us to discuss the complexities of Cook County property taxes and how investors can protect their bottom line! Molly breaks down the different methods used for property valuations. She explains what investors should know about the new Cook County Assessor Pat Hynes and how to effectively navigate the property tax appeal process. Molly gets granular on underwriting property taxes, estimating future tax liabilities on rehab projects, and understanding available incentives! She closes with her craziest tax appeal stories, and practical advice to help investors maximize their ROI! If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= C onnect 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: Molly Phelan, Siegel Jennings Property Tax Law Link: Molly's LinkedIn Link: SUCI Ep 465 - Pat Hynes Link: The Goldie Initiative Link: ULI Chicago Guest Questions: 01:54 Housing Provider Tip - Understand when it makes sense to break a lease with a tenant! 03:40 Intro to our guest, Molly Phelan! 09:57 Property valuation methods and the new Cook County Assessor. 24:14 Underwriting property taxes on redeveloped properties! 29:00 Tax appeal strategies. 39:12 Pat Hynes' economic development plan! 43:21 Estimating property taxes and incentives to be aware of. 55:55 Crazy tax appeal stories! 63:19 What's your competitive advantage? 64:09 One piece of advice for new investors. 65:01 What do you do for fun? 65:32 Good book, podcast, or self development activity that you would recommend? 66:48 Local Network Recommendation. 67:22 How can listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

October 29, 2026Episode 48859 min

Episode 488: Chicago New Construction Creating Housing with Andy Ahitow

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! ============= C onnect 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: 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.

October 27, 2026Episode 48715 min

Episode 487: The State of The Chicago Market and The Top 5 Neighborhoods with Jason Wagner

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 C onnect 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 ============= Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

October 22, 2026Episode 48657 min

Episode 486: Chicago House Flipping Thru Wholesaling, Subject-To, and Creative Financing with Oscar Medina

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! ============= C onnect 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: 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.

October 15, 2026Episode 48552 min

Episode 485: Investing & Managing In Lake County With Bill and Shannon Powers

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! ============= C onnect 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 ============= 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.

October 13, 2026Episode 4848 min

Episode 484: 3 Simple Steps To Find Deals in Today's Market with Mark Ainley

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 C onnect 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 ============= Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

October 8, 2026Episode 48356 min

Episode 483: Screening Pets in Rentals with John Bradford of Petscreening.com

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! ============= C onnect 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: John Bradford, PetScreening | Email John: john@petscreening.com 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.

October 1, 2026Episode 48254 min

Episode 482: The Future of Pilsen and Chicago's 25th Ward with Miguel Chacon

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! ============= C onnect 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: 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.

September 29, 2026Episode 48116 min

Episode 481: Multiple Financing Options For Your Next Investment With Chris Puleo

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 C onnect 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 ============= Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2026.

September 24, 2026Episode 4801 hr 6 min

Episode 480: Senior Housing Sector: Underwriting, Markets, and Opportunities with Mark Myers

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! ============= C onnect 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 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.